Skills-based career development is an approach to employee growth that maps the skills people have, the skills future roles require, and the learning experiences needed to close the gap. It moves career progress away from job titles and tenure, and toward visible, measurable capability. For HR and Talent Development leaders, it turns career growth from a vague promise into a working system.

The difference matters. Traditional career development tends to reward how long someone has held a role. Skills-based career development rewards what a person can actually do, and shows them the specific capabilities they need to reach the role or project they want. Done well, it connects employee aspirations to the capabilities the business needs most, so career planning and workforce planning finally point in the same direction.

This guide covers the full operating model: defining skills, identifying skill gaps, building role-level learning paths, enabling managers, connecting development to internal mobility, and measuring outcomes. It also covers where teams go wrong, with concrete examples you can adapt.

How Skills-Based Career Development Differs From Traditional Career Development

Traditional career development follows a ladder. An employee enters a role, accumulates tenure, and waits for the next title to open up. Promotion paths are linear, and progress is often measured by time served rather than capability gained.

Skills-based career development replaces the ladder with a map. Instead of asking “how long until the next title?”, it asks “which skills does the next opportunity require, and how do we build them?” This shifts the focus to capabilities, proficiency levels, readiness, and the future needs of the business.

This does not eliminate career paths. It makes them more transparent and more flexible. An employee can see exactly which skills separate them from a target role, and they can build those skills through more than one route.

That flexibility opens up directions a ladder cannot:

• Lateral moves that broaden a person’s skill base across functions
• Stretch assignments that build new capability inside the current role
• Project-based development that lets employees practice target-role skills before they hold the title
• Internal mobility into adjacent roles that share transferable skills

The result is a model where career advancement depends on demonstrated capability, not on waiting for a seat to open. Many organizations build on the foundations of strong employee career development programs and then go deeper into the skills layer that makes those programs actionable.

Why HR Leaders Are Prioritizing Skills Now

The pace of skill change is the clearest reason. Employers expect 39% of the key skills required in the job market to change by 2030, according to the World Economic Forum’s Future of Jobs Report 2025. That is real disruption, even though it has come down from 44% in 2023 as more companies invest in continuous learning.

When more than a third of core skills are expected to shift inside five years, static training and development cannot keep up. A fixed course catalog assumes the skills people need are stable, and they are not.

Several forces are driving this:

• AI and digital transformation are reshaping which technical and human skills carry value, with AI literacy and big data skills rising fastest
• Leadership demand keeps growing as organizations promote individual contributors into management without enough preparation
• Changing workforce expectations mean employees now treat learning and career growth as a reason to stay or leave

These pressures expose the skills gaps that show up across the workforce: areas where current capability falls short of what the business needs next. Skills-based career development gives HR a dynamic way to find those gaps and close them through targeted employee learning and development rather than generic workplace training.

There is also a competitive opening. Deloitte reports that while roughly 90% of organizations are experimenting with skills-based approaches, fewer than one in five have adopted them in a significant, repeatable way across the organization. The intent is widespread, but execution is rare, which means HR teams that build a working system now move ahead of most of the market.

Why Skills-Based Career Development Matters for Organizations

The business case is straightforward. A skills-based approach connects individual employee growth to organizational capability, which is the bridge between people strategy and business strategy.

Retention is the most immediate payoff. Career progress is the top motivation for employees to learn, and providing learning opportunities is the leading retention strategy, according to LinkedIn’s 2025 Workplace Learning Report. When employees cannot move ahead, they leave and take their skills with them.

Beyond retention, the model strengthens several parts of the talent system at once:

• Engagement rises when employees see a credible path forward
• Workforce planning improves because HR can see which capabilities exist and which are scarce
• Internal mobility increases as people qualify for roles across the organization
• Promotion readiness becomes measurable rather than guessed
• Leadership pipelines fill because future managers are developed deliberately

Each connects employee career growth to a capability the organization actually needs, which is what separates skills-based development from a generic perk.

It Helps Employees See a Clearer Career Path

Employees engage with development when they can see what comes next. A clear career path shows them which skills a future opportunity requires and how to build them, which turns career success from luck into a plan.

Vague encouragement does not work. “Keep growing” tells an employee nothing. “Here are the four skills that separate your role from a team lead role, and here is how to build each one” gives them something to act on.

Concrete transitions make the path real:

• Individual contributor to manager, where the shift is from doing the work to enabling others
• Specialist to team lead, where deep expertise must pair with coordination and delegation
• Analyst to business partner, where technical analysis must connect to influence and strategy

When employees can map career advancement to specific, learnable skills, career advancement strategies stop being abstract advice and become a checklist. Pathwise’s library of essential career skills helps employees and managers name the capabilities that matter at each step.

It Helps HR Identify and Close Skill Gaps

A skill gap is the distance between the skills a person or team has now and the skills a current or future role requires. Skills gaps across a workforce affect hiring costs, succession risk, productivity, and employee confidence.

When gaps go unmeasured, organizations overcorrect by hiring externally for capabilities they could have built internally. That is slower and more expensive, and it signals to existing employees that growth happens elsewhere.

Skill gaps in the workplace surface through several inputs combined:

1. Role requirements that define the skills and proficiency each position needs
2. Manager input on where their teams are strong and where they struggle
3. Employee self-assessments that capture how people rate their own capability
4. Performance data that shows where results fall short of expectations
5. Business strategy that signals which capabilities will matter more next year

Knowing how to identify skill gaps from these inputs is the foundation. Everything downstream, from learning paths to promotion decisions, depends on an honest picture of where capability is missing. Supporting individual skill development then becomes a targeted response rather than a guess.

It Supports Internal Mobility and Workforce Planning

• A skills inventory shows HR where capability already lives inside the organization. Instead of assuming talent must come from outside, leaders can search their own workforce for the skills a new project or role needs.
• This is where skills-based career development connects to skills-based talent management and skills-based workforce planning. The same skills data that powers career conversations also powers decisions about who can move into which roles.
• A skills inventory should serve two timeframes at once. It should show current performance, so managers know who can deliver today. It should also show future readiness, so HR can forecast which capabilities the organization will need and develop them before the gap becomes urgent.

The Core Elements of a Skills-Based Career Development Framework

This is the practical layer. A skills framework gives the organization a shared language for skills, the roles that need them, and the gaps between.

• The most important design rule: the framework must be simple enough for managers and employees to use, not just HR. A framework only specialists can read becomes a document nobody opens.
• A working framework has four parts: a skills taxonomy, role profiles with proficiency levels, a skill-gap assessment, and development actions.

Skills Taxonomy

A skills taxonomy is the organized list of skills the organization needs, grouped into categories. It is the dictionary everything else references.

Group skills into clear categories so they stay navigable:

• Role-specific technical skills, such as financial modeling or software architecture
• Functional skills tied to a department, such as demand planning or campaign management
• Leadership and management skills, such as delegation and performance management
• Communication and collaboration skills, such as feedback, facilitation, and conflict management
• Digital and AI skills, including AI literacy, data analysis, and digital tools
• Career navigation skills, such as networking, personal branding, and self-awareness

These categories help employees and managers answer foundational questions like what are skills that matter for a given role, and what are career development skills versus job-specific ones. Pathwise’s explainer on what are skills is a useful starting point when teams build their first taxonomy.

Role Profiles and Proficiency Levels

Each role or career level should define its required skills and the expected proficiency for each. A role profile is the target an employee develops toward.

Use simple, consistent proficiency language so the levels mean the same thing across teams:

1. Foundational: aware of the skill and can apply it with guidance
2. Working: applies the skill independently in routine situations
3. Advanced: applies the skill in complex or ambiguous situations
4. Expert: sets direction and coaches others in the skill

Avoid vague descriptions like “strong communicator.” They cannot be assessed consistently, because two managers will rate the same person differently. Observable behaviors work better. “Gives direct feedback in one-on-ones and adjusts a message for different audiences” can be seen, coached, and measured.

Skill-Gap Assessment

A skill-gap assessment compares an employee’s current skills against the skills their target role or level requires. The output is a short list of specific gaps, not a vague sense that someone “needs development.”

Several inputs make the assessment reliable:

• Employee self-assessment to capture the person’s own view
• Manager assessment to add an outside perspective
• Performance review data to ground ratings in results
• Work samples that show capability directly
• Project outcomes that reveal skills under real conditions
• Certifications or course completion as supporting evidence

Combining sources matters, because self-assessment alone tends to be generous and manager assessment alone can miss context. Used together, they show HR how to identify skill gaps with enough accuracy to act on.

Development Actions

Gaps should lead to specific actions, not a generic “go take some training.” A skill-gap assessment that ends with “needs leadership development” has not done its job. “Needs to practice delegation and run two stretch projects this quarter” has.

Match the action to the skill:

• Career courses for structured knowledge and frameworks
• Manager coaching for in-the-moment guidance
• Mentorship for perspective from someone who has done the role
• Stretch assignments that build the skill through real work
• Peer learning that spreads capability across a team
• Job shadowing to see a target role up close
• Rotational projects that build breadth
• Practice-based assignments that turn knowledge into habit

Structured learning anchors this mix. Pathwise’s career courses for employee skill development give employees a consistent base of knowledge that managers and mentors can then reinforce through practice.

How to Build a Skills-Based Career Development Program

This is the implementation sequence. The focus stays on the skills layer, the part that makes broader employee development programs concrete and measurable. Follow these steps in order, and resist the urge to map everything at once.

Step 1: Start With Business Priorities

Begin with the capabilities the organization needs most, not with a training catalog. Developing employees only pays off when their growth points at a real business need.

Translate strategy into capability targets first:

• More first-time managers ready to lead
• Stronger communication across teams
• An AI-ready workforce
• Better decision-making under pressure
• A stronger internal promotion pipeline
• Better cross-functional collaboration

Once the priorities are clear, you can choose learning content that serves them. Selecting courses before defining priorities is how staff development budgets get spent on skills nobody needs.

Step 2: Define Critical Skills by Role and Level

Do not try to map every skill for every role on day one. That effort stalls and the framework never ships. Start with high-impact roles or the career transitions where people struggle most.

The individual contributor to manager transition is a common starting point, because it is where many organizations lose good people to bad first-management experiences. Define the skills that transition requires:

• Communication
• Delegation
• Feedback
• Decision-making
• Prioritization
• Coaching
• Conflict management
• Strategic thinking

Mapping one critical transition well teaches the organization how to map the next one. Breadth comes later.

Step 3: Identify Skill Gaps Across the Workforce

With priority roles and required skills defined, run a practical skill-gap process across the relevant population:

1. Choose the priority roles to assess first
2. Define the required skills and proficiency for each
3. Assess current proficiency using self and manager input plus performance data
4. Identify the common gaps that appear across people
5. Segment the gaps by role, level, and team
6. Prioritize the gaps tied to the greatest business risk

Segmenting matters. A skill gap that appears across an entire team is a structural problem that needs a program. The same gap in one person needs a development plan. Treating skill gaps in the workplace at the right level keeps the response proportionate.

Step 4: Build Learning Paths Around Skills, Not Just Courses

A learning path should combine formal and informal development, not list a stack of courses. The widely used 70-20-10 learning model is a useful guide: most growth comes from on-the-job experience, a meaningful share from others, and the rest from formal training.

Blend the elements deliberately:

• Formal training for frameworks and foundations
• On-the-job practice that applies the skill immediately
• Coaching and feedback that correct course in real time
• Peer learning that reinforces the skill socially
• Reflection that turns experience into lasting capability

Pathwise’s organizational offering pairs courses with coaching, career resources, events, and community, which makes it a fit for this kind of blended employee development rather than a course-only approach. For human-skill gaps, targeted programs like communication skills training for employees slot directly into a learning path.

Step 5: Train Managers to Have Skills-Based Career Conversations

Managers decide whether the framework lives or dies. HR can build the best skills taxonomy in the world, but if managers do not use it in conversations, it stays a document.

Give managers a simple career conversation structure they can run in any one-on-one:

1. Which skills are you using most right now?
2. Which skills do you want to build next?
3. What future roles or projects interest you?
4. Which skill gaps are most important to close first?
5. What support do you need from me?

This structure turns career advice from an annual event into an ongoing habit. It connects career planning and career growth to the manager relationship, which is where most employees actually make decisions about staying or leaving.

Step 6: Connect Development to Internal Mobility

Employees need to see how skill-building connects to real opportunities. If building a skill leads nowhere, motivation collapses. The link between development and mobility is what makes the whole system credible.

Make the connections visible:

• Role profiles that show the skills each role requires
• Internal project marketplaces where employees apply skills to new work
• Career path maps that show realistic next moves
• Promotion readiness criteria based on demonstrated skills
• Stretch assignments that serve as auditions for larger roles

This is skills-based talent management in practice. The same skills data that guides development also informs skills-based workforce planning, so mobility decisions rest on capability rather than on who happens to be visible to leadership.

Step 7: Measure Progress and Improve the System

Measurement tells you whether the system works and where to fix it. Track a focused set of metrics rather than everything at once:

• Skill assessment completion
• Skill progression over time
• Learning path participation
• Course completion
• Internal mobility rate
• Promotion readiness
• Retention
• Engagement
• Manager career conversation completion

The trap here is measuring activity instead of capability. Course completion is easy to count and tells you little. The better question is whether employees are actually gaining skills and moving into the roles the organization needs. A program where completion is high but internal mobility is flat is not working, no matter how good the dashboard looks.

Example: Skills-Based Career Path From Individual Contributor to Manager

A specific example makes the model concrete. Consider a high-performing individual contributor moving toward a first management role, a transition nearly every organization runs and many run poorly.

Current Role: High-Performing Individual Contributor

The skills already present usually include:

• Technical expertise in their function
• Strong execution and follow-through
• Reliability that earns trust
• Problem-solving under pressure
• Collaboration with peers

The core development need is a shift in identity: moving from doing the work personally to enabling others to succeed. This is where many strong contributors stall, because the skills that made them excellent individually are not the skills management requires.

Target Role: New Manager

The new manager role requires a different skill set layered on top:

• Delegation
• Feedback
• Coaching
• Prioritization across a team
• Conflict management
• Team communication
• Decision-making with incomplete information
• Performance management

Notice the mix. Some are technical management skills, but most are human skills. That balance is exactly what separates a ready manager from a skilled contributor who is not yet ready.

Development Plan

A learning path for this transition blends formal and experiential development:

1. A structured course such as Manager Essentials to build the frameworks
2. Shadowing a current manager to see the role up close
3. Leading a small project to practice delegation and coordination
4. Practicing feedback conversations in low-stakes settings
5. Coaching sessions to work through real situations
6. Monthly development check-ins to track progress against the gaps

This turns a career path into a skill-building plan. The employee is not waiting for a promotion. They are building, and demonstrating, the exact capabilities the next role requires.

Common Mistakes HR Teams Make With Skills-Based Career Development

The model is simple to describe and easy to get wrong. These are the failures that show up most often, and how to avoid them.

Mistake 1: Building a Huge Skills Taxonomy Nobody Uses

The most common failure is overbuilding. Teams try to catalog every skill for every role, produce a 500-item taxonomy, and watch managers ignore it because it is unusable.

Start small. Map a few priority roles and their core skills, prove the model works, and expand from there. A framework that managers actually use beats a comprehensive one that sits unopened.

Mistake 2: Treating Skills-Based Development as Training Only

Employee training and career development are not the same thing. Training builds a skill. Career development connects that skill to a future opportunity. A program that offers courses but never links them to roles or mobility is just a learning catalog.

Employee training and development works when the training points somewhere. The course on delegation matters because it moves someone toward a management role, not because it exists.

Mistake 3: Ignoring Manager Enablement

HR cannot run thousands of career conversations. Managers do. When managers lack scripts, frameworks, and accountability, the program becomes a static set of resources rather than an active development system.

Equip managers with the conversation structure, hold them accountable for completing career conversations, and give them the skills data they need. Without this, even a well-designed framework goes unused.

Mistake 4: Focusing Only on Technical Skills

Technical skills are easy to define and measure, so teams over-index on them. But human skills are often what determine whether someone is ready to advance. The Future of Jobs Report 2025 ranks creative thinking, resilience, flexibility, agility, and leadership among the fastest-rising skills, alongside technical capability.

Build human skills into every path: communication, adaptability, leadership, judgment, resilience, and collaboration. These are frequently the difference between a capable specialist and a ready leader. Technical paths still matter, and emerging needs like AI upskilling employees belong in the framework, but they should sit alongside human skills rather than crowd them out.

Mistake 5: Measuring Activity Instead of Capability

Counting course completions feels like progress but measures effort, not outcomes. A high completion rate with no change in internal mobility or promotion readiness signals a program that is busy but not working.

Measure demonstrated skill growth, internal movement, role readiness, and business outcomes. These are harder to track than completions, and they are the only metrics that tell you whether capability is actually building.

How Pathwise Can Support Skills-Based Career Development

Each implementation step needs structured content, coaching, and resources behind it. Pathwise supports that work without HR having to assemble it from scratch.

Career Resources for HR Teams and Organizations

Pathwise’s career development resources for organizations provide structured learning, career resources, coaching, and employee development support for all levels. For HR leaders, this gives employees a consistent foundation while keeping the program scalable, supporting the framework, learning paths, and development actions above without a custom build.

Career Courses for Employee Skill Development

Pathwise career courses give employees structured learning they can plug directly into development plans. They cover practical capabilities that map to common skill gaps:

• Decision-making
• Negotiation
• Networking
• Personal branding
• Storytelling
• Manager essentials

These courses fit naturally into role-based learning paths, especially at career transitions where employees need both knowledge and frameworks before they practice on the job.

Coaching and Career Support for Higher-Touch Development

Some skill gaps need personalized guidance that a course cannot provide. Coaching fits leaders, rising managers, high-potential employees, and anyone preparing for internal advancement. It addresses the situational, human-skill gaps, like navigating a difficult team dynamic or stepping into a larger role, that benefit most from one-on-one support.

Build Career Growth Around Skills, Not Guesswork

The core argument is simple. Employees need visible paths so they know where they are going. Managers need practical tools so they can guide the way. HR needs skill data so decisions rest on capability. And organizations need a stronger internal talent pipeline so they can fill critical roles from within.

Skills-based career development connects all four. It replaces guesswork about who is ready with evidence, and it replaces vague encouragement with a plan an employee can act on. With more than a third of core skills expected to change by 2030, that shift from promise to system is no longer optional for HR teams that want to keep pace.

HR leaders ready to put this into practice can explore career development resources for organizations for structured learning, coaching, and scalable employee development support. To give employees practical skill-building inside their development plans, start with Pathwise career courses for employee skill development.

Future-proofing employee careers means building the systems that help people develop durable, transferable skills so they stay valuable as roles, technology, and business priorities shift. It is an organizational strategy, not a personal one. The work sits with HR and the leaders who decide how learning, career paths, and internal movement actually function day to day.

It does not mean promising that any single job will survive unchanged. No employer can guarantee that. What a company can do is widen the range of work each person is ready to take on, so change creates options instead of dead ends. That distinction shapes every strategy below, and it separates real career development from wishful thinking about job security.

Why Future-Proofing Employee Careers Is Now an HR Priority

Career development used to be treated as a perk. It is now a workforce resilience strategy, because the skills your business runs on are changing faster than most hiring plans can keep up with.

The World Economic Forum’s Future of Jobs Report 2025 found that employers expect 39% of the core skills workers need to change by 2030. The same report points to several forces driving that shift at once: technological change including AI, demographic shifts, economic uncertainty, geoeconomic tension, and the green transition. None of these are temporary. They compound.

When skills churn that fast, two things happen inside a company. Critical capabilities go scarce, and employees who can’t see a path forward start looking elsewhere. Building skills internally is usually faster and cheaper than buying them on the open market every time priorities move. That is the business case for treating employee career development as infrastructure rather than a benefit line item.

What “Future-Proof” Actually Means

Future-proofing is a system for raising adaptability, not a promise that roles stay frozen. The goal is employability: the ability to move into new work as the business evolves.

A few core ideas hold the concept together:

• Career resilience: the capacity to absorb change and keep contributing in a new form.
• Skills transferability: capabilities that carry across roles, like communication, decision-making, and problem-solving.
• Continuous learning: development that happens in the flow of work, not once a year.
• Internal mobility: real pathways to move sideways or up without leaving the company.
• Career ownership: employees driving their own growth, supported by systems that make it possible.

Frame it this way with leaders and you avoid the trap of overpromising. You are not protecting jobs. You are expanding what people can do.

Why This Is an Organizational Responsibility

Employees can own their careers, but organizations control most of the levers that make growth possible. Access to learning, manager support, visibility into open roles, coaching, and feedback loops are all designed at the company level. An individual can want to grow and still hit a wall if none of those systems exist.

This is where HR becomes the architect of a future-ready career ecosystem rather than a service desk for training requests. The job is to build the conditions, then hold managers and leaders accountable for using them. Pathwise’s solutions for organizations and HR professionals are built around exactly this idea: structured learning, coaching, and resources that scale development across every level instead of leaving it to chance.

Start With the Skills Your Business Will Need Next

You cannot future-proof careers without knowing which skills will matter to your strategy. The starting point is not a course catalog. It is the business.

Begin with what is changing: business priorities for the next one to three years, shifting customer needs, technology adoption, regulatory pressure, and gaps in your leadership pipeline. Those inputs tell you which skill families to prioritize. For most organizations the list includes AI and digital literacy, communication, critical thinking, adaptability, and leadership.

Build a Skills Inventory

A skills inventory gives you visibility into the capabilities you already have. You can build it from several sources:

1. Skills assessments and competency mapping against a defined skills taxonomy.
2. Manager input on what their teams can actually do.
3. Self-reported employee profiles.
4. Project history and performance data.

The aim is not a perfect database. It is enough visibility to make decisions. Even a rough capability inventory beats guessing.

Identify Future Skills Gaps

Compare current skills against the capabilities your strategy will demand over the next 12 to 36 months. Then sort the gaps by urgency:

• Immediate role requirements.
• Emerging skills tied to new technology or markets.
• Leadership pipeline needs.
• Durable human skills that transfer across roles.

LinkedIn’s 2025 Workplace Learning Report reinforces why this matters: 49% of L&D professionals said their executives are concerned employees do not have the right skills to execute the business strategy. A skills-first approach turns that concern into a plan.

Prioritize Roles Most Exposed to Change

Map which roles are most affected by automation, AI, customer expectations, or business-model shifts. Keep the language calm. This is workforce planning, not a layoff list. A useful frame is that most roles fall into one of four buckets: automated, augmented, redesigned, or expanded. Knowing which bucket a role sits in tells you what kind of career support its people need.

Build Career Paths Around Skills, Not Just Titles

Traditional career ladders are too rigid for organizations that change quickly. A title-based ladder offers one direction and stalls the moment promotions slow down. Skills-based career paths show growth even when the next title is not available.

Move From Job Ladders to Career Pathways

A fixed ladder says “do this job for three years, then get promoted.” A career pathway shows multiple routes: an individual contributor moving to a specialist track, a shift onto the manager track, a cross-functional move, or a project-based growth path. Pathways make progress visible and keep institutional knowledge inside the company.

Use Skills-Based Career Development

For each path, show the skills required, not just the job title. Define proficiency levels so people know where they stand and what comes next:

• Foundational
• Intermediate
• Advanced
• Expert

This is the core of skills-based development: employees can see precisely what to learn to reach the next stage, which turns a vague ambition into a concrete plan.

Make Internal Mobility Easier

People often leave because they cannot see their next opportunity inside the company. Internal mobility fixes that with practical mechanisms:

• Internal job boards and talent marketplaces.
• Stretch assignments and rotations.
• Shadowing and short project-based gigs.

LinkedIn’s report found that only 36% of organizations qualify as “career development champions” that use multiple tactics to support growth, and those companies are more profitable and better at retaining talent. Internal mobility is one of the clearest signals to an employee that staying is worth it.

Make Learning Continuous, Practical, and Personalized

One-off training does not build career resilience. A future-ready program blends formats so learning sticks and shows up in real work.

A strong mix includes structured courses, coaching, manager-led career conversations, peer learning, and applied projects. Pathwise’s career courses provide the scalable structured-learning layer, while coaching and community add the personalized support that courses alone cannot.

Offer Durable Human Skills Alongside Technical Ones

Technical skills age. Human skills compound. Across roles and decades, the same capabilities keep their value: communication, decision-making, negotiation, influence, storytelling, problem-solving, and adaptability. These are the skills that let someone change roles without starting over.

Investing in communication skills training for employees and leadership development pays off precisely because those abilities transfer no matter how the technical landscape shifts.

Include AI Literacy Without Making It the Whole Program

AI readiness is now part of career resilience, but a program built only on AI misses the point. Deloitte’s 2026 Global Human Capital Trends argues that technology alone is not enough: people create competitive advantage through adaptivity, creativity, and judgment under uncertainty, qualities you cannot install with a software rollout. 

Deloitte also found that 59% of organizations take a tech-focused approach to AI, and those organizations are more likely to fall short on returns than the ones that pair technology with human capability.

Layer AI learning by role:

1. General AI literacy for all employees.
2. Workflow-specific AI use for functional teams.
3. Advanced AI strategy for leaders.

That structure builds AI skills across the workforce while keeping human judgment, ethics, and creativity in the center. The goal is an AI-ready workforce that keeps its human touch, not one that defers to tools.

Turn Learning Into Application

Learning becomes credible when people use it for real work. Assign cross-functional projects, customer problem-solving, process redesign, presentation practice, AI workflow pilots, and leadership simulations. Application is what convinces both employees and executives that development is producing results rather than completion certificates.

Equip Managers to Become Career Development Partners

HR cannot scale future-proofing alone. Career growth happens, or stalls, in the relationship between an employee and their manager.

The gap here is large. LinkedIn’s 2025 report found that only 15% of employees said their manager helped them build a career plan in the past six months, down five percentage points from the year before. Managers are stretched across execution, communication, and constant change, often without the tools or time to coach careers well.

Train Managers to Hold Better Career Conversations

Give managers a simple set of prompts they can use in one-on-ones and reviews:

• What skills do you want to build this year?
• Which parts of your work energize you most?
• What future roles interest you?
• What experiences would help you grow?
• What support do you need from me?

A new manager who asks these questions consistently does more for retention than any annual survey. Build the conversation into existing cadences so it does not become another standalone task.

Give Managers Simple Tools

Manager support improves when the tools are lightweight: career conversation guides, skills checklists, development plan templates, and internal mobility maps. Heavy processes get skipped. Easy ones get used. Formal employee career development programs give managers a consistent structure so every team gets the same quality of support.

Recognize Managers Who Develop Talent

Most organizations reward managers for output, not for growing people. Fix the incentives. Track internal promotions, skill progress, engagement, retention, and participation in development conversations. And never punish a manager when a strong team member moves to another part of the business. Internal mobility is a talent win, and treating it as a loss teaches managers to hoard people.

Support Employees at Different Career Stages

Future-proofing cannot be one-size-fits-all. What a first-year analyst needs differs sharply from what a senior leader or a pre-retirement expert needs.

• Individual contributors: skill expansion, visibility, communication, and cross-functional exposure, supported by stretch projects and mentoring.
• New and emerging managers: feedback, delegation, coaching, decision-making, and change management.
• Rising and senior leaders: strategic thinking, influence, executive presence, leading through ambiguity, and AI-informed decision-making, usually with higher-touch coaching.
• Late-career and pre-retirement employees: knowledge transfer, mentoring, advisory roles, and phased transitions so hard-won expertise stays in the business.

Tailoring resources by stage signals that the company is invested in everyone, not just high-potential early-career talent.

Build a Future-Proofing Program HR Can Actually Run

Treat this as a repeatable program, not a one-time campaign. A simple five-step cycle keeps it running quarter after quarter.

1. Diagnose the current state. Review business priorities, workforce risks, skills data, engagement and retention trends, and employee feedback. Find where people lack visibility into paths or learning.
2. Define priority skill areas. Choose a manageable set of enterprise priorities. Separate universal skills, such as adaptability and communication, from role-specific ones.
3. Build learning pathways. Design them by audience segment and career stage, blending courses, coaching, mentoring, applied projects, and manager conversations.
4. Activate managers. Hand them prompts, templates, and clear expectations, then train them on coaching basics and weave reminders into review cycles.
5. Measure and improve. Track results and use them to refine skill priorities, pathways, and manager support.

Keeping the program small and repeatable beats launching an ambitious initiative that collapses after one cycle.

Measure Whether Career Future-Proofing Is Working

Connect career development to business outcomes, not just training activity. Course completions alone tell executives nothing about value. Split your metrics into leading and lagging indicators.

Leading indicators show early engagement:

• Course enrollment and completion.
• Skills assessment participation.
• Career conversation completion.
• Development plan adoption.
• Internal applications.
• Manager participation.
• Employee confidence in future readiness.

Lagging indicators show business impact:

• Retention of key talent.
• Internal mobility and promotion rates.
• Time-to-fill critical roles.
• Skills gap closure.
• Engagement scores.
• Leadership bench strength.
• Reduced dependence on external hiring.

For executive reporting, tie a handful of these to strategic priorities: how upskilling supports a transformation initiative, AI adoption, customer experience, or leadership continuity. Keep it simple enough that leaders can act on it. Coaching, in particular, links directly to outcomes leaders care about, which is why pairing development with career coaching to improve retention tends to show up in the numbers.

Common Mistakes to Avoid

A few predictable failures sink otherwise good programs:

• Treating future-proofing as a training catalog. A library of courses is not a strategy. Courses have to connect to skills, roles, manager conversations, and business needs.
• Focusing only on high-potential employees. Future readiness should be broad-based, with higher-touch support reserved for critical roles, not the only investment.
• Overpromising job security. Avoid language that implies no one will ever be displaced. Use accurate framing: build adaptability, increase options, prepare for changing work.
• Leaving managers unsupported. Expecting managers to coach careers without tools or time guarantees the 15% problem continues.
• Ignoring employee motivation. People engage when development connects to their own goals, not just company needs. Autonomy, visible growth, and practical relevance drive participation.

Next Steps for HR Leaders

Future-proofing employee careers takes more than telling people to keep learning. It requires a system: identify the skills your business will need, build skills-based career paths, make learning continuous and applied, equip managers to coach, support every career stage, and measure business impact.

Build those pieces and you create the conditions for an adaptable, engaged workforce that stays. To put structured learning, coaching, and scalable career resources behind your plan, explore Pathwise’s solutions for organizations and HR teams or review the career course catalog as a ready way to start developing talent at every level. For employees who want to take ownership of their own growth, the guide to future-proofing your career is a useful companion resource.

Internal mobility is the practice of moving employees into new roles, projects, and skill-building experiences inside their current organization rather than replacing them or hiring externally to fill every gap. In the AI era, it has shifted from a nice-to-have benefit into a core workforce strategy. The reason is simple: skills now change faster than companies can hire, and the talent needed for tomorrow’s roles often already sits inside the building.

Career mobility is the broader, more employee-centered version of that idea. It covers lateral moves, promotions, stretch assignments, mentorship, job rotations, and cross-functional work that prepare people to grow over time. 

For HR and talent leaders, building a deliberate career mobility model is becoming one of the most direct ways to protect retention, close skills gaps, and keep the workforce agile while artificial intelligence reshapes what work looks like.

This guide explains why career mobility matters now, what AI is changing about skills and career paths, and how HR can build a mobility program that produces measurable business results. It is written for people who need both the business case and a practical plan they can start using.

Career Mobility vs. Internal Mobility

Career mobility and internal mobility are related but not identical, and the distinction matters when you design a program.

• Internal mobility usually refers to the movement itself: an employee changing roles within the organization through a promotion, lateral transfer, internal gig, or stretch assignment. It is the HR and talent strategy term, and it is what most metrics track.
• Career mobility is wider. It includes the development experiences that prepare someone to move, even before any role change happens. A mentorship relationship, a short rotation, a cross-functional project, or a targeted upskilling path all count, because each builds the capability and visibility that makes a future move possible. Career mobility centers on the employee’s growth. Internal mobility centers on the organization filling roles. A strong strategy treats them as two ends of the same system. If you only post internal jobs without building the development pathways behind them, you get movement on paper and frustration in practice.

For HR teams that want to anchor this work to a single operating model, career development support for HR professionals brings the development layer and the movement layer together rather than running them as separate programs.

Why HR Leaders Are Paying Attention Now

AI is disrupting entry-level work, skill demand, and the traditional career ladder at the same time, and external hiring alone can no longer keep pace.

Gartner projects that roughly one-third of recruiting capacity will shift inward toward internal talent mobility, and that one in five employees will need to be redeployed by 2030 as new roles are created and old ones change. 

Most organizations are not ready for that level of internal movement. Gartner also identifies declining entry-level hiring as a growing pressure on HR, because AI now handles much of the lower-value work that used to train early-career employees. You can read the full breakdown in Gartner’s 2026 talent management trends.

The practical takeaway: the best future talent for many roles may already be inside the company, hidden by poor skills visibility, outdated job architecture, or managers who guard their best people. Internal mobility is how you find that talent before launching an external search.

What AI Is Changing About Work, Skills, and Career Paths

AI is not only automating tasks. It is reshaping which skill combinations matter, compressing the time people have to develop, and raising the value of human judgment.

Skills Are Changing Faster Than Job Titles

Job titles are becoming a weak unit for workforce planning because the skills inside them shift constantly. The World Economic Forum reports that nearly 40% of the skills required on the job are set to change by 2030, with AI and big data ranking as the single fastest-growing skill area, followed by networks, cybersecurity, and technological literacy. The full data appears in the World Economic Forum’s Future of Jobs Report 2025.

This is why skills-based workforce planning is replacing title-based planning. A skills taxonomy gives the organization a shared language for capabilities. A skills inventory shows where those capabilities actually live. Together they let HR spot adjacent skills, the capabilities an employee already has that sit close to a role they have never held, and use them to find redeployment options that a job-title search would miss.

Traditional Career Ladders Are Compressing

When AI absorbs routine work, it removes the early tasks that used to teach junior employees their craft. PwC’s analysis of more than one billion job ads found that entry-level roles most exposed to AI are now seven times more likely to demand traditionally senior skills like leadership and creativity, and that these “seniorised” entry-level postings grew 35% since 2019 while other entry-level roles shrank 10%. The detail is in the PwC 2026 Global AI Jobs Barometer.

For HR, the implication is direct. Employees need accelerated development, coaching, and stretch opportunities earlier in their careers, because the old slow climb up the ladder no longer exists. Structured early-career development, onboarding, mentorship, and internal project work have to do the job the ladder used to do.

Human Skills Are Becoming More Valuable, Not Less

As AI handles more analytical and routine output, judgment, leadership, adaptability, communication, creativity, and stakeholder management rise in value. The same PwC research shows AI skills now carry a wage premium of around 62%, but it pairs that finding with a clear warning that human-intensive skills are now what separate strong performers in AI-exposed roles.

Career mobility programs should therefore develop two things at once: AI fluency and human-centered capability. Treating these as competing priorities is a mistake. The most resilient employees combine both. Pathwise covers this balance in more depth in its guide to building an AI-ready workforce that keeps the human touch.

The Business Case for Career Mobility

Career mobility is a lever for business resilience, and HR leaders need that framing to win executive buy-in.

Retention Improves When Employees See a Future Inside the Company

Employees leave when they cannot see where they go next. Lack of visible growth is one of the most common drivers of regrettable attrition, the loss of people the organization wanted to keep. Gartner names regrettable retention pressure as a primary productivity barrier heading into 2026. 

Career visibility, coaching, and genuine access to internal opportunity reduce that risk. Mobility is not only about promotions; a well-chosen lateral move can re-engage someone who felt stuck. Pathwise explores this link in its work on career coaching and employee retention.

Internal Mobility Closes Skills Gaps Faster

External hiring is slow, expensive, and uncertain, especially for the fast-emerging skills every company is chasing at once. Redeployment, upskilling, reskilling, and adjacent-skill matching let you fill needs from a known quantity. 

An operations specialist who already understands the business can often be developed into an AI-enabled process role faster than an outside hire can be recruited, onboarded, and brought up to speed. Structured employee career development programs turn that potential into a repeatable pipeline rather than a one-off rescue.

Career Mobility Supports Workforce Agility

Mobility lets an organization shift talent toward changing priorities without restarting from zero. Project-based gigs, cross-functional assignments, and temporary redeployment to critical initiatives all move capability to where the business needs it. This is the practical expression of strategic workforce planning: instead of a static headcount plan, you get a workforce that can flex.

What a Modern Career Mobility Strategy Looks Like

A modern strategy rests on five pillars, and technology is only one of them: skills visibility, transparent pathways, internal opportunity access, manager support, and measurement.

Skills Intelligence and Employee Profiles

Good matching depends on good data. HR needs current information on each employee’s skills, experience, certifications, learning progress, performance context, and career aspirations. Poor data quality is the fastest way to undermine any AI-driven matching, because the system can only recommend what it can see. 

Organizations without an advanced skills intelligence platform can still start lightweight: a structured self-assessment plus manager validation for a few critical job families beats a stalled attempt to map everything at once.

Career Pathways and Role Architecture

Employees move when they can see where moves are possible. Career mapping shows the realistic next steps from a given role, including vertical promotions, lateral moves, cross-functional shifts, and project-based detours. Tie those pathways to business-critical roles and future skill needs so the map serves both the person and the organization. Pathwise breaks down the mechanics in its explainer on what career mapping is.

Internal Opportunities Beyond Job Postings

A mobility program that only posts open jobs misses most of the opportunity. Internal gigs, stretch assignments, mentorships, cross-functional projects, job rotations, and short-term task forces all build skills and test role fit without a permanent move. These opportunities need to be visible, searchable, and genuinely accessible. 

Employees often also need guidance to understand which ones fit their goals, which is where coaching and manager conversations come in.

Managers as Career Coaches

Managers can accelerate mobility or quietly block it. A manager who holds career conversations, builds development plans, gives honest feedback, and protects psychological safety moves people forward. A manager who hoards talent to protect their own team’s output stops the system cold. 

Training managers to coach, and rewarding them for developing and releasing talent rather than retaining it, is one of the highest-leverage moves in any mobility program.

How HR Can Build a Career Mobility Program

The work moves from strategy to execution in a clear sequence, and it scales to organizations at different maturity levels.

• Start by identifying the business-critical capabilities the organization will need over the next 12 to 24 months, then map where those capabilities exist internally and where gaps are forming. Align this with workforce planning so mobility is not a side initiative.
• Next, audit current barriers to movement. Ask whether employees know where opportunities are posted, whether managers discourage internal applications, and whether tenure rules or approval workflows quietly suppress movement. Check whether opportunity access is equitable across departments, levels, and locations.
• Then build visible career pathways with concrete examples of next moves, paired with learning recommendations and coaching prompts. Pilot the program with one high-priority segment, such as an AI upskilling cohort, a leadership pipeline, or a customer-facing function, and define success metrics before launch so you can refine governance and manager expectations from real results.
• Finally, connect learning to movement. Training on its own changes little. Link courses, coaching, mentorship, and project work to real internal opportunities so development leads somewhere. This is where L&D and talent acquisition collaborate on internal pipelines instead of working in separate lanes. Pathwise covers the development side of this in its guide to AI upskilling for employees.

How AI Can Support Internal Mobility Responsibly

AI helps internal mobility most where scale and visibility are the constraint: surfacing internal candidates, recommending opportunities, suggesting career paths, and analyzing skills gaps across a large workforce. It does not replace human judgment, and treating it as if it does creates risk.

• Use AI to widen the view, not to make the final call. A matching system can surface a candidate a hiring manager would never have found, but the decision should still include human review, employee consent, and a real conversation. Where possible, keep the matching criteria explainable so employees and managers understand why a recommendation appeared.
• Protecting fairness matters as much as accuracy. An AI system trained on past promotion patterns can quietly reproduce old inequities, so HR should monitor for bias, run adverse-impact checks, set inclusive eligibility rules, and audit both who gets recommended and who actually moves. The tradeoffs are worth thinking through carefully; Pathwise lays out a balanced view in its breakdown of the pros and cons of AI in the workplace.

Employee trust sits at the center of all of it. People should know how their skills, interests, and career data are used, and they should be able to set their own preferences. Mobility should feel empowering, not like surveillance. 

The LinkedIn 2025 Workplace Learning Report found that only 36% of organizations qualify as career development champions, and those organizations are far more likely to lead in generative AI adoption, suggesting that strong human development practice and responsible AI adoption tend to grow together rather than in opposition.

Metrics HR and Talent Leaders Should Track

Mature programs measure both activity and impact, not vanity numbers. Tie every metric back to a business outcome.

Mobility and opportunity metrics to track:

• Internal mobility rate and internal fill rate
• Percentage of roles filled internally
• Internal application rate
• Time to fill internal roles
• Participation in gigs, rotations, mentorships, and project assignments

Skills and readiness metrics to track:

• Critical skill coverage and skills gaps closed
• New skills developed against business priorities
• Bench strength and readiness for succession roles
• Redeployment success rate

Retention and engagement metrics to track:

• Retention of high-potential employees and retention after internal moves
• Engagement among mobility participants
• Manager support scores for mobility
• Career confidence and clarity scores
• Regrettable attrition among employees who lacked mobility options

Common Mistakes That Undermine Career Mobility

A few predictable failures stall most programs.

• The first is treating mobility as a job-board problem. Posting internal roles is not the same as building a mobility culture; without pathways, coaching, and manager support, the postings sit unused.
• The second is letting managers hoard talent. When a manager’s incentives reward keeping strong performers in place, enterprise talent needs lose. Recognize and reward managers who develop and export people, and make mobility support an explicit part of the manager role.
• The third is building AI tools on weak skills data. Incomplete profiles and outdated job descriptions produce poor matches and erode trust. Start with critical roles and priority skills, then refresh the data continuously through learning, projects, performance, and employee input.
• The fourth is ignoring equity and transparency. Hidden opportunities reward employees with the strongest internal networks and shut out everyone else. Clear eligibility rules, transparent application processes, and consistent communication keep the system fair.

Examples of Career Mobility in Practice

Concrete examples make the model easier to act on across industries.

• An operations employee develops AI fluency and moves laterally into a process-improvement role after a targeted upskilling path, a stretch project, and coaching. HR identifies the adjacent skills, the business fills a critical need, and no external search is required.
• A company creates cross-functional project gigs on an AI implementation or customer-experience initiative. Employees build new skills, managers and employees get structured feedback afterward, and HR uses the assignment to test future role fit before committing to a permanent move.

A skills inventory reveals hidden internal candidates before an external search begins, surfacing people whose capabilities never showed up in their job title. High-potential employees then receive mentoring, leadership development, and cross-functional exposure, and internal mobility becomes part of succession planning rather than a separate track.

Next Steps

In the AI era, HR cannot run career mobility as a side program. It belongs inside workforce planning, retention, learning, and leadership development as a single connected system. The practical path is consistent: build skills visibility, create transparent pathways, support and reward managers, use AI responsibly, and measure business outcomes rather than activity.

If you are ready to turn career mobility into a working operating model, explore Pathwise’s workforce development solutions to see how skills visibility, internal pathways, and coaching fit together, or connect with the team through career development support for HR professionals to map your own internal mobility strategy.

Career preparation is the process of clarifying your goals, building relevant skills, strengthening your network, and creating a plan for your next career move. It applies whether you want a new job, a promotion, a career change, or simply a more intentional path in your current role.

This guide explains what career preparation is, why it matters now, and how to build a career management plan you can actually use. You will get a six-step framework, a practical checklist, examples for different career stages, and the common mistakes that hold people back. By the end, you will know exactly what to do next.

What Is Career Preparation?

Career preparation is the ongoing work of getting ready for your next professional step before you need it. It covers self-assessment, goal setting, skill building, networking, and the habits that let you act when an opportunity or a setback arrives. It is broader than a single job search.

Three related terms often get used interchangeably, so it helps to separate them. Career planning is the act of choosing goals and mapping a route toward them. Career management is the wider, continuous practice of steering your professional life, adjusting goals, tracking progress, and making deliberate decisions instead of reacting only when something changes. Career preparation sits underneath both: it is the readiness layer that makes planning and management work in practice.

Think of it this way. Planning answers “where do I want to go.” Management answers “how do I keep moving and adjust along the way.” Preparation answers “am I ready to move when the moment comes.” A strong career development plan connects all three, so your daily effort lines up with your long-term direction.

If you want a structured way to visualize the route ahead, career mapping gives you a visual model of roles, skills, and transitions. And if you are early in the process and unsure where to begin, understanding career readiness is the natural starting point.

Why Career Preparation Matters

Career preparation matters because the job market changes faster than most plans assume, and the people who prepare in advance adapt with less disruption. Waiting until a layoff, a reorganization, or a sudden opening forces you to plan under pressure, which rarely produces your best decisions.

The data backs this up. Median job tenure in the United States fell to 3.9 years in January 2024, the lowest level since 2002, according to the U.S. Bureau of Labor Statistics. For workers ages 25 to 34, the median was just 2.7 years. People move more often than they used to, which means the skill of preparing for a transition is now a core professional skill, not an occasional one.

Skills themselves are shifting too. The World Economic Forum’s Future of Jobs Report 2025 found that employers expect 39% of workers’ core skills to change by 2030. The same report estimated that 59% of workers will need training by 2030 to keep pace. If you are not actively preparing, the gap between what you can do and what the market wants tends to widen quietly until it becomes urgent.

Preparation pays off in concrete ways:

• It builds clarity. You know your strengths, your gaps, and the direction you want, so decisions get easier.
  
• It builds confidence. When you have done the groundwork, interviews, promotions, and pitches feel less like gambles.
  
• It builds adaptability. You can respond to a reorganization or a new opening without scrambling.
  
• It builds resilience. If a role disappears, a prepared professional has a network, an updated resume, and a plan to fall back on. 

There is also a motivation effect. LinkedIn’s 2025 Workplace Learning Report identified career progress as the top reason people pursue learning. When growth stalls, engagement drops and people leave. Preparing for your next step keeps you moving, which keeps the work meaningful.

The 4 Core Benefits of Career Management

Managing your career deliberately produces four benefits that compound over time. Each one supports the others, and together they turn vague ambition into steady progress.

1. Clearer Career Goals

Career management starts with knowing what you are working toward. Clear goals focus your effort and give you a way to measure progress, so you can see how far you have come and where you still need to grow.

The most useful goals are specific and realistic. SMART goals (specific, measurable, achievable, relevant, and time-bound) turn a vague wish into something you can act on. Compare these two:

• Weak goal: “I want to advance in my career.” 
• SMART goal: “I will move from a senior analyst role to a team lead position within 18 months by completing a management course and leading two cross-functional projects.” 

Set goals that match your current situation and resources. A recent graduate aiming to become a Fortune 500 executive in five years is setting up for frustration. A graduate aiming to move from entry level to mid level in that window has a target worth chasing. For a deeper method, see the process of setting goals and why writing them down increases follow-through.

2. Stronger Professional Development

Professional development is the work of improving your skills so you perform better now and qualify for more later. It includes courses, certifications, workshops, job shadowing, and stretch assignments that push you past your current level.

The case for it is strong. With nearly 4 in 10 core skills expected to change by 2030, continuous learning is no longer optional. The practical move is a skill-gap analysis: list the skills your target role requires, rate yourself honestly against each, and build a plan to close the largest gaps first. A focused skill development plan keeps that effort organized, and it helps to know which essential career soft skills employers value across roles.

3. A More Useful Career Network

A strong network keeps you informed, connected, and visible to opportunities you would otherwise miss. It is one of the highest-return activities in career preparation, and the numbers explain why.

A 2025 survey found that 54% of U.S. workers were hired through a personal connection, and many open roles are never posted publicly at all. Networking is not a favor you ask once you need a job. It is a relationship you build before you need anything. Practical actions include:

• Attend industry conferences and events, and join conversations rather than standing on the edge.
  
• Join professional associations and alumni groups to meet people in your field.
  
• Use LinkedIn to comment on others’ posts, share useful updates, and stay on people’s radar.
  
• Reconnect with former colleagues and managers twice a year, with no agenda beyond keeping the relationship warm. 

For a fuller approach, learn how to build your career support network so it works for you over the long term.

4. More Control Over Career Decisions

The biggest benefit of career management is control. When you understand your skills, set goals, and prepare in advance, you choose your moves instead of reacting to them. That control matters most during transitions: promotions, role changes, layoffs, and pivots into new fields.

Control comes from preparation, not luck. It means having an updated resume before you need it, a network you have nurtured, and a development plan you revisit on a schedule. With those in place, a sudden opening becomes an opportunity rather than a crisis. A useful starting point is learning how to find purpose in your work, which anchors the rest of your decisions.

How to Prepare for Your Career in 6 Steps

Career preparation becomes manageable when you break it into steps. The framework below moves from understanding yourself to acting in the market and reviewing your progress. Work through it in order, then repeat it as your situation changes.

Step 1: Assess Your Strengths, Values, and Interests

Start by understanding what you do well, what you care about, and what you enjoy. Self-assessment is the foundation, because goals built on a clear picture of yourself hold up better than goals borrowed from someone else.

Use a mix of inputs:

• Reflect on past roles and projects, noting what energized you and what drained you.
• Ask trusted colleagues and managers for honest feedback on your strengths and blind spots.
• Try a formal assessment of interests, values, or work style to add structure.
• Watch for job-fit signals: the tasks you finish quickly, the problems you enjoy solving, the environments where you do your best work.
  

Step 2: Define Short-, Mid-, and Long-Term Goals

Turn self-knowledge into direction by setting goals across three horizons. Layered goals keep daily effort connected to long-term ambition.

• Short term (3 to 12 months): finish a certification, lead a project, or build one specific skill.
• Mid term (1 to 3 years): earn a promotion, switch teams, or move into a specialty.
• Long term (3 to 10 years): reach a leadership role, change industries, or build expertise that defines your reputation.
  

Write each goal down and attach a rough date. Goals with deadlines get acted on; goals without them drift.

Step 3: Research Career Paths and Requirements

Before you commit, learn what your target roles actually require. Research closes the gap between where you are and what the next step demands.

Look into the specific skills and credentials the role needs, the typical salary range, the job outlook for the field, and the day-to-day responsibilities. Read job postings for roles one or two steps ahead of you and note the requirements that show up repeatedly. Those repeated requirements become your development priorities.

Step 4: Build a Skill Development Plan

Once you know the requirements, build a plan to meet them. A skill development plan converts your research into scheduled action.

List the gaps between your current skills and your target role, then rank them by impact. Match each gap to a way of closing it: a course, a certification, a mentor, or a stretch assignment at work. Stretch assignments are often the fastest route, because you build the skill and prove it at the same time. Set target dates so the plan has momentum, and use a structured skill development plan to keep it on track.

Step 5: Strengthen Your Resume, LinkedIn, and Network

Prepare the assets that let you act when an opportunity appears. These are the tools that turn readiness into results.

• Keep your resume current, with recent accomplishments quantified wherever possible.
• Update your LinkedIn profile so it reflects your target direction, not just your past.
• Maintain your network through regular, low-pressure contact.
• Practice your interview answers before you need them, so you are not rehearsing under pressure. 

If a job search is on your horizon, review how to find a job efficiently and how to prepare for an interview so you walk in ready.

Step 6: Review and Update Your Plan Quarterly

A career plan is a living document, not a one-time exercise. Review it on a schedule so it keeps pace with your life and the market.

A quarterly review works well for most people. Each quarter, ask: Have my goals changed? Have I closed any skill gaps? Has my industry shifted? Is my current path still the right one? Adjust based on the answers. Also review whenever something significant changes, such as a new role, a reorganization, or a shift in your priorities. Regular review is what keeps you from investing months in a direction that no longer fits.

Career Preparation Checklist

Use this checklist to turn the framework into action. Work through it once to set your foundation, then revisit the bottom items each quarter.

• Define your strengths, values, and interests through reflection and feedback.
• Identify the skill gaps between your current role and your target role.
• Set short-, mid-, and long-term goals, each with a date.
• Update your resume with recent, quantified accomplishments.
• Refresh your LinkedIn profile to point at your target direction.
• Build and maintain a network of mentors, peers, and contacts.
• Create a skill development plan with courses, certifications, or stretch assignments.
• Prepare and practice your interview answers before you need them.
• Research salary ranges and requirements for your target roles.
• Schedule a quarterly review to track progress and adjust.
  

Career Preparation Examples by Career Stage

Career preparation looks different depending on where you are. The principles stay the same; the priorities shift. Here is how the framework applies across five common stages.

• Students and early-career professionals: Focus on exploration and foundations. Try internships, build a starter network through alumni groups, and develop core skills. Goals should be broad enough to allow discovery but specific enough to guide first steps. 
• Mid-career professionals (individual contributors): Focus on depth and visibility. Identify the skills that separate senior contributors from the rest, take on high-visibility projects, and decide whether your path runs toward management or deeper specialization. 
• New managers and rising leaders: Focus on the shift from doing to leading. Build people-management and communication skills, find a mentor who has made the transition, and seek feedback on your leadership, not just your output. 
• Career changers: Focus on translation and proof. Map your transferable skills to the new field, close the credential gaps that matter most, and use your network to find an entry point. A clear transition plan makes a big difference here, since people with one are far more likely to land the change successfully. 
• Pre-retirement professionals: Focus on legacy and flexibility. Consider advisory roles, consulting, mentoring, or phased transitions, and prepare the financial and skill groundwork for whatever comes next.
  

Common Career Preparation Mistakes to Avoid

Most career preparation failures come from a handful of repeated mistakes. Knowing them in advance helps you sidestep them.

• Setting vague goals. “Advance in my career” gives you nothing to act on. Specific, dated goals do.
• Skipping a skill plan. Knowing you have a gap is useless without a concrete plan to close it.
• Neglecting your network. A network built only when you need a job rarely delivers. Build it before you need it.
• Waiting for a crisis. Preparing only after a layoff or a bad review means planning under stress, which leads to worse choices.
• Never reviewing progress. A plan you set once and forget drifts out of date. Quarterly reviews keep it useful.

Conclusion

Career preparation is not a single task you finish. It is a habit of staying ready: clear on your goals, current on your skills, connected through your network, and willing to review your plan as things change. The professionals who do this well spend less time reacting and more time choosing, because they prepared before the moment arrived.

You do not have to build all of it at once. Start with one step, assess where you are, then keep moving. When you want structured support, explore PathWise’s career services to build a plan that fits your goals, or book a session with a PathWise coach to work through your next move with someone in your corner.

Ways PathWise Can Help

Whatever stage you are at, there is a path in:

• Want one-on-one guidance through a transition or promotion? Start with career coaching.
• Need hands-on help with your resume, LinkedIn, and job search? See career services.
• Prefer to learn and build skills at your own pace? Browse the career courses.
• Just getting started and not sure which fits? See everything built for individuals, or review the full range of PathWise solutions.

Ready to take control of your next step? Get in touch with the PathWise team.

An entry-level career is the starting point of a professional path: a role designed for people who are new to a field and need to build skills, not prove a long track record. These jobs usually call for little or no full-time work experience, offer training, and serve as the first rung on a longer career ladder. They are built for recent graduates, career changers, and anyone applying for a first job with limited experience.

This guide explains what entry-level means on a real job posting, why some of these roles still ask for experience, and how to qualify when your resume is thin. You will find examples by industry, the skills employers screen for, what counts as experience when you have never held a full-time job, and a step-by-step plan to find, land, and evaluate your first role.

What Is an Entry-Level Career?

An entry-level career is a role intended for someone beginning in a field, where the employer expects to teach the job rather than inherit a finished professional. The work centers on learning the basics, getting on-the-job training, and contributing under supervision. You can find these roles in nearly every sector, including business, technology, healthcare, finance, marketing, and operations.

There is a useful distinction between an entry-level job and an entry-level career. A job is the single role you take. A career is the longer path that role starts. A customer service representative position is a job; the move from that seat into team lead, then operations manager, is the career. Thinking in terms of the path, not just the paycheck, changes how you choose your first role.

What “Entry-Level” Usually Means in Job Postings

On a posting, “entry-level” signals that the role is open to people early in their working lives, typically framed as needing zero to two years of experience. The listing usually promises training, expects basic baseline skills, and assigns beginner-level responsibilities under a manager’s guidance. Reading several postings for the same title is the fastest way to see which requirements are truly standard and which one company simply added.

What you should expect to see in a genuine entry-level posting:

• A stated experience range of roughly zero to two years, or language like “no experience required” or “training provided”
• Beginner responsibilities that support a team rather than lead it
• A named manager or supervisor who oversees your work
• Baseline skills such as communication, organization, and basic software use
• Education or certification that is preferred rather than strictly mandatory

Why Some Entry-Level Jobs Still Ask for Experience

The frustrating contradiction many job seekers hit is real and measurable. As of 2025, 38.4% of entry-level jobs require at least three years of experience, a mismatch sometimes called the experience paradox. Entry-level postings that ask for no prior experience have also thinned, with roles open to people with zero to two years dropping sharply since early 2024.

Two things explain the gap. First, some employers reuse old job descriptions or inflate requirements to filter the applicant pile. Second, “experience” rarely means only full-time employment. Internships, coursework, freelance projects, and volunteer work often satisfy the spirit of the requirement. 

There is encouragement in the data: roughly 42% of applicants who lack the exact experience listed are still considered hireable candidates that employers will train. Apply even when you fall short of the stated years, and use the rest of this guide to show evidence you can do the work. For broader readiness before you apply, career preparation resources can help you close the gaps employers notice.

Entry-Level Career vs. Entry-Level Job vs. Internship

People use these terms loosely, but they describe different things, and knowing the difference helps you target the right opening. Here is how the common early-career options compare:

• Entry-level job: A permanent, paid role for someone new to a field. It includes training and beginner duties and is the most common first step into full-time work.
• Entry-level career: The longer professional path that an entry-level job begins. The job is the seat; the career is the trajectory across roles and years.
• Internship: A short-term, often temporary position, paid or unpaid, designed to give students or recent graduates supervised exposure to a field. It frequently leads to a full-time offer.
• Apprenticeship: A structured, paid program that combines on-the-job training with formal instruction, common in skilled trades and increasingly in tech and healthcare.
• Junior role: A step above pure entry-level. It assumes some demonstrated skill and gives slightly more independent responsibility, often the next promotion after an entry-level job.
• Associate role: A title that varies by industry. In some fields it is the entry point; in others, such as law or finance, it sits above entry-level and carries more accountability.

The practical takeaway: read the responsibilities, not just the title. A role labeled “associate” at one company may be more advanced than an “entry-level” role at another.

Common Entry-Level Career Examples by Industry

Entry-level roles exist across every major industry, and each opens a different career path. Below are common starter roles, what you actually do in them, the skills they build, and the next step each one tends to lead to.

• Administrative assistant (business and operations): You manage schedules, documents, and communication to support a team. You build organization, software fluency, and professional communication. Next step: office manager or operations coordinator.
• Marketing coordinator (marketing): You support campaigns, schedule content, and track analytics. You build copywriting, data reading, and project coordination skills. Next step: marketing specialist or campaign manager.
• Sales associate (retail and sales): You serve customers and learn how products are sold. You build persuasion, customer service, and goal-tracking skills. Next step: account executive or sales team lead.
• Junior software developer (technology): You write, test, and maintain code under senior guidance. You build programming, debugging, and version-control skills. Next step: software engineer or developer II.
• Customer service representative (support): You answer questions, resolve issues, and learn the product deeply. You build communication, problem-solving, and patience under pressure. Next step: support team lead or customer success manager.
• Healthcare assistant (healthcare): You support medical staff and help patients in a clinical setting. You build clinical basics, reliability, and bedside communication. Next step: licensed technician or specialized care role.
• Junior financial analyst (finance): You gather data, build basic models, and support reporting. You build spreadsheet skill, attention to detail, and financial literacy. Next step: financial analyst or associate. If finance is your target and you lack experience, study the more specific path before applying broadly.
• HR coordinator (human resources): You support recruiting, onboarding, and records. You build interpersonal skills, discretion, and process management. Next step: HR generalist or recruiter.
• Operations associate (operations): You keep daily processes running and flag bottlenecks. You build systems thinking and coordination. Next step: operations analyst or manager.
• Data analyst, junior (data): You clean data, build reports, and answer business questions. You build SQL, spreadsheet, and visualization skills. Next step: data analyst or analytics specialist.

Use these as a map. Pick two or three that fit your interests, then study real postings to learn the exact skills each employer wants.

What Skills Do Employers Expect for Entry-Level Roles?

Communication is the single most requested skill across entry-level hiring, ranking above technical ability in analyses of millions of job postings. Employers screening resumes for entry-level positions consistently look for evidence of teamwork, problem-solving, and clear communication before anything else.

The skills that move an entry-level application forward:

• Communication: Writing clearly and speaking professionally. This is the top-requested skill in entry-level postings.
• Teamwork: Working well inside a group and supporting shared goals.
• Reliability: Showing up, meeting deadlines, and following through without being chased.
• Problem-solving: Thinking through an issue and proposing a workable answer.
• Digital literacy: Comfort with email, spreadsheets, collaboration tools, and the software a role uses daily.
• Customer orientation: Understanding and serving the needs of clients or users.
• Basic technical skills: The specific tools a field uses, from a coding language to a CRM.

One fast-rising signal deserves attention: AI literacy. More than a third of entry-level jobs now ask for AI skills, nearly triple the share from a year earlier. AI literacy means knowing what these tools can and cannot do, how to write a useful prompt, and how to check the output. It is not yet the top skill employers want, communication still leads, but it is climbing fast and worth building. To present any of these well on paper, review which good skills to put on a resume actually match the roles you are targeting.

What Counts as Experience When You Have Not Had a Full-Time Job?

Experience is not limited to a paycheck from a full-time employer. Employers accept many kinds of evidence that you can do the work, and skills-based hiring has made this more true than ever. Nearly two-thirds of employers now use skills-based practices for entry-level professional roles, and many have dropped GPA as a screen entirely.

What counts as experience, and how to frame it:

• Internships: The strongest non-employment signal. Describe the project, the tools you used, and the outcome you contributed to.
• Coursework and class projects: A capstone project, research paper, or group assignment shows applied skill. Name the deliverable and the result.
• Volunteer work: Organizing an event or running a nonprofit’s social account demonstrates real responsibility. Quantify it where you can.
• Part-time and seasonal jobs: Retail, food service, and gig work build reliability, customer skills, and teamwork that transfer to professional roles.
• Freelance projects: Paid or unpaid client work proves you can deliver. Keep samples and link to a portfolio.
• Certifications and micro-credentials: A completed certificate in a relevant tool or method signals initiative and baseline competence.
• Clubs and student leadership: Leading a team, managing a budget, or planning logistics maps directly to workplace skills.

The phrasing matters as much as the activity. Write each resume bullet around three things: what you did, what tools or skills you used, and what result you helped create. “Managed the social media for a campus club, grew followers 40% in one semester” beats “responsible for social media.” A strong resume turns scattered experiences into proof.

How to Find and Land an Entry-Level Career

Landing a first role is a sequence, not a lottery. Applying randomly to hundreds of listings wastes effort; a focused process wins. Work through these steps in order. For the full tactical playbook, see how to find a job.

Choose Two or Three Target Roles

Pick two or three specific roles that match your interests and skills, then concentrate your energy there. Focus beats spray-and-pray because it lets you tailor every application and learn the field deeply. Studying a single career direction also helps you map a longer path; a career plan for your early 20s is a useful frame for choosing where to aim first.

Match Your Resume to the Job Posting

Tailor your resume to each posting instead of sending one generic version. Pull the skills and keywords the listing names, then mirror them honestly in your bullets. Lead with transferable-skill phrasing: “coordinated a five-person group project on deadline” speaks to teamwork and reliability even without a job title behind it. Include education, internships, part-time work, volunteer roles, certifications, and technical skills.

Build Proof Before You Apply

Create evidence that you can do the work, especially if your resume is light. Useful proof includes:

• A small portfolio or set of samples relevant to the role
• A class or personal project that mirrors real job tasks
• A completed micro-certification in a tool the field uses
• Documented volunteer or freelance work with a clear outcome

Proof closes the gap that the experience paradox creates. It gives a hiring manager a reason to choose you over an equally inexperienced applicant.

Use Job Boards and Your Network

Search established job boards and professional networking platforms to find openings, and use those same platforms to connect with people working in your target field. Networking matters because many roles are filled through referrals before they are widely advertised. A short, specific message to someone in the role you want often does more than a hundred cold applications.

Prepare for Entry-Level Interview Questions

Walk in ready to show enthusiasm, coachability, and fit, since employers know you are new and are hiring for potential. Prepare specific stories from your projects, internships, and part-time work that show how you solved a problem or worked in a team. A structured approach to how to prepare for an interview will help you answer common questions with evidence rather than generalities.

How to Tell If an Entry-Level Role Is a Good Opportunity

Not every entry-level job moves your career forward; some are dead ends with a fancy title. Before accepting an offer, weigh the role against criteria that predict growth. A good first role builds skills you can carry anywhere and gives you a manager who actually develops people.

Signs a role is worth taking:

• Real training: Structured onboarding and ongoing learning, not “figure it out yourself.”
• Manager support: A supervisor who coaches rather than just assigns work.
• A visible promotion path: Evidence the company promotes from within, since internal advancement is a common route up from entry-level.
• Transferable skills: Work that builds abilities valued across employers, not just one company’s quirks.
• Fair, realistic requirements: A posting that matches its title instead of demanding three years for a beginner role.
• Pay transparency: A stated salary range and a willingness to discuss it openly.
• Culture fit: A team and pace where you can do your best work.

If a role scores well on training, manager support, and a promotion path, it is usually worth taking even if the starting pay is modest. Those three factors compound over the first few years.

Common Mistakes to Avoid When Applying for Entry-Level Jobs

Most rejections trace back to a handful of avoidable errors. Job seekers who fix these compete far better, even against candidates with more on paper. The frequent mistakes:

• Applying too broadly: Blasting a generic resume to hundreds of roles signals effort but produces weak, untargeted applications.
• Ignoring networking: Skipping referrals and professional connections cuts off the channel that fills many roles before they post.
• Using a generic resume: Sending the same document everywhere ignores the specific skills each posting names.
• Underexplaining projects: Listing an internship or project without the result wastes your strongest evidence.
• Skipping experience that counts: Leaving off volunteer work, freelance gigs, or leadership roles throws away proof you can use.
• Not following up: Failing to send a short thank-you or status note after an interview lets stronger-follow-up candidates pass you.

When Should You Move Beyond an Entry-Level Role?

Most people stay in an entry-level role for one to two years, but the right timeline depends on your learning curve, not the calendar. The signal to move is when growth stalls, not when a set number of months passes. Once you start your first role, applying solid tips for your first job early will speed up how fast you become ready for the next step.

Signs it may be time to move up or move on:

• You consistently perform the role well and have results to show for it
• You have mastered the core skills the job teaches
• Your responsibilities have expanded but your title and pay have not
• You no longer see a clear path to grow where you are
• An internal promotion or a stronger external role is realistically within reach

Moving up does not always mean changing companies. Many people advance fastest by raising their hand for more responsibility where they already are.

Conclusion

An entry-level career is a starting point, not the whole journey. The roles open to beginners build the skills, evidence, and relationships that carry you into bigger work, and choosing one with real training and a clear promotion path matters more than the first salary number. Treat your first job as the foundation: gather proof, target a few roles well, and move up when your growth stalls.

If you want help choosing or landing your first role, explore PathWise career services for resume, job-search, and interview support, or build the underlying skills at your own pace through our career courses. For a plan built around your specific goals, work one-on-one with a mentor through PathWise coaching, or see everything available to early-career job seekers on our solutions for individuals page.

Career coaching at the moment means using a coaching insight, question, or feedback cue during a real workplace situation instead of waiting for your next formal session. It turns reflection into action when feedback lands, conflict flares, a decision looms, or stress spikes. The skill is simple to describe and hard to do under pressure: pause, choose a better response, and act before the automatic reaction takes over.

Most people already know what good behavior looks like. The gap is timing. You remember the advice an hour after the meeting, not during it. Learning to apply coaching in real time closes that gap. You stop saving your best thinking for the calm moments and start using it when it counts.

Career coaching in the moment, defined: Applying a coaching lesson, prompt, or behavior during a live situation rather than after it. It connects day-to-day reactions to longer-term career growth by helping you respond on purpose instead of on impulse.

What Is Career Coaching at the Moment?

Career coaching at the moment is the practice of acting on coaching insights while a situation is still unfolding. A coaching session gives you frameworks, language, and self-awareness. Coaching at the moment is where you spend them. The value of a session is not the hour you sit in it. The value shows up in the next hard conversation, the next piece of critical feedback, the next time you want to react and choose not to.

This matters because workplace coaching produces measurable results. A meta-analysis of 39 randomized controlled trial samples covering 2,528 participants found a moderate, statistically significant effect of coaching across leadership and personal outcomes, with the strongest effects on goal attainment and self-efficacy. 

Seventy percent of people who receive coaching report improved work performance. Those gains depend on transfer: moving what you learn from the session into the actual moments where behavior gets decided.

It helps anyone whose job involves other people, which is nearly everyone. Individual contributors use it to handle feedback without getting defensive. Managers use it to stay steady when a one-on-one turns tense. People navigating a career transition use it to make clearer decisions under uncertainty. The common thread is real-time pressure, and the common skill is responding with intention.

When Should You Use Coaching in the Moment?

You use coaching in the moment whenever a situation triggers a fast emotional reaction and a slower, better response is available. These are the points where your default behavior and your intended behavior split apart. Naming them in advance makes them easier to catch.

Common workplace coaching moments include:

• Receiving critical feedback. A manager points out a gap and your first instinct is to explain or defend.
• A tense one-on-one or meeting. The temperature rises, someone interrupts, and the conversation starts to drift off course.
• Imposter syndrome before a high-stakes task. You feel underqualified and want to hedge, over-prepare, or pull back.
• A missed deadline or visible mistake. The urge is to over-apologize or assign blame instead of fixing the problem.
• Workplace conflict. Two people want different things and the disagreement starts to feel personal.
• A career decision. You face a choice about a role, project, or path and feel pressure to answer immediately.
• A performance review. You hear a rating or comment that stings and want to argue the point in the room.

The pattern across all of these is the same. Something lands, your body reacts, and a small window opens where you can still choose your response. Coaching in the moment is the discipline of using that window. The more situations you can name ahead of time, the faster you recognize them when they arrive.

The Pause-Name-Choose-Act-Review Model

The Pause-Name-Choose-Act-Review model, or P-N-C-A-R, is a five-step coaching model you can run in seconds during any real situation. It is built for repetition under stress, not perfection. The goal is to use it often, not flawlessly. It works in a hard email, a difficult meeting, or a moment when you are tired and want to react.

Each step does one job. Together they interrupt the automatic reply and replace it with a deliberate one. Self-regulation and empathy are the two emotional intelligence skills that most strongly predict job performance, and this model is a practical way to exercise both.

Pause

Take one breath before you respond. That single breath is the difference between reacting and choosing. When a sharp comment lands or a meeting goes sideways, your first job is simply to notice your reaction instead of acting on it. The pause does not need to be long. One slow breath buys you enough space to think.

Example: Your manager cuts off your update with a blunt correction. Instead of replying instantly, you breathe once and let the first wave of defensiveness pass.

Name

Name what you feel and what you need, in plain words. “I feel rushed.” “I feel defensive.” “I feel unsure.” Naming the emotion lowers its intensity and restores access to clear thinking. This builds self-awareness fast, and self-awareness is the foundation every other coaching skill sits on.

Example: You silently note, “I feel embarrassed, and I need to understand exactly what went wrong.” The label alone takes the edge off the reaction.

Choose

Pick the smallest useful response. Not the perfect response, the smallest one that moves the situation forward. Ask yourself one question: “What would better look like in the next two minutes?” That question converts a coaching insight into a concrete next action.

Example: Rather than defending your whole approach, you choose to ask one clarifying question about the specific issue your manager raised.

Act

Take the next step right away. The window for a deliberate response is short, so act while it is still open. A small action taken in the moment beats a perfect plan you carry out later, because the moment is where the behavior actually registers with other people.

Example: You say, “That’s fair. Can you give me one example of what you’d want done differently?” You have now turned a stinging comment into useful information.

Review

Capture the learning later, when the pressure is off. Spend two minutes recording what happened, what you felt, what you did, and what you would try next time. This is where in-the-moment practice compounds into real career development. Without review, every situation is isolated. With it, you start to see patterns.

Example: That evening you note that direct feedback triggers defensiveness, and that asking for one example reliably calms you down. Next time, you reach for that move faster.

Examples of Coaching Moments at Work

Coaching moments are easier to handle when you have language ready before you need it. The scripts below pair a common situation with a specific in-the-moment response. Adapt the wording to your own voice. The point is to have a first move that is better than your default reaction.

Receiving critical feedback

Your instinct is to explain why the criticism is unfair. The better move is to get specific so you can actually use the feedback. Direct, specific feedback is far easier to act on than vague impressions, so ask for it.

• Say: “Thanks for telling me. Can you give me one example of what you’d like me to do differently next time?”
• Then: Pick one behavior from the answer and test it in your next meeting or email.

Handling a tense meeting

When a discussion heats up, the urge is to push harder or shut down. The better move is to slow the room and separate the issue from the people. Leaders who consistently build trust and empathy see turnover rates around 40 percent lower than peers, and steadying a tense room is one way that trust gets built.

• Say: “I want to make sure I understand your point before I respond. Can you walk me through it again?”
• Then: Restate their position in one sentence before you offer yours.

Making a career decision

Under pressure, the instinct is to answer immediately so you look decisive. The better move is to buy time without stalling. Anchoring the choice to your own values and priorities keeps short-term pressure from steering a long-term decision.

• Say: “This matters, so I want to give it real thought. Can I get back to you by tomorrow morning?”
• Then: Write down the decision, the options, and which option best fits your goals before you respond.

Preparing for a difficult conversation

Before a hard talk, the instinct is to script every word or avoid the conversation entirely. The better move is to clarify your one goal and your opening line. If you feel stuck before you even start, working through why you feel stuck first can free up the energy to begin.

• Say (to yourself): “My goal is to fix the pattern, not to win. My first sentence is the impact, not the blame.”
• Then: Open with the specific impact: “When the report came in late, the client meeting got pushed, and that’s the part I want to solve.”

How to Be More Coachable in Real Time

Being coachable means you can take in feedback, ask clarifying questions, try new behaviors, and reflect honestly on the results. It does not mean accepting every suggestion you hear. It means staying open long enough to learn from the situation before you decide what to do with it. People who are coachable get the most from coaching at the moment, because they convert insight into change quickly.

Coachability in real time comes down to a few habits:

• Default to curiosity over defense. When feedback feels sharp, focus on the meaning, not the tone. Ask, “What is the one useful point here?”
• Separate impact from intent. A coworker may deliver a message poorly, yet the impact can still be real and worth addressing. Name the impact and you can change the pattern.
• Ask for specifics. When feedback is vague, request a single concrete example. Examples remove guesswork and tell you exactly what to repeat or stop.
• Use a simple feedback prompt. “What should I stop, start, or continue?” gives the other person an easy structure and gives you a clear answer. For more language you can reuse, the art of feedback covers how to ask for and act on input well.
• Show humility without self-criticism. Openness to growth is a strength. Treating every piece of feedback as proof of failure is not, and it shuts down learning.

Humility is the quiet engine here. The most coachable people are not the ones with the least to learn. They are the ones most willing to be seen learning.

Coaching, Mentoring, Therapy, and Manager Feedback: What’s the Difference?

These four supports overlap, which is why people confuse them, but each does a distinct job. Knowing which one you are in helps you set the right expectations in the moment.

• Coaching is performance-focused and forward-looking. A coach helps you find your own answers, build specific skills, and create an action plan within a defined timeframe. The coach asks more than they tell.
• Mentoring is development-focused and relationship-driven. A mentor is usually someone more senior inside your field who shares experience, perspective, and connections to guide your broader career journey. Mentoring tends to be less structured and led by the mentee’s questions.
• Therapy addresses mental health, emotional healing, and patterns that often have roots in the past. It is delivered by a licensed clinician and is not a substitute for, or the same as, performance coaching.
• Manager feedback is evaluative and tied to your role. Your manager assesses your work against expectations and has authority over outcomes like ratings and assignments, which coaching and mentoring do not.

The practical takeaway: a coaching moment with your manager is different from a coaching moment with a coach, because your manager also evaluates you. When you notice which relationship you are in, you can choose the right response, whether that is asking a coach to help you think or asking a manager to clarify an expectation.

How to Track Progress Between Coaching Sessions

Career development is shaped less by big goals than by what you do in the small, repeated moments that build your reputation. The way to make coaching in the moment stick is to track it lightly and consistently between sessions. A short record beats a perfect system you abandon after a week.

Keep a simple moment log. After a notable situation, write four things:

1. The situation. One line on what happened.
2. What you felt. The emotion you noticed in the moment.
3. What you did. The response you actually chose.
4. What you’d do next time. The one adjustment you want to test.

Then run a weekly review. Once a week, read your entries and look for a single theme. Maybe you avoid conflict. Maybe you over-explain. Maybe you delay decisions. Pick one micro-skill tied to that theme and practice it for seven days. That is improvement you can actually feel, and it gives your next coaching session a clear focus.

Pattern recognition is the real payoff. One tense meeting tells you little. Eight weeks of entries show you exactly which situations trip you up and which responses work. If you want help turning those patterns into a longer-term plan, working with a career coach can connect your daily habits to bigger career moves.

How Pathwise Coaching Can Help

Coaching in the moment is a skill you build with reps and feedback, not one you master from an article. The hardest part is staying consistent and spotting the patterns you cannot see on your own. That is where structured support helps. A coach gives you language to use under pressure, a sounding board for real decisions, and an outside view of the habits driving your results.

Pathwise supports real-time growth at whatever stage you are in:

• Want a coach in your corner? Explore career coaching with Pathwise to practice these skills with someone who can spot your patterns, or view coaching packages and pricing.
• Need help with a specific milestone? Pathwise career services cover resumes, interviews, and the concrete steps between where you are and where you want to be.
• Prefer to learn at your own pace? The self-guided career courses let you build skills on your own schedule.
• Just getting started? See how Pathwise works for individuals navigating their next career move.

If recurring moments at work keep tripping you up, book a conversation with the Pathwise team to talk through your situation and decide which path fits you best.

A career legacy is the lasting impact your work, leadership, relationships, and values leave on people, organizations, industries, and communities. It is the part of your professional life that keeps creating value after you change roles, retire, or move on. Your legacy shows up in the people you developed, the systems you built, the standards you raised, and the values others now associate with your name.

Most people picture a career legacy as something to think about near the end of a working life. The more useful view is simpler. A legacy is the sum of repeated choices, not a final chapter. The mentor you support this year, the process you fix this quarter, and the values you model in hard moments all become part of what you leave behind. 

This guide defines the idea in plain terms, shows career legacy examples across different roles and stages, gives you copy-ready legacy statements, and walks you through a short framework and worksheet to define your own.

What Is a Career Legacy?

A career legacy is the durable mark your professional contributions leave on others. It answers a direct question: when you are no longer in the room, what continues because you were there? That answer can be a stronger team, a better way of working, a standard you helped set, or a group of people who advanced because you invested in them.

It helps to separate three related ideas. A professional legacy covers the full scope of your work output, the products, companies, and results that outlast your tenure. A personal legacy is broader, including the character and values people remember, both inside and outside of work. 

A leadership legacy is narrower and specific to those who lead others. It is measured by what survives a transition: the people who grew under you, the culture you shaped, and the decisions that still hold up after you leave. Most careers produce all three at once, in different proportions depending on the role.

The reason this matters now is practical. Gallup reports that only about 30% of U.S. workers feel strongly connected to their organization’s purpose, down from 38% before the pandemic. Defining the legacy you want gives your daily work a direction that pay alone does not. It also makes your choices about career mapping and role moves easier, because you have a clearer test for what counts as progress.

Why Your Career Legacy Matters Before Retirement

Legacy is not a late-career topic. Treating it as one wastes the years when you have the most influence to shape it. Your legacy is built through repeated actions, so the earlier you name what you want it to be, the more of those actions point in the same direction.

There is hard evidence that meaning, not just money, drives how people experience work. Gallup’s research found that employees with strong purpose in their work are far more engaged than those without it, with roughly 50% engaged compared with only 9% among those with low purpose. 

The same body of research shows that employees who find their work meaningful report being significantly more motivated than those who find little meaning in what they do. Purpose and legacy are tightly linked. When you know the impact you want to leave, the work in front of you feels less like a transaction.

Thinking about legacy early changes concrete decisions. It shapes which roles you accept, which relationships you invest in, which skills you build, and how you behave under pressure. A professional who wants a mentorship legacy starts sponsoring people in year three, not year thirty. 

A leader who wants a cultural legacy writes down values and builds them into hiring and reviews long before any farewell speech. The point of finding purpose in your work is to act on it now, while you still have decades of repeated choices ahead.

4 Ways Professionals Build a Career Legacy

Professional legacies tend to form in four areas. Most people contribute in more than one, and the strongest legacies usually combine several. Use these categories to spot where your own impact is already growing and where you might want to invest more.

The four ways professionals build a career legacy are:

• Building or improving organizations
• Developing people
• Advancing a profession or industry
• Creating social or community impact

1. Building or Improving Organizations

This legacy lives in the companies, teams, and systems you create or strengthen. It includes founders who start durable businesses, operators who fix broken processes, and executives who leave an organization healthier than they found it. The test is whether the thing you built keeps working after you step away.

Examples of this type of impact include:

• Founding a company that continues to employ people and serve customers for decades
• Rebuilding a failing department into a high-performing team
• Designing a process, playbook, or system that outlasts your tenure
• Preserving and strengthening a culture you inherited rather than dismantling it

Ask yourself: what part of this organization will run better because I was here? If the honest answer is “nothing that will survive my departure,” that is a signal to focus your energy.

2. Developing People

This is often the most lasting legacy of all, because people carry your influence into rooms you will never enter. It covers mentorship, day-to-day management, sponsorship, and formal coaching. Developing people compounds, since those you raise often go on to raise others.

The data here is striking. Employees with mentors are significantly more likely to be promoted than those without one, and mentorship is consistently linked to higher retention and job satisfaction. Building a people-development legacy can look like:

• Mentoring junior colleagues toward roles they did not think they could reach
• Sponsoring people for opportunities, not just advising them
• Coaching team members through hard transitions and decisions
• Creating a team culture where development is expected, not optional

Strengthening your own leadership skills directly expands this kind of legacy, because better leaders develop more people, more effectively.

3. Advancing a Profession or Industry

Some legacies reach beyond a single employer. This category covers innovation, standard-setting, and thought leadership that raise the bar for an entire field. It is how a profession ends up better off because you practiced it.

This legacy can take several forms:

• Inventing or popularizing a method others adopt
• Helping write or raise the standards your industry follows
• Publishing work, research, or teaching that shapes how others practice
• Mentoring across organizations, not just within your own

For senior professionals, this kind of cross-industry influence often depends on visibility and credibility, which is where executive presence becomes a practical tool rather than a vanity concept.

4. Creating Social or Community Impact

The fourth area is the social good your work makes possible. It includes volunteering, nonprofit leadership, work on diversity and inclusion, sustainability efforts, and advocacy for underserved groups. This legacy is measured by who is better off in the wider world because of how you spent your professional energy.

Common forms include:

• Leading or building nonprofit organizations that serve a community
• Advocating for groups who lack a voice in your industry
• Embedding sustainability or ethical practice into how a business operates
• Using professional skills to solve problems outside the profit motive

7 Career Legacy Examples from Leaders

The clearest way to understand legacy is to see it in real careers. The following leaders, all featured on the Career Sessions, Career Lessons podcast, each built a different kind of legacy. For each, consider the legacy type, what they built, who benefited, and the lesson you can apply.

• Michael Alter, co-founder and former CEO of SurePayroll. He built SurePayroll over 20 years into a company large enough to be acquired by Paychex, then moved into teaching entrepreneurship to graduate students at the University of Chicago. His legacy spans organization-building and people-development. The lesson: a legacy can have a second act, where the skills you used to build something get passed to the next generation.
• Kim Crider, Major General, US Air Force (Retired). She did foundational work behind the US Cyber Command and the US Space Force while leading thousands of service members across a 35-year career. Her legacy is industry-shaping and people-leading at scale. The lesson: some legacies are institutions that protect people you will never meet.
• Jason Krantz, CEO of Definitive Healthcare. He built two healthcare data and analytics companies from the ground up, with his current company employing over 700 people and advancing how the healthcare industry uses data. His legacy is organization-building repeated deliberately. The lesson: a legacy can be a pattern of building, not a single venture.
• John Judge, nonprofit CEO. He committed his career to the nonprofit sector, from the Boy Scouts to Habitat for Humanity, the Appalachian Mountain Club, and The Trustees of Reservations, leading the last two as CEO. Along the way he built relationships in underserved communities and became a lobbying voice for protecting environmentally sensitive areas. His legacy is social and community impact. The lesson: choosing a mission over margin can be a legacy in itself.
• Rohini Dey, founder and advocate. During the pandemic she launched Let’s Talk Womxn to help women restaurateurs, growing it to chapters in 13 cities with over 650 members. Earlier, as a board member of the James Beard Foundation, she helped found the Women’s Leadership Program and mentored hundreds of women toward executive chef roles. Her legacy blends entrepreneurship, mentorship, and advocacy. The lesson: you can build a business and lift an entire group of peers at the same time.
• Bill Boor, CEO of Cavco Industries. He speaks openly about building not just homes but jobs, and about his responsibility to preserve the ethos he inherited, both at Cavco and in his earlier role leading the Great Lakes Brewing Company. His legacy is stewardship of culture and organizations. The lesson: protecting a good legacy you inherited is as valuable as creating a new one.
• Danny Warshay, educator and entrepreneur. He scaled his own entrepreneurial knowledge to help hundreds of startups and taught the entrepreneurial process to thousands of Brown University students, many of whom launched their own ventures. His book, See, Solve, Scale, extends that reach further. His legacy is teaching and people-development. The lesson: knowledge shared deliberately multiplies far beyond what you could build alone.

Very different leaders, very different legacies, one consistent theme: durable impact on people, organizations, or the wider world.

Career Legacy Examples by Career Stage

Legacy is not reserved for executives. Every career stage offers its own way to leave a mark. Pathwise’s audience spans individual contributors, new managers, rising leaders, the C-suite, entrepreneurs, coaches, HR professionals, and those approaching retirement, and each can start building intentionally now.

Career legacy examples by stage include:

• Early-career individual contributor: becoming the person who documents the knowledge no one else writes down, so the team runs better after you move on.
• New manager: building your first team culture deliberately, setting the tone for how people treat each other and grow.
• Rising leader: sponsoring high-potential people into stretch roles and defending good standards when it would be easier to let them slide.
• Executive or C-suite: embedding values into hiring, reviews, and strategy so the culture survives your transition, and planning succession early.
• Entrepreneur: building a company designed to outlast you, with leaders capable of running it without you.
• Coach or HR professional: designing development systems that keep producing better people long after any single program ends.
• Pre-retirement professional: transferring knowledge, documenting why decisions were made, and naming and preparing successors before you go.

For professionals seeking structured support in defining this, Pathwise’s resources for individuals are built around exactly these stages, including career courses and career services that map to each one.

Sample Career Legacy Statements

A career legacy statement is a single sentence that names the impact you want your work to have. It is a useful anchor for decisions and a clarifying exercise on its own. Here are copy-ready examples grouped by the kind of legacy you might want to leave. Adapt the wording to your own voice.

• The mentor: “I want to be remembered as the person who helped others see and reach potential they did not know they had.”
• The builder: “I want to leave behind organizations and systems that keep working well long after I am gone.”
• The innovator: “I want my work to change how my field solves a problem, so the standard is higher because I practiced it.”
• The community advocate: “I want my career to leave my community measurably better off than I found it.”
• The ethical leader: “I want people to trust that the right thing was always done, even when no one was watching.”
• The coach: “I want to develop people who go on to develop others, so my influence compounds beyond me.”
• The industry shaper: “I want to raise the standards of my profession so the next generation starts further ahead.”
• The team-culture leader: “I want to build a team where people do their best work and treat each other well.”
• The knowledge-sharer: “I want to pass on what I learned so others avoid the mistakes I made.”
• The retirement-transition leader: “I want to leave my role stronger than I found it, with capable successors ready to carry it forward.”

How to Write Your Own Career Legacy Statement

Writing your statement takes five steps. Work through them in order, then compress your answers into one clear sentence. The goal is a statement you would be comfortable having read aloud at the end of your career.

The five-step framework is:

1. Values. Name the two or three values you want people to associate with your work, such as integrity, generosity, rigor, or courage.
2. Audience. Decide who you most want to serve or affect, whether that is your team, your customers, your profession, or a community.
3. Contribution. Name the specific contribution you want to make for that audience, the change you want to cause.
4. Behaviors. Identify the repeated behaviors that would actually produce that contribution, since legacy is built through actions, not intentions.
5. Proof. Decide what evidence would show the legacy was real, such as people promoted, systems still running, or standards adopted.

Then connect the three core elements, the people you serve, the values you model, and the contribution you make, into one sentence. For example: “I want to be the leader whose integrity and investment in people leave behind a team that keeps growing strong leaders after I am gone.”

Career Legacy Worksheet: 6 Questions to Clarify Your Impact

Use these six prompts to move from a vague sense of legacy to a concrete one. Write a few sentences for each. The answers feed directly into the statement framework above and into your longer-term career mapping, and you can go deeper with Pathwise’s career resources when you are ready.

1. Who do I most want to help through my work, and why them?
2. What problems do I want to spend my career solving?
3. What values do I want people to associate with how I work?
4. Who has invested in me, and how could I pass that forward?
5. What would still be working or growing a year after I left my current role?
6. What is one action I could start this month that points toward the legacy I want?

If your answers feel thin, that is useful information. It usually means a value or audience is still unclear, and it is worth sitting with the question rather than forcing an answer.

Common Mistakes to Avoid When Defining Your Legacy

A legacy goes wrong in predictable ways. Watching for these mistakes keeps your effort honest and grounded.

The most common errors are:

• Making it about ego. A legacy built to be admired tends to be brittle. The durable ones are about what continues for others, not how you are remembered.
• Staying vague. “I want to make a difference” is not a legacy. Without a named audience and contribution, there is nothing to act on.
• Tying it to a title. If your sense of impact disappears the moment you lose a job title, it was never a legacy. Legacy lives in people and outcomes, not org charts.
• Waiting for “someday.” Treating legacy as a retirement project means missing the years of repeated choices that actually build it.
• Confusing activity with impact. Being busy is not the same as leaving something behind. Tie your effort to evidence that will outlast you.

Define the Legacy You Want to Leave

Your career legacy is being built right now, through the choices you make this month, not the ones you imagine making decades from now. The professionals who leave the strongest legacies are the ones who named the impact they wanted early, then made repeated decisions in that direction. A clear definition turns a vague aspiration into a set of actions you can start today.

The fastest way to move from reflection to a real plan is to work through it with someone. Start a conversation through Pathwise career coaching to define your legacy, values, and next career chapter with a coach who can hold you to it.

If you would rather start on your own first, two resources fit naturally with this work:

• Build the skills behind the legacy you want: Pathwise career courses help you develop the leadership and people-development strengths that most legacies are built on.
• Get structured, hands-on support: Pathwise career services and the broader resources for individuals give you tools to turn the worksheet above into a concrete career plan.

C-level leadership skills are the strategic, organizational, financial, and interpersonal capabilities executives use to set direction for an entire company rather than a single team or function. They include strategic thinking, executive communication, decision-making under uncertainty, financial acumen, and the ability to lead people through change. These skills separate functional managers from enterprise leaders who own company-wide outcomes.

The shift into the C-suite is less about doing your old job better and more about doing a fundamentally different job. A vice president is measured on a business unit. A chief executive is measured on the whole enterprise: its strategy, its culture, its capital, and its long-term survival. The skills that earned the promotion are rarely the skills that sustain the role, which is why so many capable leaders stall at the threshold of senior leadership.

This guide breaks down what C-level leadership actually requires, how executive roles differ from management, and the twelve competencies that matter most. According to research compiled by Quarterdeck, leadership development programs return an average of seven pounds for every one pound invested, yet only 11% of business leaders believe their development initiatives produce meaningful results. The gap between potential and outcome usually comes down to which skills get built, and how deliberately.

What Is C-Level Leadership?

C-level leadership refers to the work of senior executives who hold “chief” titles and carry enterprise-wide accountability. The C-suite typically includes the Chief Executive Officer (CEO), Chief Financial Officer (CFO), Chief Operating Officer (COO), Chief Information Officer (CIO), Chief Marketing Officer (CMO), and Chief Human Resources Officer (CHRO). Each owns a function, but all share responsibility for the performance of the organization as a whole.

The defining feature is scope. A C-level executive sets enterprise strategy, allocates capital, shapes organizational culture, and answers to the Board of Directors and shareholders. The role trades narrow functional depth for cross-functional breadth and collective judgment.

It helps to see where the C-suite sits relative to the levels below it:

• Manager: focuses on team execution and day-to-day delivery.
• Director: owns functional leadership and the performance of a department.
• Vice President: drives business unit performance and connects strategy to operations.
• Senior Vice President: integrates multiple units and prepares for enterprise scope.
• C-Level Executive: sets enterprise strategy and owns company-wide outcomes.

Understanding this ladder matters because each rung demands a different mindset. Many professionals try to reach the top by perfecting the skills of the rung below, which is exactly why the transition is so difficult.

How Executive Leadership Differs From Management

Management keeps systems running. Executive leadership decides which systems should exist in the first place. That is the core distinction, and it reshapes nearly every daily habit.

Managers optimize within a defined scope. They hit targets, coordinate people, and solve problems handed to them. Executives define the scope itself. They choose markets, set the strategic intent, decide what the company will not do, and accept accountability for bets that may not pay off for years. 

The World Economic Forum notes that modern executives increasingly succeed through integration, collective judgment, and the ability to navigate enterprise-wide trade-offs rather than functional expertise alone.

A few practical differences stand out:

• Time horizon: managers think in quarters, executives think in years and decades.
• Information quality: managers act on relatively complete data, executives decide with gaps and ambiguity.
• Influence model: managers have direct authority, executives rely heavily on influence without authority across peers and the board.
• Accountability: managers answer for their team, executives answer for the enterprise and its stakeholders.

If you are early in the climb and still learning to lead people directly, the foundations matter first. Our guide on becoming a manager for the first time covers the habits that make later transitions possible. For the broader principles, the piece on what defines leaders and leadership sets useful context.

Why C-Level Leadership Skills Matter

Strong executive skills are not a vanity credential. They change measurable business outcomes, and the data on this is striking.

Emotional intelligence alone accounts for 77% of leadership effectiveness according to research summarized by Kapable, making it one of the strongest predictors of executive success. Leaders with high self-awareness are 32% more effective, and those who regulate their emotions well are 28% better at resolving conflicts and managing crises. These are not soft luxuries. They directly affect decision quality, retention, and trust.

The cost of weak skills is just as concrete. Between 60% and 70% of change initiatives fail, and the difference between success and failure usually traces back to leadership capability. Projects with excellent change leadership reach a 73% success rate, compared with 39% for those run poorly. Capital is wasted not because strategies are wrong, but because executives cannot carry their organizations through the transition.

The stakes rise as scope grows. A flawed decision by a manager costs a project. A flawed decision in the C-suite can cost the company. That asymmetry is why executive leadership development deserves deliberate investment rather than chance.

12 Essential C-Level Leadership Skills

The most useful way to think about executive capability is in four families: strategic, organizational, influence, and financial. The twelve competencies below span all four. For each, you will find what it is, why it matters, an example, and how to build it.

Strategic Thinking

Strategic thinking is the ability to see patterns across markets, competitors, and time, then set a direction that creates lasting competitive advantage. It is the signature skill of enterprise strategy.

Executives who think strategically connect dots others miss. When Satya Nadella took over as CEO of Microsoft, he reframed the company around cloud computing and a “growth mindset” culture, a strategic bet that reshaped the entire business. To develop it, study your full company the way an investor would: read the strategic documents, listen to earnings calls, and learn how revenue, costs, and competitive positioning actually fit together. Practicing vision setting on smaller initiatives builds the muscle for larger ones.

Executive Communication

Executive communication is the skill of conveying complex ideas with clarity to many audiences at once: employees, the board, investors, and the public. Leaders with high emotional intelligence communicate with measurably more clarity, which is why this skill compounds with so many others.

The test of executive communication is whether a complicated strategy can be made simple without becoming wrong. Strong executives tailor the same message for a board committee and a frontline team without losing the core. Build this by seeking board-level and investor relations exposure early, and by practicing structured storytelling. Our leadership communication skills guide breaks down the specific techniques that travel well into senior roles.

Decision-Making Under Uncertainty

Decision-making under uncertainty is the ability to commit to a course of action with incomplete information and accept the consequences. Executives rarely get clean data, so this skill defines the role.

A reliable executive decision-making process keeps quality high even when speed is required:

1. Gather the available information quickly, accepting it will be incomplete.
2. Analyze the risks and the cost of being wrong.
3. Evaluate two or three realistic scenarios, not just the preferred one.
4. Consult the stakeholders whose buy-in or expertise matters.
5. Decide, and communicate the decision clearly.
6. Monitor outcomes and adjust as new information arrives.

The discipline is not avoiding mistakes. It is making reversible decisions fast and irreversible decisions carefully.

Emotional Intelligence

Emotional intelligence is the capacity to recognize and manage your own emotions and read the emotions of others. Given that it accounts for the largest single share of leadership effectiveness, no executive can afford to treat it as optional.

High emotional intelligence shows up in conflict, pressure, and feedback. An executive who stays composed during a crisis steadies an entire organization. Building it starts with honest self-assessment: a 360-degree feedback survey often reveals blind spots that performance reviews miss. Coaching accelerates the work, with structured programs reported to cut stress by 24% and improve performance by 26%.

Financial Acumen

Financial acumen is fluency in the numbers that drive the business: budgets, capital allocation, margins, and risk. Even non-financial executives must read a balance sheet and understand what creates and destroys value.

The CFO owns the model, but every C-level leader makes financial trade-offs. Capital allocation, the choice of where to spend limited resources for the highest return, is among the most consequential executive decisions. Develop this by participating in the budgeting process, studying your company’s financial statements, and learning how your largest shareholders evaluate performance.

Executive Presence

Executive presence is the blend of confidence, credibility, composure, and communication that signals a person belongs at the top table. It is often the difference between being capable and being trusted with scope.

Presence is built on substance, not theater. It combines gravitas under pressure, clear communication, and the credibility that comes from consistent judgment. Emotional intelligence is its foundation, which is why composed leaders project authority without forcing it. Our dedicated guide on executive presence goes deeper, and the related piece on professional presence covers the earlier-career habits that build toward it.

Change Leadership

Change of leadership is the ability to move an organization from one state to another while keeping people engaged and performance intact. With most change efforts failing, this skill carries enormous weight.

The executives who succeed treat change as a human process, not a project plan. They communicate the reason for change relentlessly, address resistance directly, and sequence the transition so people are not overwhelmed. When Mary Barra led General Motors through its pivot toward electric vehicles, the challenge was as much cultural as technical. Build this skill by leading progressively larger transitions and studying why past efforts stalled. Our guide on how to lead through change lays out a practical framework.

Talent Development

Talent development is the work of building the next generation of leaders, including your own successor. Executives who hoard capability create bottlenecks, while those who build pipelines multiply their impact.

Succession planning is the clearest test of this skill. A strong executive can name who would step into each critical role and what that person still needs to learn. Develop it by mentoring deliberately, delegating real authority rather than tasks, and treating workforce planning as a strategic priority. The leadership pipeline is built years before it is needed.

Stakeholder Management

Stakeholder management is the ability to align the competing interests of boards, investors, employees, customers, and regulators. Executives operate at the intersection of these groups, often without direct authority over any of them.

The skill is part diplomacy, part transparency. Board communication, for example, requires giving directors enough detail to govern without drowning them in operational noise. Build stakeholder alignment by mapping who holds influence over your initiatives, understanding what each group needs, and engaging them before you need their support rather than after.

Innovation Leadership

Innovation leadership is the capacity to drive new ideas, products, and business models while managing the risk that comes with them. In fast-moving markets, standing still is a decision with consequences.

Jensen Huang built NVIDIA into a leader in artificial intelligence computing by betting early and repeatedly on technologies that had no guaranteed market. Innovation leadership balances bold bets with disciplined experimentation. Develop it by creating space for measured risk, rewarding learning from failed experiments, and staying close to emerging shifts in your industry.

Risk Management

Risk management is the discipline of identifying, weighing, and mitigating threats to the enterprise before they materialize. Executives are paid to see around corners.

This spans financial, operational, reputational, and strategic risk, increasingly including cybersecurity and AI governance. An EY survey found that AI adoption is outpacing governance, with risk awareness among the C-suite remaining low even as deployment accelerates. Build this skill by running scenario analyses, stress-testing major decisions against worst cases, and treating corporate governance as a source of resilience rather than a compliance chore.

Organizational Agility

Organizational agility is the ability to help a large company sense change and respond quickly without losing stability. It is the antidote to the slowness that often comes with scale.

Agile executives build structures that adapt: clear priorities, fast feedback loops, and a culture that treats change as normal. Organizational resilience comes from this balance of speed and steadiness. Develop it by simplifying decision rights, reducing the layers between a signal and a response, and rewarding teams that adapt rather than wait for permission.

How to Develop C-Level Leadership Skills

Executive skills are learnable, but not by accident. They are built through deliberate exposure, honest feedback, and structured practice over years.

A practical development path looks like this:

• Adopt a whole-company mindset. Learn how every function creates value, not just your own. Read corporate strategy, follow the numbers, and understand the competitive landscape.
• Seek broadening experiences. Take roles and projects that fill gaps in your track record rather than reinforcing existing strengths.
• Get an honest evaluation. Use a 360-degree feedback survey and a leadership coach to surface blind spots that performance reviews miss.
• Build a personal board of advisors. Senior roles get lonely, and a trusted circle of advisors keeps your judgment sharp and your perspective grounded.
• Invest in structured learning. Given the strong returns leadership development can produce, formal courses and coaching are among the highest-leverage uses of an aspiring executive’s time.

For a broader foundation, our guide on how to improve leadership skills covers the fundamentals, and the overview of the 20 qualities of a good leader maps the traits worth cultivating early. Setting a clear strategic intent for your own development turns vague ambition into a plan.

How AI Is Changing Executive Leadership

Artificial intelligence is rewriting what C-level leadership requires, and the change is happening fast. Executives now need fluency in how AI reshapes strategy, workforces, and decision-making.

The adoption numbers are decisive. The Conference Board’s 2026 C-Suite Outlook found that 82% of CEOs are more optimistic about AI than a year earlier, and AI now outranks every other investment priority. Yet enthusiasm is not the same as readiness. Enterprises without a formal AI strategy report just 37% adoption success, compared with 80% for those with one.

The leadership implications are significant:

• AI is now a CEO-level responsibility. Ownership of AI strategy has shifted decisively toward the chief executive, signaling that this is enterprise strategy, not an IT project.
• Adoption creates friction. Roughly two-thirds of executives report that generative AI has caused division inside their companies, making change leadership and stakeholder management more important, not less.
• Upskilling is non-negotiable. Around 90% of C-suite professionals intend to build their own AI skills within a year, recognizing that data-driven decision-making is becoming a baseline executive competency.

The executives who thrive will treat AI as a tool for sharper judgment and workforce transformation, while keeping the human skills, emotional intelligence, communication, and ethical risk management that machines cannot replace.

Common Mistakes Future Executives Make

Most stalled executive careers trace back to a handful of avoidable errors. Recognizing them early is itself a competitive advantage.

• Staying parochial. Clinging to a single functional identity, sales, finance, or operations, signals you are not ready for enterprise scope.
• Optimizing for being liked. Senior roles require unpopular decisions. Leaders who avoid conflict erode their own credibility.
• Neglecting financial fluency. Non-finance executives who cannot read the numbers lose influence in the rooms that matter most.
• Skipping the feedback that hurts. Dismissing 360-degree input or coaching leaves blind spots that grow with seniority.
• Underestimating culture. Treating change as a logistics problem rather than a human one is why most transformations fail.

The pattern across all five is the same: applying the habits of a lower rung to a higher one. The fix is to deliberately practice the new job before you hold it.

Final Thoughts

Reaching the C-suite is an achievement, but staying effective there is a different discipline entirely. The twelve competencies in this guide, spanning strategy, organization, influence, and finance, are the ones that distinguish executives who lead enterprises from managers who run functions. They are learnable, measurable, and worth building long before the title arrives.

The deciding factor is rarely talent. It is whether you build these skills deliberately or leave them to chance. PathWise gives you a structured path depending on where you are and how you prefer to work:

• Want one-on-one guidance? Our executive and leadership coaching helps you work directly on the competencies that matter most for your path.
• Prefer to learn at your own pace? Our career courses build the same skills through structured, self-directed programs.
• Mapping your route to the C-suite? Explore how PathWise supports individuals across every stage of the climb.
• Developing a team or leadership pipeline? See our solutions for organizations and HR professionals.

Not sure which fits? Reach out to our team and we will help you find the right starting point for your next move.

Sports management careers cover the business and operational side of sports: running teams, marketing events, planning games, representing athletes, crunching performance data, and leading athletic programs. Most of these jobs happen off the field, in front offices, athletic departments, agencies, arenas, and tech firms rather than on the court or pitch.

The field is broad, so the right path depends on your strengths. If you like logistics, operations roles fit. If you like persuasion, marketing and sponsorship fit. If you like numbers, analytics fits. This guide explains the main career paths, what they pay, the degrees and skills employers want, and the practical steps to break in. By the end, you will know which lane suits you and how to land your first role.

What Are Sports Management Careers?

Sports management is the practice of running the business, operations, and administration of sports organizations. It spans professional teams, college athletics, recreation departments, sports agencies, marketing firms, and technology companies. The work keeps the games running, the revenue flowing, and the athletes supported.

The field splits into several functions. Team operations handle scheduling, travel, and rosters. Athletic administration leads programs in schools and colleges. Sports marketing builds fan engagement and brand partnerships. Event management runs the games and tournaments. Athlete representation negotiates contracts. Analytics turns data into decisions. Each function has its own entry points and skill demands.

Most roles share a base of business judgment, communication, and managing many moving parts under deadline. Playing experience helps in coaching or scouting but is rarely required. Far more positions reward marketing instincts, financial sense, project management, or technical skill. To map where your abilities point, career mapping gives you a visual model of roles, skill gaps, and the steps between them.

Sports Management Career Paths at a Glance

Sports management career paths fall into six broad groups based on the core skill each one rewards. Knowing the group narrows your search before you ever read a job description.

• Operations and logistics: team operations, facility operations, event management. These roles reward planning, scheduling, and calm execution under pressure.
• Sales and marketing: sports marketing, sponsorship, ticket sales, fan engagement. These roles reward persuasion, creativity, and an understanding of fan behavior.
• Data and analytics: performance analytics, business intelligence, sports data science. These roles reward statistics, programming, and the ability to translate numbers into action.
• Athlete support: athletic administration, wellness coaching, player development. These roles reward leadership, empathy, and program building.
• Legal and representation: sports agents, contract advisors, name, image, and likeness (NIL) consultants. These roles reward negotiation, contract knowledge, and relationship management.
• Technology and innovation: sports tech product roles, wearables, broadcast and fan experience. These roles reward engineering, product sense, or data skills applied to sports.

The sections below walk through the most common roles, where you would work, what qualifications help, and how pay breaks down. Salary figures vary widely by league level, geography, employer, and revenue model, so treat published occupation data as a baseline rather than a promise.

Team Operations and Management

Team operations keep a club running day to day. Staff organize travel, scheduling, equipment, and game-day logistics. At higher levels, operations leaders weigh in on roster decisions, budgets, and contracts. The work is fast and seasonal, with long hours around games.

You would work for professional or minor league teams, college and high school athletic departments, or sports leagues. A degree in sports management or business helps, along with strong organization and communication. Internships and assistant roles are the usual way in.

Entry-level coordinators often start modestly, while general managers in major professional sports can reach six or seven figures. Most people enter through an unglamorous first job and prove themselves on game days.

Athletic Administration

Athletic administration runs sports programs inside schools, colleges, and community organizations. Administrators hire coaches, manage budgets, raise funds, and represent the department to the public and media. The role blends leadership with operations.

You would work in high schools, colleges, parks and recreation departments, or community sports leagues. A degree in sports management or education helps, and master’s degrees are common at the college level. Leadership and budgeting experience matter more than playing background.

Pay rises sharply with the level of competition. High school athletic directors earn less than their counterparts at large universities, where athletic directors can clear six figures. Volunteering or working in a college athletic department is a reliable starting point.

Sports Marketing and Sponsorship

Sports marketing promotes teams, events, and athletes. Marketers run advertising campaigns, manage social media, coordinate fan engagement, and structure sponsorship deals. The job rewards creativity and a sharp read on what fans respond to.

You would work for professional teams, colleges, marketing agencies, sporting goods companies, or media outlets. A degree in marketing, communications, or sports management fits, and digital marketing certifications help. Sales-heavy roles often pay commission on top of base salary.

The U.S. Bureau of Labor Statistics groups much of this work under marketing managers and market research analysts. Marketing managers had a median annual wage of $161,030 in May 2024, and the broader advertising, promotions, and marketing managers group is projected to grow 6 percent from 2024 to 2034. 

Market research analysts had a median wage of $76,950 and are projected to grow 7 percent over the same decade. Building a marketing portfolio through clubs, internships, or volunteer projects is the fastest credibility builder, and knowing what are good skills to put on a resume helps you present that work well.

Event Management and Facility Operations

Event management plans sporting events from setup to teardown. Event staff handle ticketing, security, vendors, and entertainment. Facility managers oversee the venue itself: maintenance, scheduling, and the logistics that keep a stadium or arena working.

You would work in stadiums, arenas, college campuses, event companies, or sports federations. Event planning experience and a degree in sports or event management help, and certifications like the Certified Meeting Professional credential add weight.

This work maps closely to the meeting, convention, and event planner occupation, which had a median annual wage of $59,440 in May 2024 and is projected to grow 5 percent from 2024 to 2034, faster than the average for all jobs. Volunteering at tournaments, marathons, or campus events builds the experience and contacts that lead to paid roles.

Sports Agents and Athlete Representation

Sports agents negotiate player contracts and endorsements, manage public relations, and advise clients on career decisions. The work demands deep industry knowledge, legal fluency, and total dedication to a small client roster. Trust is the currency.

You would work at a sports agency or independently, and increasingly in NIL consulting or athlete unions. A law degree or MBA often helps, and player associations certify agents in many leagues. Most agents start with minor league or amateur clients and build a reputation through results.

Top agents can earn millions, but that tier is rare and slow to reach. The realistic path starts small, with internships and a focus on learning the business side of contracts and negotiation before chasing marquee clients.

Sports Analytics and Data Science

Sports analytics turns performance and business data into decisions. Analysts build predictive models for coaching, scouting, ticketing, and marketing. The field has grown as teams and betting platforms compete on the quality of their data.

You would work for professional teams, sports analytics firms, media companies, fantasy sports and betting platforms, or colleges. A degree in statistics, computer science, or data science helps, along with programming in Python or R and genuine sports knowledge. A public portfolio matters more than a brand-name employer early on.

The closest national benchmark is the data scientist occupation, which the Bureau of Labor Statistics reports at a $112,590 median annual wage in 2024. Sports analytics roles range widely below and above that depending on level. Presenting work at analytics conferences, using publicly available datasets, is a proven way to get noticed.

Esports Management

Esports management runs competitive gaming the way traditional sports management runs leagues. Managers coordinate teams, tournaments, and live events, and handle sponsorships and fan engagement. The audience skews young and digital, so community presence counts.

You would work for esports teams and leagues, colleges, gaming companies, or tech firms. A passion for esports and the platforms behind it is the baseline, paired with experience in event planning, marketing, or coaching. A degree in sports or esports management helps but is not mandatory.

Pay spans a wide range depending on role and the size of the organization. Immersing yourself in gaming communities and organizing events, even small ones, builds the digital footprint that hiring managers look for.

Sports Technology and Innovation

Sports technology builds and manages the products that teams, athletes, and fans use. The work covers wearables, performance tracking, training tools, broadcast tech, and fan-experience platforms. It sits at the intersection of sports knowledge and engineering or product skill.

You would work at startups, professional teams, technology companies, or broadcasters. A technical background in coding, engineering, product management, or data helps, combined with an understanding of sports performance or fan behavior. Crossover projects that link the two domains stand out.

Compensation tracks the broader tech market more than the sports market, so it often runs higher than other sports roles. Staying current on emerging tools is part of the job, since the products change fast.

NIL Consulting

NIL consulting helps student-athletes earn money from their name, image, and likeness. Consultants manage sponsorships, social media, and contracts, and they keep athletes inside the rules. The work blends branding, marketing, and compliance.

You would work for NIL agencies, athletic departments, or marketing firms. Knowledge of branding, contract basics, and social media is essential, often paired with a sports management or marketing degree. The rules change often, so staying current is the core of the job.

NIL is governed by a shifting mix of National Collegiate Athletic Association (NCAA) policy, state laws, institutional rules, and ongoing litigation and settlements. That uncertainty is the defining feature of the field right now. Treat compliance guidance from the NCAA and individual schools as the source of truth, and avoid giving athletes legal advice you are not qualified to give.

Sports Management Salaries and Job Outlook

Sports management salaries vary widely, so the most reliable approach is to anchor each role to the closest occupation the Bureau of Labor Statistics tracks, then adjust for league level and location. Pay in major professional sports sits far above pay in high school or community settings for the same job title.

Here is how several adjacent occupations looked in the most recent federal data, with 2024 median annual wages and projected growth from 2024 to 2034:

• Meeting, convention, and event planners: $59,440 median, 5 percent growth (faster than average). This is the closest match for event and game-day roles.
• Coaches and scouts: $45,920 median, 6 percent growth. This covers on-field development and talent evaluation.
• Market research analysts: $76,950 median, 7 percent growth (much faster than average). This maps to fan research and sponsorship analytics.
• Marketing managers: $161,030 median, with the wider marketing-managers group projected to grow 6 percent. This reflects senior sports marketing leadership.
• Data scientists: $112,590 median. This is the nearest benchmark for sports analytics roles.

Two caveats matter. First, the average growth rate for all occupations over this period is 3 percent, so every role above outpaces the broader job market. Second, these are national medians across all industries, not sports-only figures. A marketing manager at a major league franchise and one at a regional brand can earn very different amounts. Use these numbers as a floor for research, then supplement with current job postings in your target city and league.

Do You Need a Sports Management Degree?

A sports management degree helps but is not required for most roles. It signals familiarity with the industry and opens campus recruiting pipelines, yet many professionals enter from adjacent fields and do just as well. What matters more is matching your education to the function you want.

Several degrees map cleanly onto specific lanes:

• Business or marketing suits operations, sponsorship, and sports marketing roles.
• Communications suits public relations, media, and fan engagement work.
• Data science, statistics, or computer science suits analytics and sports technology.
• Law or an MBA suits athlete representation and senior business roles.
• Kinesiology or exercise science suits player development and wellness coaching.
• Event management or hospitality suits event and facility operations.

If you already hold a degree in one of these fields, you likely do not need a second one in sports management. Certifications, internships, and a portfolio often close the gap faster and cheaper. A focused skill development plan lets you target the exact competencies a role requires instead of paying for a broad credential you may not need.

How to Choose the Right Sports Management Career

Choose your sports management career by matching the work to your strongest natural ability, not by chasing the most visible job. The field is wide enough that nearly any business or technical strength has a home in it, and the people who pick the right lane early advance faster than those who drift.

Start with an honest read of where you do your best work:

• If you stay calm under deadlines and like coordinating people and resources, target operations, event management, or facility roles.
• If you persuade people and read audiences well, target marketing, sponsorship, or sales roles.
• If you think in numbers and enjoy building models, target analytics or sports data science.
• If you lead and develop others, target athletic administration or player development.
• If you negotiate well and understand contracts, target athlete representation or NIL consulting.
• If you build products or write code, target sports technology roles.

Once you know the group, pressure-test it against reality. Talk to people doing the job, read current postings to see what employers actually ask for, and try a small project or volunteer role in that area. The goal is to confirm the fit before you commit years to it. A structured look at essential career soft skills can also reveal which lanes already play to your strengths.

How to Get Into Sports Management

Breaking into sports management follows a repeatable sequence: pick a lane, build evidence, network, and apply to entry roles. Most people who struggle skip the first step and apply broadly to jobs they are not positioned for. Narrowing first makes every later step easier.

Use these steps in order:

1. Choose your lane. Decide which of the six groups fits your strengths so your effort points in one direction.
2. Build experience early. Volunteer, intern, or work part-time in any sports-related setting. Game-day staffing, campus athletics, and local event work all count.
3. Create a portfolio or track record. Marketers build campaigns, analysts publish data projects, operations people document events they ran. Evidence beats a resume line.
4. Network deliberately. Join professional groups, attend industry events, and request informational interviews. Many sports jobs fill through referrals before they are posted, and a strong career support network is often the difference maker.
5. Apply to entry roles. Operations assistant, ticket sales representative, marketing coordinator, event assistant, athletic department assistant, and data intern are common first jobs.
6. Prepare for interviews. Sports employers test both fit and follow-through, so how to prepare for an interview is worth the time before you walk in.

If you are early in the process and unsure where to begin, broad career preparation lays the groundwork, and a clear method for how to find a job keeps your search organized once you start applying.

Skills Employers Look For in Sports Management

Employers in sports management hire for a consistent set of transferable skills that apply across nearly every role in the field. Technical knowledge gets you considered, but these skills decide who advances.

The most valued skills cluster into five areas:

• Communication: writing clearly, presenting to stakeholders, and managing relationships with athletes, sponsors, media, and fans.
• Organization and project management: juggling many deadlines at once, a core demand in operations and event roles especially.
• Analytics and data literacy: reading numbers and making decisions from them, now expected even outside analyst roles.
• Leadership: hiring, motivating, and developing teams, central to administration and management tracks.
• Marketing and commercial sense: understanding how the organization makes money and how fans behave.

Two patterns hold across the field. Communication and organization show up in almost every job description, and data literacy has spread from analytics into marketing, operations, and even coaching. Strengthening these areas early gives you leverage no matter which lane you choose.

Pros and Cons of Sports Management Careers

Sports management careers offer the chance to work in a field you love, but they come with real trade-offs that are easy to overlook when the games are exciting. A clear view of both sides prevents an expensive misstep.

The advantages are genuine:

• You build a career around sports, an industry many people are passionate about.
• The field is varied, so you can move between operations, marketing, analytics, and more as your interests shift.
• Demand is growing, with most adjacent occupations projected to outpace the average job market through 2034.
• Skills transfer well, so experience in one role often opens doors to others.
  

The drawbacks are just as real:

• Entry-level competition is fierce, and many first jobs pay modestly.
• Hours are long and seasonal, with heavy demands around games, tournaments, and events.
• Pay varies enormously, and the high salaries you hear about belong to a small group at the top.
• Geographic flexibility helps, since the best openings cluster around teams and venues.
  

The honest takeaway is that sports management rewards people who enter with a specific plan and build experience before they need it. Treated as a deliberate career rather than a fan’s dream, it pays off.

Final Thoughts

Sports management is not one job but a family of them, united by the business and operations behind the games. The right path comes from matching your strongest ability to the lane that rewards it, then building proof through internships, projects, and a network before you apply. Federal data shows steady growth across the adjacent occupations, so the openings are real for people who prepare.

The people who break in fastest are not the biggest fans. They are the ones who picked a lane early and built evidence for it. If you are not sure which lane fits or how to start, that is the work to do first. Map your strengths against the six career groups, then build the experience and connections that get you hired.

PathWise helps you do exactly that. Work one on one with a coach through our career coaching to choose your lane and pressure-test it against real roles. Use our career services to sharpen the resume, portfolio, and interview prep that sports employers screen for. Or move at your own pace with our career courses to build the skills a target role demands before you apply.

Most teams don’t fail because they lack talent. They fail because they’re not having the conversations that matter.

In this episode of Career Sessions, Career Lessons, I sit down with workplace culture expert, consultant, and author Gustavo Razzetti to discuss his new book, Forward Talk. Gustavo argues that the biggest threat to team performance isn’t conflict—it’s silence. When concerns go unspoken, tensions remain unresolved, and difficult issues are avoided, organizations accumulate what he calls “conversational debt.”

This conversation explores why people often stop speaking up, why agreement isn’t the same as alignment, and what leaders and team members can do to create healthier, more productive conversations.

In this episode, you’ll learn:

• Why teams often struggle because of avoided conversations rather than a lack of talent
• What “conversational debt” is and how it compounds over time
• Why employees frequently stop speaking up—not because they’re afraid, but because they believe nothing will change
• The difference between agreement and true alignment
• How groupthink, blame, and avoidance keep teams stuck
• Why psychological safety alone isn’t enough
• Practical ways leaders and team members can foster more honest, productive conversations
• How high-performing teams create cultures that encourage participation and shared ownership

Tune in every week for more episodes like this. Subscribe on Apple Podcasts, Spotify, YouTube, or follow Career Sessions wherever you’re listening.

Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/gustavo-razzetti

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Watch the episode here

Listen to the podcast here

How To Overcome The Conversational Debt That Holds Teams Back, With Gustavo Razzetti

Defining The Concept Of Conversational Debt

Most teams do not fail because they lack talent. They fail because they do not have the necessary conversations. Think about all the meetings that you have been in, and I have certainly been in some where everyone nods and agrees and leaves, only for nothing to actually change, or worse, where the real conversation is happening afterwards in the hallway or in a messaging platform or behind closed doors somewhere.

Our guest, Gustavo Razzetti, argues that this phenomenon is much more than bad communication. He calls it conversational debt. The hidden cost of avoiding tensions, unspoken concerns, and the decisions that never really get made. The interesting part is that we assume that people stay silent because they are afraid to speak up. I am sure there is some truth in that. Gustavo’s research also suggests that something far worse is going on. People are silent because they do not believe speaking up will matter.

That sense of pointlessness erodes trust, it kills momentum, and it keeps even the smartest teams stuck. In his new book, Forward Talk: The Bold New Method For Getting Teams Unstuck, Gustavo lays out a practical approach for turning conversations from something we avoid into something that actually drives progress. We are going to explore why teams get stuck, why psychological safety may not be the full answer, and what it really takes to create conversations that move both people and organizations forward.

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Gustavo, welcome to the show.

Thank you for having me.

We are going to dive right in. You have a new book out, which talks about teams. I know you argue that teams often do not fail because they have a lack of talent, but because they are not having the right conversations, which is a pretty bold claim. We would love to hear you talk a little bit more about the conversations that we’re missing in our teams.

I’m talking about strategic conversations. Not the coaching, the how-to communicate clearly and so on and so forth. My focus is on teamwork. There are conversations, not one-on-one, but collective conversations. What is missing is basically the difficult conversations, the topics that we do not want to address, and the different perspectives. Sometimes, we look like we are aligned. We look like we are all on the same page. Simply because we do not want to rock the boat. We do not want to upset our manager. We do not want to look like, “You’re not a team player for speaking truth to power or challenging the status quo.” Those conversations that are missing at some point are going to explode.

You make the point that these conversations compound over time in a nonlinear fashion, and there is a bit of exponential growth to them if you let them linger for longer.

There is a phenomenon that most people work a lot with teams in workshops and consulting, and they always have the illusion that things are going to happen magically. When I have a one-on-one conversation, everyone knows what is happening, but then when they get together in the room, no one wants to address those issues. I call this compounding effect conversational debt. It is like, “We are making some money. Maybe I overspend, maybe go out for dinner too frequently. We see nothing is going to happen until the credit card statement comes, and we see that the debt starts to pile up.” The same happens with teams. We think, “It is not a big deal,” but when you have not a big deal, one after the other, then it becomes a big deal.

That phrase conversational debt really resonated with me. It captures the essence of it perfectly. As I think about my own experience working in the corporate world for several decades, when you have those situations where people just do not talk about the things that are really necessary. The elephants in the room, or whatever you want to call them. It just gets worse and worse. The point where the team is for all practical purposes, even if they are getting along, it is a dysfunctional team.

The best way to address conflict is when it starts, and the next best moment is now. The more we keep waiting, the more it is going to get out of hand. We have that fantasy that a conflict disappears, and it does not. I work with leaders who do not want to have those hard feedback conversations with team members because they do not want to go through that tense conversation. They do not want to go through that moment in which people get upset, or maybe they are not going to like them as leaders, whatever.

I always tell them the person who is having some kind of performance issue knows. They know that you are not happy. They know that you are looking at them, frustrated. They are waiting for that conversation to happen. It is like a couple that is going through a rough patch, and both know that they need to sit and say, “How are we going to relaunch our marriage, our partnership?” Someone has to go first.

One thing that I thought was more of a bold claim, I guess I know I used that phrase a minute ago. You make the point that people often do not speak up, not because they are afraid to speak up, but because they do not see the point. That is dark in a way that people have just, in essence, given up on their teams.

Overcoming Pointlessness Versus Just Fear

It is dark, but it is also clear, and it gives us a different kind of path. The point is when leaders say, the team is not speaking, I always say, were they speaking in the past? Try to get when you started. At the first meeting you had with them, did they share their concerns? Did it tell you what was wrong with the former leader? Probably they did. People at some point stopped sharing their perspectives, and this is because nothing has changed. This is very interesting because people usually think that people do not speak up because of fear or because of their culture.

I have seen a lot of cultures that are really nice where people are happy, leaders promote and nurture a safe environment, so people feel safe. No one wants to basically rock the boat. They do not want to create any friction, so people do not speak about, “Your leaders are going to listen.” They are going to hear your concerns, but then there is no action, no change. It is like those employee engagement surveys that we complete every twelve months, twice a year, whatever the cadence is. After sharing, nothing changes. I would continue to raise my hand and share my opinion if nothing mattered.

For people who are sitting in a team, that gets to be a very frustrating existence. I can think of times when I have been there. You feel like you’re talking to a wall, or you make a controversial point, or you bring up something that will create a sense of conflict and tension in the room. Everybody else just looks down, and your peers leave you hanging out there.

It becomes not a team discussion anymore, but it is you and the boss going to engage on this topic, or is the boss just going to move on and change topics? When that happens enough, they just change topics. You just realize, what’s the point of bringing these things up? You are not going to pay any attention to them anyway. That is where I feel like you have hit a person on a team who has just given up for all practical purposes.

It is a paradox because it is like you are shooting yourself in the foot, because if you do not raise the issues, once again, those issues are going to harm you and the team as well. There is an interesting point about what you were saying. We talk about the walls. Of course, the manager plays a big role, and probably many of your audience are managers, but there are also people who are not in a position of power, but still contribute to this kind of defeat mindset. I always say agreement happens in the room.

Alignment is what happens after, because we can all agree when we are together, but then, when we implement, are we really aligned with the implementation? During those water cooler conversations with my team members, we start saying, “I do not care about this.” We are feeding that darkness using the term that you used before. It is not just the boss who is the problem. Sometimes our own colleagues pulled us down.

Teams are teams. You use a sports analogy. You can blame the coach on the sideline for everything that goes wrong in the game, but there are five in basketball, eleven of you, and a soccer football team out there on the field, the pitch. If you are not working well together, you cannot really blame the coach for that. Again, thinking about my own experience, I have sat through meetings where teammates are really not carrying their weight of making the team effective. Even a well-intentioned boss is going to struggle unless they get that dynamic right. This idea of individual agency comes with this. You have got to take some ownership. Even if you are a team member, you cannot just put all the blame on the boss and say this team is not working and it is all their fault.

We contribute both to the harm and to the solution, or part of the solution and part of the problem. Part of the problem, part of the solution. Agency is a keyword they just brought up because I think that people do not realize their contribution. Silence is contagious. When I am going to raise my hand, and then I see no one speaking, then I say, “Maybe it is not the right move to make.” When I facilitate workshops, and I ask a question, people start looking at each other and say, “Something is going on here.” On the other hand, when someone takes that action, they act with courage, they break the silence, and they ask a question. They are blunt in front of others. They are also modeling that positive behavior.

When that happens, it feeds the opposite cycle. You can have a negative cycle that compounds debt. You can have a positive cycle that compounds interest, conversational interest. If you want to use the opposite of your conversation with that phrase.

Totally. If you do not mind me asking, in your experience, because you mentioned earlier that you have seen those teams where people are shutting each other down by looking at each other like, “This is not the right moment. We do not want to get there.” What are the signals that you observe working with teams when the opposite happens?

It happens in one of a couple of ways. Either somebody in the right tone says, “Mary, I know you were expressing some concerns the other day. Share those.” There is a little bit of putting the person on the spot when you do that, but done in the right way, it gives them the confidence that you are going to support them because you have already said, “I want to hear what you have to say. I know you have an opinion on this, one teammate to another, not in the position of leader.”

The other way is when somebody does bring that up, and somebody else then comes on top and says, “I have been thinking about that as well,” or “That is an excellent point,” or asks the question and just allows the conversation to get some oxygen in it. When it is just one person making that point, and you get crickets, nobody says anything, and people are not making eye contact. That is where I think it feels really awkward and where that debt does accrue. I have seen it work both ways, but it is definitely harder to get that dynamic going, which obviously is the point of your book.

Sometimes we think that it is harder, but it is not as hard. There is this thing called the vulnerability loop to a point in which the second person is as important or even more important than the one who starts the conversation. I am going to say, “Maybe not naming Mary,” but saying, “I heard that some team members had some concerns about the deadline, the timeline. This project feels a little bit like we are rushing it. It is too complicated.” Someone says, “Yes, I heard the same when someone builds on that conversation.” The rest say, “Now we can jump too.” That second person plays a huge role in building that loop.

For sure. Your book is called Forward Talk: The Bold New Method For Getting Teams Unstuck. Help us understand what you mean by forward talk and how it creates this kind of team construct that you are arguing for here.

Of course, we want, and leaders want, and you, as a team member, want to move forward. The most important thing is that teams get stuck in conversations because most of those conversations are focused on the past. We have, for example, one pattern that is to blame. When all our conversations are about that bad hire, the bad decision the team or the leader made, or a project that went wrong, or maybe we never completed it, or we had to redo it, whatever the case may be, that blame drags people into the past, and we cannot get over it.

Implementing Forward Talk To Neutralize Groupthink

Rather than focusing on how we can improve from that mistake, what have we learned? We get stuck on who screwed up. Avoidance is also the same because, building on our conversation, “Nothing happened in the past. I stopped caring. I am going to keep myself silent, or I am not going to really speak up my mind. I am going to just adapt.” The other pattern is groupthink. It is the most deceiving of all because it looks like we are moving forward, but we are just moving on.

We just want to go along with the team, we want to agree, we rush decisions without having the proper conversation. We are dancing around the issues simply to be a team player or just to “Let’s move on.” That is why decisions never stick. Forward talk is about conversations that not only focus on moving into the future, making progress, but also do that by addressing the real issue, not ignoring it, not tackling it superficially.

You talked about groupthink perhaps being the one that is most deceiving because you think you have got agreement, but you really do not have agreement. Which one do you think happens most often?

It all depends on the type of culture. In cultures that are more nice, groupthink is the one that you see the most often. In cultures that are driven by fear, blame is the easiest pattern because when there’s fear, someone’s going to get punished. We would rather not be the culprit. We find someone else or even another department.

You also feel that psychological safety isn’t necessarily the answer.

I have been working with psychological safety before it became a thing, following Amy Edmondson’s work for over eight years or more. I have been training people, facilitating stuff, but going through the research of my book, and also working with teams, I realized that it is not a complete solution because psychological safety focuses on the context. We need to create a safe space for people to speak up. Two things are happening. First, as we mentioned before, some companies are safe, but that still does not mean that they want to hear the truth.

They want to hear the perfect truth, the illusion of alignment. Second, the concept of psychological safety has become a little bit weaponized, both from leaders and team members. I have a lot of team members saying, “This team is not safe, so I am not going to speak up.” They use it as an excuse because, in the end, they are part of the problem. They are not doing anything to change it. They are using the excuse that it is not safe enough. They are not accountable.

That is a really fair point. A lot of things end up getting taken too far and used in a way that ultimately is not constructive. Certainly, the concept of having a team environment where people can speak freely, share opinions, be vulnerable, and bring up conflict if that needs to be brought up. Say the unpopular thing. All of that is important at the same time. I have seen situations where people have said, I do not really feel psychologically safe. Therefore, they are just casting blame on the system as a defensive mechanism. Exactly what you said.

They are removing their agency, right? The point is not with the framework. It is how the framework has been turning into something that basically is not helping some teams, but also, there is an additional layer in my research identified, like three groups. Some people are susceptible to psychological safety. If the environment is safer, they tend to speak more. If it’s unsafe, they speak less. There are team members who, regardless of whether it’s safer, do not participate. There are people who, even in unsafe environments, speak up because of their personalities.

For somebody in our audience who is listening or watching and is having their own team experiences like this. We talked a little bit about being that second voice and the powerful effect that that can have. What are some of the other ways that a team member sitting in one of these meetings can help turn the conversation in the right direction?

Two things come to mind. The first is becoming more aware of the patterns. I always like to say forward talk is like a direction. No team is perfect. We are always going to have a little bit of blame. We are going to have a little bit of avoidance. The point is not having those patterns. The point is when those patterns become the team’s norms, and we default to those. We are going to have better and worse days. When we start seeing how the conversations happen through those three lenses, are we avoiding the topic?

Are we focusing more on blaming people or other people, or maybe even the customers, instead of trying to solve the problem, focusing on the system? Are we trying to find a solution that maybe, for example, a group thinks. It is about finding the safest idea instead of the idea the team really needs, because we want an idea that everyone is going to support, instead of the idea that is going to be a little bit uncomfortable, but it is the one that we need. This is the first thing.

When you start noticing the patterns, you can start sharing that with the team members and say, “Guys, I think we are getting too much into this.” Not judging, not finger-pointing, but at least it creates awareness. The second and quick intervention is what I call reframing conversations. Many times we have, we tried that, and it is not going to work, or it did not work in the past. How can we make it work, considering that the conditions have changed? For example, you reframe it into an opportunity.

We cannot make this decision because the leader is not in the meeting. What decision can we make with the power that we have? We do not have a budget. What can we prioritize? We make money or fund this project. Many conversations get teams stuck because they feel absolute, and they focus on a problem. Reframing the conversations, turning that obstacle into an opportunity, trying to see the other side, and not getting stuck. You turn into a question to explore.

You have done a lot of work with teams for the ones that you have seen that are really high performing. What else do you see them doing that really stands out both in and outside the room?

First, it is important that leaders realize that their role is to facilitate, not dominate, conversations. That comes to letting go of what happens in the room, being more intentional about tapping into the collective wisdom, and also admitting that they are not right or they are not the only source of truth. I was writing an article about this in Mark Zuckerberg’s AI version, so people can access the CEO 24/7. That is built on the idea that the CEO is always right and is the source of answers. High-performing team leaders are not in that position. They are in the position of curating the information through their teams rather than being the ones who provide the solution.

You’re hitting on a couple of things that really resonate with me. One is the idea that we are in this era where the idea of star CEOs really seems to be particularly prominent. When you have a star CEO, to me, that is a weak team because it has a singular dependency on one person. Even if that person is legitimately a star, I mean, sometimes it is, they are so controlling that nobody else really gets any air to speak or to express their own opinion or to take their own actions. The idea of the star CEO just works against everything that a team really should be about, which is a collection of people trying to achieve more than they would have been able to do if they were working independently.

Even if they see us as stars, they should not play the star part. They should let their team thrive.

I was coincidentally listening to Stanley McChrystal’s book, Team of Teams. At the very end of the book, he talks about the leader as a gardener. It was a good analogy. I have not heard before, just this idea that you’re tending to something. You are nurturing it. You are not growing the vegetables or the fruit or whatever you’re growing. You are not making the flowers.

You are tending to them. You are creating the conditions for your garden to grow. If you think about it in that construct, you’re going to play a very different role than if you’re the controlling, top-down, micromanaging leader. That difference really stood out to me as a very relatable metaphor for thinking about the role that a leader needs to play if they really want to bring out the best in everybody on their team.

That is the culture. It is an environment where you want other people to flourish. You just need to nurture it, not take over it.

Let’s talk a little bit more about the broader organizational context and just some of the things that I will say exist outside of the team itself and the broader culture of the organization that is creating these conditions where people just feel like it is not worth speaking up, pointless, or otherwise.

There are two takes on that. The other day, I was facilitating a workshop, and there were like 600 senior managers, and I asked them, what is your stronger sense of belonging? One extreme had your team, the people that you work the most frequently with and are closest to, or the larger organization, and everything in between. The vast majority of people say that their strongest sense of belonging and their connection was with their teams. The larger culture plays a big role and influences a lot of patterns when it comes to conversations. In the end, you can have a very toxic organization and still have great subcultures that are healthy or semi-healthy. Conversely, you can have a very healthy organization and have pockets that are really toxic or harmful or silent.

I am curious to get your view in terms of the orientation of the individual to the team versus to the organization. Is one necessarily better?

Probably, but I want to think more about what the natural tendency is, because I think that leaders need to work with the energy we’re talking about in the garden. If a tree wants to move in one direction, it can push. They are going to look for where the sun is. You should not fight against that. That is nature. Nature is that we have a stronger sense of belonging to the people that we are closer. You get connected to the place that you live, the sports team that you follow, your neighbors, then your family, and your friends. The closer that community, the stronger that sense of belonging. That is human nature.

When we want to create an identity, especially for companies that have tens of thousands, even hundreds of thousands of employees, it is very hard to make sure that everyone has the same pattern, the same agreements, and they all look alike. Actually, by trying to do that, we basically erode people’s uniqueness. It is easier to create that connection and have stronger subcultures at a team level than trying to force one identity that is going to bring us around to us. We need to bring the connecting tissue between those subcultures and the larger org.

Think about teams that are so team-centric. Almost to the point where they are ignoring the broader context. Positively or negatively, I think that can be pretty unhealthy because it does not scale particularly well. It could be that the team becomes very set on doing something that is misaligned with what the broader organizational culture or purpose is about. At the same time, I think it is unrealistic to expect people to gravitate more naturally to a big organization because they are not dealing with the 10 or 100,000 people that are in their company every day.

They are dealing with the ten people that are on their team and how to balance that centricity. If you want to call it that in terms of my centricity to my team and my centricity to the broader organizational purpose, I think it is one of the hardest parts to get right in terms of having team focus, because you do not want them to act in isolation. You also do not want them to completely ignore the ten people around them.

You capture it brilliantly. You do not want to impose your organizational identity. You do not want to isolate teams into their subculture. It is a balance. In my book, I talk about the three key elements of culture. Those are basically the three key elements of commercials that are conversations about alignment, belonging, and collaboration, or I call them the ABCs of culture. When it comes to alignment, what’s our purpose, value, what are we in business for? What’s the impact? Everyone should be on the same page.

I do not care which business you are in or which unit. When it comes to how we do the work, the collaboration, that is more up to the team to decide what is going to work for them. We talk about being innovative. Innovation does not mean the same for your legal team, your procurement team, your finance team, or your product team. It is different. The belonging, that emotional side, is a combination of both how leaders lead at a company-wide level and also how teams operate on their own.

You have worked with teams all over the world. When you go in and work with a team that is maybe not where they should be or where they want to be, what do you see as the tension to separate the ones that then head in the right direction versus the ones that just stay stuck?

Utilizing The Team Heartbeat Exercise For Alignment

What changes is that they move conversations from their head to the room. A lot of people are building narratives around their team members. They’re really totally off, and sometimes getting that narrative outside helps a lot. I am going to share a very basic exercise. One thing I call the team heartbeat. I ask. From the moment you join this team until today, capture all the highs and lows, then identify what are the key events that happen on each of those. That creates a pulse or heartbeat of the team.

When people share with each other, you start to realize that maybe a project that was limited in terms of budget and timing or whatever for you was exciting. You start to see how people react to different events. When you can bring all those perspectives together in terms of how we perceive the same events, the same experiences, but through our different personalities and roles, you start to create a very interesting context for people to realize that, “Maybe we are seeing the same movie, but everyone is getting hooked in different parts, and we love certain parts.” Sometimes we hate all the movies.

In that exercise, I would imagine what is particularly valuable is seeing what people agree on highs? What do people agree on lows? They are all bringing up the same situation, but they are seeing it differently. You probably also got some things where I thought this was a particular high that nobody else happened to notice, or a low that nobody else happened to notice. That is insight as well. It helps you see different people’s perspectives because you go into the room, you have your meetings, but then you all go off and do your own thing, and you’re living different experiences day to day. You’re only having that shared time every now and then. I am sure you see a lot of that in your work when you go through that exercise.

You said something that is really interesting. Imagine that, for example, the leader says, “This moment was fantastic.” They realized that no one else cared. It could be either that you’re clueless or that your communication skills are not there. Maybe the moment was great, but you make it about yourself. You want to be the hero in the narrative, not the people. People did not like it. There is a lot to learn from those things.

You made a point earlier about narratives. We are forming these narratives. We are interacting with our peers. We are saying some things, we are not saying some other things. We are walking away from every meeting with a point of view about where people are coming from. We have these opinions about teammate A, teammate B, teammate C that could be accurate or perhaps completely inaccurate.

Unless you start to vocalize some of those things and test them and figure out whether you have got a shared view of reality, you run the risk that you do not. That is where this idea of conversational debt comes back to what you talked about earlier, can really pile up because it just means that the team is not really having a shared sense of consciousness, if you will, about how all of this really ought to be interpreted.

If you do not know what the problem is, all solutions are going to fail. Conversation is the first step towards understanding what is going on. That is why we fail. When there’s silence and leaders in particular, but also team members, avoid the real issue, people are going to fill the void with narratives. In most cases, they are not going to be good. People start filling that void with lots of crazy stories. When we start a conversation that we fear, people say, “It was not that bad.” That is the realization that most people have. There is a lot of research that shows that the people who went through hard conversations most of the time do not regret it and actually feel that “That went much, much better than I thought it would.”

That is true a lot of the time, as you are saying that you have this belief that if you bring something up, it is going to be this huge issue. I will say 7 or 8 times out of 10, it ends up being less of an issue than you thought it would be 2 or 3 times. Maybe it becomes a bigger issue than you thought. If that is the case, then you really need to have the conversation.

It is like overspending, and I do not want to check your credit card statements. It is going to be here. Probably when you open, say, “I thought it was even worse.”

That is where the debt’s really going to pile up. Not conversational debt, real debt.

Yes, sir.

For our audience, what would you want people to walk away with? One mindset shift or one tool in their toolkit to help their teams be more effective?

Cultivating Individual Agency And Positive Cycles

First, the notion of regret. There is a lot of research from Daniel Pink that says that we do not regret what we tried, what we did. We usually regret what we did not do. You are not going to regret a conversation even if it goes wrong. You are going to regret the idea of I should have, I wanted to, but I never did. The second thing is that you’re part of the problem.

We talked a lot today about conversational agency in plain English. Own your part. Do not complain if you are not sharing your truth. If you are not asking the right questions, you are also part of that silent culture. You are also part of the problem. We need to stop waiting for someone else to do that. We need to go first. We need to model the courage we want to see in others.

If everybody starts doing just a little bit of that, you start to get the different kind of compounding effect that creates some of the positive energy that you need to then help the team become even more effective, more willing to confront hard topics together, more willing to speak openly. That’s what we are really all aiming for. That is what’s going to drive high-performing teams.

I know people are saying, “You are saying this.” It sounds easy. I am not saying start with the hardest conversation. It is like exercising. You have to build muscle. We built the muscle of avoidance. Now we need to start training and start building the muscle of participation, the muscle of conversations.

Your book is out. I look forward to seeing how the book launch goes and how it does. I wish you the best with everything. Thanks for being on the show with me.

Thank you for hosting me, and thank you for the conversation.

—

Takeaways from the conversation just now with Gustavos. First, the biggest risk in teams is conflict. It is actually silence. Teams do not underperform because people disagree. They do so because people stop speaking up. Often it is not fear. It is the belief, even a deep-rooted cynicism, which I said was kind of dark, that saying something will not actually change anything, which is not where you want your team to be.

The second thing is that unspoken issues do not disappear. They compound. This is what Gustavo called conversational debt, and it builds over time, just like interest would on a loan that you owe. Each conversation adds to misalignment, adds to frustration, and eventually these things turn into major failures that will feel sudden, but they really were not, and they were completely predictable. Third, alignment is often an illusion.

Just because everybody nods does not mean everybody really agrees, and getting real alignment is both a shared understanding and a genuine commitment. Even when people initially agree, as Gustavus said, agreement happens in the room, and alignment happens afterwards. There is a big difference between the two. Finally, better conversations require courage, not just frameworks. The exercise he suggested, I think, is a great one in terms of looking at highs and lows and how everybody views that.

At the end of the day, for teams to really work together, there has to be the courage to speak up. That means everybody has to have that sense of owning their part, being willing to express unpopular opinions, to engage and challenge honestly, even when it is uncomfortable. Culture does not really change until behavior does, and that requires everybody owning their part. I invite you to subscribe to Career Sessions on Apple Podcasts, on Spotify, and on YouTube. If you found this discussion enlightening, and I hope you did, please sign up for my membership community, which is called PathWise, and my newsletter, PathWisdom. Thank you.

Important Links

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• Forward Talk: The Bold New Method For Getting Teams Unstuck
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About Gustavo Razzetti

Gustavo Razzetti is the bestselling author of Remote, Not Distant, Stretch for Change, and his forthcoming book, Forward Talk. Gustavo is a culture strategist, workshop facilitator, and keynote speaker with over 25 years of experience—first as a marketing and advertising executive, now as CEO of Fearless Culture, a culture design consultancy. He’s facilitated more than 1,500 workshops with leadership teams at Mars, Microsoft, Merck, the Inter-American Development Bank, and hundreds of organizations across the world.

Razzetti is the creator of the Culture Design Canvas, now used by over 500,000 practitioners worldwide, and the Forward Talk framework. He helps teams surface issues early, challenge groupthink, and turn avoided conversations into decisions that stick. His work has been featured in The New York Times, BBC, Forbes, and Fortune. He’s a regular contributor to Psychology Today. His most recent book, Forward Talk: The Bold New Method For Getting Teams Unstuck, was released on May 5, 2026.

Most people spend a huge portion of their lives at work. So why do so many of us dread it?

In this episode, JR speaks with Debbie Lovich, Managing Director and Senior Partner at Boston Consulting Group and author of Make Work Work, about why employee engagement has remained stubbornly low for decades despite billions spent on leadership training, culture initiatives, and workplace transformation programs.

Debbie argues that making work better doesn’t require another grand strategy or organizational overhaul. Instead, it comes down to a handful of daily leadership behaviors that create more human, enjoyable, and productive workplaces.

Their conversation covers:

• Why most leadership training fails to change behavior
• The connection between employee joy, performance, and retention
• The five daily practices that help leaders create better workplaces
• Why employee experience should be treated like customer experience
• How co-creation can replace traditional change management
• The role of middle managers in shaping workplace culture
• What leaders get wrong about AI and the future of work
• How anyone—not just senior executives—can improve the culture around them

If you’re a leader, manager, or employee who wants work to be more meaningful, productive, and enjoyable, this conversation offers practical ideas you can put into action immediately.

Subscribe to Career Sessions on YouTube and wherever you get your podcasts for weekly episodes like this.

Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/debbie-lovich/

—

Watch the episode here

Listen to the podcast here

Why Work Feels Broken (And How to Fix It), With Debbie Lovich

The Stagnation Of Global Workforce Engagement

If we’re honest with ourselves, a lot of us would say that the answer to that question is no. Workforce engagement with a proxy for satisfaction has hovered around 30% in the United States for many years. It’s even lower in other parts of the developed world. If you think about it. It’s a huge failure that we can’t do better than that. What’s fascinating is that we’ve never had more books or frameworks or leadership training and even shows like this one about how to make work better. Hundreds of millions of people just go through the motions every day at work and that’s terrible.

My guest, my friend in HBS classmate Debbie Lovich has spent over three decades working inside some of the world’s biggest organizations. She has been at Boston Consulting Group, advising leaders who genuinely want to create workplaces that are better but they haven’t figured out how to translate that intention into everyday behavior in a way that truly makes a difference.

The problem isn’t that these leaders aren’t trying or that they don’t care. It’s that they’re focused on the wrong things. The way they’re going about it is making things even worse. In her new book, Make Work Work, Debbie introduces five daily practices that when done consistently can transform how people experience work.

It isn’t about launching a big transformation or rolling out yet another HR program. It’s about what leaders can do every single day. In this episode, we’re going to talk about why work feels so broken to so many people, what it takes to create joy at work and how any leader or honestly, any of us can take part in changing our workplaces for the better. I’m J.R. Lowry. This is Career Sessions.

—

Debbie, welcome back to the show. This is your second time with me. You must be especially brave.

Maybe especially lucky.

We will leave that up to the interpretation of our audience. Let’s get going. You have a new book out. You spent 30 plus years working at the Boston Consulting Group and advising organizations. What finally pushed you to write a book now?

Defining The Concept Of Radical Employee Centricity

If I look at the ark of my career, I spent the first part thinking that smart people did strategy and operations and the softies did people stuff. Halfway through my career, I realized that, “If I look at all the projects I did for clients and the work I did for clients. They definitely had a great impact, but they didn’t have as much impact as I aspired for them to have.” I started to look at what got in the way. What got in the way? People, leadership, culture, ways of working and behavior.

I started to say, “I have to address this stuff.” I went into work on the people’s stuff. My first client was BCG, and I found out that changing behavior is anything but soft. It is hard, especially senior leader behavior. When you have dozens, hundreds, thousands of leaders, to get them all work differently and to drive value creation. That was the coolest thing I could be doing. That’s what I’ve been doing for the past decade and a half.

In the last decade, I started focusing on what I call radical employee centricity. Which is if you treat your employees as important as you treat your customers and shareholders, there’s tremendous value on lock for the company. It’s not just you employees nice because it’s the right thing to do. Employees who enjoy their work can create so much value. I discovered this thing. I’ve written about it. Now, I want to get those two ideas, the leadership piece and the employee value. They sort of skate together because what is the easiest way to unlock employee value, to make work enjoyable, or the title, my book to make work work?

What’s the easiest way to do that? It’s leaders and what leaders do every day. That’s what the book is for. It’s to get this message out there. Every leader has in him or herself, the ability to make work enjoyable for his or her people and her team or her organization. In doing that, they could unlock so much value for their organizations besides just making the people’s lives better every day.

What’s interesting about this, all these business books have been read. We’re doing training for leaders and employees. Yet, as you point out in the book, work still sucks for a lot of people. What are we getting wrong?

Why Traditional Corporate Training Often Fails

First of all, training doesn’t work. I tell people, and you will appreciate this. You don’t get in shape by watching an exercise video from the couch. Nor do you get in shape by going to a spa for a week because you’ll go back to sitting at your desk all day or your sedentary life. You also won’t get in shape by saying, “I’m going to go to Pilates every morning at 5:00 AM,” because you’re going to hit snooze and you’re not going to go. The way you get in shape is by walking to work, doing walking meetings, building fitness that’s doable into your natural rhythms and routines.

What organizations spend billions on is the spa, the watching an exercise video from the couch or Pilates classes that nobody goes to. It doesn’t take and so the secret to building muscle, to building leadership case stability is not doing off-site, training and webinars. The secret is to make small changes in your day-to-day work that build habits and build muscle. People could understand that work could be better. They understand that leaders could be better, but the answer they’re putting against it, the solution just doesn’t take.

There’s certainly a heavy emphasis on behavioral science that underpins your five practices. The idea that you’ve got to make it simple, habitual, and do it consistently or you’re not going to continue to do it over time. That’s where a lot of these things fall down. A lot of leadership books are at 50,000 feet. They’ll talk about these big thematic things. They don’t bring it down enough to what you can do. A lot of other books do a decent job of that. Your book certainly is very focused on saying, “These are five practices. They seem simple. They’re not as simple as they seem if you want to put them into practice and you’ve got to make them into habits.”

It’s also interesting because there are a lot of books out there that give you a checklist and do these things. One of the things about the five behaviors in the book, the five practices that help them take is that they’re rewarding to do. They’re multiplicative in their impact. This is like doing something that just gives energy and in return, gives you back energy. Hopefully, people get addicted to doing these things because they’re so rewarding to do. You see the multiplicative impact right away.

Let’s get into them. I’ll rattle them off and then I’ll let you explain each of them in turn, celebrate someone, go see and help, be interested, co-create, and do it first. Let’s go through them.

Celebrating People And Embracing Servant Leadership

Let’s start with celebrate someone. I start that chapter with the story about this very senior leader I worked with whose team was not productive, bad morale, and bad culture. I interviewed all of his senior directors one-on-one and they were like, “He hates us. We’re never good enough for him.” This was in a pharmaceutical company, a biotech company. They’re all clinical geniuses. I go back and I tell him, “Your team thinks you hate them.” He’s like, “What? I have the best team on the planet.” I’m just, “When have you told them that?” He goes, “They don’t need to hear it. They know it.” I’m like, “No. They need to hear it.”

This is to celebrate people, every time you have a positive thought about someone, tell the person. Be like,” J.R, you are so awesome because I don’t know how you created this show in your spare time while you work full time. You are this runner, hiker and walker. Where do you find the time for it? It’s amazing.” That’s a specific compliment. I happen to believe that, and it’s true. It’s genuine. Don’t make stuff up or say, “You’re great.” The move. If you think anything positive at any time about anyone you work with, let them know.

By the way, it doesn’t have to just be your team underneath you. It could be your peers. It could be your boss. Bosses are lonely, but you got to get the balance. We know from behavioral science that people need to hear something like five positive things to every negative thing to feel good about themselves. Yet, we’re not saying the positive things. Go see and help is built on servant leadership. If you remember that from agile methodologies.

It’s the notion of going to where the work is and helping people out. What I tell executives is, “You’re meeting at these gleaming corporate headquarters or fancy hotels and you get together all day for your executive meetings. You’ve gotten so disconnected from what’s happening at the rock face of the work. Instead, why don’t you do your meeting in a manufacturing plant or in a retail store or in a distribution center? Before the meeting, go out on the floor and talk to people. Ask them, “How can I make your job easier? What can I take off your plate? What gives you straps?”

When you get to your executive meeting, talk about it at the meeting. I talk about Hubert Joly, who I’m so privileged to have worked with. Hubert was the CEO who turned around Best Buy when Amazon got into consumer electronics and they started going online. If you remember, there was Circuit City, RadioShack, and Best Buy. Circuit City and Radio Shack were out of business. Hubert took this very employee-centric mindset.

Before he took the CEO position, he worked in the stores. He just spent time with the front line and learned what we can do as an organization to help them be more effective in their jobs. He’s written in his wonderful book, The Heart of Business. Everything I needed to know about turning around Best Buy was coming from the front lines. That’s the go see and help. Get on the floor and help folks.

As I was reading that piece, I was thinking back to when I was at Fidelity. This goes back many years. We would do meetings. I can’t remember how frequently we would have them. Maybe every 6 or 8 weeks or maybe every quarter. We would go to a different site to do the meeting, to your point. Most of our organization were call center reps. Thousands of people answering, in that instance, calls from people who are participating in a benefit plan that Fidelity administered like a 401(k) plan or a pension. Every time we met, we would have our meeting but then we’d spend time with the management team there.

We do events with the employee population. They loved the fact that all of us came to them. Even if we didn’t spend a ton of time with them, we were certainly being visible to them. I made a huge difference in those circumstances and it certainly reinforced for me the value of getting out there and being visible to your employees. Make sure that you’re breaking through the layers of management chains and hearing about what their experience is like.

That’s exactly right. You’ve got it. I worked with a client years ago who was big pharmaceutical company. Pharmaceutical companies have huge sales forces. They always have an open territory. The executives would go out for a week a quarter and go sell. That was magical because they were helping out the district manager who was short-staffed. They also were in tune with what it was like at the rock face of the customer interaction. The reaction you get, like what you said, when you were out in the call centers, people loved it. That’s the energy. Remember I said, these are positive things. It makes you want to do it again because people are so happy to see you. It makes them feel like rockstar. It is reinforcing energy.

For sure. Let’s go to the third one, be interested.

Developing Genuine Interest In Employees As Individuals

This is just asking people about themselves. Being interested in the people on your team as a human. Not as a worker. What do you do outside of work? How do you end up here? Where’s your family from? What do you do for fun? What do you want to do long term? What are your career goals? People want bosses and leaders who care about them. You then remember the details. In my contact information for people, in the notes section, I write down the details. The next time I talk to them, I could be like, “How’s your son’s college applications going?” They’re like, “Debbie, remember that?”

It’s being interested in their lives. I get a little bit of push back when I talk about this. Some people are not comfortable talking about themselves. They may be very introverted. That’s fine. Make it safe. Talk about yourself first and don’t go deep to say, “Here’s what I’m doing on the weekend. What are you doing?” If you offer about yourself, that’s also generous. It makes it psychologically safe for them to offer about themselves. It shows your interest in people. It helps people feel valued, not just as someone who does great work but as a whole person, part of your team.

For a lot of leaders, it’s uncomfortable. You get some who are great at walking the floor. They remember people’s names. They remember the details. They can make it seamless. They light everybody up and bring energy. Others are so awkward about it. That it just feels like a horror show for all parties involved. Having a repertoire of questions that you can go to or having a method of engaging people in a way that doesn’t feel awkward for them or awkward for you and your style. It takes time to develop. A lot of leaders are interested in their people and their certainly time constraints.

They can’t engage is deeply in every conversation that they would probably ideally like to be able to. It making the most of those little moments, whether it’s passing somebody in the hallway or bumping into them, going in or out of the bathroom even or in the cafeteria or in the elevator. There’s lots of opportunities for those 30 second conversations that will bring a little bit of extra lift to somebody’s day if you take advantage of them. There’s also the people who just don’t. You stand in the elevator next to CEO and they don’t say a word to you. That’s the thing you’re going to remember. That they didn’t say a word to you. They didn’t even say hi.

The elevator is so funny. The BCG office in Boston, we have floors eight to the top. There are people who get out before but as soon as we hit eight, I’m like, “This is the BCG express. I’m Debbie. Who are you guys?” People appreciate it. It warms it up. These are colleagues, but you’re right, it is awkward. By the way, it’s awkward for the CEO, too. Maybe they don’t know how to do it but they know everyone knows that. You almost have to.

 You almost have to. At the same time, I see a lot of senior leaders who are like, “Pretend there’s nobody in here with me so I can be alone with my thoughts for just a second.” The phone has become the ultimate cure for social awkwardness and unfortunately, it’s making it worse.

Again, as soon as you do all these practices, the positive instant feedback you get just gets you hooked on it. I like talking to random people in the elevator who are all colleagues of mine. I know we have something in common. I like that. I like getting to know people, which is great. The problem starts when people are like, “Debbie, you introduced yourself to me yesterday or last week.” I’m like, “I’m sorry, my brain. Please remind me of your name again.” You got to be okay with that.

You do. I’m terrible at remembering names and I work at it and work at it. Age is not helping that. I will just say to people like, “I’m terrible at remembering names. You may have to tell me your name again, but I will remember you.” It helps take some of the pressure up. It’s admitting a little bit of weakness and vulnerability in a way that people can relate to and it in my case, it’s not just made up.

Prioritizing Co-Creation To Boost Adoption And Engagement

That’s right. It makes you so human as a leader. Even saying, we’re interested. That’s the third. The fourth is co-create. Co-creation is a little harder. Co-creation is more anything that you were working on as a leader that’s going to impact some group of employees, have someone at least someone at best a couple of those employees on the team with you working on it. What happens is as we make these top-down changes, these off to the side projects, these Gen AI use cases. We’re like, “Let’s roll them out.”

They never get adopted the way they should be because they don’t work as well as they should be because you haven’t gotten adequate input from the people who are getting it. The world gets this with consumer products. There’s so much customer level, interaction, piloting, alpha beta, gamma, feedback loops co-creation with customers. It’s so ironic when it comes to work. We don’t do that. Every change we do at work, re-org, new technology deployment, new workstream, and new approach impacts people.

We got to do the same customer stuff with our employees and that could take lots of different forms. It could take a couple and put them on the team. Create an employee advisory panel and have the team off to the side that’s doing this read out to them every week like they’re the client or do a focus group with them. I’m working with a client. We’re doing a huge transformation program and we literally communicated to the entire organization we want your ideas. There’s a website they can go to put their ideas in.

Every idea is categorized and routed to the right leader. The person gets a response like, “Here’s what we’re doing with it and why. Can we talk more? Here’s why it doesn’t work, but thank you. Keep them coming.” Is it energizing? There’s a whole goal of these behaviors. By the way, it’s to unlock employees, and joy which unlocks value creation for the company. This stuff makes it feel like we’re all in this together.

This co-creation is a little harder to do because you’ve got to pull the people on your team or you have to create the advisory panels or you have to create the infrastructure to make people feel a part of everything you’re doing, then it’s not top down. When you do this, remember Jim Whitehurst, from our section? He wrote a book called The Open Organization after he went from Delta Airlines to Red Hat. He saw Red Hat. That company was all co-creation. He’s like, “What is my job as CEO if everyone’s self-motivated and doing their own work?”

What he realized, and he wrote in his book is something like change management is for when you’ve done a bad job at the work. If you do the work in the wrong way and you need to convince people it’s in their best interest to adopt it. That’s changed management. If you do real co-creation, like, “Change what? This is just how we do things.” That’s the fourth.

In the scheme of things, frankly, that one is more than a little bit harder. It’s a lot harder for most people. First of all, leaders feel like they have to have all the answers and they don’t necessarily want to feel like they have to go out, solicit and put on them. They want to move quickly. They think engaging employees in the process slows them down.

They don’t think employees will have a valuable perspective. All those reasons that people put in their heads about why they can’t, shouldn’t or don’t want to do this stuff. It’s a lot harder and it’s countercultural in a lot of organizations. I talk about Red Hat build on a usage of an open source platform Linux, in their case. That’s how that whole company was built and grown.

It’s in their ethos. We’ve seen more of that open source mentality in the era of the internet. This crowdsourcing and all of the things out there from Wikipedia that are about people working together to make something better than it could ever be with people working individually on their own. It’s still grudgingly finding its way into most of corporate America. That is about a leader’s egos and their processes and their willingness to make time for this early rather than doing, and fear. That’s why this one is the hardest of the five.

I agree. Here’s how I’ve been working around it. It doesn’t have to be all the way to a Red Hat total crowdsource company. Literally, an email box where people can send ideas and you staff someone to respond to them. That’s super easy to do. As a leader to any team, you just need to start saying, “Make sure you have the employees impacted. Have a voice on that team. Here are a couple ways you could do it.” Making Red Hat is definitely very hard, but there are baby steps that get you a lot of the way there, but you’re right in what you said. It’s a mindset thing.

What’s helped me on the mindset thing, is the customer discovery wave. You do this with your customers. Why not do it with your employees? By the way, our customers choose every day how much energy to bring to work. Can you turn your customer stuff, which you already have, on your employees? We got customer journeys, design thinking, segmentation, personalization, AB testing, crowdsourcing and customer feedback. You can’t buy a product without customer feedback. How many times do we ask employees for feedback? Once a year or twice a year. Long surveys that nothing happens as a result. I just need to pull them over to say, employees are customers, too. Your spot on that mindset is the issue.

Let’s go the last one.

The Power Of Leading By Example (Do First)

Do first. I start this chapter with the story of this new Starbucks CEO who takes the job at Starbucks, but says, “I’m going to still live in Southern California and private jet up to Seattle whenever I need to be there. By the way, I need everyone to be back in the office.” Disconnect. This is not the only reason Starbucks is totally failing, but it can’t help.

On top of that, “Here’s my ginormous pay package,” while the average person is Starbuck’s is barely earning a living wage.

That’s it. You can’t ask anybody to do anything that you don’t do first. You want everyone to adopt Gen AI and rethink how they spend their day and their work streams. You better do it first and talk about it. Talk about how hard it is, how rewarding it is and how scary it is. Once you start doing it and you see how people react, it will become addictive.

This one is ultimately about role modeling. Role modeling or showing people is a lot more powerful than just telling them to do something because you’re showing them that you’re willing to do it, too.

By the way, if you can’t do it, you’ll think twice before asking everyone else to do it.

For a leader who’s reading and saying, “This sounds great. Where do I start?” Where should they start?

You just start by starting. I literally would start with the celebrate them. That’s the easiest one. You have a positive thought about anyone. Say it. Coach the leader of the big transportation company. People even use abusive words about him. I had him start doing that, celebrate them and people were literally sending me notes like, “Whatever you did to Sam,” and it was nothing. The cultural ripples, the performance and the energy. That was amazing.

It’s about feedback, positive or negative. You said the ratio was 5 to 1. I’ve heard some people say it needs to be up closer to 10 to 1. The point is, you need to be delivering those specific bits of positive reinforcement all the time. Don’t leave a meeting. Don’t be in an enemy meeting without mentioning things. Don’t be in a one-on-one without mentioning these things. Don’t be in the elevator without mentioning these things.

Have the ability where you’re constantly giving some little piece of specific positive reinforcement. In the scheme of things, I won’t say it’s always easy but it’s the one that gives you back to the point you talked about earlier, that dopamine hit for yourself. I gave a person positive feedback. That felt good to them and it feels good to me. It makes you want to keep doing more of it. If you can get that cycle going, then it becomes easier to do some of the other things like being interested in working way up to probably the hardest one, which I still think is co-create.

Remember, the meta goal here is to have an organization where everyone is excited to be there every day. Which doesn’t mean every minute of work is joyful. It’s not, but on average. When people say, “Do you enjoy your work?” Your answer is yes. Did you enjoy your work this week? Your answer is yes. Did you enjoy work? Mostly yes. Sometimes we could have bad days. My research shows when employees enjoy their work, they are half as likely to quit.

They are anywhere from 2 to 4 times as motivated to bring their best to work every day. In a recent piece I put out an BHR, they sell 25% more per hour than people who don’t enjoy work. There is value on the table just like the customer revolution decades ago. I believe we’re on the precipice of the employee Revolution. The value on the tables there. The unlock can be tiny little things that become multiplicative. Start by starting.

We need something, because employee engagement haven’t moved in the last generation 25-30 years. Everything we’ve been trying is not working. It goes back to what you said earlier in the conversation that all these big programs, the training, the books, and the retreats, none of that’s working in the way that we want it to. We’ve got to try something else. The idea of small practices matters. Let’s we talked a little bit earlier about leaders, but for a mid-level manager or mid-level person, what can they do to help bring this into the culture of their organization?

Mid-level managers are so important in my mind because they are the providers of this emotional context in which their teams live. They’re the coaches to the frontline manager to help them drive it. A mid-level manager has to role model this. They need to coat their frontline leaders in doing this. They also have to give feedback up high. If a mid-level manager is doing this, in one part of organization and they start seeing performance, this beautiful work that works, performance morale or performance motivation, virtuous circle going. Their group will perform better than others.

That will send the message up high. This is applicable to a front-line supervisor, a mid-level manager, and executive. Ironically, it’s also applicable to individual contributors and employees. You could give a compliment that’s genuine. You could ask the peer how they spend their weekend. You could say, “I heard something’s going on incorporate. Let’s find a way if we can get our voice heard.” You could change the dynamic. I’ve had junior people on my teams change the dynamic all the time. You’re not a victim.

If you’re going to work every day and you’re not happy. You’re quite quitting, your job hugging or whatever you’re doing. You have enough of a relationship with work. It may be tactically necessary because you need a paycheck. At the same time, you don’t want to live in that situation. Work or careers are too long to have anthe us the mentality and constantly be looking over your shoulder and worrying about it. Everybody needs to change that dynamic. We’ve made work so utterly unenjoyable for so many people that it’s like a hollow form of capitalism in a way.

Imagine this. You’re one of these employees who are working for the paycheck. The place is terrible. You feel like, “I can’t do anything about it,” and then imagine something small good happens. There are new snacks in the cafeteria. If you take a minute to write a note to whatever leaders in charge of that and you say, “Thank you. That made a huge difference. If you’re open to other ideas, I got plenty.” You can do something. By the way, that’s not a complaining way to do it. You have to find a little thing to say thank you about and say, “If you want more, we could give you more.”

I know you do a lot of writing and thinking about the future of work more broadly. Apart from applying practices like the ones you described in your book. What else do you want to see in the workplace in the future?

Applying Human-Centric Practices To Future Technology Deployment

I’m still pushing for more enjoyable work. It is critical when it comes to Gen AI, agentic AI and this whole technology explosion. In my heart of hearts, most organizations are going about this wrong. They’re pushing technology for productivity. Productivity alone as opposed to saying, “Here’s your work. Here’s what this technology can do. How could it make your work more enjoyable? How can it take away the stuff that sucks your soul?”

By the way, customers and employees are all different. One person’s joy is another person’s toil. I worry where we’re going with technology. This whole thing about making work work, if we approach AI in the same way, co-create with employees, focus on helping them in their work, celebrating people who find ways to do it. The productivity will solve for itself.

We’re at this crossroads of how you decide to deploy it. Everything in the book and everything that I’m trying to push around moving from transaction track to work that works gets magnified with this. It could go much worse or much better with AI. That would be my last message. This is not separate from your technology agenda. It has to be the core of your technology agenda.

Something is disruptive as AI can be disruptive in a good way or disruptive in a bad way. The jury is still out on how we’re going to see this play out. That’s what everybody’s focused on and worried about.

The jury is still out on how we’re going to see this play out, but we all have agency. Especially as leaders to drive how this is going to play out. We can make sure it plays out in a much more human-centric, employee-centric and people-centric manner. I want every leader to be the cause to tip the scales to make a come out the way it should come out.

Agency is an important point. From the leader all the way down to the front line, you have to have agency in your professional life. Otherwise, it will happen to you. Odds are, it will happen to you in ways that you don’t always like. If you want to tilt the odds in your favor, you’ve got to take ownership.

You’ve got it.

The book comes out in November 2026. It’s available for pre-order.

It’s called Make Work Work: The 5 Daily Practices of the Employee-Centric Leader. It’s out at Amazon, Barnes and Noble or wherever you buy your book. Thank you for helping me amplify it, my friend.

You are more than welcome, Deb.

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What should we take away from our discussion with Debbie? First of all, work doesn’t improve through big programs. It improves through small daily behaviors. That’s the premise of her book and the five practices that she covers. The way that you as a leader show up or you as an individual show up, matters more than any strategy, deck or culture initiative. It’s the small behaviors that compound over time or compound across people in a way to become meaningful.

Second, we didn’t talk about this so much but, certainly, a key highlight that Debbie mentioned right at the end. That the idea of an employee is a better goal than employee engagement. We use employee engagements as the measure that’s been out there for 25 or 30 years that Gallop came up with. There’s a big difference between being engaged, which means checked in and truly enjoying your work. When people truly enjoy their work, it drives better performance, better retention and better innovation.

The third is that five practices are simple, but they’re not automatic. Celebrate someone, go see and help, be interested, co-create, and lead by example. The power in doing them consistently even if you don’t always do them perfectly. Pick a place to start. Don’t try and make it like a New Year’s resolution where you throw yourself into something and you stop doing it by the second Friday of January. This has to be something that you work on bit by bit over time.

Fourth, is it culture isn’t just about what leaders say. It’s about what people experience. This is where this idea of employees as customers that Debbie talked about. The transaction trap, the us the mentality, all of that comes into play. You want a workplace for people want to contribute. Who wants to work in a workplace where it feels like us them all the time?

Finally, importantly, is that everybody plays a role and everybody has agency. If you are C-level leader, a middle manager or even an individual contributor, you can bring these practices into action in your team, in your organization and all of that adds up in making your organization a place where people enjoy coming to work. I invite you as always to subscribe to Career Sessions on Apple Podcasts and Spotify or YouTube. If you found this discussion enlightening, sign up for my membership community, which is called PathWise and our newsletter PathWisdom. Thanks.

Important Links

• Debbie Lovich on LinkedIn
• Boston Consulting Group
• Make Work Work: The 5 Daily Practices of the Employee-Centric Leader
• Hubert Joly
• The Heart of Business: Leadership Principles for the Next Era of Capitalism
• The Open Organization: Igniting Passion and Performance
• PathWise on LinkedIn
• PathWise on Facebook
• PathWise on YouTube
• PathWise on Instagram
• PathWise on TikTok
• PathWise on Twitter

About Debbie Lovich

Deborah Lovich is a Fellow at BCG Henderson Institute, Boston Consulting Group’s think tank, leading the thinking on the Future of Work, with a focus on “making work work” for all stakeholders by adding radical employee centricity to organizations priorities including reshaping work with GenAI.

Debbie has spent the last half of her 30+ year consulting career working across industries and countries on the human side of transformation. She does the hard work of changing cultures and leader behaviors from the C-suite to the front line to enable sustained value creation. After COVID-19, Debbie led BCG’s thinking on the future of work. As GenAI is reshaping work, organizations and industries, Debbie is showing her clients how being employee-centric will enable them to get the most value from these new technologies. Debbie has also applied her expertise internally at BCG, where she led the development and rollout of the firm’s global predictability, teaming, and open communication (PTO) program, an initiative implemented to improve BCG’s culture and employee work–life balance. She has been a frequent contributor to Forbes, as well as Harvard Business Review, Sloan Management Review and a TED speaker.

Most people see careers as ladders to climb. Mohamed Isa sees them as mountains to explore. In this episode, Mohamed shares his remarkable journey from working as a cleaner in a bank to becoming the youngest CFO of a publicly listed company in Bahrain. Along the way, he learned that success isn’t about following a predetermined path—it’s about taking calculated risks, continually reinventing yourself, and creating opportunities where others see limitations.

JR and Mohamed explore:

• How a cleaning job became the foundation for an extraordinary career
• Why taking career risks can accelerate growth
• The difference between having a large network and having the right network
• How to think about reinvention through seven-year cycles
• Why careers don’t need to follow a linear path
• What “peak leadership” means and how to build a lasting legacy
• How mountain climbing became a powerful metaphor for life and work

This conversation is a reminder that where you start doesn’t determine where you’ll finish. Whether you’re feeling stuck, considering a career change, or simply looking for inspiration, Mohamed’s story offers a powerful perspective on what’s possible when you combine ambition with action.

Tune in every week for more episodes like this. Subscribe on Apple Podcasts, Spotify, YouTube, or follow Career Sessions wherever you’re listening.

Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/https://pathwise.io/podcasts/mohamed-isa

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Watch the episode here

Listen to the podcast here

From Cleaner To CFO (and Beyond): Lessons On Reinvention And Risk, With Mohamed Isa

Our guest has a story that will make you rethink what is actually possible in a career. Mohamed Isa did not begin his career in a position of privilege. He began as a cleaner in a bank, working quietly and in the background, observing a world that he was not yet part of. Instead of accepting that that was his lane, he treated it as a vantage point, as a way to get himself into university and beyond. What followed was not luck. It was a series of deliberate climbs.

From those early days, Mohamed went on to build a career at Unilever, earn his CPA, and eventually become the youngest CFO of a publicly listed company in Bahrain in his late twenties. On paper, it looks like a pretty straight ascent, but as you will hear, the reality was a lot more complex, filled with reinvention and resets and things like that. Mohamed is not somebody who just climbed the ladder.

He actually questions whether the ladder is even the right metaphor. He talks about reinvention in cycles, about treating life more like a series of experiments, and about operating in what he calls your peak leadership mode. Most interestingly, he often compares the whole journey to climbing a mountain, not just reaching the summit, but knowing when it is time to choose a different one. We are going to talk about that journey from cleaner to CFO, from structure to experimentation, from success to reinvention.

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Mohamed, welcome to the show.

Thank you so much, JR.

The Early Experience As A Bank Cleaner

It is good to have you. Let us dive right in. I know from our past discussions that you started your career working as a cleaner at a bank. What do you remember most vividly about those days? At that point, did you have any sense of where life might take you?

I remember the cleaning job very vividly. I remember going to a point where the bus would come and pick us up from the diplomatic tower and the diplomatic area in Bahrain. We would go to clean two floors in the bank. It was an investment bank. I cannot remember the name, but it was an investment bank. We would normally go from 6:00 PM to 10:00 PM. Most of the staff would be out, but some of the hardworking staff would be there, and they were all dressed nicely, wearing ties and looking very elegant. We were just in different types of overalls. We did not have a uniform.

That was funny for me. A company should have a uniform. I remember going there and vacuuming the carpets, cleaning the windows and making them very shiny, just like my head, if you can see. Collecting the mugs from the tables and washing them. The funny thing is, I did not wash the toilets. That was good. It was not part of my job description, but being serious, even if I had to wash the toilets, I would have washed the toilets because, after all, this is the job I had to do to get money to go to university. That was the main objective.

Get some money into my pockets so that I can buy some new clothing, shoes and other things. In high school, you could just wear anything and go to school. In university, you want to give the right impression. In fact, I had a strategy. I do not know how I came up with that strategy. I was very elegant in my dress. I had all these not-so-expensive shirts, and I bought a few ties, so when I went to university, all the professors thought I was working for a bank. My treatment was different from that of the other classmates I had, and that was the start of my career.

Cleaning, I did not see it as something shameful. I thought I had to do what I had to do, as simple as that. The staff, one of them in particular, was very polite and he was very recognising. One night, I had the courage to ask him, “What do you think I should join? Should I get a bachelor’s degree in management or in accounting?” He gave me the most beautiful answer. He said, “Regardless of your degree, make the most out of it.” That was advice I will never forget.

Did you know at that point that you wanted to have a career like the one that you have had, or did it still feel distant to you?

To my surprise, I had decided to become an accountant at the age of thirteen. Let me tell you the story. I have a preferred uncle, and he used to be a volleyball player. He used to get all these fancy shirts, T-shirts and shoes. I was the tallest one in the family, and I would get all these T-shirts. Not only that, I would sneak into his room and sometimes just steal some candies and chewing gum. One time, I saw a career guide published by the Rotary clubs in Bahrain, and it had the title, the job description and what qualifications you needed.

At the bottom of the page, there was the salary. Because in our family, cash was so tight, I was just looking at the salaries and flipping through the pages. At that time, the accountants made the most money. I looked up the title of the page, accountant, and I thought, “This is me.” When it was time to select my stream in high school, I did not go into science. I went to commerce. Eventually, I obtained my bachelor’s degree in accounting. The career choice was made early on, literally based on the money.

Becoming The Youngest CFO At Twenty-Six

Fair enough. I think that is probably how a lot of kids decide what they want to do, or at least come up with an initial idea of what they want to do. You ended up becoming the youngest CFO of a publicly listed company in Bahrain. Walk us through how you got from that kid cleaning offices in an investment bank and then going to university to becoming the youngest public company CFO.

It happened in a very nice way, and the sequence was very simple. I worked at Unilever for a few years. I came back to Bahrain, and I joined Gulf International Bank and I joined for a very brief period, only two months. Someone from Bahrain, whom I met in Jeddah when I was based in Jeddah, working with Unilever, gave me the hint about the CFO job. He said, “Give me your CV. I will pass it to the team, and hopefully it will work out.”

I was very reluctant because when I was growing up, we had this advice. You should stay in a job for a certain period. You should not be jumping from one job to another. I was from that school. When he hung up, I thought I would never send him the CV. He called in the afternoon. He said, “Where is your CV?” I sent the CV, and at that time, I used to have a Yahoo account. I still remember the email exactly word for word. “Dear Ali, although I am not very excited about this, please find my CV. Regards, Mohamed.”

I received a call immediately from Ali, and he said, “Just tell me, should I pass it or not?” I said pass it, and that is how I went into the interviews. We had three rounds of interviews. I met the chairman, the CEO, the outgoing CFO, the investment director, and the property development director. I had so many signs from God not to join that company. Just give you one example, or maybe two. The day I had my second interview, I was waiting next to the building. I received a message from the investment director saying that the wife of the CEO is having labour.

We were rescheduling the meeting, and I thought, “That is a sign.” I went back to the bank, and that day, Bahrain experienced what we know as Black Monday, where there was an electricity outage. I thought, “This is another sign from God not to join this company.” I thought, “I am just making this up in my mind.” The first sign was that I was going through another interview, but this time the company wanted to take me and show me the assets they owned.

One of them was a man-made island called Tala. We were there in a four-wheel Jeep, and we got stuck in the mud. I thought, “Now this is a sign.” The CEO was so good. He said, “How about this day in the office?” I felt I could work with this gentleman. If he had this incident and he is making fun, I can work with that. Despite all these signs, I said, “Let me go and try this out.” I ended up staying there for more than eleven years.

What is interesting to me about that story is how persistent they were in keeping you pulled in because a lot of companies, a lot of people, like the guy that you sent your CV to, he could have just said, well, you do not seem very interested in this. I am not going to use my own personal capital to help you unless you are really committed. He pushed you into it anyway.

I am very thankful to him to this day.

How did you get from Unilever to becoming the CFO of a publicly listed company?

In Unilever, I had a strategy because I knew if I stayed very long in Unilever, I would not be coming back to Bahrain. I wanted to come back to Bahrain. My strategy was that when I passed the CPA exams, I would come to Bahrain. I had made two calls, one to a friend of mine who was working in the Gulf International Bank, and another to someone who was working with what we now know as our capital. I had two job interviews on the same day. One clicked immediately, the recruiting manager, the VP, she was not there to test my knowledge or anything.

She was fascinated by the work I did with Unilever. She was saying, “Tell me more about this and that.” I just got the offer on the second day. I just told you how I went from GIB to the investment bank. It was a very risky decision. All my career decisions were risky. Leaving Bahrain was risky. Leaving Unilever, a very well-established company, to join a bank in Bahrain was a risky move. Going from the bank to a newly started company, that was risky, but I think I have always been able to have this mindset. So what?

Let me try. Let us find out what happens. All the time, I had these friends whom I trusted. I called someone from Oman. His name is Nazar. We used to work together at Unilever. I told him about this jump because I was a credit analyst at Gulf International Bank. Jumping from a credit analyst to CFO, that is a big jump. He had asked me a smart question. He said, “Do you think you have a 30% chance of succeeding? I told him, “I think more than that.” He said, “Just do it.” That is what I did. That is how I became the youngest CFO of a publicly traded company in the Gulf. I was 26 at that time.

The Importance Of Cultivating A Strategic Network

As you went from your pre-university job to university and to Unilever into that CFO job, were there times that you felt like you were in over your head and did not really belong in the track that you were in?

I did not feel that. The reason is that I always did my homework. I always had calls with people outside the company to ask for tips, for advice. For example, when I was a CFO for the first time, I had to deal with external auditors, and I had never dealt with external auditors in my life. Yes, I dealt with internal auditors. I called my previous manager, whose name is Majeed, and I said, “Man, these guys are coming within three weeks. What should I do?”

He just kept telling me to do this and this. This is what I used to do, cultivating contacts and then using these contacts to help me succeed in my career. I attribute whatever I have reached today to my contacts, and I can name these individuals who have shaped my career. One time, I did a trail and I ended up having only eight people take me to where I am today. People think you need to have a very big network. I do not think so. You need to have the right network.

I think you are highlighting the importance of having a few people in your network who will really go to bat for you, to use an American expression, who will open doors for you, create opportunities, and back you when you need it. It is sponsorship, right? That goes beyond a network, goes beyond mentorship, having that level of sponsorship. The fact that you can pinpoint back to eight people who created opportunities for you is a really good thing and probably something not a lot of people would be able to do in terms of having that level of sponsorship.

I totally agree with you. Sometimes I think I am lucky, but sometimes I tell myself, this is not luck. You have been working. I remember when I was a CFO, we had the annual report of the company, and I enjoyed writing the CEO message and the chairman’s message myself. I did not give it to an agency or a marketing department. I used to write them myself. To issue the 2004 annual report, the CEO told me, “I like this, but I need something at the end.” I said, “What do you need?” He said, “I need an inspirational quote.” I said, “Let me find something for you.” I shortlisted ten inspirational quotes for him. He chose this one. It said, “Luck is a preparation meeting opportunity,” as simple as that.

It is a good way of describing it. It is about creating your own luck. You were doing that.

I am sure you have heard this phrase or expression, “If they do not invite you to the table, build your own table.”

You got your CPA along the way as well. What led to the decision to get that, and why did you decide to get it?

When we grew up, the general plan for us, the accounting students, was to work for a Big Four company and then clear the CPA exams, stay with them for five years and then jump into banking. That was the general plan. For me, Unilever was advocating other qualifications, CMA, Certified Management Accountant, and CIMA, which is the UK version of the UK. I was not inclined to go to the UK because the journey is very long.

In the CPA, you get four exams, and in the UK version, you get fourteen. Why should you go for fourteen? The decision was very clear. I was a very research-oriented student. I used to visit the public library we had in the university, and we used to get The Economist and Business Week. I would go to these magazines, and I would see the advertisements, how many times the CPA would come and how many times the ACCA would come. Ultimately, the CPA was more in demand at that time. That was the decision. Pursuing whatever I saw in that little career guide, I was just going full speed.

Was getting your CPA about building your own capabilities? Was it about conveying credibility in the space by having the certification, or was it about giving you confidence that you had that knowledge of accounting?

We had a very strong bachelor’s degree program at the University of Bahrain. The CPA was not something difficult for me. Yes, it had the taxation, which we did not study, but I know many people who do not have professional qualifications who are performing at the highest level. I can imagine the previous manager I had, Majeed, whom I consulted for the auditors. He does not have a professional qualification, but he is that kind of guy who knows what he is doing. Sometimes, the only reason you get the qualification is for the other side to have confidence in you, for the other side to see the credibility. I know many people who do not have professional qualifications, and they are doing very well. Does it help? It tells a lot.

I think sometimes, certainly, there are fields where having a professional certification is a requirement. As for practising medicine as an example, there are other fields like coaching, which would be a good example where having the certification may or may not be important to you. If you are able to build a client base without it, then it does not really matter. If you feel like you need the training or need the credibility to build your client base, then it becomes important. A CPA is probably somewhere in between. It is certainly in some places, like if you wanted to work for a Big Four, they are certainly going to push you to get your CPA. To be a CFO of a firm, it may or may not matter.

Depending on the sector, even in Bahrain, the central bank, they will have its own qualification requirements. You cannot be ahead of a department if you do not have this or that. For whoever is watching this or tuning in to this, you need to know the profession you are entering. You need to know what the requirements are. You need to know, you need to study, you need to ask. That is what I am trying to say.

The Seven-Year Cycle Of Career Reinvention

Let us talk a little bit more about some of the things you have done since then. I know you are a big believer in reinvention. You talk about the seven-year cycle. Where did that come from?

That seven-year cycle came from the story of Prophet Joseph. When he was installed as the treasurer of Egypt, he had this idea that the harvest would last for seven years, and after the harvest, there would be a drought. He managed the situation over there. Seven years are enough for someone to reinvent themselves, and you cannot reinvent yourself overnight. Seven years is a good time. If you are changing careers, you will need to establish yourself in seven years. If you are going out on your own as an entrepreneur, it will not happen overnight.

You need to be very patient. Seven years is a very good time to reinvent. I like reinvention because you can be the same person 20, 30 years from now, but what is the point? One of the most beautiful expressions that I have heard in my life was by someone called Ralph Zangara. He was in a documentary film. He said this, and it fully resonated with me back in 1998. He said, “We are a gift from God. What we become is a gift to God.”

Talk a little bit about how you have reinvented yourself over the years.

You have the cleaner, you have the student, you have the Unilever regional finance manager, then you have the credit analyst, and then you have the CFO. After the CFO, I am now a speaker, an author, and a traveller. That is what I do. In between, I do coaching, consulting, and sit on boards. Sometimes I sit on the boards of companies. Sometimes I sit on boards of professional associations. Now I am sitting on the Bahrain Customer Experience Association and the Bahrain Management Association. As I said, we need to cultivate a diverse set of experiences.

I do not want to be that person when you meet me in the future, and you tell me how many years of experience you have, and I say 25, for example. In reality, it is just one multiplied by 25 years. I cannot tolerate that. That is why reinvention is very important to me. I do not know what will happen next, because now I am pursuing mountains and pursuing speaking. Yesterday I was tuning in to your latest episode. You said something very important. You said, “If you are under 55, you still have many jobs to come.” I thought, “Yes, why not? Fifty-five is young.”

We are living longer. We are going to be working longer. It changes the dynamic. You do not have to work for the same company or in the same profession anymore. Some people want to do the same thing. I was just staying at an inn in England, and the innkeeper had been doing that job for 37 years. That is a long time. That is what he wanted to do. There are others, and I probably would count myself among them, who like to do different things every so often. It comes back to whether it is a seven-year cycle or whatever. For me, that just keeps me energised. It does not have to be this ladder. It does not have to be this if you want it to be.

I have a book over here that is called The 100-Year Life. They predict it will be normal for us to live until a hundred. What would you do if you lived to a hundred? We need to think about that.

For some people, that means they will have a longer retirement. They can afford it. For other people, it means they are going to need to work longer. That is something that we are all contemplating right now. Fifty-five is really not that old.

It boils down to what personality you have. Are you an adventurous person or are you a play-it-safe person? Let me just sit down here, I am getting a good salary, everyone respects me in this job, so why bother? There is nothing wrong or right. It is just the personality.

Talk about some of the topics that you write and speak about. I know you have written quite a bit.

I wrote about public speaking, customer experience, and leadership, but my first book was about investor relations. It was the first book about that subject in the Middle East. As a CFO, I practised investor relations, and I studied it or researched it in my MBA, and I converted my MBA into a book. We were pioneering. I am very proud to say that I am not being boastful over here, but other companies were just copying what we were doing. I was practising. I was writing about it, and I was a practitioner at the same time. I like to write about practical things. I do not like to give theories. You need to give people what they need to succeed, as simple as that.

How many books have you written at this point?

The published ones are 21. We are printing one next week, and I am printing another one, which documents my ten-year journey outside the corporate world. In May, it is called No Title No Limit. Initially, I thought, let me write a ten-article series about what I did since I left, and I will share them on my blog and on LinkedIn. As I evolved, when I reached article eight, I thought, no, I should be expanding all of this. I doubled the count of words, and I increased it from 10 to 14 chapters, plus the intro and the closing of the book. In essence, this is a book I want to hand to my children, my nephews, my nieces as a way to inspire them because now they see what I have. They do not know what I went through. I write to help people.

It is good that you are demonstrating for the next generation in your family what is possible, what you can achieve.

Last night I was attending an online course. It was the US time, so it was very late for me, but I kept just pushing myself to not sleep. They said something very interesting. They said business is a belief. If you have the belief, then business will work. The same principle applies to our careers, to our lives. If you believe the thing, and if you work for it, you will achieve it. That is what I want to show them. Everything is possible.

Mountain Climbing As A Motivator For Life

You use mountain climbing analogies in the speaking that you are doing. What does the climb represent to you in terms of your life and your career?

The climb represents energy. The climb represents passion. The climb represents challenging yourself. One way of getting to work out and be more physical is to have a mountain in my head that I want to climb. That is the motivation. I know I have to generate more funds to go, so I have to work harder to get more speaking engagements, and that is the mountain. For me, it is the biggest driver of my life as we speak, the mountains. I am pursuing the Seven Summits challenge, where I have to climb the highest mountains on each of the continents.

In the US, it would be Mount Denali in Alaska. Being fit, having the money, and enjoying the journey, writing about it, I am telling you, this all started with a two-week expedition to Everest Base Camp back in 2022. Those two weeks, it changed my life, and I fully mean it. I am writing an adventurous novel. It is called The Summit of Unity, where six climbers from the Gulf States go on a climb to Everest. I never read a novel in my life, so this is what the mountain did. The other thing I have is the Peak Leadership model. The research is now around 290 pages.

I can have a one-day workshop or twelve days of training on the methodology I developed. This is reinvention. When you have a passion for something, good things will happen. The other day, I was visiting my mom, and I was talking to Claude AI, and I said, “Go and search what are the books are available about Everest in Arabic, not in English.” It turned out there was only one, and I know the author of that book. Immediately, I thought, “This is my opportunity. Let me write not only about Everest, but also about this is the twist I have that most others do not have. I have the executive experience, I have the mountaineering experience, and I have the writing experience.”

My next target for this year is to write my first Arabic book. Not in my imagination, I thought I would write an Arabic book, because I always write in English. Because of the mountain, now I am writing an Arabic book, and it will be something totally different. I will be distilling the history of Mount Everest for the last hundred years in one book. With each chapter, you will have a leadership lesson at the end. It will be something totally different, not available in the market. This is what I want people to find. What they are passionate about. Find the thing that will make you work day and night without being tired.

Defining Peak Leadership And Leaving A Legacy

Is that what peak leadership is for you, or is it something different?

Peak leadership for me is leaving a legacy. This is the top of my peak leadership model, leaving a legacy, just like the book I am writing now for my children, my nieces, and my nephews. What legacy do you want? Do you want to be the trailblazer? Do you want to be that person who came on this earth and left it without anyone noticing? That is peak leadership. Start with self-leadership, because if you cannot lead yourself, you cannot lead others. That model has six different levels of leadership capabilities and ultimately leaves a legacy.

Leaving a legacy is something that I think a lot about at this point in my career, because there are, in all likelihood, more years behind me than there are ahead of me from a professional standpoint, at least. You start to think you have limited shots left. What are you going to do with that time? How do you make sure it has as much impact as possible? It is why I started to do Pathwise and this podcast, and all of us want to leave some form of legacy. Some of us are more committed to it than others. Some of us take more action than others.

It is great that you are doing this beautifully, J.R. I am not sure how many people you are inspiring because, as you know, all people will come and comment on your show or like it, but I am telling you, your impact is more than what you imagine.

All of us can have some impact, right? The size of the ripple effect that we create. Some people create a large ripple effect and leave a true impact on the world, positively or negatively. Other people leave a smaller ripple effect, but all those ripple effects add up. That is what advances humanity.

That is the compounding effect.

For somebody who is tuning into this and feeling stuck in their career, what would you tell them that they should be thinking about in terms of driving towards some form of reinvention?

Call someone, meet someone, sit with them, share with them. What are your worries? What are your feelings? What is happening in your life? Tell them where you want to go. Two days ago, I was talking to someone. He wants to take over his father’s business, and he wants to pick my mind on this. I said, “I need two things from you. I need you to think like a dentist. Show me the picture with the broken teeth, with cavities, and then show me the Hollywood smile.” If you know these two points, then you can work out the details.

If you do not have any idea of where you are going or what you want to do, it would be very difficult, or even for well-intended people to help you. You can have access to people who can help you, but you need to have that clarity about where you want to go. From there, you start calling people, having coffee with them. I had so many coffee conversations, and some of these coffee conversations led to business opportunities. If you are stuck, get unstuck, do something. Do not wait.

Sitting around waiting for something to happen to you is usually not a recipe for success. Last question, if you were going to go back and talk to that version of yourself who was cleaning that bank as a teenager, what would you tell them?

I would tell him you are in for so many surprises, good ones and bad ones. At the end, just enjoy the journey.

Good advice. Mohamed, thank you for doing this. I appreciate what you are doing and what you are aspiring to do in terms of the legacy that you leave and the impact that you have in your speaking and your writing.

Thank you so much. It was my pleasure. I wish all the audiences, the viewers, all the best in their career transitions and their career growth, and take charge.

—

What are the practical takeaways from my discussion just now with Mohamed? First, where you start your career definitely does not define your ceiling. This is probably the most important point, but how you respond to the opportunities that are put in front of you is really important. Think about Mohamed’s own story that he talked about in terms of his transition into Unilever and from Unilever into the company that he ultimately became the CFO of. It was not just about ambition, but it was also about awareness, discipline, and purposeful action, about listening to opportunities that were presented to him. He did not just wait. He studied, he prepared, and he stepped into things as they came to him.

Second is that careers are not singular. They are not just a steady climb up a ladder. To his point, they are cycles of reinvention, whether seven years or otherwise. One of his central theses is that our careers need not be linear. Every few years, you ought to be IRS-assessing and relearning and sometimes starting over, as I have done and he has done over the course of his career. People who thrive long-term are the ones who lean into that and are willing to evolve and not just keep doing the same thing again and again and again.

Third is that ownership is the difference between drifting and building. Rather than letting his career happen to him, Mohamed made intentional choices, whether pursuing a CPA, shifting into leadership, or jumping into something that he was perhaps more than 30% confident in, but certainly not 100% confident in. All of that mindset of ownership, as he said, compounds over time. Finally, peak performance is about the legacy that you leave.

It is about continuing to grow, to learn, and try, test, and adapt. His mountain climbing analogy reinforces that success is not always about one perfect path to that summit. Sometimes it is about choosing different climbs, about learning, about adapting. Sometimes it is about learning when to turn back because that summit might not be right for you, or the conditions might not be right for you. As always, I invite you to subscribe to the show on Apple Podcasts, Spotify, or YouTube. If you found this discussion enlightening, please sign up for my membership community, which is called Pathwise, and our newsletter, PathWisdom. Thanks. See you next time.

Important Links

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About Mohamed Isa

An internationally recognized keynote speaker who inspires, engages, and transforms, Mohamed Isa energizes audiences worldwide with heart-moving stories and performance-driving strategies. Known for his dynamic style and relatable storytelling, he delivers experiences that stay with audiences long after the applause fades.

As an award-winning keynote speaker, Amazon bestselling author, and former CFO, Mohamed bridges the worlds of business and inspiration with effortless credibility. Fluent in Arabic and English, he connects with audiences across cultures, empowering leaders and teams to think higher, act faster, and achieve more. With expertise in leadership, employee engagement, and customer service, Mohamed delivers content-rich keynotes that combine practical business insight with authentic storytelling. His sessions are not just motivational; they create measurable change and help organizations strengthen culture, performance, and purpose.

What sets Mohamed apart is how he lives the lessons he teaches. From standing at Everest Base Camp to summiting Mount Kilimanjaro and trekking Mount Kosciuszko, his expeditions mirror the challenges leaders face every day. His attempt on Mount Elbrus reminded him that leadership is not only about reaching the top but also about knowing when to pause, adapt, and protect the team.

Before becoming a full-time speaker and trainer, Mohamed built a distinguished corporate career. As Chief Financial Officer of a dual-listed investment bank, he managed a balance sheet exceeding USD 500 million. He led transactions worth more than USD 350 million in exits, equity, and debt financing. He has served on multiple boards, mentored startups, and advised Fortune 500 companies, bringing a wealth of practical experience to every stage he steps on.

Consistently praised for his energy, clarity, and authenticity, Mohamed Isa does more than deliver talks; he delivers results. He creates experiences that inspire people to climb their own Everest.

Most people think overwhelm is a productivity problem. Corrie LoGiudice argues it’s something much deeper.

In this episode, JR speaks with Corrie LoGiudice, author of The Five Overwhelm Culprits, about why so many high performers feel exhausted, disconnected and stuck — even when their lives look successful on paper. Corrie explains why burnout is often misdiagnosed as a time-management issue, and why the real causes of overwhelm usually stem from deeper problems like misalignment, lack of clarity, weak support systems and chronic self-neglect.

Their conversation covers:

• Why overwhelm is more than “having too much to do”
• The five root causes behind burnout and chronic stress
• How work and personal life pressures compound each other
• Why high performers often confuse exhaustion with success
• The difference between burnout and misalignment
• How intuition helps people recognize when something is wrong
• Why women experience overwhelm differently than men
• The role resilience plays in navigating major life changes
• How to recognize overwhelm before reaching a breaking point
• Why meaningful change either happens by choice — or happens to you

Subscribe to Career Sessions wherever you get your podcasts for weekly episodes like this.

Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/corrie-logiudice

—

Watch the episode here

Listen to the podcast here

How To Escape Overwhelm And Redefine Success, With Corrie LoGiudice

Overwhelm Is Driven By Five Deeper Root Causes

This conversation is about something almost everybody feels at some point but very few people are willing to name or say out loud, I’m overwhelmed. The kind where to the outside observer your life looks successful but internally, alarm bells are going off. You may be checking all the boxes of career, family, friends, hobbies and interests but you feel like you’re barely holding it all together. My guest Corrie LoGiudice has spent years unpacking that exact experience in her new book, The 5 Overwhelm Culprits.

She argues that overwhelm is more than about being overly busy. It’s driven by five deeper root causes, the lack of clarity, confidence, community, conditioning and consistency. What makes her perspective different is that it doesn’t separate work life and personal life. As she puts it, most people, especially women, aren’t managing one set of demands. They are managing potentially two full lives at once. Corrie’s work is grounded in real experience operating at a high level while also going through some difficult and deeply personal chapters.

She’s turned that into a practical framework that’s now helping thousands of people rethink how they approach success, burnout and change. In this episode, we’re going to dig into those five overwhelm culprits, why so many high performers feel stuck even when things look great and how to start making meaningful changes without blowing up your entire life. I’m J.R. Lowry. This is Career Sessions. Corrie, I am glad to have you here with me.

I’m so excited to be here. Thanks for having me.

You have a new book out. You open your book with a line, “I am so exhausted. I’m pissed off.” What was the moment where you’re overwhelm turn from something that you were managing into something that you had to confront?

It happened for me on the Belt Parkway in New York. I was going through the commute and I’m sitting on the Belt Parkway right outside of JFK Airport. It’s 7:00 AM. My GPS is basically frozen in time. I would get stuck in this section of road so often, I would check into it on Facebook like I was checking into a place. It’s like, “I’m on the Belt Parkway but the GPS is frozen in time.” I’m thinking to myself how I missed my son’s entire morning routine. I’m thinking about the long day ahead and about how maybe if I’m lucky, I’ll get to see him for an hour that night when I get home at 7:00 at night.

I was commuting four hours a day, so two hours there and two hours back. I remember looking around at everybody and all the cars around me. This is New York rush hour. It’s hundreds of cars. It’s thousands of people who are all stuck in the exact same position as me. I remember thinking to myself like, “This can’t be it. We’re all choosing to do this? This doesn’t make any sense to me. Why am I signing up for this?” It ultimately became a topic of conversation I brought to my therapist later where we were talking about my commute.

I had this feeling. I called it weird. something felt off. Ultimately, I learned later. It’s because I was misaligned. I wasn’t busy for the sake of being busy. I was taking action in so many different capacities in so many different ways that it didn’t make sense to me. It’s like, “Why am I doing this?” It became a topic of conversation I brought to my therapist and then later, led to me in the career that I’m doing now. That was the big turning point for me.

I have one kid who she and her husband, both commuted every day from New Jersey and in New York. I think New York’s got its own special form of rat race. The commutes are harder. There’s nothing easy about managing that day-to-day existence. It brings up something that you talk about in the book, which is that everybody talks about personal life and work life.

Often, they talked about the fact that they’re distinct from each other but you have to confront all of this stuff collectively. The idea of bringing also your professional and your personal sense of being overwhelmed together. Why do you think this gap exists? Why are we getting this point wrong in the way that we’re looking at this problem?

For so many years, it was separate. What ultimately has happened and has been in the last couple of decades. Our workplace has changed so quickly that work and life used to be separate. You had one parent that was working outside the home. One was taking care of kids or one was responsible for the home. It’s very distinct. You had work and you had personal. Now, it’s more common to be dual income than it is to be a single income and dual responsibilities across the board. What’s happened is expectations have compounded. Not reduced. At the same time, traditional advice still treats them separately.

It’s inconvenient for employers to acknowledge that your personal circumstances are having an impact on you and some are more in light than others, obviously. It doesn’t contribute to the company’s bottom line to worry about how long your commute is or how much stuff you’ve got going on. Whether you’re the parent in charge of your kids PTA or soccer team or whatever that case may be. it’s this systemic form of denial willful ignoring of it all.

I couldn’t agree with you more on that.

For you, as you were working this through with your therapist and starting to figure out what this meant. What did you feel like you were missing up until that moment of realization? What do you think other people are missing when they are having one of those moments where they are drowning? It ought to be more visible to them and to the people around them.

Apart with the drowning that’s exceptionally frustrating. Ultimately, it’s a misdiagnosis. What everyone’s telling us, it’s like, “You’ve got a time management problem. It’s a productivity problem. If you color code this and get this calendar and whatever else, then things should be able to work.” That’s not the problem. The problem is mental load across roles. When you look at women in particular in leadership roles when you think just about their responsibilities at work.

Usually, they’re responsible for themselves and their direct reports, then carrying into that. Again, the personal side, you can’t take out of it. There are also responsible a lot of times for scheduling things for their spouse, children and all the other things in addition to that. It’s an overall mental load problem. There’s also expectations in society now. When you look at, you know the Pinterest era, things having to be perfect and being at every single event. Not saying no to things because you’re expected to be there.

Women are in this position where you feel that we’re drowning because we have all these expectations that keep coming on us that we didn’t necessarily raise our hands and say, “That sounds fun. Let’s do this.” Also, the solutions in the way people are trying to sell it for them is through a calendar. That’s ultimately not going to work. You have to find the root of why they are feeling this way to be able to address it.

Five simple hacks won’t solve anything and having a color-coded calendar. It’s probably one of those things. This small step in the right direction but nowhere near sufficient. How much of this do you think is personal? How much is structural given what you’ve just said?

I believe it’s both. One plays into the other. The challenge is we treat overwhelmed like it’s a personal problem and all the solutions are personal. Especially in this day and age, a lot of the issues are structural. Best example I can think of off the top of my head and again, I’m going to bring it back to the caregivers. The standard workplace works 9:00 to 5:00 but school drop off is at 8:00 and we pick them up at 3:00. That’s a structural problem. It is both. You can’t solve the structural problem by giving them a personal solution. Depending on what the situation is.

The Five Overwhelm Culprits: Clarity, Confidence, Community, Conditioning, And Consistency

Let’s get to your book. You’ve got five overwhelm culprits that you talk about in your book. Do you want to run through them? The clarity, confidence, community, conditioning and consistency. That’s the list but you can put the color around all that for us.

The thing that’s great about the overwhelm culprits in particular because we were talking about structural versus individual. These work for individuals, as well as teams and organizations. It works across the board and you’ll see how I describe them. The first one is lack of clarity. It’s not so much knowing what it is you want but having alignment and understanding why you want it. For individuals like me and the car all those years. The reason I was going through the four-hour day commute was because I wasn’t aligned with my why. I was working for my family’s business. I was heading it up after fifteen years.

I love the work that I did, but the thing that changed, my real why was my son. By saying yes to that career, I was saying no to my son. My clarity was the big one for me on that. The second one is lack of confidence. It’s not so much knowing what you want and why you want it. You have to believe that you could do or have it. For a lot of folks that got stuck in cycles of imposter syndrome and things like that, that is the reason for this. Even in terms of teams. Looking overall at a team. If a team doesn’t believe a goal is possible, you have to do something to bridge that belief gap before you’re going to see them perform.

The third one is lack of community. The famous motivational speaker Jim Brown once said, “We are the average of the five people we spend the most time with.” If the people we are spending the most time with don’t know how to do what it is we want to do or don’t believe it’s possible or don’t support you in doing whatever it is you’re going to do because it’s not going to benefit them in some way, shape or form. You’re going to stay stuck and you’re going to stay overwhelmed. You’re being exact same place that you’re in now. That’s a big one.

The fourth one is lack of conditioning. When I say conditioning, it’s your physical and mental health and wellness. By the point you reach burnout, it’s too late. What we’re looking to do is to identify where in your health and your wellness are you drinking enough water. Are you getting physical activity? Are you taking care of your mental health? What time and space do you have to be able to meditate, journal or talk to a therapist?

Especially high-performing women. This is the first one that gets snot to the side because we’re so busy focusing on everybody else’s needs that we put our own last. The problem with lack of conditioning in particular in leadership is if you’re not paying attention to your physical, health and wellness, you become the bottleneck in every single system that you’re in. It’s because you’re not running at your top capacity. It’s important.

Lastly, it’s lack of consistency. In order to achieve what it is you want from where you are now, you have to be able to take action over and above what you’re currently doing to get it. Consistency is one of the easiest ways to do this. It helps with things like the mental load like we are talking about before. A lot of this comes down to systems, habits, routines, and organizations. How are your systems supporting you to be able to take action on your worst days? Not necessarily your best days.

All of these of course are interrelated as well. For somebody who’s overwhelmed, can they pick up and try and focus on one first or do they have to confront them in a holistic fashion?

Usually, you can determine which one is your culprit based on where you’re stuck. If you’re not sure on what your next step is, it might be clarity. If you don’t believe that you could do something, it’s probably confidence. That’s a good place to start. I do have an overwhelmed corporate quiz, which is great. That’s definitely very helpful. Even just in describing the five culprits, a lot of times, when people are listening to it, they’ll hear one and they’re like, “That resonates for me.” That’s usually the best one to start with.

I do recommend starting with one which is clarity. It’s the foundation will culprit. It ties into a lot of different ones. The system is designed in a way that you do pick it up where you need it. I’ve done keynotes where I’ve had people in the audience come up to be saying that they saw me at an event six months ago. They had a completely different set of takeaways hearing the exact same content because their culprit was different or their seasonal life was different.

That’s interesting. Having worked on this with people and deliver these keynotes and done your coaching work. Do you find that any one of them is misunderstood by people that requires the most going deeper?

I would say lack of conditioning because it’s the first one that pretty much anybody puts on the side. If you’re a high performer, you’re always putting everybody else in front of you. You got to view it almost like an athlete. If you’re not fine tuning that physical and mental element, you’re not performing at your talk capacity. This is very much the case for women in a lot of the interviews featured in the book. They say variations of the same thing where they feel like they’re not fully 100% in one place.

Escape Overwhelm: High performers spend so much time taking care of everyone else that they forget the truth: if you’re not fine-tuning your mind and body, you’re limiting your own potential.

They’re like, “I’m not fully at home when I’m at home. Mentally, I’m checked out and think about stuff at work. I’m not fully at work because I’m mentally checked out and thinking of things there.” That’s a direct reflection of you need to work on lack of conditioning. You need to create that time and that space for your brain to find down to be able to process so you can be fully present.

Personal Experience Of Surviving Trauma Shaped The Framework

Framework is practical and certainly clear. I know you also draw in some pretty deeply personal experiences. How did those shape the five categories for you more generally?

It was through life experience. The way it ended up happening, it was from having to survive while I was leading. I was leading as a corporate SVP. In the timeframe I was looking at, I left this abusive marriage. Later on, I had experienced this suicide loss. I had a therapist who was like, “You should figure out how you were able to do this and apply it here.” It was very much like a workshop process going through it. In looking at different situations but in a way similar in terms of them through line, in terms of trauma, there were different situations but they were the same patterns that showed up over and over again.

Each time I was starting off, I didn’t have any clarity on what I wanted next or for the next phase of my life. In each situation, it was showing up that I wasn’t necessarily confident in certain areas or I didn’t have the right support people. It became very clear that those were the five to go after. I ended up using it in like a trial and navigating my suicide loss.

Through that experimentation, within months of having lost by then partner, I found the man that I ended up marrying. I started my business and I did a whole bunch of other things that most people would have taken years to be able to unpack and figure out. It’s because I had the right support systems in place. I knew exactly what I needed to allow myself the space to be able to heal and process. Also, to still continue to perform.

It sounds like a fast timeframe to have worked through everything you just described.

It was very fast. That’s the reason, too. I had gone through this same thing when I had gone through my divorce. My therapist at the time was like, “I have other patients that can’t do what you’re doing. If you could figure out how to teach people how to do it, you can impact a lot of lives.” At that point, I was still in my family’s business. I was expected to take it over. The seed had been planted that I started thinking about, what would it look like if I did do this work? After my suicide loss, that’s when I decided, “Let me go all for it,” because I didn’t want to sit in the car for hours every day.

Let’s come back to that car and sitting in the car for four hours every day. A lot of people are chasing what you call the illusion of success. The idea of having things that look perfect on paper in terms of profession, family, kids, partner, hobbies and friends. All of that stuff that creates this sense of success but they know inside something is wrong. You described feeling off early in our conversation. How do you tell the difference between, “I just signed myself up for too much and I got to start saying no more to know something more deeply is wrong here?”

The biggest way to look at it is depletion versus misdirection. When you’re burnt out, you have no desire to do anything. You want to get away from it all. You want to run. You want to escape. You don’t have any excitement in regards to the future. Where when you’re a misalignment, the energy is there but there’s friction. For me, sitting in the car, that energy was there. I love the work that I did. I love working for my family’s business. I build a career. I enjoy the work that I did, but there was friction. There was friction in that commute and sitting there. It didn’t sit right. It’s through that misdirection of energy that you could tell me difference.

For somebody who is feeling that sense of things, it’s often hard to break away from the status quo. You get into the cycle. You’re on the hamster wheel. Why is staying stuck so often more appealing than confronting change, even when we’re deeply unhappy?

It’s much easier to stay unhappy that it is to face our fears. A lot of times, you’re dealing with fear of the unknown or fear of disrupting different relationships. You don’t want upset people. For me, I didn’t want to upset my dad. “You’ve been preparing me for many years for this. I don’t think this is for me.” Predictability also feels safer. When you go into the unknown you make a big change. You don’t know what’s going to ultimately end up happening. People choose what feels safe for them and a lot of times, not necessarily what makes them happy. That requires a lot of internal clarity and self-awareness to figure out.

The Process Of Breaking Inertia And Trusting Intuition

How do you when you’re working with your clients coach them through that process of breaking the inertia?

One of the biggest things that I do with my clients when first starting with them is getting them to trust their intuition. The way that we do that too is when we’re exploring a topic. Let’s take values. It’s one of the first things that will go through. We determine personal values. I asked them to pick four out of a list of say 105. You would think I asked them to commit to a 3-year life plan. They put so much time and attention into it.

It’s a matter of when you look at the words on paper. Which one gives you a gut feeling? You can either feel it in your stomach. Some people feel it more in their chest, but there’s a feeling before your brain starts going, “This is so-and-so’s valuable or this is a line with my partner’s. I should choose this.” Usually, your tuition is whatever the first thought crosses your head before your brain starts spiraling. The more that you can learn to trust that very first answer, the more an alignment you’ll be with your intuition overall.

Is that how you get people to separate out what they want from what they feel like other people expect from them?

Yes. A lot of times, too, we’ll also explore why is this your value and having them explain it. If it ties into, somebody else shares it. Why is that important? If this person wasn’t part of the equation, would this still be your value? Help them gain clarity from there. Asking why is an excellent question in terms of coaching to get you four levels deeper to the root of what you’re looking to uncover.

Do you think this is a harder process for women than it is for men?

I do it for a couple of different reasons. In general, women aren’t necessarily nurtured to trust their intuition. We’re nurtured to be exceptionally safe. Even little girls versus little boys. We praise the little boy. They jump from the top of the stairs. You’re like, “He’s daring.” The little girl does it and we’re like, “What are you doing? You’re going to break your leg.” Women, in general, were encouraged to be helpful. We’re encouraged to be kind and take care of people. None of that has anything to do with your intuition.

Where little boys, is this a good idea? Basically, trying to train them to be leaders through making decisions, trying and failing. Little boys get more flexibility with versus girls. I do think that intuition is much harder for women to grow and nurture. Women do tap into it and I don’t necessarily want to say it’s because of empathy, but because of other ways that women process emotion and feelings. As well as situations and problems that they’re intuition becomes very powerful compared to the way that men may process the same situation.

Even for people who are coming into adulthood now. There’s probably still gender norms that are being imposed on kids growing up that affect how they behave as adults and confront some of these things when they run into them as adults. Come back to the idea of success in the hamster wheel. What are some of the other lies that we often tell ourselves about success?

The biggest one that I see is this belief that success is tied to sacrifice. You can’t have one without the other. This is something that was modeled for me. I’m a 4th-generation entrepreneur. I learned everything I learned from my father and my uncle who learned from my grandfather. Watching how they ran our family businesses was work hard and play hard. It was 70-80 hours a week in the office. It was a long commute. That’s why I thought it was normal. It was a lot of missed school concerts and things like that on my side that my dad might be on a business trip.

That’s what I thought the definition of success was because my family is successful. What I’ve learned since then because I wasn’t going to sit in a car for four hours a day. You can still have your own version of a line of success. There’s a big difference between being successful for the sake of success as well as being aligned with what it is that you’re working towards. When you design it intentionally, it’s possible. I run my business now 20-hours a week. Everything is designed around my kids. It is entirely possible to have that level of success. I would say I’ve been more successful in my career since I’ve left and started my own thing than I was before. That’s the biggest lie that I’d be telling my kids, for sure.

Change Either Happens By Choice Or You Are Forced Into It

You talk about the fact that change can happen in two ways. Either you choose it or you’re forced into it. How do those two paths choosing it versus being forced into it tend to lead to different types of outcomes?

It’s the same outcome but different experiences. You have two ways. The first one is you can make a conscious choice like, “I’m going to change. I’m going to quit my job. I’m going to apply for this other job that I’m not sure if I’m qualified for, but it would be great if I got it.” You could be forced into it through what I call a pivotal life moment. Pivotal life moments are things like I described before such as divorce or suicide loss. It could be you losing your job or any number of things. That’s your life after the event is different than it was before. That’s a force change.

There’s so many people who will not change their job until they’re laid off. That’s a force change. You’re ultimately leading to the same thing. You could either choose to get a job and change your job or you could be laid off and then have to go and find a job. The experience is very different because through the choice, there’s a certain level of empowerment. There’s a certain level of confidence that you build by taking the chance, going through and doing things that have it go according to plan.

When you go through the pivotal life moment or forced way, the experience isn’t as bright and shiny. You’re having to learn as you go. You’re scared you didn’t want to do this. There’s a lot more fear involved with it. You can lead change. You could decide like, “I’m going to make this change proactively,” or you can end up recovering from it. Either way, you can get the same outcome but they’re two very different experiences.

Resilience comes into play here as well. Giving some of the stories you shared about yourself and you share in the book. How does that factor into this whole notion of confronting your overwhelms?

Resilience to me is evidence that you’ve built the capacity to be able to handle hard things. For each and everything that I personally went through and there was a lot in a five-year timespan. Every single time that I successfully navigated it, it built my confidence. I vividly remember this to the day that I lost my partner to suicide. I was the one to find him. I remember standing on the lawn of his apartment and thinking to myself, “You’ve been through hard things like this before. You’ll get through this.”

There was a certain level of confidence that I was going to be able to navigate it. It had I not gone through the other situations before that were not the same situation but had similar undertones and lessons. I never would have had that level of confidence going into it. It’s that moment where you know deep down I can do this again. That’s true resilience.

To your point, every challenge that you face makes you a bit stronger. It gives you a sense of pattern recognition of, “I know what this feels like. I’ve been here before. I’ll get through it.” Having those challenges in life, painful as they are in the moment, they do help you get through lesser situations in the future more readily than you would have otherwise.

I’d also probably add to that. We were talking before about deciding to make a change or waiting for a pivotal life moment. When you’ve gone through situations like that in the past and you’ve successfully survived in and built that confidence. It makes making those proactive decisions so much easier because they seem like nothing in comparison to what you went through. It’s helpful too in terms of what risks you take to be able to better yourself moving forward.

How do you recognize the signals when you’re feeling a sense of overwhelm sooner so that it doesn’t hit a breaking point?

Most of the time we know that we’re overwhelmed. There’s that moment that you’re like, “It’s just too much.” The way I like to describe it is like a computer having too many tabs on. You open up too many tabs on the computer and it starts to run slow and then eventually it freezes up. We all have that moment when it comes to your own personal overwhelm.

You have to do a shutdown to get it to work again.

I tell everybody to do a brain dump because it’s the same thing. You take what’s in our head and put it on paper instead so it doesn’t have to live there. That would be the first sign. You feel yourself because overwhelm erodes your performance, your productivity, and your presence. It happens with time very slowly. It’s hard to know when you’re in the moment, but you do know that breaking point when you just can’t process.

From what you’ve said, intuition plays a role here, too. You’ve got to trust you into your interaction more than some people are comfortable doing.

Intuition is so important for all the things that we’re talking about.

For somebody who feels like they’re in a breaking point moment, what’s the first piece of advice you give them in terms of where to start?

To shift from a future focus vision, which a lot of us high performers were always thinking about like next quarter or next year or a five-year plan. It’s to shift from that future focus vision to shifting to today. This is something too that I could speak to. My capacity currently is very low because I experienced family lost and this was the very first thing I did. It was from, “We’re going day by day.” Instead of monthly or weekly. Even my team knows. Everybody knows we’re shifting day by day because your overall capacity is lower. You need time and space to be able to process what’s going on.

This is helpful and it removes pressure from you. It gives you that space. You naturally know when the time is to start shifting back to that future focus because you’re going to start to get excited. Once you finally have the time to cross and move through whatever it is you’re moving through that’s overwhelming. You’re going to naturally start to shift forward again. That’s when you just go back to business as usual. To start and take all that pressure off yourself and shift to what would make today a successful day and leave it at that.

I’m sorry for your loss. When you’re confronted with something like that, it’s probably a bit easier to downshift. When there isn’t something that slams you in the face like an illness or a death or some other catastrophic thing that happens in your life. It’s harder to call the moment and say, “We’re downshifting.”

You can’t expect yourself to be able to perform at 100% if you’re experiencing something like that. It’s also a good mindset shift to know that you’re 50% now, if that’s 100% of what you can give. It’s still 100%.

True. For your kids who might be reading this book but at some point, in their future. What do you hope has changed about the way that we think about success and are overwhelmed by the time that they hit adulthood?

I dedicated the book to my kids and the dedication is for my children. You never learn to confuse exhaustion with success. I would love for them to stop equating exhaustion with success the same way that I did. To move away from tracking and basing their performance on output and more shifting to alignment. Whether or not these actions were taken are aligned and having an impact. That they don’t feel that they are two people, employee versus a human or one whole human.

Overall, overwhelm is recognized a bit earlier than it is now. I feel we’re in a scenario where everybody is talking about the burnout crisis. Unfortunately, once you get to burn out, it’s too late. We have the ability to be able to solve this by looking at how we handle overwhelm. My hope for my kid’s generation is, success doesn’t end up costing them their lives and their health.

We all want our kids to be happy first and foremost. It’s hard to be happy when you’re exhausted. I know your book comes out on May 12th, 2026, The 5 Overwhelmed Culprits. I wish you the best with the launch. It’s an exciting time when you’ve got a book about to be birth into the world. Thanks for joining me and for sharing your story with some of its deeply personal moments. Also, your framework and help people apply it to help them break out of the cycle that they might find themselves in.

Thank you so much for having me. It’s been great.

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What should we take away from the discussion with Corrie? First of all, being overwhelmed isn’t a time problem. It starts with clarity. What stood out for me is this idea that it’s more than about just having too much going on. It’s often a sign that something deeper is off. It could be clarity, consistency, conditioning or any of those five things. If you don’t know what matters most or why you’re doing it or you’re not taking care of yourself or you’re not able to do things as consistently as you want to be able to do them. It creates this slippery slope.

It’s a non-linear slippery slope. Burnout is non-linear. The longer you let it go, the worse it gets. The longer you let misalignment go, the worse it gets. It’s harder in an almost exponential way to recover from that if you let it go on too long. The second thing was our conversation about success and this idea that success and exhaustion should be the same thing. You can have a life that looks great on paper and still feel completely drained by it. A gap between the external perception of success in our internal alignment and happiness is where a lot of overwhelm lies.

If there is that misalignment, that can be a real signal to you that something in your life needs to change. The last thing is this point around the fact that change either happens by choice or it happens to you. You may ultimately get to the same outcomes as Corrie was saying, but the process to get there will be different and will feel different if you choose it. Such as choosing to leave a job versus if it happens to you, such as getting laid off or waiting until you get laid off.

Again, coming back to what I said a second ago. The earlier that you learn to listen to your intuition, your energy and your body signals, which can show up in a variety of ways. The more likely you are to make changes on your terms, versus having them first on you. I invite you to subscribe to Career Sessions on Apple Podcasts and Spotify or YouTube. If you found this discussion enlightening, sign up for my membership community, which is called PathWise and our newsletter PathWisdom. Thanks.

Important Links

• Corrie LoGiudice
• Corrie LoGiudice on LinkedIn
• Corrie LoGiudice on Instagram
• Corrie LoGiudice on YouTube
• The 5 Overwhelm Culprits: Strategies to Save Your Sanity Without Sacrificing Your Success
• PathWise on LinkedIn
• PathWise on Facebook
• PathWise on YouTube
• PathWise on Instagram
• PathWise on TikTok
• PathWise on Twitter

About Corrie LoGiudice

Corrie LoGiudice is a keynote speaker, high-performance coach, and entrepreneur who helps high-achieving women turn their overwhelm into a catalyst for confident leader- ship. After navigating a series of life-altering events—including divorce, loss, and walking away from a senior executive role—she rebuilt her life one intentional choice at a time. Her signature Overwhelm Culprit framework was born out of that season and has since helped thousands of women clarify their next step, speak up powerfully, and lead fulfilling lives.

She’s been featured on TEDx and in outlets like Forbes, Thrive Global, Business Insider, Girlboss, and more. Through her company, Corrie Lo & Co, she delivers keynotes, workshops, and coaching to powerhouse women and the companies that want to retain and grow them. Her client roster includes organizations like Michelin, Vonage, Impossible Foods, SHRM, Na- tional Grid, and dozens of women’s leadership associations across the country.

Most companies don’t fail because they’re outcompeted. They fail because they succeed. In this episode, JR speaks with Eric Ries, author of The Lean Startup and Incorruptible, about why successful organizations so often lose their mission, values and long-term vision. Eric explains how modern corporate systems incentivize short-term extraction over long-term value creation and that the problem isn’t necessarily bad leaders, but structures that slowly corrupt organizations over time.

Their conversation covers:

• Why “shareholder value” became the dominant philosophy
• How companies like Costco resisted short-term pressure
• The hidden incentives that destroy great businesses
• AI governance and what OpenAI and Anthropic tell us about the future
• How founders can design companies that survive beyond them
• What employees and consumers can do to help companies stay true to their mission

If you’re interested in the impact of capitalism on leadership and innovation, make sure you tune in.

Subscribe to Career Sessions on YouTube and wherever you get your podcasts for weekly episodes like this.

Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/eric-ries

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Watch the episode here

Listen to the podcast here

Why Success Can Destroy A Company, With Eric Ries

Companies Don’t Fail Because Their Out-Competed, They Fail Because They Succeed

Most companies don’t fail because they are out-competed. They fail because they succeed. It’s a bit of a mind-blowing concept, isn’t it? These are the companies that grow, scale and attract capital. Sometimes almost imperceptibly something changes. The mission starts to get diluted or the company goes in a different direction. Short-term incentives take over. The very systems that ultimately enabled success start extracting value from these companies rather than creating new value.

I’m sure you can relate to this in terms of companies that you have worked for or that you have dealt with in your life. What’s unsettling is that it’s not about the people. The people are not bad. It’s just that the system is designed that way. Our guest Eric Ries has spent more than decades shaping how companies are built. His first book The Lean Startup was a monster. It fundamentally changed how founders think about product development, experimentation, and innovation.

In his new book Incorruptible, he’s taking You on something much bigger. He’s arguing that the real problem isn’t how we build products. It’s how we build companies. His core argument is that most organizations are structurally incapable of staying true to their mission. This is corruption. Not in the legal sense, but in the sense of value extraction. It’s the default outcome. More importantly, he’s proposing something radical that we can design companies to resist.

Governance isn’t just a formality. It’s part of the product. The most important thing you’ll ever build is not the product but your organization itself. In this episode, we’re going to talk about why good companies go bad and what it takes to build a great company that stays great. Whether it’s possible to scale without losing your soul and your company.

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Eric, welcome to the show.

It is my pleasure. Thank you.

We’re going to dive right in. Let’s talk about Incorruptible. The court argument, as I took it away from the book, is that companies don’t fail because the people are bad. They fail because the systems are bad. When was the moment that you had an a-ha moment about that?

I’ve been at this for a long time. I’ve helped a lot of people start companies. I have personally helped create billions of dollars of personal wealth for founders. I’m talking about very significant success and I have zero jealousy of those people. I’m so proud of them and so happy for them with the access they’ve had. I’ve also had to see the dark side of this and I’ll tell you the story. I’m working with a friend of mine. Someone I admire and he got completely screwed by his investors. A classic story.

He was a very values-driven person. He built this incredible ethos in the company and made so much money for his investors. At the end of the day, it wasn’t enough. They wanted more. They were so focused on squeezing every dollar out of it. They got out of the company. Tale as old as time. He licked his wounds and he went through the trauma of that. I was there to help him and support him as best I could. It was sad watching up close. Anyway, he got over it. I’m proud of him and he’s back at it.

He’s incomprehensibly rich. What does he want to do with his free time? Does he want to go buy an island and hang out in the Bahamas? No. He wants to get back in the saddle and do it again. He’s creating a mission-driven company with tremendous social promise. I asked him, “Given what happened to you, what steps do you plan to take in this next company to make sure it doesn’t happen again? Are you considering any governance changes?” He looked at me with his blank expression. He was like, “What?” The answer is no. He’s going to do the same thing over again.

It was heartbreaking to make. Maybe it’ll be fine this time, but I had this sinking feeling. I was like, “This is crazy.” What I realized when I reflected on it later, he has internalized this whole story as his personal failing. That’s how the media tells the story. It’s like the founder versus the activists. The this versus the that. Who won? Whoever’s more savvy is whoever won. This savvy person must be right. Since he’s so focused on it as a personal matter, he’s blind to these systemic forces that he was up against.

As a result, he doesn’t even see that he wasn’t presented with a range of options of which he selected the best one for him and his organization. He was told, “This is the only and best way forward. We have to do better. This is not okay.” If we keep going around and around like this, we’re going to keep having this same result and I can’t let that happen.

You talked about a number of things early in the book that set the stage for this. The whole first part is essentially companies that have gone through situations like what you described. You use a definition of corrupt. That’s not just about illegal behavior but about this idea of value extraction. People who are looking to take as much value for themselves out of your company as possible. Even if it ends up meaning that the company gets destroyed, or that it loses its mission and drifts off into some different form of itself. Why does this happen?

The Adoption Of Value Destroying Best Practices And Financial Gravity

It’s very important to call the behavior corruption. That’s not a new thing. Many of the ways that we make money now in the world are celebrated as legitimate ways of making money. Our grandparents would have seen them as not just morally dubious but they would have been actual crimes. We have legalized so many forms of gambling and value destruction. We have locked a lot of investors into this prisoner’s dilemma. Since every investor thinks every other investor is trying to squeeze all the money out for themselves.

If you don’t get in and out first, you’re going to be the one left holding the bag. The reason it happens is we have made a civilization level wrong turn. Many of the so-called best practices that we teach boards, leaders, executives, founders, investors, everybody about how companies should be built, operated and structured. Not only are they not best practices. They’re literally value destroying but we teach them as if they were immutable laws of capitalism or of business or of whatever.

If you can look out the window now, my guess is you can see a tree older than most of these best practices. They are a very recent invention. It was shocking to me how much research we have. They’re not just inefficient but quite valued destroying. At the same time that we have witnessed the financialization of the economy over the last 100 years, we have adopted this set of best practices that is designed to make organizations weak.

That the outside pressure that is growing, thanks to the financialization, is more and more likely to collapse. To the point now where almost everyone I talk to, they’re not startup people or corporate governance people. They will tell me stories about this for rapacious behavior. I can’t remember who told me this. I think he was going to a restaurant and he was at his favorite restaurant. He took a bite of the food and he’s like, “This doesn’t seem right. Something’s wrong.” He was with a friend he’s like, “Hold on. I need to check something on my phone. I think this restaurant’s been bought by private equity.”

He pulled it up on his phone, he’s like, “I could taste it.” I’ve told that story a lot now. Several people have come up to me to tell me that they know what restaurant I’m talking about. They’ve each named a different restaurant. I call this phenomenon financial gravity. This pressure that companies are feeling to always act in this extractive way. It has blossomed out of the private sector and is now infecting everything. You see it in hospitals, non-profits, governments, Unions and universities. It’s an illness. We can’t ultimately build a civilization that can endure if we’re constantly pushing everything into this short term extractive mindset.

You think about some of the examples that are played over the last 20 to 25 years. The privatization of prisons, as an example. Which seemed like a great idea and then turned into a completely horrible idea. All the private equity companies are buying up care homes. Rolling them up and turning them into something less than they used to be for arguably our most vulnerable population. It’s all over the place where you’ve just got this ruthless overly aggressive form of capitalism.

That’s taken root. To your point, we support this. What I learned in business school back in the early ‘90s, was to maximize shareholder value. It ignores the fact that you’ve got employees, a community, and potentially other stakeholders as well. In some ways, the people who are all about shareholder value, you think that the companies that focus on those other things are stupid. That’s the argument that you make. You had a lot of great examples in the book. Maybe go through one or two that got this idea of staying true to mission and some of the things that they’ve done to protect that.

I had forgotten about this story until just now. For a long time in Silicon Valley, our favorite airline was Virgin America. Richard Branson had an American offshoot of Virgin Atlantic. It was a separate airline and because of American regulations, he could not be the majority owner. I happened to be in DC one day having meetings with regulators and academics and all kinds of people. I was working on this thing called the long-term stock exchange. I’m trying to get it approved.

I had a whole day. I’m walking around with my legal entourage and having these grand poobah theoretical meet discussions like we’re having now about shareholder primacy and short-termism. It was amazing when I was talking to these fancy people. They were utterly contemptuous of the idea that there’s a problem that needs fixing. Anyway, I go to check in for my flight and I happen to be in DC on the day that the board of Virgin America over Richard Branson’s objections decided to sell the airline.

They agreed to emerge to what he opposed. It’s what we call a killer acquisition. I’m checking in for the flight and there’s all these baggage handlers and flight attendants hanging around the checking counter. I said, “I heard this will be this merger. What do you guys think about it?” The baggage handler turns to me and is like, “Corporate greed. Once you take a company public, short-term pressure.” They just gave me the whole thesis.

They were so much more educated than all these fancy people I spent the whole day meeting with. They understood both the human consequences of these choices which are dire but also the financial consequences. They were just like, “This is a valued destroying act being done in the name of shareholders for short term profit.” It was wild to me how many of us, normal people, seem to understand this well and yet our most elite people are deeply confused.

The protagonist of the book is a guy named Sol Price, who anyone in retail will know. He is the father of modern retail. Many of his competitors sprung out of his own ideas. Walmart and Costco was based on his ideas. Anyway, his original concept was called FedMart. Everything you love about Costco was pioneered at FedMart in San Diego starting in the 1950s. He had twenty years of unparalleled growth. It was like a classic product market fit up in the right story. He believed that his purpose was to be a fiduciary to the customer.

If you’re a discount retailer, you are taking financial responsibility for your customers. Quality and discounting was in the blood of the organization that he built. That’s why Costco to this day has capped margins. He believed in treating his employees well. He always paid higher than the necessary prevailing wage. Anyway, he was a good employer and someone who understood this simple fiduciary commitment, “Customers first, employees second and shareholders third.”

After twenty years of unparalleled growth, were his investors happy? Were they satisfied? Were they pleased that this ethos was producing these results? No. They weren’t. They wanted more. They wanted conventional practices. They wanted to raise prices and use the trustworthiness that Sol had built to steal this value for themselves. Giving it away to customers made them uncomfortable. This still goes on now. A couple years ago, a Wall Street analyst wrote this about Costco without irony. They said, “Costco is taking money that right fully belongs to shareholders and investing it in the customer experience.”

That’s supposed to be a criticism. Anyway, investors didn’t like it and they had the votes to get Sol Price out. He comes to work one day in 1975 and the locks on his office door have been changed. The critical thing about the story, shareholder primacy claims to be acting in the best interests of shareholders to help them make the most money. Yet in these patterns, when you do the shareholder primacy thing, you often make things worse for the shareholders. Not better.

FedMart was bankrupt within seven years. They just utterly destroyed it. When they fired him from FedMart, he knew he could do it again and he did. He created a company called Price Club. He took one week off and his new office for Price Club was in the same building as FedMart. He got to the office upstairs and said, “Let’s go. Let’s do it again.” He did it again. Ultimately, his disciple who came to Price Club with him was a guy named Jim Sinegal. He’s the founder of Costco.

Eventually Price Club and Costco merged to create the Costco you know now. That’s the clearest and easiest contrast of, if you build the structure properly, to build this ethos and defendant, you create an awful lot of value in the world. If you don’t, if you insist on the conventional playbook, you will get this golden goose phenomena.

The Governance Class Attacking Successful Companies Like Costco Over Shareholder Primacy

You make the point. For all of the people who are naysayers that Costco had it all wrong, it’s massively outperformed the S&P 500.

It’s something like 60X over the 40 years since it went public. Again, it’s very important to understand this. We have something that I call the governance class of our society. This is an unelected set of elites who sit on boards, who work at law schools, and corporate governance specialized judges. It’s a very small group of people who decide things like what is the purpose of an organization. These people operate with no democratic accountability. Creating rules that have never been subject to any legislative action or referendum. Things like the Revlon Doctrine in Delaware. The court decided one day that this is how it’s going to be going forward.

Although, people like to blame Milton Friedman for this turn of events. It’s not clear to me that Milton Friedman is any more of the cause or the symptoms of this club just deciding that this is how it should be. Every once in a while, these groups of governance experts get together and decide that some company practice that makes the company more resistant to outside pressure is wrong. For example, there was this project called the Harvard shareholder rights project. That was going after companies like Costco. That had what are called classified boards.

This is one of the many defense mechanisms you can have for outside pressure. A study was done that showed that of the 90 companies that they pressured to do this campaign. They cost something like $100 billion of value loss. It’s incredibly destructive, this behavior. Costco was there. Crosshairs for a while and it wasn’t just a Harvard shareholders project. There were a bunch of groups that have tried these attacks and what I call the governance fortress of Costco.

What’s incredible about their arguments is that they require you to close your eyes to the actual facts on the ground for the arguments to make sense. Here’s the argument. If you don’t have the board of directors accountable to shareholders, then management will become what’s called entrenched. Entrenched means managers are going to start serving themselves. They’re not going to be interested in performance anymore. They’re not going to care about their investors.

Why is it bad? It leads to poor performance. I get that. That makes a lot of sense on paper. By the way, it’s not a true argument. If you understand why people would make it in the abstract and if you had a poor performing company that was also an entrenched company. I get it. These same people were using these same arguments and the same attack on Costco. One of the highest performing companies in the whole stock market.

This whole debate to me has become almost surreal in the degree to which it has become an abstraction fully divorced from people’s live realities from our ethical and moral frameworks. That is so important to us as a human species but also, to the economic facts on the ground. It’s become completely unhinged.

You’ve got to ask this question. You’ve come up in Silicon Valley. You’ve dealt with a lot of venture capitalists over the course of your business career so far. You can probably name billionaires whose houses you’ve been to. Do you worry that this turns into a little bit of your own Jerry Maguire moment?

I expect a certain amount of flack and blowback. I’ve been getting that my whole career. People thought Lean Startup was nuts and they came around to the end. It’s interesting. I was nervous. It’s because of Lean Startup, I’m a big advocate for testing iteration scientific methods. I was like, “I can’t just write this book by myself in a cave. I got to show it to some people and get some feedback.” The first people I showed it to were all mission driven entrepreneurs.

It took me a while to work up the courage to show it to some VCs. I have to admit because I was a little bit worried. Earlier drafts of the book, it was hard for me to get the tone. There are a lot of stories in this book that involve investor malpractice. There’s also a lot of stories that involve founder malpractice. People are like, “You think founders should rule the world.” Not really. The evidence is good. There’s problems with that, too. We’re talking about something called the architecture of institutional longevity.

What structures can we build organizations to so that they can last for a long time? That by definition cannot be about any individual person because we’re talking about organizations that endure beyond the human lifespan. I was still a little nervous. I sent it to one of my mentors. Someone I respect. A real Silicon Valley OG who helped build Silicon Valley in the first place. I wasn’t sure what he was going to say. He didn’t read it for a while. I was like, “He hates it.” I was bracing myself.

On the day that the manuscript was due to my publisher, I was literally hours from hitting send on the final draft. He called me out of the blue. My phone rang. I saw him on the caller ID and I was like, “What’s he going to say?” I was so nervous and it was incredible. He was kind. He was like, “This book spoke so much to me.” People have forgotten that Silicon Valley used to have a real mission driven ethos.

It had been overrun in recent years by these mercenaries who preached profit extraction above all but they are destroying what made Silicon Valley great. It made me feel like he saw this as a restoration of Silicon Valley’s true principles. That was such a boost to me. I was like, “It’s going to be alright.” Since then, a lot of investors have read the book and found it compelling. I’ve been very grateful for their support.

I want to talk a little bit about the Lean Startup foundation to anybody who’s starting a company in terms of how people build products and created the vernacular of MVP among other things. Now that you’ve got this new book Incorruptible that’s about how you build companies for long-term success. What do you think about the two? What’s the relationship that you envisioned for the two books?

They are deeply related in a way that I find a little bit embarrassing. You mentioned Star Wars. One of the funniest jokes on the whole internet I think is this Reddit meme that’s been going around for years now. It’s Anakin and Padmé in four boxes. Box one, you have Anakin. He says, “I’m going to change the world.” In box two, Padmé says, “For the better, right?” In box three, you see Anakin with his grin on his face. On the fourth box, she says, “For the better, right?” I just thought that joke was so funny because in the tech industry, that’s so us.

We’ve built so many companies that are like, “We’re going to change the world.” It was like, “Did anybody specify for the better?” After a while, I stopped finding the joke funny though because I thought it was obvious that we were trying to change the world for the better. Everyone should know that. I had someone ask me once, “Hot shot, did you specify for the better in the Lean Startup?” I was like, “I did. How dare you ask me such a question?” I was like, “Did I?”

I went and got a copy off the shelf. I found that right there at the end of the introduction, it says, “Such and such that the next generation of founders will have the tools they need to change the world, period.” I didn’t specify for the better and I thought, “What have I done? I fell into the same trap as everybody else.” We were frankly naïve. We thought we could build these companies to the mission driven, vision driven template and no one would try to steal it from us.

We were encouraged in that delusion by many advisors such as bankers, lawyers, VCs and so many people. We’re just like, “Don’t worry about it. It’s always too early to worry about that. You can always fill it out later.” When something would go wrong, it would always be like, “If only you trusted the right people. If only you had been a little more savvy.” It’s a trap that many of us fell into, myself included.

I’ve been trying over the course of all of my books to create a business culture that is more scientific, more humane and more rooted in long-term values. Somehow, despite my best efforts, I got sucked into the mania, too. This is a very needed corrective to those mistakes that I don’t take full responsibility for, but I take my part for sure.

Ultimately, that meme and what you were just saying, we all make this assumption that you’re going to change the world for the better. It does need to be said.

The reason it’s so important to say is, when you look at startups or Silicon Valley companies, when they’re pitching investors. They’re like, “Rah, rah, rah. I am a world changing and world eating technology.” You’re like, “That’s interesting. You’re changing the world. You’re reshaping the face of reality to your values. Do you have any moral responsibility for the outcomes of your choices?” It’s like, “No. I’m just a little technology. I make databases.” Give me a break. Pick a lane buddy. Either you’re a world beater, man up and take responsibility for your actions or delegate that to somebody else.

Don’t go around lobbying the government. If you don’t want a moral responsibility. Don’t expect the upside rewards of all this power. We’ve seen the worst of both worlds. The socializing of risk and the privatizing of gains. Taking these negative externalities and profiting from them. It’s something that people should be embarrassed to have profited from. Not something to brag about.

AI Governance: Learning From Social Media Failures And Demanding Moral Responsibility

We’ve got a timely example of how all of these forces are playing out with AI now. You talk in the book about how OpenAI and Anthropic are set up as examples to create public trust. Look at what happened with Anthropic in terms of its debate with the US government about how the technology can be used. I’d not heard this quote before, but I liked it. “Most fears about AI are best understood as fears about capitalism.” How do you think this is going to play out?

AI is full of uncertainty. Part of the reason it’s so interesting is that for the first time in a long time, really high business stakes depend on the answer to empirically testable philosophical questions. Which has always been true to some degree, but it’s wild now. For example, everything going on with generative AI is powered by something called the scaling laws of a technology called Transformers. So far for years, every time we’ve increased the amount of computational effort, we put into these models. We get a corresponding return in their capability.

If you tell me, whether this is an unbounded exponential curve or an S curve. I can tell you a lot about the future. If it’s an S curve, if you tell me what year it will level off. I will tell you a lot about the future because this is truly the philosophical state of the art. We are probing the nature of the universe as a fundamental attribute of the universe. Anything we did in a particle accelerator. If anyone thinks they know what’s going to happen here, they are guessing. Nobody knows.

One day, the S-curve will probably level off. If it’s next year or 10 years or 100 years from now, it makes a huge difference to all the questions people want to know about what’s coming with AI. The uncertainty we feel is given by the fact that this technology is so unsettling. It’s changing our ideas about what intelligence even is. Many post-modern abstruse academic theories are going to turn out to be empirically testable.

Anyway, it’s an interesting time. Now, to question Anthropic and open AI. There’s something about this technology. It’s a visceral danger that has made this generation of founders as much more wary of how it should be controlled. It has a lot to do with the fact that social media came right before. Many of the actors, investors and players in this drama are veterans of the social media wars. Even though they unpublic are all talking about how great social media turned out to be because it made them super rich and private. Everyone acknowledges social media has been an absolute disaster.

It’s a society. Our sense of the truth has been utterly fragmented and that is not healthy. Those same rapacious companies that control social media. What if they control AI? Scary. It is telling that we’ve had a big debate about AI safety and governance and how it should be governed. I tell the story in the book. I was once doing an event at the Vatican. I was invited to speak on this panel. It was me and eight people in this giant panel. I looked down the row and every major AI company was there.

It was Anthropic, OpenAI, Google, Meta, Palantir, and Cohere. I looked down the road and I realized, “There’s not a single company on this day with me who has standard governance.” Not one. It’s considered too dangerous. No one would feel ethically responsible doing it. It’s absolutely impossible to imagine. I do think that’s important. Now, we’ve all had a bunch of governance failures already in AI. The founding of Anthropic had to do with a disagreement with OpenAI about the path forward on AI safety.

The recent experience you mentioned with Anthropic and the DOD, leaving aside who’s right, who’s wrong in politics. That also is a very complicated situation. Honestly, I don’t even think Anthropic is the main actor in that story. It’s mostly a story about government overreach and the DOD. To me, it was a very significant thing. Again, regardless of how you feel about the rightness or wrongness of what they did. Anthropic was willing to say, “We will turn down $200 million over a point of principle.”

You could say they were wrong to do that or right to that. In our modern world, it is very rare to see a company that can say no to even $1 of extra profit, let alone hundreds of millions of dollars. In fact, one of their competitors swooped in and grabbed up the contract the second they said no. I thought that was notable. When they did that, I’m sure they did not know what the consequence of doing that would be. They’ve been subject to government retaliation. They’ve been called a lot of names in public by a lot of very powerful people.

People are under rating what a big deal it was. They did this without knowing at all what the result would be. It’s also interesting to me and very validating for these is the book. They have received all these benefits that they could not possibly have foreseen. I remember someone sent me a video the day after they did it. The whole sidewalk around their entire headquarters in San Francisco was chalked up with messages from the public just saying, “Thank you for doing the wrong here.” That doesn’t happen very often with tech companies even in San Francisco. Let me tell you.

Claude rocketed to number one on the App Store. There was this incredible surge of customer loyalty. Even when we disagree with them, we admire companies who stand for something. Being willing to stand for something, in the face of genuine cost, is one of the most important ways to build trustworthiness in a company.

This book relates to the Lean Startup. The Lean Startup was chock-full of great advice for people who are starting companies on the ground perspective. This book operates at more of a system level in terms of how the economy and the capitalist world is set up. For somebody who’s thinking about their career journey, what would you want them to take away from the book that would be helpful to them in terms of how they think about what they choose to do professionally and how they navigate this uncertainty?

I’m glad you asked this question. Although, it is true that the first part of the book has this more theoretical discussion, so did Lean Startup. People forget this. The first chapter of Lean Startup is not about MVPs and pivots, but about the history of management. I believe my whole style of writing is to lay a very solid theoretical foundation. Whether the reader likes it or not. I notice that a lot of people come to my books and that’s not what they’re looking for. They want the practical tools, but I give the practical tools, too.

Here’s my promise to the reader. Every technique in this book is something you can do today. Nothing requires you to wait for some regulatory change or get permission from that. They’re all actual things you can do. Every technique is given in theoretical form but also in story form. We have actual case studies of real-life companies that have done it. We have a lot of academic evidence that these techniques work because many of these techniques are new. Although, for most readers, they have never heard of this before.

I always say, “Only because it’s new to you, doesn’t mean it’s new.” Your question about someone thinking about their career and employee. First of all, if you’re a founder and you’re in it now, like if someone’s reading now and you’re either thinking of or you just started a company. You can skip part one if you need to. Read part two. The book is drawn into three parts Part two is the blueprint and is chapter by chapter. Every chapter is specific actionable techniques you can adopt. The earlier you adopt, the better. Not to say that if you’re a late stage company, you can’t adopt them but the easier, the earlier.

If you’re not a leader or a founder yet, like you’re someone earlier in your career or you’re not sure what your role in this change is. I wanted this book to be useful. I put it in the subtitles. It’s subtle but it’s there. The subtitle of this book is Why Good Companies Go Bad and How Great Companies Stay Great with an ellipsis with my little nod to Good to Great. For those fans of the great Jim Collins. There’s the why readers and the how readers. They’re both equally important.

People don’t realize this. They always say, “Why would I read a book that’s for the founder?” You might be a future founder. The first thing you need to understand is almost all the great founders in this book, the ones who created breakthrough success that not only made a lot of money, but created this tremendously positive change in the world. Most of them had a pre-existing ethos that they brought with them into entrepreneurship. If you’re that person, you need to be developing those ideas and you’re understanding now. As soon as possible. Don’t wait.

Secondly, and this is what part three of the book is about, especially the last few chapters. We all have more power in this economy than we think. Part of the magic of late stage capitalism is to make everyone feel this empowered and helpless. This thing seems inevitable and super powerful, but we don’t realize this system is obsessed with the EU. Which means, every action you take is somebody’s OKR.

You cancel a service. You buy a thing. You are willing to pay $0.3 extra for the higher quality product. I guarantee you. It’s somebody’s job to notice. You refuse to work at a bad company. You ask the right question in a job interview. The next thing you know, those questions are being discussed by the board of directors because they’re obsessed with getting top talent. If you have questions, they need to have answers. There’s so many simple, practical, easy things that individual people can do.

You don’t have to be that courageous even. Put your toe in the water and see what it is like to lean into this other interpretation of what organizations are, what business can be. I have found in my own career and in the many people I’ve counseled and mentored over the years that this can lead to very surprising change. Even if you feel like you are utterly powerless or utterly helpless. Give it a try. If you need to, read part three of the book first. That’s okay, too.

Key Takeaways: Designing Your Company For Institutional Longevity And Enforceable Mission

There is a heavy manifesto component to the book. That was seen true of the Lean Startup. I said to a colleague of mine after reading it, “This book is going to make a big splash.” Partly because it’s you and the ideas are pretty powerful and pretty timely for us to be talking about now. I wish you all the best with your launch and thank you for your time.

I appreciate it. Thank you so much.

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Fascinating conversation with Eric. Let me just try and boil down a few of the key points. The first point is about this idea of designing your company and not just building it. People think about building a great company but you have to design and make sure that what you’re building will last. If you’re a founder, culture, talent, and your personal philosophy aren’t necessarily enough. You’ve got to think about ownership structure, board, composition, and incentives and all of those things.

All of that will determine whether the company survives in the way that you envisioned it. Whether it’s mission survives and maybe whether it even itself survives. Second is this idea of invisible drift. We didn’t talk about it explicitly. Certainly, some of the examples of companies veering off course. We talked a little bit about FedMark and how that company was taken away from the original vision and ethos that Sol Price had when he founded it. There’s other examples in the book.

Johnson & Johnson is one that gets mentioned that Eric walks through about how it went from a very strong ethos to having lost that ethos. Particularly as it related to as best this and talcum powder in the lawsuits that have happened over that. It’s important to be thinking about if you feel like you were overly focusing on short-term gains instead of long-term value, this is not a random occurrence. This is happening all over the place. It’s a structural signal that the system, maybe your system, and your governance model are pulling you off course.

Third is just the important concept of making your mission enforceable. Not just aspirational. Again, there’s a lot of concepts that Eric introduced in the book that we did not have time for that allow you to make sure that what you create will last. Even last beyond your lifetime as a founder. There’s examples of that he covers as well. Finally, it’s this idea that, in some ways, the more likely you are to win, the more likely you may end up being to lose. Success increases risk because it brings the financial players to bear. You’ve got a plan for early.

The more valuable your company becomes, almost the more pressure that it will face to extract that value. You’ve got to build protections before you need them. It’s almost impossible to start worrying about this too soon. Those are the key points for founders or people involved in startups. If that’s not you, you should also consider some of the key lessons for Eric’s book in terms of companies that you choose to work for and how you design the trajectory of your career. We talked a little bit about that at the end.

Otherwise, you could find yourself working for a company that you feel ends up being soulless and feeling completely uninspired by that. I invite you as always to subscribe to Career Sessions on Apple Podcasts and Spotify. You can also subscribe to our YouTube channel. If you found this discussion enlightening, sign up for my membership community, which is called PathWise and our newsletter PathWisdom. Thanks.

Important Links

• Eric Ries on LinkedIn
• Eric Ries on Facebook
• Lean StartUp Co.
• The Lean Startup
• Incorruptible: Why Good Companies Go Bad… and How Great Companies Stay Great
• Jim Sinegal on Facebook
• OpenAI
• Anthropic
• Google
• Meta
• Palantir
• Cohere
• Good to Great
• PathWise on LinkedIn
• PathWise on Facebook
• PathWise on YouTube
• PathWise on Instagram
• PathWise on TikTok
• PathWise on Twitter

About Eric Ries

Eric is the creator of the Lean Startup methodology, practiced by individuals and companies around the world. He is the author of New York Times bestseller The Lean Startup, The Startup Way, and The Leaders Guide (funded by one of the top Kickstarter book campaigns of all time). He has founded a number of startups, including LTSE, where he is currently Executive Chair and Chairman of the Board, and IMVU, where he served as CTO. He has also advised on business and product strategy for startups, venture capital firms, and large companies across many industries.

Most people think success comes down to talent, timing, or even luck. But Kyle Austin Young suggests it could be a numbers game. In this episode, he explains how to think about success through the lens of probability so you can actively improve your odds over time.

JR and Kyle explore:

• Why your goals have hidden probabilities attached to them
• How to reduce the likelihood of failure
• The power of repeated attempts
• When to power through to achieve your goals, and when to pause
• Why differentiation is critical in today’s market

This conversation reframes success as something you can engineer. Whether you’re early in your career or reevaluating your next move, this will help you make smarter decisions and create better outcomes over time.

Tune in every week for more episodes like this. Subscribe on YouTube and follow Career Sessions wherever you’re listening to this.

Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/kyle-austin-young

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Watch the episode here

Listen to the podcast here

How Successful People Actually Think About Risk, Failure, And Opportunity, With Kyle Austin Young

Most people think that success is about talent and timing, maybe even luck, but what if that’s not the complete picture? What if success is less about being extraordinary and more about playing the odds better than everyone else is doing? My guest, Kyle Austin Young, has built his work around this deceptively simple idea, which is that success is a numbers game, not in a shallow hustle way, but in a deeply strategic sense.

How do you take more shots, yes, but more importantly, how do you take better shots? How do you position yourself so that, over time, the math starts to stack up in your favor? Kyle is a contributor to Harvard Business Review and Forbes and Fast Company and Psychology Today, and his perspectives aren’t just theoretical. He’s lived through setbacks, he’s been laid off a couple of times, and he’s used those experiences as a way to rethink the realities of his career journeys.

In our conversation, we’re going to unpack the hidden math behind success, what people get wrong about it, and what they get wrong about resilience, and how to tilt the odds in your favor, whether you’re early in your career or rethinking your next move because success is really a numbers game. The question is, how well are you playing it? Kyle, welcome and thanks for joining me.

Thank you for having me. I’m excited to be here.

Fundamental Misunderstanding About Success As A Numbers Game

Yeah, absolutely. Let’s jump right in and talk about your book. The title is simple and yet provocative. What do people fundamentally misunderstand about success being a numbers game?

There are a few things we misunderstand, but I think at the basis a lot of people don’t realize that every goal that they’re pursuing has two hidden numbers attached to it. Their odds of success and odds of failure. I think one of the reasons why we spend so little time thinking about that is we assume that our odds are unknowable, unchanging, and therefore irrelevant.

I wrote this book to help people realize that there are ways that we can actually wrap our minds around our current odds of success. If we do that, we can then actually improve our odds of success. In the context of a single goal, that can change your outcome, but over the context of many goals, that can change your life. I think the fundamental misunderstanding just starts with recognizing that this is even possible.

Obviously, all of this is about probabilities. As you say, probabilities of success and probabilities of failure. What are some of the variables that people should be trying to influence?

The Counterintuitive Strategy Of Thinking Negative And Probability Hacking

Well, what I find to be one of the most straightforward ways to improve our odds of success is to do something that’s a little counter-intuitive. I’ve found that when most people are pursuing a big goal, the advice they’re usually given is to think positive, don’t worry about what could go wrong, that’ll just discourage you. If it’s meant to happen, it’ll happen. Just pursue your goals with gusto, and that’s the most reliable way to succeed. I encourage people to do the exact opposite. I literally encourage people to think negative.

That’s a big part of the probability hacking process, because we can understand probability a little bit like we’ve traditionally understood matter. This idea that matter can’t be created or destroyed, but it can be transferred and rearranged. The odds that we want are currently hiding in our potential bad outcomes. If we think about a game where we’re flipping a coin, if it lands on heads we win, tails we lose. There’s a 50% chance we’ll win and there’s a 50% chance we’ll lose because it might land on tails.

Now, I don’t know how to influence a coin toss, but in real life, there’s typically things we can do about the bad outcomes that are hogging some of the probability we want. As we make those risks less likely to materialize, we boost our odds of getting what we’re actually looking for. My framework is ultimately designed to help people identify what are the potential bad outcomes, how can we use our creativity to take some of those risks off the table. If we do that intentionally over the course of the goal, I give people ways to break it down into a diagram, and if we do it step by step, we can end up with dramatically better chances of getting what we want.

What are some of the specific ways that you can reduce the odds of a bad outcome so that something becomes more of a good bet?

Practical Application Of Reducing Bad Outcomes (First Job Example)

Yeah, if you’re open to it, let me do this in the context of an example. This won’t have any numbers in it. I tell the story in the book. It’s the story of how I got my first job out of college. This was many years ago. I’d just graduated with this undergraduate degree and I wasn’t really inspired at all by the opportunities that I was seeing. I decided to do something really audacious.

I decided I was going to apply to become the product development director at a health organization. I’m 21 years old. If I get this job, I’m managing people in their 50s, 60s, 70s, people who could have been my grandparents at the time. I decided to apply for this job, and I got the interview, and so I had a real chance. Even at this point in my career, I wanted to ask the question. “What can I do to improve my odds of success?”

This was before I was a consultant, before I wrote this book, before I did any of this stuff. I said, “Let’s see what we can do,” and so I tried to identify what are the bad outcomes that might happen instead of the outcome I wanted. At this point, all I needed was a job offer. I already had the interview, so there was just one step left. I identified three risks, three big threats to my success.

The first was that the hiring squad might take one look at me and just think, “He’s too young. There’s no way somebody this young can manage the department.” I needed a way to try to minimize that risk. A lot of people would say, “Well, there’s nothing you can do about that. You know, you could lie and say you’re older than you are.” I wasn’t going to do that. “You could, I don’t know, wear a paper bag over your head.”

A lot of people look at an obstacle like that and say there’s nothing you can do with it. I found something I could do, which is I grew a beard. That simple change to my appearance made me look a good bit older than when I didn’t have the beard. It took some of the edge off when I walked into the room. It wasn’t like “Who’s this kid? Where did he come from?” It looked like maybe I could pass for somebody a little bit older than I was.

Another risk that I identified was they might be concerned about my lack of experience, which was real. I had just graduated from college and I was up against candidates who had a few decades on me in terms of their work experience and all of the things that they’d done over that time. Again, I wasn’t going to lie, but I did want to ask myself the question, “What can I do to take some of the risk out of that?”

“What can I do to maybe reframe the conversation so that it’s not just a conversation about how I don’t have any experience?” I actually typed up a plan for how I was going to turn this product development team around, and it was so thick I had to have it spiral bound. It was a book. I took it in with me, a bunch of copies, and I handed it out to every person I interviewed with.

When they would ask questions about my resume, I would just redirect it to be a conversation about my vision for the future of the department. They’d say, “Tell me about a time you overcame adversity,” and I’d say, “Well, let me tell you how I’m going to overcome adversity as it relates to this thing that the product development team is dealing with.” that was a way that I de-amplified some of that risk.

The third and final threat that I perceived was the thought they might be concerned I just couldn’t get along with the existing team because of the generational gap. “Is he going to be able to fit in with this group of people?” I did something that I’ve continued to use since then a really great strategy. I asked if the team had read any books lately as a group.

They said a few titles, and I went out and read every single one. What that did is when I was then in these interviews, I could speak their language. I knew their jargon, I knew the frameworks that they were referencing, I understood their goals better. I found myself in a group interview at one point. It was me and some of these other candidates. They were all much more experienced than I was.

One of the books the team had read was called The Whuffie Factor. Not a lot of people are still reading The Whuffie Factor, I don’t think, but it was a book about how brands generate social capital. Somebody presented an idea and I said, “You know, I think that’s the idea that could get us a lot of Whuffie.” I remember looking around and the other candidates, their eyes are bugging out of their head. “What on earth did this kid just say? What is Whuffie? What’s he doing?”

I looked at the existing team members, and they’re laughing. They knew exactly what I was talking about. They just read that book. When it was all said and done, I got that job. At 21 years old, I became the product development director at this health organization and it completely changed the trajectory of my career. I would later encounter a couple of layoffs and that led to the consulting.

That was just such a massive leap forward for me. What made that possible was thinking negative. What made that possible was recognizing that the odds that I wanted were hiding in my bad outcomes. Those were the things that could have happened instead of what I wanted. I did everything I could to take those things off the table and ultimately got what I was after, which was a really unlikely opportunity.

I hear two things in what you said. One is you were directly confronting the negatives. Objections that people were going to have. Anybody who’s in this sales process will certainly say that that’s a key thing that you often have to do to make a sale. You were trying to convince them to hire you, so it is a form of a sale. Any process where you’re trying to influence somebody or sell somebody, being ready to confront the objections is a key thing. I think that’s one thing you certainly did.

I think the bigger thing listening to what you’re saying is you stacked the odds in your favor by going the extra mile. Coming in with a playbook. Most people think, “I’ll do that after I get the job.” You did it before you got the job. As somebody who’s hired a lot of people in my life, having somebody who’s come in and actually thought about it, that makes a huge impression because you’re saying, “I’ve already thought about this and I’m deeply committed to the success of this and I haven’t even gotten the job yet.”

To me, that just stands out a ton. It’s part of what you’re saying, which is you’re both reducing the odds of a bad outcome, but you’re also pushing some things onto the likelihood of a good outcome. You’re managing both halves of that coin flip, if you want to go back to your analogy of the coin flip from a few minutes ago.

I think that’s absolutely true. I think what’s key about this framework is I know there’s a lot of people out there who want to go the extra mile. They want to work hard, they want to do everything they can to succeed, but they aren’t necessarily sure where they should be investing their time. I encourage people to create what I call a success diagram. It’s just a list, left to right, like a map of, “Here’s everything that’s going to have to go right in order for me to get what I want.”

For each thing that we need to go right, beneath it I then make a list of the things that could go wrong. “What are the potential bad outcomes that could happen instead of what I want?” when we have that out in front of us, it gives us a really powerful opportunity to take a bird’s-eye view and ask the question, “What can I do about these bad outcomes? In what areas can I go above and beyond?”

Otherwise, we all know that person who’s working really hard, maybe they’re not getting the results that they want. Sometimes we feel like we are those people. That’s because to some extent, it’s not really about how hard we’re working, it’s about are we working hard on the right things? I find that whenever everything’s done in the context of what has to go right in order for you to get what you’re looking for and what could go wrong, we make sure that we see a good return for the efforts that we’re putting in.

A lot of people seem to want certainty before they act. How do you get them comfortable with operating without it?

The Power And Limits Of Multiple Attempts To Achieve Unlikely Success

I think I start by just making it clear that you are operating without it whether you like it or not. I’m sorry to bust the illusion of certainty, but you never had it. Also, in the book I talk about the power of multiple attempts. I had the opportunity to interview somebody who played on the 1980 US men’s Olympic hockey team, the “Miracle on Ice.”

I show, using numbers, how this was called this miraculous thing that the United States beat the Soviet Union when they were so outmatched. As an individual event, it was. If you look at the fact that they played 9 times total, the US won 2, the Soviets won 7. That’s not a miracle. Going 2 and 7 in a 9-game rivalry, that’s not a crazy outcome at all that you would win 2 out of nine games. That’s just a difference in ability, a difference in skill.

I try to illustrate for people that through the power of multiple attempts, we can accomplish things that seem unlikely. I think that’s something that takes a little bit of the edge off when it comes to failures when you recognize that almost all of the big success stories that we’ve seen in history, or maybe not all, but many of them incorporate this element of repeated attempts.

We think about the arts, and we think that the most successful artists are the ones who are the most talented. We realize that Mozart, who maybe we know 5, 10 pieces of music that he composed, he composed over 600 pieces of music. We think of these people as being incredibly talented, and they are, but there’s also a component in this that they just tried over and over and over and gave themselves so many opportunities to find success.

One more story I tell in that same vein. Thomas Edison. When he’s trying to invent the incandescent lamp, it all comes down to finding a practical filament. He needs something that can get hot enough to glow without catching on fire or snuffing out so quickly that there’s no point in even trying to have one of these in your home. He’s up against a number of other inventors who are trying to do the exact same thing.

It wasn’t that he had an idea no one else had thought of. It wasn’t necessarily that he was even significantly more talented than they were. What he did that they didn’t do is he experimented with 6,000 different filaments to find 1 that worked the best. He actually found that carbonized bamboo, which is probably not the first thing you’re going to try, that was the one that incandesced the longest without catching on fire.

He ends up being awarded these valuable patents that change the trajectory of his career. Through repeated attempts, we can find unlikely success. What we need to realize is once we have that success, it changes our odds in a long list of subsequent goals. Even if we succeed through this inglorious process of trying over and over again, that doesn’t change the fact that once we have the success, we have the ability to then go chase bigger goals with much better odds.

You hear these stories. Van Gogh was famous for just taking a brute force approach, like, “I’m going to learn to be a great painter if it takes me my entire life,” and he just painted and painted. Edison, I think famously said something to the effect of, “I haven’t failed a thousand times” or whatever the exact expression that he used to describe the fact that it took him a long time to get to where he ultimately got with trying to invent a workable light bulb solution. How do you know when you’re trying to brute force your way through this and just giving yourself a lot of attempts? When does that persistence become irrational? How do you know when the odds just aren’t worth playing anymore?

One way that we can get a sense of our odds of success is to create a success diagram but then put some numbers on it. Ultimately, we can understand our odds of accomplishing a goal as the odds of each individual thing that has to go right multiplied together. I’ll give a really simple example of that. Let’s say that you’re training to run a marathon. I just ran my first half-marathon.

You hire a running coach and she says, “I can get you ready by race day, but there’s three things you’re going to have to do. I need you to eat, sleep, and train according to the regimens I’m going to create for you. If you stick to all three of those things, you’ll be ready, but if you don’t, if you cheat on even one of them, I’m not going to be able to get you ready to run such a big distance in a short amount of time.”

If I’m going to create a success diagram for that, there’s three things that have to go right. I need to eat, sleep, and train according to these parameters, and if I do those things, then I’m virtually guaranteed success according to this running coach. Let’s just put some really easy numbers on that. Let’s just say we think it’s 70% across the board. 70% chance I’ll eat the way I’m supposed to, 70% chance I’ll sleep the way I’m supposed to, 70% chance I’ll train the way I’m supposed to.

This is where a lot of people fall into a trap called averaging. We assume that if we feel good about our individual steps to accomplish a goal, we can feel good about our odds of the goal in its entirety. That’s not true. In reality, we can’t average these numbers, we have to multiply them. What’s really surprising to a lot of people is if you multiply that out, .7 times .7 times .7, you learn that you only have a 34% chance of accomplishing this goal.

At first, it seems like such a slam dunk, but it’s actually not. This is a predicted failure. You might succeed, but we don’t expect you to succeed. We expect you to make a mistake in one of these three areas and ultimately not be ready on race day. We have an opportunity to get some sense of our odds of success when we break it down into its component parts and try to make some estimates of how likely are each of the things that I’m going to need, how likely are those to ultimately come to fruition.

There are some other rules that can help us estimate. You know, we’re not going to have all the information, but we can know that our odds will never be higher than the odds of our most improbable prerequisite. If there is one thing that has to happen, has to happen in order for you to succeed, and it’s incredibly unlikely, then your overall odds are going to be even lower than that because it’s not the only thing that has to go right.

We can start to get a little bit of a sense of, “Is this a 1-in-10 type of goal? Is this a 1-in-100 type of goal? Is this a 1-in-1,000 type of goal?” In some cases, if you’re Thomas Edison looking for a practical filament, it’s okay if it’s a 1-in-6,000 type of goal because it’s not that hard necessarily to just experiment with these different filaments. You’ve got a timer, it’ll tell you which one works the best.

Is it practical, though, to start 1,000 businesses and hope that one of them is successful? Probably not. That’s probably not a practical goal. You’re absolutely right that we want to get a sense of what this number is in our lives. We can’t necessarily do it exactly, but when we break it down into its component parts, we find that we can get a pretty good estimate and at least know to some extent what the limit of our opportunity is. “Here’s best-case scenario.”

There are times where that tells us that maybe this isn’t a goal to prioritize right now. Ask yourself the question, “Which one of these should I be going after right now?” a lot of times when we order our goals by how likely we think they are to happen and prioritize the ones where we have a real shot, we can then improve our odds at some of those things that might currently seem more far-fetched.

How did you come to all of this? How did you put together this philosophy? Obviously, there’s a lot of statistics and math involved in it, but how did this become core to the way that you think about success and failure?

I think a lot of people’s origin stories, it wasn’t the story that I designed for myself. When I got that job as product development director, I thought that I’d set myself up for a pretty fantastic career. For the first few years I had. I had a lot of success. Ultimately there was a round of layoffs that I was included in. I moved across the country for another job. There was a round of layoffs that I was included in.

By the end of it, I’d had two pretty visible, pretty respected leadership positions and all I had to show for it were two layoffs. The first time, my wife and I just bought our first home, that wasn’t ideal. The second time, we were in the process of adopting our daughter, which is a pretty famously expensive process, and so twice I had to sit down my wife and say, “I lost my income.”

At that point, I didn’t want to just stay on what felt like this hamster wheel of, “Get another great job, lose it. Get another great job, lose it.” I had some friends who were really generous with me. It was pretty well known after the second layoff that I had four job offers the next day. People knew that I was still in demand and that was really helpful.

Some people reached out to me and said, “I’ve heard that you’re trying to decide which one of these four jobs to take. What if you took a fractional role with each of the organizations, positioned it as consulting, and then put yourself in a position where you’d have a more diversified income?” that was over a decade ago, but I took that advice. One of the biggest things I carried with me into that consulting career was I learned through the layoffs that it wasn’t just a question of my personal performance when it came to my job security.

It was possible to do a really good job, get great performance reviews, and then still find myself without an income very suddenly. Ultimately, what I realized was if I wanted to do everything I could to stay gainfully employed, it wasn’t just about what I was doing. It was also about whether the projects I was involved in were succeeding or failing, even if that meant going outside of maybe the scope of my job description.

“What could I do to make the project successful, to make sure the company had money, to make sure that I was in a position where I could still be okay?” that’s what led to this idea of when I would enter into a new consulting project, I would make a diagram where I’d list out everything that had to go right in order for the project to be successful.

Sometimes that just meant asking the right questions. “Have we thought about this? What are we doing about this risk over here?” I wanted to take a higher level of responsibility and put myself in a position where I was doing everything I could to make the team succeed, realizing that that was going to be the thing that ultimately kept me employed.

Ten years down the road, how does this impact how you think about the trade-off that somebody might be considering between having one full-time job versus the path that you’ve chosen, which is to have multiple income streams and different consulting projects? How do you think about that trade-off?

It’ll be different for different people. I can tell you my story. In my life, I now probably make maybe six or seven times as much as I did when I was a product development director, so there’s no cap on your income, there’s an opportunity for tremendous growth in that vein. There is some diversification, which is really nice. You will go through the experience of losing clients more in this model because you have several clients.

You’ll get laid off more often, so to speak. However, you have this diversification, so when it happens, it’s not as big of a deal, and that’s something that’s been helpful for me too. Financially been very rewarding for me. I can’t guarantee that everybody would have that same success. I’ll also say that a con that I do experience is you have 6 or 7 retainers at any given time, there’s always going to be a client who’s having a great day and there’s always going to be a client who’s having a terrible day.

If you want to go on vacation, you can do everything you can to minimize the risk of something catching on fire while you’re gone, but you’ve got maybe 7, 8, 9, 10 different organizations that need nothing to catch on fire for a week, and so in that sense, the odds work against you. You’re always on a little bit. I enjoy what I do. It’s unique every day, lots of different experiences. I get to learn from a lot of different people, so it makes me better at what I do. It’s been a great fit for me. I think ultimately, people are going to have to answer that question for themselves because there is some work to get to where I’m at, and you need to decide if that’s an investment you want to make.

Using Setbacks For Intentional Self-Reflection And Reinvention

Coming back, you had some setback moments. You talked about the couple of layoffs. When somebody has a setback moment like that, what advice would you give them to try to regain a sense of control?

What I have found every time I’ve been laid off, and I really mean this, is it has always helped me reinvent in a way that’s been really positive. It’s just an unexpected call to self-reflection of, “Okay, I designed a life that isn’t going to go the way I thought. Now let’s pause and ask the question. ‘Is there anything I wish was different?’ because we’re going to have to find a new job anyway.”

Success Thinking: Every time I’ve been laid off, it’s pushed me to reinvent myself in a positive way. It’s really an unexpected invitation to self-reflection.

In some ways, I think it can be a really helpful thing for people to have those types of setbacks because it forces us to think more intentionally, which we can do without the setback. You can be gainfully employed and stop and ask the question, “Is this the job I want? Is this aligned with my values? Is this putting me on the path that I want to be on?” I find that I tend to just get caught up in the day-to-day.

I’m on my to-do list, I’m in the entrepreneurial sense, working in the business, not on the business or in my life, not on my life. It puts us in a position when we’re laid off where we have to pause and ask that question. For me, I live in Nashville, Tennessee, which I’m very thankful for because of a layoff. That’s the reason that I ultimately moved here. I don’t know if I would have made that move otherwise.

I think it’s been a really good move for my family. I think I would have just kept working in that job that I started with. Whether you’re encountering a setback or not, I would encourage you to pause and ask those big questions of, “Is how you spent yesterday the way you want to spend your life? If not, then maybe there’s an opportunity for change,” and I don’t know if that’s ever more apparent than when we’ve been laid off because it takes away that fear of losing what we have. We already lost what we have. We’re on the other side of that fear. Now it’s just a question of what do we want?

One of the things you talk about speaking of pausing is pausing goals. What do you mean by that and what’s the advantage in it?

There’s been a little bit of a movement lately telling people to quit their goals or if they have too many goals, quit goals. I think that’s nonsense. I don’t know why you would ever need to quit a goal. Just pause it. Just say, “I’m not actively pursuing this goal right now,” but that doesn’t mean you won’t ever pursue that goal. I wanted to write a book since I was like eleven. That’s a goal that I’ve had for decades and decades.

It wasn’t even close to realistic at that time. It wasn’t close to realistic when I was a product development director or when I was an operations manager. It became realistic when after a decade of consulting and writing for Harvard Business Review and Forbes and Psychology Today, people were coming to me saying, “How do you think about this? Teach us the framework that you’re using because we’re seeing results from you that we’re not seeing from other people.”

That’s when I finally had the opportunity to write the book. I’m not as big a fan of quitting. I’m a bigger fan of pausing. I think you can do it really intentionally, and it’s in this same context of a success diagram. For the goal that you’re pausing, write down everything you can think of that will have to go right for you to accomplish that goal, start thinking of some of the things that could go wrong.

Just hang on to that sheet of paper. Keep it nearby. What that allows you to do is then live your life and you can passively collect the advantages you’ll need to one day pursue that goal. In the same thing of the context of me writing that book, I had an opportunity at one point to take on a project that wasn’t going to pay very well, but it was going to put me in close contact with a number of literary agents.

I knew what my goal was. I said, “Yeah, I would like to do that.” Why? I knew that someday I wanted to write a book, and I knew that one of the things required in order to achieve that goal was I was going to need to have a relationship with some literary agents. When that opportunity came up, I took it. We have an opportunity to pursue goals like that where it’s not necessarily the thing that’s at the top of our to-do list, it’s not on the front burner so to speak. However, as we’re going through life, we have an opportunity to meet people, connect with people, and gather up some of the advantages that we’ll need to one day move that goal back to the active list instead of the “someday” list. That’s why I believe in pausing.

You’re going to fail, right, along this journey. When you fail, how do you make sure that you get as much value out of that as possible?

Repurposing Assets From Failed Goals For New Outcomes

For me, it goes back to the success diagram. It goes back to looking at what steps have already been accomplished in pursuit of this goal because then we can ask the question, “How could we maybe reposition some of the assets we’ve accumulated in pursuit of something different?” In the book, I tell the story of these friends who I believe were former paypal employees, and they decided that they were going to start an online dating site together.

This was at a time when the internet was much newer, and they wanted to differentiate themselves by giving people the ability to upload a video just introducing themselves to other people who might want to maybe go on a date with them. That was cutting-edge technology at the time that they were doing this. They’re trying to get people to use the service, give it a try.

They’re running advertisements, they’re paying people money just to create an account, just upload a video and say, “Hey, I’m Kyle, here’s a little bit about me, here’s what I’m looking for,” and they just couldn’t do it. They couldn’t get enough people to start using the service to ultimately then go out and run advertisements and say we have all of these people looking to find love. Finally, they decided that they were going to not necessarily quit the goal, but repurpose it.

They were going to try to take what they’d already accomplished and use it toward a different outcome. The biggest thing they’d accomplished was they’d given people the ability to upload videos to the internet and anyone could do it. You didn’t have to be a programmer, you didn’t have to be a computer scientist, you could record a video, put it on the internet. That was crazy.

Instead of using it in the context of a dating website, they decided to broaden their scope and let anybody upload videos to the internet. Ultimately, they called it youtube. It was a failed goal, so to speak, that was incredibly lucrative, incredibly successful by many standards because they stopped and they didn’t run away from it. A lot of us run from failure.

Something goes poorly, “I don’t want to think about that, that’s embarrassing. I don’t want to be associated with that.” Instead, they recognized that there were a lot of smaller accomplishments that had happened in pursuit of that failure. Those accomplishments were still valuable. They could still be used in other places. Ultimately, they just took what they’d built, pointed it toward a different outcome, and were able to achieve enormous success.

I think a lot of us have left tremendous value behind when we try to distance ourselves from our failures. I encourage people to use that success diagram to remind them of, “Here’s all the things we’ve learned, here’s all of the assets we’ve accumulated. Is there something different we could do with these advantages that we’ve worked so hard to get?”

Avoiding Sameness Through Strategic Differentiation And Credibility

I know you write a lot about standing out as well. Why do so many people in business seem to default to sameness?

I think one of the biggest reasons. The people who are responsible for differentiation or at least image are often incentivized in a way that’s out of alignment with what might be the company’s best interest. If you think about like an established organization, if you’re an employee who’s responsible for that brand’s image, do you want to be the person who walks into your boss’s office and says, “Boss, I took a big risk today, but it might pay off for us?”

Most people don’t want to do that. That’s a weird conversation to have. To some extent, that is the price of being a little bit of a renegade when it comes to your branding. You have to be able to stand up to your superiors and say, “I’m taking risks. I’m doing things that might go really well or might not.” in reality, I think a lot of the employees in those roles find themselves in positions where it might be smarter for them to just play it safe and say “I’m following best practices,” and then if something goes poorly, they can blame it on the economy or blame it on some market force versus it all coming back and saying, “Maybe you shouldn’t have taken that big risk.”

I think that what’s important is, again, if we know exactly what we want, we know what it’s going to take to get it, we know what could go right, we know what could go wrong, we can take a lot of the risk out of a rebrand. We can take a lot of the risk out of being different and make sure that, just like we weren’t wanting to work hard for the sake of working hard, we aren’t trying to be different for the sake of being different. We’re being different in the areas where we need to be different.

How would you suggest that people practically speaking can differentiate themselves, particularly if they’re early in their career?

It depends to some extent on the industry that you’re in, but to some extent, I would encourage you to go back and ask the question, “What is the problem I’m trying to solve for my customers? How are other people solving it? What are just the biggest remaining frustrations that people have? What are they still mad about?” Are they mad that they don’t get enough one-on-one support? Are they mad about the prices they’re paying? Are they mad that there’s certain features that don’t exist?

That’s your biggest opportunity for differentiation. It’s not just, “How do I be different?” It’s, “How do I be different in the context of my customers’ goals?” when you recognize that, it can put you in a really powerful position. If you don’t have access to that information, you aren’t sure what to do, then I would just tell you to default to incredible customer service. If you are just killing it from a customer service standpoint, then in my experience, you’re going to automatically beat out so many of your competitors.

Also, put yourself in a position where some of that innovation will happen because if you’re taking your customers’ concerns really seriously, it’s going to lead to improvements in your product suite. I find that when you demonstrate that you are bought into your customer’s success, you care as much about their success as they do, they’ll keep you along for a long time.

Last question, coming back to the idea of success odds. If you had to give one piece of advice to someone about maximizing their long-term career upside, what would it be? Stacking the odds in their favor?

I think that one of the biggest things we can do right now is give ourselves some external indicators of credibility. I think that credibility is just becoming more and more important. Being a writer for the Harvard Business Review opens a lot of doors for me. Letting people go to the Penguin Random House website and see my book opens a lot of doors for me. We’re looking for ways to be different, and I think when we’re different in ways that feel credible, that’s really important.

Right now, we have more information than ever before. The differentiator is, is it credible information? Can I trust this information? Whatever you can do to go out and pursue those goals that put you in a position where people recognize, “This is somebody who has some authority in this space. This is somebody I can trust to help me distinguish the signal from the noise,” is going to be really powerful for you. Your skills are going to matter a lot, but what you’re looking for is these sources of credibility. I think those are the things that, even though they feel a little arbitrary, they set you apart in a world that often blends together.

To me, this whole idea of reducing the odds of failure, increasing the odds of success, it’s so intuitive, and yet people don’t really go through that mental exercise in any aspect of their life in terms of trying to stack the odds in their favor. That’s ultimately the key message you’re trying to convey to them.

Yeah, it’s uncomfortable to think about the things that could go wrong. We want to just imagine it going right. There is a skill that’s hidden within all this, that you have to learn how to be uncomfortable for a little bit. What I have found is when you identify the risks to your success, if you’re willing to sit in that discomfort for a little while, the solution almost always presents itself.

I was looking for just an example in the book. I knew I needed a case study for something. I was in an airport and I walked past a Ben & Jerry’s, and I thought, “I’ve been to Vermont, to the Ben & Jerry’s factory. I’ve seen the graveyard of all their failed flavors. I know that they had a really iterative process to succeed. I bet this is a story I can work with.”

I went back and sure enough, it worked great, made it into the book. It just comes with being willing to be uncomfortable for a little bit, trusting that you will figure this out. Not everything, but you’re going to put yourself in a position where you’re going to have ideas, you’re going to have options to choose from. You don’t have to be afraid of acknowledging that there are threats to your success.

You can trust that over time and through collaboration with other people, you’re going to be able to find some of those answers. A success diagram makes asking for advice a lot easier because you can share a context. “Here’s what I’m after, here’s what I think has to go right, here’s what I perceive that can go wrong, help me think this through.” that’s a lot better than just saying, “What would you do if you were me?”

Absolutely. Thank you, Kyle. It’s been a fun conversation, certainly a thought-provoking one, and I appreciate you making time for it.

I’ve enjoyed it. Thank you.

Alright, really interesting conversation. What are the practical takeaways from my discussion with Kyle just now? One, and I think most importantly, is this idea that success isn’t just about working harder, it’s about increasing your odds. That involves looking at both what it’s going to take to succeed and what could get in your way, the things that could cause you to fail.The people who are doing this best, they’re not necessarily the most talented people, but they’re designing their decisions and their actions and their environments to tilt probabilities in their favor over time. I think that’s the key message from Kyle’s book.

Second, and he talked about this in his own experience, setbacks can feel like detours but they also provide data. When you have a disruption, like the layoffs that Kyle went through, or failures that are in a business strategy, you can use them to recalibrate. To recalibrate your strategy, to think about your positioning, and to take smarter shots going forward.

Finally, differentiation, as we talked about at the end, is really an advantage. Whether you are thinking about this individually or you’re thinking about this from the perspective of a business, in a crowded market, blending in kills your odds.Standing out, sometimes even imperfectly, dramatically increases the chances of meaningful opportunities.

We see this with people who’ve overcome odds and doing things that nobody thought that they could do. Take some of those lessons to the way that you think about your own career journey. I invite you to subscribe to Career Sessions on Apple Podcasts and Spotify. You can also subscribe to our youtube channel, and if you found this discussion enlightening, sign up for my membership community, which is called Pathwise, and our newsletter Pathwisdom. Thanks, see you next time.

Important Links

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• The Whuffie Factor
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About Kyle Austin Young

Kyle Austin Young is an award-winning strategy consultant for leaders and teams in a wide range of fields. At the core of his methodology is a powerful system for accomplishing big, meaningful goals that focuses on understanding and changing your odds of success. The nicest compliment Kyle has ever received happened unexpectedly when the phone rang during dinner.

The biotech CEO on the other end was brief. “I just felt like I should tell you that you’re the first consultant we’ve ever worked with who did exactly what he said he was gonna do.” That was nearly a decade ago, and it has set the tone for everything since.

We often talk about burnout, quiet quitting and disengagement at work, but underneath these trends is something deeper: loneliness. In this episode of Career Sessions, Tracy Brower joins JR to unpack the growing crisis of disconnection at work and why it’s affecting everything from performance to mental health.

They cover:

• Why loneliness is rising in the age of remote work and social media
• Why work is still the #1 place people build friendships
• How leaders can create belonging
• The need for both strong ties and weak ties
• How to build a network that actually leads to opportunities
• Simple ways to feel more connected starting today

This conversation breaks down the science of connection and how it shapes your career, relationships, and sense of purpose.

Subscribe and follow Career Sessions on YouTube and wherever you get your podcasts so you never miss an episode.

Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/tracy-brower

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Watch the episode here

Listen to the podcast here

The Hidden Cost Of Loneliness At Work, With Tracy Brower

Widespread Loneliness And Work’s Historical Role In Connection

Over the past few years, we’ve heard a lot about burnout, quiet quitting and the changing relationship that people have with work. Underneath many of those conversations is something deeper and arguably more fundamental, which is loneliness and the lack of community that people are experiencing. Research suggests that roughly half of people feel lonely. They lack a sense of belonging in their lives. While that feels like it could be a personal issue, it definitely has real implications for our health and our well-being. That impacts our careers.

At the same time, work has historically been one of the primary places where we as adults form relationships. We form friendships and communities there. Many people meet their closest friends through their workplace. Some even meet their spouses or partners. Themes become support systems and, in some cases, work provides a structure and shared purpose that helps people feel connected.

Some people though are arguing that we’re expecting too much from our workplaces. It’s asking them not to provide income but meaning, belonging and friendship. Others argue that connection at work is exactly what drives engagement, satisfaction and innovation. What roles should work play in helping people build friendships and community? What does it mean for leaders and teams and the way that we think about networking and professional relationships?

My guest Dr. Tracy Brower is a Sociologist and Author of the new book Critical Connections. She explores the science and practice of friendship, belonging, community and inner work. She you look at why human connection matters so much and how the same principles that shape our friendships can also shape how we lead, collaborate and build meaningful professional networks. I’m J.R. Lowry and this is Career Sessions.

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Tracy, welcome to the show.

Thank you. Thanks for having me.

You are my first second time guests. It also coincide with being about 200 episodes in. It’s opportunity for me to get back and reconnect with people who I spoke with before.

I’m looking forward to our conversation. Thanks for having me back.

Let’s dive eight in. You’ve got a new book to talk about the growing crisis of loneliness and the lack of belonging that a lot of people are feeling. Why is this become such a widespread issue?

Causes Of The Growing Loneliness Crisis

Critical Connections: Build Relationships and Harness the Power of Community in Work and Life

This is a huge issue. I’m right about it in my new book called Critical Connections. The timing is exactly right. We are so lonely. Fifty percent of us say that we’re lonely. Issues around mental health have reached record highs. Those have everything to do with connection, community and belonging. The reason we’re facing a lot of that, first of all, we have elevated convenience over connection. We don’t talk to the barista. We ordered on the app. We don’t talk to the checkout person. We get the delivery at our door.

Those superficial relationships and superficial interactions are highly correlated with the sun’s of community. We’re losing that. That’s one. Another issue is just social media and all of our virtual connections, which is like empty calories. We might have 50,000 connections but to have someone we can count on is a different thing. Some of that has replaced our experiences in real life and the time that we’re investing in real life.

The third issue was about work. Seventy-five percent of people make their friends at work. We feel seen at work. We feel connected at work. Even if it’s not idyllic, work is still a source of that connection and community. As we’ve become more distant, as we’re working hybrid and working remote, we know there are terrific benefits to some of those. Also, that causes us to feel a greater sense of disconnecting and loneliness.

Where their particular demographic that stood out to you, whether it’s young professionals, men, or remote workers that were more effective by this than others?

For sure. The demographics are incredible. Twenty-seven percent of young men say they do not have a friend. That demographic of young man is striking. Older people a lot of times struggle more with loneliness. Adolescents can struggle more with loneliness. In fact, there’s some interesting data at the adolescent level about when people work too hard on having too many friends, versus the quality of friendship. That is true for all of us.

There can also be certain demographic moments where things can be isolating. If we’re starting a new job and we haven’t reached those levels of connection yet. It can be if we move into a leadership role from an individual or contributor role. That moment, that situation and circumstance can cause us to feel more disconnected. Sometimes young parents can feel more isolated. There are definitely both demographic and situational drivers. That all points to how are we intentional about creating some of these connections.

This is a social issue at its core. Why should a leader or an organization care about the idea of loneliness and connection? Especially as it relates to their workforce.

The Business Cost Of Lonely Employees

There is so much data on this topic. There’s brilliant data by an organization called Sunny Workplace. They do work on engagement and retention in the drivers of productivity. They found that for every lonely employee, it costs about $13,300 a year. That’s based on attrition, absenteeism, and loss performance. When we feel connected to other people, we work better. We contribute better. We feel a greater sense of obligation in a positive way.

There’s a business case toward belonging. The other thing is that when people have more friends at work, they tend to perform better. It’s because we have line of sight to who is seeing our deliverable, who is involved in, what we’re creating and how we’re connected. There’s higher level of retention when we feel connected to people. We’ve all seen the data that having a best friend at work is critical or staying with the organization. That is still true. It’s been validated. It’s been replicated.

We’re big part of the reason that we stay with an organization. It’s because we feel connected. Another big reason that people leave is leadership. They don’t feel aligned with leaders. They maybe don’t feel recognized or appreciated by leaders. When leaders are intentional and cognizant about creating those connections among their team members and with themselves. It drives a lot of great outcomes from productivity, retention and performance to things like engagement and commitment.

Why Work Is A Powerful Place For People To Make Connections

You are saying that work is a place where a lot of people tend to make their friends. You said 75% of people say that they make friends at work. Why is work such a powerful place for people to make those connections? How is it changing now relative to maybe what would have been the case in the past?

Work is indeed a critical place that we make connections. There’s a few different reasons for that. One, work is someplace that we have a longer-term relationship. An average people still change jobs and organizations very frequently. We’re up to about 12 to 18 months that people change jobs or change organizations. You still get a sense of continuity over time. You get to know somebody for that 12 months or 18 months. That is a driver of relationships, that continuity. That’s one of the reasons that work is a place we make friends and connections.

Another reason that we make friends and feel connected at work is because we see the outcomes of our work. There’s that line of sight. That makes a difference as well. Another reason that we make friends at work is that we connect but with at a task and a relationship level. Task-wise, I’m counting on you to get the thing done and you’re counting on me to show up. We have that task level relationship that keeps us interacting frequently. Frequency is an element that’s important in relationships.

There’s also a relationship part of the way that we interact at work. We see each other at the coffee machine and I say, “How did your move go?” You see me at the beginning of the meeting and you say, “How’s that new grandbaby?” We have both task and relationship going on. The other thing that makes work an important place where we create connections is because we see ebbs and flows. I see you on the day when you walk in and you’re on top of the world. Things are going well. I see you on the day when you’re struggling and I can reach out and be supportive. All of those elements drive those connections and start to solidify relationships.

Given what you said earlier about the fact that people aren’t talking to their barista. They’re just ordering and picking up as they run through the coffee shop. They’re ordering food online and meeting somebody at the door. All of those things that take away those opportunities for small talk, we’ve lost those. People aren’t going to church as much as you to 1 or 2 generations ago. You don’t have those other mechanisms for forming relationships. It makes work more important. I also had somebody say to me that we’re asking too much of our workplace now. It’s impossible for organizations and leaders to fill in all these gaps. I’d love to hear your thoughts on that debate as well.

The Employer’s Critical Role In Creating Conditions For Well-Being

That is a debate indeed. One of the things that employers are recognizing is how critical their role is, whether they want the rule or not. People are struggling so much with well-being. We talked about not only is loneliness at a record high but mental health issues are to record high. If people aren’t at their best, they can’t bring their best. They can’t perform as well. Workplaces end up having to serve a role in terms of supporting people. It’s being available for people, leading effectively, and being a source of information for people. Also, creating the additions for well-being through those connections, relationships and community.

The important thing too is to think about those outcomes. Maybe an organization wants to help connect people because they care deeply about people and they want to do the right thing. They may recognize, “We’re going to get better retention, better productivity and better performance when we help connect people.” Whether you’re doing this for altruistic reasons or an organization is doing connection and community for less altruistic reasons. It’s still the right thing to do. One other thing that is helpful as I think about the way that we frame this.

I always like to say, “Leaders aren’t responsible for people’s well-being. They are responsible to create the conditions for well-being.” We all have to be responsible for our own well-being, connection and health. All of that. Our organizations and our leaders can take the responsibility to create the conditions that make it better for us in order to do that.

Thinking about my own experience as a leader, it feels like it’s gotten harder. We went to the whole COVID period and we got more willing to talk about mental health, well-being and how everybody was doing. Probably back slit on that a bit since then as everybody’s come back into the office. It does feel like you need to be looking out for people’s well-being and mental health. The expectation is there more than it used to be.

Back to the beginning of my career. Nobody cared whether I was having a good day or bad day. It was a different environment and now we do. It does put a lot of pressure on the workplace and the people who are responsible for that workplace to at least make sure that they’re creating the right conditions. Hopefully, contributing positively, too, but at least not contributing negatively.

You think that’s an important point and a couple of accounts. There is data that 69% of people say their leader makes more of a difference to their mental health than their doctor or therapist and on par with their partner. As if leaders didn’t have enough demands and expectations. We can also say to ourselves, “As a leader, I have a great opportunity to contribute positively.” That’s one.

Another is, it is important that we validate that leader expectation, leader demand, and leader experience. Statistically, less people want to get into leadership. More people are saying, “I might want to leave leadership” If we take a minute and take that deep breath collectively and say, “Leadership is legitimately harder now. Here’s how we’re supporting leaders. Here’s how we’re providing resources for leaders. As well as the people that report to them.” That’s an important piece that leaders feel that level of support and validation.

You talked in the book about trends like quite quitting and job hugging built around an individual having a negative view of work. Whether maybe specific to their situation or a negative view to the idea of work in general. How does that affect their ability to form connections at work or outside of work?

That negative view on work makes a big difference because we tend to think that all work is bad or work is a grind. That will separate us from our opportunity to feel like we’re making a difference. We all have an instinct to matter. We want places to express our talents, capabilities and make a contribution. If we have that negative view, it gets in the way of us fully participating. It gets in the way of us fully feeling like we can provide deliverables and express our best with our teams.

Loneliness At Work: That negative view of work makes a big difference. When we see all work as a grind or something bad, we cut ourselves off from the opportunity to feel like we’re making a real impact.

On the other hand, if we have a more practical view of work, I’m going to have some days that are good and other days that are not so good because work is stressful sometimes. That’s normal. That contributes to our ability to be more realistic in the work environment. Feel more connected with others because we’re coming with our best in mind that day. I don’t think we want to take an idealistic view of work. As we said, they’ll be good days and bad days.

If we recognize that work is an avenue for us to contribute, to express our talents and our skills and to be with other people and meaningful ways. That contributes not only to connection but to our suns of a steam and to our suns of engagement. Feeling engaged at work is a good feeling. We feel like we’re making a difference. All of those contribute to each other, engagement, connection and the performance that were able to contribute.

Is this is a generational thing? It’s been a long time since I started in the workforce but I don’t remember feelings like I just did the idea of work in general. It feels like more people are having that relationship with work. What’s your sense from the research you’ve done?

This is situational because over time we’re thinking a lot harder about, “Do I like what I’m doing? What am I doing? How often am I working?” That is different than a more automatic view of, “I show up. I work from 8:00 to 5:00 every day.” Situationally that has changed. The other interesting thing is if we look at the generational differences. We, in different generations, have similar preferences for what we want from work.

The big difference is our priority order is different. The number one thing that youngest generations want from work is build social capital, get mentoring and build my career. We all care about that but that’s what youngest generations care about. Mid-generation, kids, elder care, partners, threatening the needle, connecting the dots, the number one thing that generation want from work is support for performance.

Get in, get out, do the daycare dash at 5:00, or do the elder care dash at 5:00. Get things done because there’s a lot to do. The number one thing older generations want is to leave a legacy. Be part of organizational memory and mentor others. Again, we all care about those things but it’s the priority order that makes a difference in terms of what we want most. The takeaway message is it’s different by generation. It’s different situationally. We can create the conditions in the work experience for connection that meets lots of these needs across generations and across life stages.

Let’s talk a little bit more about what leaders and organizations have to do to foster this. In the book, you outline five core attributes of a strong community such as purpose, shared values, information flow, belonging and leadership. How can somebody who is in a leadership position in an organization, help bring those ideas into their day-to-day?

This is important. As a leader, when you are imparting purpose, you’re reminding them of how they matter uniquely to the big picture. You’re reminding them how that big picture relates to human beings. Reinforcing a sense of purpose at a personal level is a big deal. It’s being clear about values. We talk about this all the time. When you demonstrate values and that strong commitment to values, that goes such a long way.

Five Core Attributes Of A Strong Community

People don’t believe what you say. They believe what you do. I worked with a leader years ago and he used to say to his team, “You’re              behaving so loudly I can hardly hear what you’re saying.” We know this intellectually, but the other thing is that leaders have a laser on them. People over index on, “What did they say? What did they do? How are they behaving?” When leaders are modeling the way toward that behavior, that makes a huge difference.

Information flow is another one like openness, sharing, and knowing appropriately what to share. One of the things we know and with so much going on in the world, people are increasingly looking to their organizations as a single source of truth. It’s like, “This thing just happened. What does this mean to our organization, to my job and to our roles around here?” When leaders cannot offer certainty but focus on clarity, that makes a huge difference.

When leaders offer belonging in terms of a relationship that they form with individuals and the relationships they foster among the team. The last one is, as a leader, sometimes, you think you have to have all the answers. When leaders demonstrate humility, when their open to other people stepping in, and stepping up when the time is right. That emergent leadership, that shared leadership is also characteristic of great communities and is the way that leaders can put that into practice.

You also talked about the importance of admitting mistakes as a leader and showing that you are open to learning as other attributes that people are looking for that contribute to this sense of community in the workplace.

This is huge. There’s this wonderful concept of intellectual humility. Data suggests that people will trust you more if you are super expert and have a strong point of view and when you have appropriate humility. If you are all super expert strong point of view with no humility, your credibility will decline. People will perceive you as arrogant. They won’t be as open to listening to you. If you can mix those two, it’s cool.

They have a strong point of view and a firm stands and clarity about your passion and your expertise. When you can ask questions, when you can admit mistakes, assume that you don’t have all the answers and that other people have critical information and bring those into the room and into the conversation. Ask for feedback. Those are real drivers of trust, credibility and a strong community. When we can not only feel great direction and feel confident in our leaders. Also know that our leaders are open to input and open to feedback that helps us drive forward as a community more effectively and build those relationships more effectively as well.

With respect to friendships, not necessarily your Leader relationship. You talk about the importance of a few things including humility, transparency and consistency. We’ve talked about a few of these already but maybe not consistency in terms of how that factors in what would also be relevant to a leader relationship, too.

One of the main things we want from leaders is presents and accessibility. Be in distractible. Be present with me. Be accessible. You don’t have to be 24/7. With presence and accessibility, we build trust. Predictability and consistency is critical in all relationships in building trust. That is one of the biggest variables that builds trust. We want legibility. We don’t value as much. The people who are great poker players, we might value them but it might be harder to develop a relationship. If they’re great poker players. We can never read them.

As humans, we prefer people we can read. We prefer people who are more understandable to us. Predictability and consistency is part of that legibility. Neurologically, we prefer certainly. We shy away from ambiguity. When we have a leader that we at least know what to expect, it may not be everything that we want, but at least we know what to expect in terms of predictability and consistency. That’s a big deal. It’s interesting ideas. Consistency, predictability, accessibility, and presence go a long way in all relationships including leader relationships.

Intellectually, when you work with somebody who’s all over the map, you have no idea what to expect. At least, when you’re working with somebody who’s consistently a jerk, you know that’s what you’re going to be dealing with and you’re ready for it. If you don’t know whether you’re going to get the jerk or the cheerleader on any given day. How do you even mentally prepare yourself for that? That made sense to me in that context.

I want to talk a little bit about some of the learnings that we can take away from your book in terms of networking. You talk about bonding relationships and bridging relationships. It would be great if you could define those for us. Also talk about for somebody who wants to build a professional network. How should they think about this idea of similarity and diversity? Which are inherent in those bridging and bonding terms.

The Importance Of Bridging And Bonding Social Capital

I love this concept of bridging and bonding. Bonding social capital is when we have social capital relationships. People we can get advice from and we can get support from within our team. That is bonding social capital. Bridging social capital is those same kinds of things outside of our team like in another department, another organization or another part of our lives. We need both bonding and bridging social capital.

I love the concept of super high ways and dirt roads. If you have a relationship with somebody in your organization in another department and you have coffee with them now and then. That’s cool. That’s awesome. It’s a dirt road. You’re carving a dirt path back and forth as you get together for coffee. If you have super high highway relationships in an organization, that means that lots of people in my department have relationships with lots of people in your department. We’re pulling each in. We’re getting together and getting advice. We’ve got all these relationships across the organization. That is more like a superhighway.

That gives you tons of social capital, both bridging social capital and bonding social capital. You have more people that you can rely on. That tends to create resilience in relationships and in the organization. You’ve got all those sources of support, advice, ideas, suggestions and performance. It’s cool to think about both bridging and bonding social capital. As we think about similarities and differences, our human instinct is to be attracted to people who are more similar to us. That’s called homophily. It’s just instinctual.

People who look like us, sound like us and think like us tends to be our first birds of a feather, stick together behavioral preference. There is research that went about 50% of our network is different than us. That tends to be the greatest mix for well-being and happiness. We need those people who are just like us and speak the same language literally and figuratively. We need people who challenge us, different from us, press us, help us to think differently and challenge our thinking. That both difference and similarity is a big driver of meaningful connections and meaningful communities.

As we’re building networks, we want people who are cheerleaders. We want people who are safe haven support that we can let down our here and lean on their shoulder. We also want challenging relationships. People who will tell us, “You can do better in. You have spinach in your teeth. I have an idea for you about how you can be better.”

We need people who are advocates for us. We need people who are different from us. That we can learn from and think differently about ourselves so that we can be even better at expanding our capabilities. Bridging and bonding social capital as well as both similarities and differences help us not only build strong communities, but also be more resilient ourselves and in our organizations.

The Concept Of Strong Ties And Weak Ties

You also brought up another concept about strong ties and weak ties that I thought was relevant as well to the idea of networking.

You can think about your connections in concentric circles closest in. You have your 2 or 3 closest people and your 5 closest and you’re 10. Out to about 150 is our maximum number of connections based on our neurology. Weak ties are those ties that are further out. They tend to be statistically the sources for new opportunities, new jobs, and promotions. Even opportunities in our personal life or are volunteer life.

The reason for that is, by definition, they have access to information that are closer ties don’t. Our closer ties tend to have access to the information that similar to the access we have. Weak ties are the people that we may not know as well. We know them well enough for them to call and say, “I saw this cool opportunity, or did you know about this?” Maybe to advocate for us like, “You should think about so and so. You should know someone so and so.” Those weak ties tend to connect us. That’s for new opportunities come from very significantly.

People talk about the importance of looking at your second order connections in LinkedIn because they will have visibility into a broader range of opportunities than your first order connections who are most likely to be in your function or industry. It makes sense. A lot of people need that prodding to think more broadly because they have this negative view of networking.

We can think about more positive view of networking if we’re thinking less about what we’re trying to get and more about what we’re trying to give. Sometimes it’s hard to ask for help or ask for something. When we’re more focused on, “How can I be curious about somebody? How can I be empathetic? How can I understand more about their situation and make a contribution to them?” That can help take some of the it out of networking because we know there’s definitely that feeling about networking.

When I think too, it’s less about being transactional and more about being long-term in our relationships. This isn’t just like, “I want to capture as many business cards in the conference.” That’s super transactional. That’s about quantitative networking. If we can think about, who can I meet? Who can I learn from? Who might I have something to contribute to? That helps with the networking outlook.

Simple Actions To Build Stronger Relationships At Work

For somebody who wants to build stronger relationships at work that they could start right away. What are two or three simple actions that you would recommend?

One, lean in and get to know people. Invite somebody for coffee. Start up a conversation with somebody when you’re in line in the café. Lean into creating those connections at work. Another thing we can do is take initiative and raise your hand to do the next project or the adjacent project in the organization. It’s a myth that we bond most through team building that is purely social. It’s great. Escape rooms or pasta making classes are all great. Keep doing those.

We bond more significantly when we’re doing tasks together. We’re rolling up sleeves, solving problems, and creating new ideas or new innovations. Take the initiative to raise your hand to get involved in that next project. It’s both taking the initiative socially like, “Let’s have coffee. Would you be my mentor?” From a task relationship as well.

Loneliness At Work: We bond more deeply when we do tasks together—rolling up our sleeves, solving problems, and creating new ideas or innovations.

For somebody who wants to just work more generally on building connections and building community, any last thoughts that you would have come from your book or otherwise?

We need to be empowered. Sometimes, we wait for the phone to ring or wait to get invited onto the project. When we realized the power of our personal agency, when we reach out or take action, not only is that correlated with mental health. It’s also correlated with more opportunity for connection. That other thing to remember is it’s a flywheel. If we feel super disconnected, it can be hard to take this first step over the threshold figuratively speaking.

When we take that first step, it gets easier and it will get easier. It will build our social skills. People are reporting statistically that social skills are declining. They feel less confident. They feel less ability to connect but the more you connect, the easier it is to connect and will build that muscle again. Both as individuals and teams and as a society.

I hope we build those muscles again because having a world where everybody just sits in their house or there’s everything they need or works remotely and doesn’t talk to anybody is clearly not good for humanity. Sometimes, it feels like that’s a direct work at it.

I know. It’s so true. It’s that old movie Wall-E, where Earth is destroyed and everybody leaves. They’re just sitting watching VR headsets in their athleisure suits. That’s not where we want to go. We need to be connected and that will make us our best.

It will. Thanks for being with me. It’s great to have you back as a guest, Tracy. Congratulations on your new book Critical Connections. I wish you well.

Thank you so much. Thanks for having me.

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What are the practical takeaways for my discussion with Tracy? First, relationships are not a soft part of work. As she said in the conversation, there are linked to performance. One of the big themes from her work and her book is a connection isn’t a nice to have. When people feel a sense of belonging, when they trust their leaders, when they feel known by their colleagues creates engagement, collaboration, innovation and retention. That drives performance. Relationships ultimately are key part of how work gets done well.

Second, work is still one of the most powerful places to build communities. Seventy-five percent of people say that they build friendships through work. Even though people sometimes say that works shouldn’t be responsible for helping people create friendships. The reality is, shared goals, repeated interactions, mutual challenges, rolling up sleeves and the things that Tracey was talking about toward the end.

Those are important ways for these relationships to develop. Organizations can’t manufacture friendships. As she said, they can certainly create the environments or connection is more likely to happen. People are more likely to feel that good sense of healthy well-being. Doing that is ultimately to their advantage given the link to performance.

Third, strong careers depend on both close relationships and broad networks. What we are talking about toward the end there about the importance of having strong ties and weak ties, similar relationships and diverse relationships. People who are close to you can provide trust and supporting collaboration. People who are less close to you can provide new ideas, information and opportunities. The people who are most resilient and managing their career cultivate all of these kinds of relationships.

Finally, connection is built through small behaviors. Not big gestures. The traits that make somebody a good friend, being consistent, open, humble, and curious are the same things will make somebody a trusted colleague or a leader. Building meaningful professional relationships comes down to everyday behaviors such as listening well, showing appreciation, sharing credit, making people feel valued and heard. I invite you to subscribe to Career Sessions on Apple Podcasts and Spotify. You can all subscribe to our YouTube channel. If you found this discussion enlightening, please sign up for my membership community, which is called PathWise and our newsletter, which is called pathWisdom. Thanks.

Important Links

• Tracy Brower
• Tracy Brower on LinkedIn
• Tracy Brower on X
• Tracy Brower on TikTok
• Tracy Brower on Instagram
• Critical Connections
• Sunny Workplace
• PathWise on LinkedIn
• PathWise on Facebook
• PathWise on YouTube
• PathWise on Instagram
• PathWise on TikTok
• PathWise on Twitter

About Tracy Brower

Dr. Tracy Brower is a PhD sociologist studying happiness, work-life fulfillment and the future of work. She is a Global 50 Thinker and her new book, Critical Connections, is available for preorder now. She is also the award-winning author of The Secrets to Happiness at Work and Bring Work to Life. She is the vice president of workplace insights with Steelcase and a senior contributor to Forbes and Fast Company. Her work has been translated into 25 languages and her TEDx talk has been viewed 8.6 million times. You can find her on LinkedIn, X, TikTok, Instagram or at tracybrower.com.

Most productivity advice skips right past the most obvious lever: sleep.

In this episode, JR speaks with Nathalie Walton who leads growth at Better Sleep, the app that’s become the go-to sleep tool for 65 million people around the world.

Nathalie’s path here wasn’t linear. It started with her own experience during pregnancy where she came to realize that there was a frustrating gap in support for women’s health. That led her to found Expectful, a platform for fertility, pregnancy, and early motherhood, and eventually to Better Sleep, where she’s helping scale something that genuinely changes how people feel day to day.

JR and Nathalie get into:

• Why sleep isn’t something you can bank or borrow against
• How Better Sleep built real trust with its users in an era when most health apps cut corners
• Why expanding access to care (especially for women and underserved communities) is one of the most important problems anyone in healthcare can be working on right now

If you’re interested in health, startups or optimizing your performance at work and in life, you don’t want to skip this episode.

Find and follow Career Sessions on Apple Podcasts, Spotify, and YouTube.

Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/nathalie-walton/

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Watch the episode here

Listen to the podcast here

Why Rest Is the Original Performance Tool, With Nathalie Walton

Sleep is crucial to our well-being, and yet more people than ever are struggling to get the rest they need. Researchers increasingly recognize that sleep is not just about feeling rested. It is deeply connected to our mental health, physical health, and productivity, which is why we are covering it on a show about careers and professional development.

Sleep has also become one of the fastest-growing areas in digital health, with companies racing to build tools and technologies to help people sleep better. Our guest is at the forefront of that movement. Nathalie Walton is a leader in the sleep and digital wellness space and is currently helping guide the growth of BetterSleep, the world’s leading sleep wellness app, now serving an astonishing 65 million users worldwide.

Previously, Nathalie founded Expectful, a platform that supported women through fertility, pregnancy, and early motherhood with meditation, evidence-based content, and mental health tools. In our conversation, we are going to be talking about the growing importance of sleep, what it takes to build a trusted consumer health brand, and how mission-driven founders are expanding access to healthcare.

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Nathalie, welcome.

Thank you so much. I am so excited to be speaking with you.

I am looking forward to the conversation as well. Let us get right into it. You are focused on sleep. Why has sleep become such a major focus in the health and wellness space?

Over the last few years, sleep has no longer been seen as a luxury. It is the core pillar of health because it influences our mental clarity, emotions, resilience, immunity, and even long-term health conditions like heart disease, diabetes, and obesity. Finally, fortunately, people are starting to understand that improving sleep is one of the most effective ways to enhance their overall wellness and longevity.

Some Of The Biggest Misconceptions About Sleep

What are some of the biggest misconceptions that people have about sleep?

Some of the biggest misconceptions that people have about sleep are that you can just catch up on sleep over the weekend. Consistency is critical. I have been in many environments where the attitude is “sleep when you are dead.” That is not really an option because if you do not sleep, that could lead to premature death. While others focus on quantity rather than quality, having fragmented or restless sleep could be just as harmful as not getting enough hours. What people really underestimate and what they get wrong is how poor sleep affects their mood, focus, and decision-making in daily life. Particularly as you are thinking about your career and how to be at your best, it can have a very negative impact.

How BetterSleep Uses Technology To Help People Sleep Better

Obviously, there has been a lot of change in the space with new technologies, particularly wearables and mobile apps. How is that changing how people approach their sleep monitoring and sleep improvement?

It is actually a wonderful improvement. Technology is giving people insight into their sleep patterns in ways that have not existed before. I am wearing one right now and running a company that helps people track their sleep. What is great and something we do at BetterSleep is that we help provide actionable guidance. Technology is only effective when it is paired with thoughtful, human-centered strategies. Data alone is not going to help your sleep. You have to know what to do with it.

What are some of the things that you would suggest to somebody who is struggling with sleep using your app or something else and is realizing that they are not getting the quality of sleep that they need?

We have some fantastic advisors on our board at BetterSleep, and I speak with them regularly for this type of advice. They have shared that you start with consistency. Go to bed and wake up at the same time every day. That really puts you in a state to be able to get the right sleep that you need. Additionally, there are other things that you can do. You can reduce your screen time. You can reduce blue light before bed and create a cool and dark sleeping environment.

One of the most important things is taking care of your mind because Better sleep does not start right before you go to bed. It starts during the day. Something that I have done for the last ten years is meditate during the day. I just found some time to calm my brain. Research shows that finding some way, whether it is meditation or breathing practices, that you can implement during the day, helps you get better sleep at night. I would say consistency and good sleep hygiene in terms of a cool, dark room, but also taking care of your mind and stress throughout the day.

Where does your company, BetterSleep, fit into all of this? What do you provide? How does the business model work? What is the experience like for an individual using it?

BetterSleep is a subscription app. Most of our downloads happen between 10:00 PM and 3: AM. People either cannot sleep, or they are waking up in the middle of the night and say, “What do I do?” We have incredible content that enables people to get back to sleep or get to sleep. We have the military method, which is a counting method that helps you get back to sleep. We have a lot of breathing exercises, but one of our most beloved features is this custom sound mixer, so that you can create the right sound mix to get your best sleep.

Maybe this is a little bit odd, but I find the sound of a drying machine very soothing. My custom mix is a dryer going off, and then I have fire crackling in the background. I do not even know where that comes from, but you can create an infinite amount of sound mixes, whether it is white noise, blue noise, or green noise. That is what we do in terms of helping people get to sleep. In terms of helping people understand their sleep, we have a feature where you are able to record your sleep.

Let us say you or your partner is a snorer, and you want to see if something is happening in the middle of the night. Do I have a lot of disturbances? You can come to our app, press record, and in the morning, we will share with you what sleep disturbances you have had. What I love about this feature is that you do not have to pay several hundred dollars for a wearable. It is immediate.

It is the content to help you sleep, it is insights, and we are starting to connect you to medical providers to help you understand your sleep. If you used a recorder and we saw that you are snoring or that you are gasping in the middle of the night, we can then connect you to providers who can help you understand whether you have sleep apnea, and all of this is covered by insurance. Ultimately, we are creating this sleep ecosystem to help you get your best night’s sleep forever.

Sounds like a lot of different things coming together to provide a comprehensive individual customer experience.

Yes, because ultimately that is what you need, as no two people have the same sleep issues. There is no generic solution, and that is why it has to be customized for the individual.

Sleep: No two people have the same sleep issues. There is no generic solution, and it has to be customized for the individual.

How Nathalie Used Real-Life Challenges To Build Companies

I know this is not your first dive into the health space. You were running a women’s health company focused on helping people through pregnancy that was inspired by your own difficult and life-threatening pregnancy. Can you share that story and how it has affected your path as a founder?

In 2020, I had my son, and I had a challenging, high-risk pregnancy. I was in the hospital multiple days a week and had a very complicated birth. I found that to be a harrowing experience because it was isolated, and mentally it took a serious toll on me. I was not sure if I was doing everything I could for my baby. There is a certain burden that I hope very few people face, but unfortunately, I know many women do face, where you have this responsibility of keeping someone alive and keeping yourself alive.

My experience exposed that there is a large gap in maternal care, particularly around postpartum and mental health support. Going through that vulnerable period made me understand how women are underserved and how critical access is, particularly from that empathetic support. It was that lived experience where I realized, “I have the power to solve this challenge.” It is a big challenge because statistics show that over 50% of women struggle in postpartum. Not only did I have that lived experience of solving a problem, but I knew that it was a big problem that was worth solving.

Why do you think this is still the case? We have been talking about this for a long time, that there are gaps in women’s health care relating to pregnancy and postpartum. It feels like we talk about it, but it has not really gotten to where it needs to be. I am curious to get your view on why.

There are many nuances as to why we have not gotten to the root cause yet, and it is very frustrating. Personally, I was very surprised by how fragmented the care is. We do not have anyone responsible for looking at it holistically. On the mother’s side, you go to the OB, and everything is about the baby. Is your baby healthy? Is your baby safe? That is critical and should not go away. At the same time, you want the mother’s doctor to look at how she is doing on a mental health level.

That is just separated from the entire process. You have people solving for one area when this requires a holistic solution. Some companies are starting to solve this, but they are small. There are a couple in Portland, some in LA, and in San Francisco, but at least on the national level, healthcare is fragmented. That is how the system is incentivized right now. It is a shame because many women slip through the cracks, and it does not need to be that way.

It really does not. How did that shape the mission and design of Expectful?

Everything that I have done previously is that, together, in the community, you can solve systemic gaps. Expectful was built around community and sharing stories. If you think back six years ago in 2020, so much of pregnancy on social media and in blogs was just the rosy picture of a new mom with a bundle of joy. We were one of the first platforms to start talking about the realities of motherhood, like the mental challenges, and making it acceptable to say, “I am struggling, and I need support,” or “I have had a harrowing pregnancy and how do I survive?” or “I have postpartum depression and thoughts of harming myself or the baby.”

At the time, that was not really discussed. How I have thought about improving healthcare, particularly those that can be stigmatized, is by being vulnerable and sharing the reality of what it is like. That is something that I did at Expectful, and it is something that I am doing now at BetterSleep by talking about what it is really like to struggle with sleep problems or mental health in pregnancy. I believe that the more that you share these stories, the more you help people realize they are not alone. This is a large problem, and there are other people facing this. When you help educate people in that way, it helps give them tools and create resources to solve the problems. In that sense, it is through community and vulnerability that you solve these massive issues that people are facing.

Building Credibility With Your Customers

Every company that starts out has to work on building credibility, but it is especially important to build trust when you are operating in the health and wellness space. How do you focus on building credibility with your customers?

This is a core pillar of how I lead companies, particularly in the health and wellness space. Many companies are not built on credibility. I think about doing this from a scientifically evidence-backed approach. How I got that credibility is that I partner with experts in the field who have medical degrees and are scientists. When it is applicable, I do research. At Expectful, we ran multiple research studies with tier-one research institutions that showed using our product led to decreased episodes of postpartum depression and increased milk production. At BetterSleep, I am working with two incredible doctors, Dr. Shelby Harris, who is a women’s health sleep specialist, and Dr. Aric Prather at UCSF.

Building credibility involves bringing in evidence-backed approaches and building a board of people who have been in the space longer than you have to help guide the creation of products. As I am thinking about the evolution of BetterSleep, I have weekly sessions with our advisors where I get their feedback. It’s like, “What do you think about this approach? Is this out there? Is there evidence for this?” It is through their lived experience in supporting thousands of patients that I can take that learning and build it into a commercial product.

Sleep: Building credibility involves bringing in evidence-backed approaches and gathering a board of people who have been in the space longer than you have.

Dealing With Regulatory And Insurance Issues In Digital Health

What are some of the other challenges that you face in building a digital health company relative to the normal things you encounter when starting a firm from scratch?

I would say the biggest challenge I face in this space is regulation. There are regulatory issues, privacy standards, and medical accuracy. At the same time, you are addressing behavioral change. That combination is inherently difficult. Unlike other startups before this, I spent a lot of time in commerce. Trust and safety in your health is non-negotiable.

You can get someone a sweater that does not look good, but you cannot give them medical advice that does not make sense. Every feature, every message, and every interaction that you build needs to meet the highest standard and be evidence-based. That is the biggest challenge I find in building a digital health company. Yet it is still so rewarding, and I would choose to do so every day.

What lessons from Expectful have you brought into BetterSleep?

Expectful was a community of the most vulnerable population, new moms. What I am bringing to BetterSleep is empathy and personalization. I learned the experience of building supportive experiences, listening to users, and integrating community and education alongside technology to improve health outcomes. I am fortunate that I had that experience at Expectful to bring to BetterSleep as we are scaling the company.

I know you have spoken about democratizing healthcare. What does that mean in practice?

This was core to my mission at Expectful and is core at BetterSleep. It is about access and making sure that everyone, regardless of income levels, gets access to the same tools that everyone else gets access to. Not everyone can afford a wearable, but everyone should have access to insights into their sleep to understand. Do you have sleep apnea, which can have many detrimental effects on your health?

What I love about building digital tools is that you are providing access at scale because the cost of subscription is very reasonable compared to a wearable or a concierge service. We are truly building for the masses. People use us in the US, India, and other countries. What I love about this digital health lowers the bar for access, and you can get the same data. Maybe you do not get as many insights, but at the highest level, you get what you need to know to help you make better decisions. Ultimately, that is what is helpful.

Here in the US, it really feels like people will not do anything that insurance does not cover unless it is an emergency. Are you getting any traction with insurance companies in terms of their willingness to cover the costs of something like BetterSleep?

There is a long process to get something covered by insurance. In order for it to be covered by insurance, it needs to be a digital therapeutic. We are not necessarily going down the pathway of becoming a digital therapeutic. That being said, we are owned by Betterhelp and Teladoc, which do offer products that are covered by insurance and are rapidly increasing their growth. It is through our relationship with our parent company that we are giving other tools that are critical to sleep, like mental health support.

They go hand in hand. We have partnerships with our parent companies to enable people to get access to other solutions that support their sleep, including our Sleep Apnea partners that are covered by insurance. As a consumer app, we cannot be covered by insurance by our nature. Our ecosystem enables us to get people to connect with the products that will help them sleep better. Those are covered by insurance. That is critical to our mission.

It seems paradoxical. It is the same thing with exercise. Sleep is critical to your health. Exercise is critical to your health. Eating well is critical to your health. Yet it feels like our entire system is built around expensive reactive things rather than preventive things.

You are 100% right. Our healthcare system is sick-based, and because of that, you have tremendous costs. Healthcare costs are so high because many doctors are afraid of medical malpractice and running tests that are not necessary, which spikes costs. You create this vicious cycle of a healthcare system that does not work for its people.

How Education Can Level The Playing Field And Change The Narrative

What are some of the other barriers that you think need to be removed to return to this idea of equitable access to health care, irrespective of income level?

A big part of it is education. That is one of the tools that can really level the playing field. That is something that we aim to do at BetterSleep. When I look at sleep in particular, there has been a narrative in the press of, I do know, probably since I started working almost twenty years ago, this warrior person grinding it out. Now you have everyone talking about 996, which is working nine hours a day, six days a week. That is unhealthy.

You have people saying that is the path to freedom and the way to go. When I think about it, that is a really dangerous narrative. When I think about how we prove outcomes, it is about education. It is about education from the same population that is sharing these difficult messages of 996 and the warrior mentality. The more that we can equip influencers, executives, and celebrities about what good health actually looks like, the more we can slowly start to change the narrative.

As more people continue on the path of living this unsustainable life and see the dangerous repercussions, where behavior leads to an unhealthy outcome, perhaps some type of disease, that is when we will probably start seeing the narrative and the education shift. We should not wait for that to happen. We should get ahead of it and help with it now.

Social media paints a picture of extremes, irrespective of the space that you are in. It is not helpful when it comes to things related to your health, whether it is mental health or beauty. I think the startup community has always been a bit extreme in terms of its expectations. Tech has had some extreme expectations, but then it grows.

You see a big company like Google that probably had that mindset in the beginning, now turning into any other big company where employees want to work 40 hours a week. There are certainly things that are working against the idea of getting good, healthy sleep. Hopefully, more and more people will start to recognize it and actually take action toward it.

That is my sincere hope.

The Role Of Founders In Closing Gaps In Healthcare

There is so much money going into this space from the venture capital community, and some of it is around longevity, the idea of the hundred-year life being the norm. What role do you see startups and entrepreneurs playing in closing some of these gaps in the healthcare space?

Founders can solve problems around issues that we have seen personally. That is really important because I am a woman and a woman of color. Certain health conditions impact me and my population in ways that do not impact the rest of the population. I hope that founders can take the problems that they have faced that VCs might not be aware of, and help educate them.

For instance, when I was fundraising for Expectful, I raised $4.2 million in my first 90 days on the job after I took over the company. I will never forget some of the calls that I had with prospective venture capitalists who would say, “Moms are fine after birth. What are you talking about? This is not a problem.” What worried me was that some of these VCs had partners who were about to give birth. I cannot really think of many women who would say that mothers’ mental health is great.

It is just not. When you have people who have lived this experience, and they have a conviction and a point of view, they have the ability to tell a story and help everyone understand what the problem is. If they have the capacity to get capital and build a solution for it, I think we are going to start to see many challenges that have been underserved being served. That is a beautiful thing. It is an exciting time to be alive, and we are able to solve some of our most challenging problems.

Sleep: When you have people who have lived this experience and get capital to build a solution for it, we will start to see many underserved challenges being served.

Areas Of Women’s Health That Require More Attention And Investment

What are some of the areas of women’s health that you think still need more focus, innovation, and investment?

There are many. Maternal mental health is an area that continues to be underserved. There is menopause support, hormonal health, and chronic conditions like PCOS. These are really large problems. There is also room for products that integrate behavioral, physical, and emotional well-being. We are just at the very beginning days of solving for women’s health. I am grateful that there are companies like Maven that have paved that path.

Women make up 50% of the population. When you think about things like menopause and perimenopause, I recently saw a statistic where 60 million women are going to go through that in the US, and we are not building for that. That is a large TAM and something that people go through for many years. I am grateful that there is a light being shone on it and that we can start innovating in that space more.

Back to the question I asked you earlier in the conversation about why it is still like this? I guess it is just because historically, the medical profession doctors were men. The researchers whom people listened to were men. The people making investment decisions were men. Men can only empathize and relate so much. There is no substitute for actually experiencing some of these health challenges. It takes women pushing for this and having to yell louder to get the investment in the areas you are talking about. Everybody goes through these changes, whether it is pregnancy or perimenopause. They have been areas of underinvestment historically.

They have. One thing that people forget, even though it is frustrating, and I do not want to say this as an excuse, but change does take time. If I look back ten years ago, a lot of these companies that were solving women’s health issues did not exist. Over the last six years, even since I started building Expectful, I have seen a huge growth in these companies. Change takes time. I understand the historical barriers, but we are making progress, and that is something that we should celebrate. We have to just continue to do this. Great companies are not built overnight. They take decades to build. With patience and continuing to advocate for the problem, I think we will start to see change.

More generally, what do you think the future over the next 5 to 10 years looks like in the digital health space?

It is undeniable that AI is going to have a large impact on the health and wellness industry. What I worry about in terms of AI is that people start to treat AI as a substitute for actual care. That becomes very dangerous. Going to ChatGPT or Claude for all of your answers can yield good advice, but sometimes it cannot. Over the next several years, we are going to see many companies go out of business because they might not stay relevant with the innovation in AI.

I hope that, despite this, builders continue to layer on an empathetic human-led layer and connect to actual practitioners. That is going to be the differentiator. While I have a gloomy outlook of the future, I am also hopeful that we can leverage AI to improve human-led empathy and connection to care providers so that people get better care at a more accessible price point. Our overall health continues to improve. That would be my hope.

Why You Should Prioritize Restorative Sleep

My hope too. Last question. Bringing it back to your customers and my audience, what is one thing that you would suggest to people that would have an outsized impact on improving their health?

From my vantage point of running a sleep company, I would prioritize restorative sleep. It affects every part of your health. Your mental clarity, mood, immunity, and long-term disease risk. Improving your sleep is one of the fastest ways to see meaningful improvements in overall wellness. On top of that, it helps you stay away from sugary snacks, which lead to other challenges. Prioritizing restorative sleep is one of the most effective things that you can do to prioritize your health and well-being.

We will leave it with that. Thank you for sharing your story and your insights, and for the work that you are doing to make health and wellness more accessible to people everywhere, and for the focus on women’s health as well.

Thank you so much, J.R. I really enjoyed this conversation.

I did as well.

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What do I want you to take away from my discussion with Nathalie? First, sleep is foundational to our health, whether physical health, mental health, wellbeing, performance, or productivity at work. It is not something that you can catch up on. Consistency is a key part of the equation, and small changes to sleep habits can have a large impact on how we feel and function. Not just in our personal lives, but at work too.

Second, and I think you heard this from her story, some of the most meaningful professional journeys start with personal experience, and what Nathalie went through while pregnant highlights how identifying a problem and experiencing it firsthand, especially one that affects your health or your wellbeing, can lead to building solutions that really resonate with millions of people. They’ve got millions of people using the BetterSleep app every day.

Third, especially in the space of digital health, trust is essential. You cannot take a cavalier attitude that is frankly happening in a lot of other companies towards your consumers. You really have to combine evidence-based information, thoughtful design, transparency, and relatability to earn that trust. It’s funny and interesting that the most beloved feature is the sound mixes that can help people fall asleep. Obviously, that’s a way that BetterSleep has built trust.

Finally, expanding access to healthcare, particularly in areas like women’s health or for those who are low-income or in remote areas. To me, it’s one of the biggest opportunity areas in the healthcare space today. I remain hopeful that through things like telehealth, which we’ve all gotten used to since COVID, wearables, apps, and other things, we will improve people’s ability to monitor and manage their health with help from a medical professional without having to go to an emergency room or urgent care.

Thanks again to Nathalie. I invite you to subscribe to career sessions on Apple Podcasts or Spotify. You can also subscribe to our YouTube channel. If you found this discussion enlightening, please sign up for the Pathwise membership community and for our newsletter, which is called PathWisdom. Thanks, and see you next time.

Important Links

• Nathalie Walton on LinkedIn
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• Expectful
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About Nathalie Walton

Nathalie Walton is a consumer technology executive, founder, and investor working at the intersection of health, wellness, and modern family life. She is currently a General Manager at BetterSleep, where she leads a multi-million-dollar subscription business focused on sleep and mental wellness. Previously, Nathalie was the CEO and Co-Founder of Expectful, a leading mindfulness platform for fertility, pregnancy, and motherhood, which was acquired by Babylist. Earlier in her career, she held leadership roles at Google, eBay, and Airbnb. Nathalie’s work and perspective have been featured in Vogue, Forbes, and Fortune. She holds an MBA from Stanford and a bachelor’s degree from Georgetown University.

In this episode of Career Sessions, Career Lessons, JR Lowry sits down with Gabriel DeSanti and Alex Dworsky, co-founders of Staj, a platform built around a simple but powerful idea: What if you could experience a career before committing to it? They explore why traditional career decision-making is often based on limited information and how that leads many people to feel misaligned years into their careers. Drawing on Gabe’s experience trying nearly 200 different jobs and Alex’s background in corporate America, they discuss how career exploration can shift from guesswork to intentional experimentation.

They cover:

• Why most people choose careers without truly understanding them
• How short-term “career experiments” can provide clarity
• Practical ways to explore new industries without prior experience
• Why curiosity and initiative matter more than a perfect resume
• How to build credibility quickly when pivoting careers
• The role of networking and real-world exposure in unlocking opportunities

They also share insights from building Staj and what they’re learning about how people test and transition into new paths.

If you’re early in your career or considering a pivot, this conversation is for you.

Follow Career Sessions for weekly insightful episodes just like this.

Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/gabe-desanti-alex-dworsky/

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Listen to the podcast here

How To Explore Careers Without Guesswork, With Gabe DeSanti & Alex Dworsky

Broken Traditional Career Decision-Making Process

Choosing a career is one of the biggest decisions we make and yet it’s one that a lot of us make with surprisingly little information. Think about it. We had down a path based on advice from friends or family. Maybe a class or an internship but mainly, it’s a lot of guesswork. We rarely get to see what a job looks like day-to-day before we choose that path. This is a big reason why a lot of us end up wondering as we get into a job, whether we’ve chosen the right direction for ourselves.

Our guests are trying to change that. Gabe DeSanti and Alex Dworsky are the co-founders of Staj. A platform built around a simple powerful idea. What if you could experience a career before committing to? Gabe has been on a mission to build the world’s longest resume. Trying out shops across a wide range of industries to better understand what different careers can involve. This journey of experimentation became a big part of the inspiration behind Staj.

Alex has spent her career inside Corporate America seeing first-hand how careers are built and how people often end up disconnected from the work they’re doing. Along the way, she noticed that many of them were trying to make this life defining career decisions without real exposure to the jobs, industries and people behind them.

In our conversation, we’re going to be talking about why traditional career exploration is often broken, how people can run small career experiments to figure out what they want to do, and how someone can break into competitive industries without traditional credentials. More importantly, we’re going to focus on practical advice. Things you can do to explore new paths, make better career decisions, and build a career that fits who you are. Whether you’re just starting out or well into your professional journey. I’m J.R. Lowry and this is Career Session.

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Gabe and Alex, welcome. Thanks for joining me on the show.

Thank you for having us.

Thanks for having us.

Let’s get right into it. You started Staj because you felt like the traditional approach to choosing a career is broken. What’s wrong with the way we’re doing it?

Careers Chosen Without Self-Understanding Or Clarity

A lot of people choose their careers when they have no idea what they want to do in their lives. They either listen to their college career people or their parents or whatever they think is right for them. When you’re 22, you don’t know what you want out of life, what you want to do and what you’re good at. It doesn’t give you an opportunity to try it before you commit to something. The job market or a career placement doesn’t align with how people are working.

Do you think this is an element of being linked to Gen Z and what they want out of work? Is there still a COVID hangover that we’ve all felt psychologically has been continuing to his generation of people entering the workforce? Is this something that’s gone back for than that?

It’s gone back further. I’m not Gen Z. I’ve seen it when my generation arrives at the time that they’ve been working for 10 to 15 years. It’s not aligned with their passions or what they want out of life. I’ve seen it with anybody who have been in a job for a little bit too long. It’s not giving them the passion that they want back. It gets people excited to realize that there’s more out there than what they’re doing. Maybe they can do it and make money and be successful.

It does go back farther than just our generation as well. We’re seeing it more now because of the internet and our access to so much. People are able to connect on the fact that maybe we are aligned in the careers that we’re supposed to be in. It’s more of open discussion topic now more than ever.

There’s probably a lot of truth to that. I’m Gen X and on the old side of Gen X. When my generation was starting in the workforce, we had no clue what we wanted to do either. We stuck with it more. Maybe this generation is willing to do and that’s maybe worth the shift has happened. Do you think the companies have a role in this, too? What are they doing that’s contributing to this lack of alignment in terms of what they’re offering and what people are looking for?

Lack Of Real Job Exposure Before Committing To Careers

When you’re in an interview, you don’t get any sense of what the job is like. Even if you were to talk to one or two people that might be on your team. It’s trial by fire. You’re lucky if it aligns with what you want to do, but I don’t know if want to join a company. You experience it while you’re in the seat. It might be a little bit too late if that doesn’t align with what you want to do. When you’re interviewing, you’re interviewing with a couple people. You don’t get a good sense of the culture or the people that you might be working with. There has to be a better way to know what you’re getting yourself into before you start.

It’s always hard to know up front what a job was going to be, even if you have done something some more to it before you may not have worked in that similar culture. It’s hard to convey all that in an interview process.

Careers Without Guesswork: It’s always hard to know upfront what a job will be like. Even if you’ve done something similar before, you may not have worked in that same culture.

Gabe, that brings us to you. You’re on a mission to create the world’s longest recipe. From what I can see on LinkedIn, you’re succeeding pretty well so far. You’ve tried a whole bunch of jobs across a very broad range. What motivated you to start experimenting with careers in this way?

It’s a bit of a journey experience in my bones and at my core. I’m a content creator. I love to make videos. Before I was a content creator, earlier in my life, I went to trade school. In trade school, you have to try all the different trades before you pick the one that you’re going to get certified in or the one that you’re going to study for the four years that you’re there.

Going back to that time in my life, I was so curious. I genuinely enjoyed trying all at a country even if it wasn’t the one that I ended up pursuing. I remember being at that time in my life and being like, “I wish I could try everyone’s job.” Even though there’s 8 or 10 years between my time in trade school and when I started this series of trying all different jobs. That thought came back to me eventually. It was something that always stuck with me. That was a big part of how I got started.

What jobs have you done that have completely changed how you maybe thought about that profession?

Career Experimentation Through Job Shadowing And “Stages”

I’ve gone to work with such a wide range of jobs now for almost 200. Every room that I walk into, I walk into it with like my curiosity just open. I’m going in and I’m taking away something from every situation. Some jobs that stand out to me are the more untraditional ones, where people created almost a role for themselves

An example of that is a dog excursion role. There’s not a job title for this. It’s essentially this guy who takes this group of dogs from New York City and brings them hiking every single day for five days a week in Upstate New York. He then brings him back to the city and drops them all off at their houses. It’s like an extreme dog walker as an example of that. It’s not a role that you think of when you think of maybe even being in the pet industry or working with animals. It was a role that he liked created for himself out of a need that he identified.

He started as a traditional dog walker and over time he was like, “These dogs need more exercise. I wonder if I could bring them on a hike.” He started bringing one dog on a hike and then two dogs. Now he brings twenty dogs on a hike at the same time. Alternatively, there’s another woman. Her name is Cindy. She makes guitars out of old New York City building wood. She’s not just taking a guitar template, putting it on a CNC machine and building it.

She’s finding and sourcing this old building wood and then she’s making guitars fully custom and fully by hand from that. That’s for artistry. These people who just dreamed up this thing and put it into action. That’s incredible. I see that in more traditional ways as well of people who are doing one career and then they completely switched up their career. Even though it still might be a traditional pass, but the creativity is what it all comes back to of what people can dream up for themselves. That’s the best part of what I take away from it.

For somebody who’s thinking about doing one of these internships, you’ve done 200 of them. Which is just an astonishing picture, by the way. What can they go into these things doing so that they get as much out of the experience as possible and get his best the sense that they can?

Learning From Real-World Career Experiments And What People Don’t Like

It helps if you have a genuine interest or even just an inclination of interest in an industry. Our hope is when you walk into a new internship or into Staj or into a job shadowing experience, you don’t have to fall in love with it. There’s so much value in identifying afterwards. I didn’t like that at all. Being open to whatever’s going to happen during that day or during that time, you’re going to get the best results. Whether it’s positive or negative being, “I don’t like this.”

To your point, if you go in into one of these conversations with an open mind and build that into the view of, what do I like to do and what do I not like to do? It certainly will help. I would imagine there’s other things you have to be thinking about. Probably there are some awkward conversations. Especially with somebody’s people doing these one-off things like, how much money do you make doing this? For a lot of people, the money part is an important part of the equation.

It absolutely is. That’s what we hope people can learn. Even in my content, I open the videos with this very vulnerable question of, “How much do you make in a year?” It gets people in to watch the video but it’s also that educational component. It’s like, “You can make $200,000 bringing dogs on a hike? You can make $15,000 making guitars?” It is important for people to learn that information and to put that information out there so people know what’s possible.

Understanding Career Values Beyond Just Job Titles Or Money

Also, it’s not just the money but, do I get to work with people? Do I get to be creative? Can I be outside all day? It’s understanding what your values are and see how that aligns to this potential job opportunity.

How do you make sure, Gabe, when you’re having these conversations that you’re not getting people at one end of the spectrum? One of the things with the influencer market in particular is everybody thinks they can make tons of money. The reality is that, the vast majority of people will never make much money at all doing that. There’s that extreme hockey stick phenomenon. When you’re doing all your interviews, how do you sense check whether this person is an extreme case?

I feel like I hold the whole process very close to my heart. When I reach out to somebody or when I find the person who I’m going to go to work with, even though there’s not like a formal pre-interview. The interview starts from the minute I send that message and maybe get a message back. How long does it take for them to respond? What is their sentiment when they respond? Are they excited? I can gauge what their personality is.

I’m typically trying to find people who are making content about their job. That’s how I find a lot of the people that I end up filming with. Most of the time, they’re just simply making videos because they either are hoping to maybe make that a new part of their business or they want to educate the market on what it’s like working in their industry. I find that those people are typically great people to interview for my videos. It also gives me a sense of their personality.

Alex, how did the two of you come together? What led to the creation of Staj?

My brother is a chef. Before you get a job at a fine dining restaurant, you work in the kitchen for a day. It helps you see if you’re good fit for the kitchen. If the chef likes you, they test your skills. It’s part of the interview process. That’s called Stajing. It’s a French word that means internship. It is such a fascinating concept for me. It inline so well with the fact that you don’t know what you’re getting yourself into before you take a job. Me being in Corporate America, we don’t have that type of experience.

While I was in the midst of Corporate America and seeing people start their own companies, it made me excited to get a better understanding of what other people are doing and how they got started. It helped me take a dive into entrepreneurship. I was trying to figure entrepreneurship while speaking to other entrepreneurs and understanding what this is like and what I have to do. As you probably know, J.R, it’s not just an idea. You have to learn finances, marketing, operations, QuickBooks and accounting.

While I was trying to figure out the marketing aspect of it, I realize that’s not a strength of mine. I came across Gabe’s profile on Instagram. Everything he’s doing by building the world’s longest resume and trying other jobs and showing people what it’s like to work in other industries aligned so well with Staj. I reached out. We shared a couple messages and we met in person. It was so perfect because we aligned on so many things. It was exactly what he wanted to build as a next step to his brand and content. We’re like ying and yang with each other. He’s content and marketing. I am finance and Ops. We come together and have this perfect union while we’re building this thing together.

How does your business model work? Describe it on both sides. Both for the hosts who are offering these stajes and the people who are looking to try something out.

We call it a job shadowing marketplace. We have stajes where the people who want to shadow and host to the people that will be shout out. The business model works where the staj will pay a four-hour experience and that’s in person. We give a commission back to the host to incentivize them for their time and to keep working with us. What’s great about that is that both sides can get what they want out of the experience.

As a next iteration, if the host is looking to hire, if this stock experience is part of an interview process, for example, then we take a recruiting fee if they get hired for a full time job. That’s the today iteration. We’re in our building year because we’re still trying to figure out are use cases in our demographic. We’re offering stajes for free for 2026 to collect a lot of use cases and customer stories. We are planning on taking it to universities, to corporations to figure out where the gap of the market is, what type of demographics see value in this and how to create a recurring revenue model.

What are you hearing so far from the people who have done one of these staj assignments about what they’ve learned both good and bad about whatever job they wanted to try out?

I love the bad part, too. That’s what’s helpful. It’s to see the not-so-nice part about it. A lot of the stajes that we’ve done almost scratched an itch that they were trying to figure out how to scratch. Our stajes were ones that are working in Corporate America, full-time jobs for the last 10 to 15 years. They’re like, “I’ve always wanted to be a private chef or I always wanted to understand what it’s like to work in floral design.”

They’re able to do it. It’s not so glamorous as they think it’s going to be. It’s a lot of hard work but with the ones that they got their hands dirty was such an interesting view for them. The floral design satj was like, “I liked it as a hobby. It’s not something I want to do full-time.” As the private chef, for example. He has worked over and over again with that chef as his help, as his staj. It’s so cool to see. While he’s still keeping his full-time job, he’s slowly entering into the cooking world and getting more experiences. Eventually, he’s going to take the leap. It helps people get that jumping off pad or a little bit more research on like, “Is this something I want to do?” It’s a hobby or this is something where I want to quit my full-time job and do it.

So far, do you have any sense of what the percentage of people who have that yes-no reaction after they’ve had this experimentation?

Since it’s such a new concept, it’s people who are trying out their hobbies where they want to see if it’s possible to do a full-time. A lot of what we have to do is teach the world on, “This is something that’s part of your career exploration process.” If we’re able to get into universities and college space, it’s going to be a lot more informative for students because they have to pick a career path. They have to start after college somewhere.

Where the people were working with now are the Millennials, the 30-year-old, 40-year-old, and 50-year-old to our little bit more risk adverse because they have a mortgage or a family that they have to pay for. Where once we’re able to delve into the university market, we’re going to get a lot more yes-no or interesting facts that come up after these types of experience to see that they don’t want to go down a career path that they always thought they should.

Obviously, we have vocational schools and then we have schools like a Northeastern that has a work and studying method of co-ops where you get a little bit of opportunity to try some different things. There isn’t this existing experimentation market that’s available to allow people to do internships or job shadowing in a massively scaled way. There’s a gap in the market and leads to people making decisions that then they want to later reverse. That’s separate from your point from a minute ago, Alex about the hobby factor. The people who want to think about doing something that may be is just up until then been their hobby.

They’re in a moment where like, “Can I monetize this? Can I make this my life?” That’s a scary dumb. If you are going to quit your stable career and move to something that doesn’t necessarily give you as many benefits as you had before, you should be a little risk adverse when you make that decision.

Talk about situations where people are contemplating a career change. What have you learned in your work so far about the practical ways that somebody with no connections in an industry can get exposure to something? Whether it’s doing a massage or otherwise.

Using Curiosity And Values To Explore Career Options Intentionally

The most important thing for somebody to do is figure out what they want. What aligns their values? What don’t they like? What do they like? What are they interested in? What are they good at? Find people you’re interested in that are doing the thing that they love or are a potential mentor that has navigated this change or career path before. Be bold and reach out to them. Literally, 10 times out of 10, we get positive responses, especially from hosting.

I love this. I was just in their shoes. I know exactly what it’s like to make a career switch or reach out to someone online that I don’t know. They are always willing to give their time and information back because it is hard. It’s also super empowering to be able to make that switch. As long as you have the confidence in boldness, reach out to whomever you find online or a mentor that can guide you in the right direction.

Some of the bad questions or the good questions like, how much money do you make, how hard is it, what didn’t you know about this industry that you can tell me now? It’s getting in person and getting a clear view of what you’re getting yourself into is the best way to start. I know all the people that Gabe and I spoke to are always willing to help    and introduce you to more people. They take you on the journey that they went on themselves. It’s such a beautiful flywheel effect where you meet one person. They introduce you to more and then you have this incredible range of network and mentors that you can reach out to.

This question has two parts and it depends on what part of your life that you’re in. If you’re more experienced in your career, your picture of that experience is going to be different than someone who is younger in high school still or maybe just entering college. It is a bit of a different conversation. When you’re younger, you might have a little more of a risk tolerance to try something new than when you are older.

Some basic ways that I’ve seen people just even begin to test interests because it’s all about experimentation. You need to experiment to even identify, “I like this or I don’t like this.” Some ways that I’ve seen people get that very entry level even before internship, school, or job shadowing is workshops. Applying and going to one day workshops in different fields is a very easy access point no matter where you are. It’s typically pretty cost effective as well to test something and do it with your hands.

Aside from that at a little more of a higher-level trade school is something that’s not talked about enough and I wish that it was. It was such a huge influence on me and such a huge part of my life. That’s what we are trying to do with Staj. We recreate what that looks like but in a non-formal setting. Those are some of the ways that we see that exposure to Industries.

Particularly in the trades, where you get a little bit more of a vibe senses feel of what a job is like than you do in an office-based job. As you’ve probably read in the news, as I’ve been reading in the news, there’s a lot more need for people to work in the trades. With AI eating office jobs, maybe we’ll have a little bit of more of a shift to people back into that space.

It’s funny with our stajes that we’ve schedule. We make sure that we schedule the day where there’s something that they could shadow going on so they can get a good idea of what the job is outside of the boring admin work that we all have to do. It allows them to see it’s more dynamic than just boring corporate jobs.

Coming back to this pivot thing for a minute. For somebody who’s trying to make a pivot, what are the best ways for them to demonstrate credibility?

Building Career Credibility Through Curiosity, Initiative, And Exploration

The best thing that our stajes have provided his curiosity because these are such dramatic shifts from what they’re doing. We see a lot of people that are successful in Staj or successful in a career transition is hunger and curiosity to understand 100% of what’s another industry like. To do the Staj experience, reach out to people on their own, do workshops or trade schools. That requires a lot of self-determination and hard work.

All that requires, at least in the beginning, is just as long as you’re curious, hungry and interested in learning something new. That will lead to what your passionate about. If you can find your passion, you do these experiences. You talk to people. That helps you build credibility because you can go into a conversation, perhaps an interview with this experience behind you. I’ve reached out to these mentors.

I have done in-person experiences with these different types of platforms like Staj or trade schools. It proves to the person that you’re speaking to or hiring that you are excited and interested in the thing that you want to do. That leads to a very successful worker. If you are always willing to learn and have the self-motivation to learn, then you’re going to be golden wherever you want to get a job.

Adding on to Alex’s point there. We’ve seen that being more of a well-rounded with access and touch points into different industries and different expertise outside of even what you’re applying for. That does demonstrate the credibility that a lot of these companies are looking for. Even if the things that you’ve touched outside of the role you’re applying for, even if they don’t relate to the things that you’re applying for. Having those well-rounded outlooks in those perspectives bring credibility to your resume.

You’ve got companies who are doing internships. Particularly the ones that do a lot of entry level hiring. They use these summer internships and winter break internships as a way to let people test drive. Also, for them to get a sense of how these people might be as full-time hires. What else would you like to see companies doing to support what you’re doing or to support this idea of career discovery and experimentation?

Careers As Test-Drives And The Importance Of Real-World Exposure

I would love to see them do internships that place people in different roles within the company during the time of that internship. Not just leaving them in this one role during that entire month. I would love to see them work for different roles in that month. If it is a test drive, then let people test drive. It should be a two-way street or a two-way interview almost for that month. Ultimately, you want your people to be working in a place that they’re the most passionate about.

Careers Without Guesswork: People can try different roles within that month. If it’s a test drive, let them test drive—it should be a two-way street, almost like a mutual interview. Ultimately, you want people working where they’re most passionate.

I completely agree. They also should not just give the interns the work that they don’t want to do. I don’t think that valuable at all. They should let more different roles but also connect with leaders or full-time people in that space. Hear from the people that are doing the job rather than the intern manager.

I think about some of the places that I’ve worked. We’ve had some of these rotational programs weak to weak as you were describing, Gabe. Maybe you do 3 or 4 or 6 months at a pop if it happens to be over your first year or two in a job. People who are in those programs love them because they get to see these different things and work with different groups. They get a better sense of what they think they would fit with.

A lot of times, the groups that are the recipients of these interns want them for longer because they have to invest in getting them up to speed and trying to get something out of them. That’s one of the tensions that exists in all of this is. How can you construct something that gives you a meaningful sense of whether this person might be a good fit for your organization at the same time give them a good view of what it’s like. It’s a hard thing to manage because managers have other things to do including the boring stuff. There isn’t always that perfect opportunity to mesh all of this together and have everybody walk away going, “That was a valuable learning experience for us.”

Completely. There’s a big gap in that market.

Coming back just to the broader idea of career discovery, how do you see things changing going forward? Particularly for this Gen Z population and not far behind them, the Gen Alpha population that’s entering the workforce?

There’s going to be new ways to learn and there’s already new ways to learn. People are learning from videos on the internet. Something as simple as that is going to be something new that needs to be adapted to not only the workplace but to our educational systems. Our education system is designed for generations that were way before us. I just think that the model needs to evolve. I don’t necessarily have to solve for that. In terms of creating new workers, it needs to evolve in there needs to be more access to what work looks like.

It’s a hard problem to solve. It’s not something that the two of you or Staj alone are going to solve even if you’re wildly successful. It’s a societal thing that we’ve got to figure out.

Some of it as we’ve talked about in the conversation is a bit unique to this generation and the dynamics that have been at play over the last 5 to 7 years. Some of it is also just an age-old problem of helping people figure out what they want to do with their lives.

It’s a match between that and then keeping up with the pace of new technology and offerings. What the job market was like ten years ago versus now is vastly different. It’s going to be insanely different in 10 and 20 years. It’s also merging. The age-old question of, “What do you want to do with your life?” With, what tools are available for me? What new job Industries are open that my parents never had access to?

For someone who wants to be more intentional about designing their career, what else besides curiosity would be important to their mindset?

Figure out you actually like. What do you want to do? Do you want to make a lot of money right from the get-go? Do you want to be creative or work with people or work remote? Be crystal clear on exactly what you want, what drives you and makes you happy. That helps you lead in the right direction of what you’re prioritizing and value out of careers. When you are trying different jobs, whether it’s a yes or no. It will lead you in the right direction.

One of the things that comes to mind for me, willingness to be adaptable. This idea that you’re going to be doing one thing or even that you have to do one thing you’re entire professional life. It’s out the window. Being able to constantly be in this mode of thinking about the next year, the next three years, or the next five years and what you want to be doing and how you might have it or how you might want to pivot is going to be something that this generation of people entering the workforce now is just going to have to have deeply ingrained in their heads.

Redefining Career Paths As Experiments And Embracing Micro-Failures

I’ll just add one more thing on top of it. Modifying your thoughts around failure when you’re exploring these different careers. It could feel like a failure if you’ve identified something and then you realize, “I don’t like that.” You feel like you have to start over. A lot of people put a lot of pressure on that decision and just shift. It can feel like a failure. Society can make you feel like a failure for not figuring it out the first time. Ultimately, it is a long journey. That failure is only a failure if you stop there. Taking that and just jumping to the next thing and then jumping to the next thing. Those little micro failures, which is what I call them, are going to lead you in the right direction.

Is there anything that we haven’t talked about that the two of you would want to leave our audience with?

It’s such an interesting time with all these new technologies and insight into other people’s jobs, roles and industries. Take a good look at what makes you happy and what you want to do with your life. Also know that there’s not one career. We live a very long life. There’s a life where you can do three different things throughout your whole career. That’s so cool and powerful to be able to do all these different things and scratch all your different itches.

Our goal at Staj is to help you figure that out and be your career guide. It’s up to you on what you want to do and what makes you happy. Know that it’s not a one-size-fits-all but it’s also that you can do one thing and switch. There’s so many different ways that you can go out there into the world and make money and help people. You need not to limit yourself.

Gabe and Alex, thank you so much for your insights and for the work you’re doing to help people, whether young or old, make better more informed career decisions and contemplate whether they are in the right path and maybe if they want to make a change.

Thank you so much.

Thanks for having us on, J.R.

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What should you take away from the conversation I had with Gabe and Alex? First, think of your career less as a single big decision and more is a series of experiments. Instead of trying to pick the perfect path from the outset, look for ways to experience different roles through shadowing, short projects and conversations with people who do the work. Real exposure will give you clarity that job descriptions never will. Second, remember that what employers are often looking for is signs of curiosity and initiative.

More than perfectly constructed career paths, building something, exploring different industries or taking on projects outside your formal role can show that you’re proactive and adaptable. Third, don’t rely on assumptions about careers that you haven’t seen up close. The day-to-day reality of a job is often very different from the way it is described. The more that you can observe and learn from people who are already doing the work, the better decisions you’ll make.

Finally, careers are built through conversations as much as applications. Talking with people in fields that you’re curious about, asking good questions, learning from their experiences could open doors and create opportunities that you’d never find just through a job posting alone. There’s a strong link here to networking and the importance of making it a regular part of your professional activities. I invite you to subscribe to Career Sessions on Apple Podcasts and Spotify. You can subscribe to our YouTube channel. If you found this discussion and lightning, sign up for my membership Community, which is called PathWise and our newsletter PathWisdom. Thanks.

Important Links

• Alex Dworsky on LinkedIn
• Alex Dworsky on Instagram
• Gabriel DeSanti on LinkedIn
• Gabriel DeSanti on Instagram
• Staj
• PathWise on LinkedIn
• PathWise on Facebook
• PathWise on YouTube
• PathWise on Instagram
• PathWise on TikTok
• PathWise on Twitter

About Gabriel DeSanti

Gabriel DeSanti is an award-winning content creator, visionary storyteller, and Co-Founder of Staj. Known as the builder of the world’s longest résumé, Gabriel brings unparalleled authority to the exploration and celebration of the world’s most overlooked, unconventional, and extraordinary careers. With a digital presence that reaches over 1.5 million followers, he shines a spotlight on hardworking individuals across industries—partnering with global powerhouses such as the NHL, Remitly, and the City of Las Vegas to champion the value of every job. Through Staj, Gabriel is redefining the traditional internship by creating immersive, hands-on job-shadowing experiences that offer real-world exposure and daily access to diverse career paths. His work not only challenges outdated career narratives but also empowers millions to embrace nontraditional routes, pursue meaningful work, and discover purpose in what they do every single day.

About Alex Dworsky

Alex Dworsky spent her career inside corporate America, seeing firsthand how careers are built—and how often people end up disconnected from the work they’re doing. Along the way, she noticed a consistent gap: people were expected to make life-defining career decisions without real exposure to the jobs, industries, or people behind them.