AI upskilling for employees is the process of training your existing workforce to understand, use, and work alongside artificial intelligence tools in their day-to-day roles. It is not about creating data scientists or AI engineers. It is about building enough applied knowledge across departments so that every employee can use AI to do their job faster, smarter, and more effectively.

For HR and L&D leaders, this is no longer a future-planning exercise. It is a present-tense operational challenge. The tools have landed. The workflows are changing. The question now is which skills to build first, in what order, and for whom.

This guide lays out a practical priority framework for HR teams that need to move beyond awareness campaigns and build genuine AI capability across the workforce.

What AI Upskilling for Employees Actually Means

AI upskilling for employees focuses on applied knowledge: how AI tools work, where they create value, and how to use them effectively in real workflows. It sits between basic digital literacy and full technical AI training.

A customer service rep learning to use AI to draft responses, summarize tickets, or flag sentiment is being upskilled in AI. A financial analyst learning to query an AI tool for data patterns instead of running manual reports is being upskilled. Neither needs to understand machine learning models. Both need confidence, judgment, and enough foundational knowledge to use these tools without making costly errors.

This is distinct from AI reskilling, which typically means preparing an employee for an entirely different role. Upskilling builds on what someone already does. Reskilling reimagines what they do. Both are necessary, but upskilling at scale is the more urgent starting point for most organizations.

The scope covers three overlapping categories: AI literacy (understanding what AI is and is not), prompt engineering (knowing how to get useful outputs from AI tools), and applied AI judgment (knowing when to trust, question, or override what AI produces). Most employees need progress in all three, but the depth varies by role.

Why the AI Skills Gap Is a Strategic Risk HR Cannot Afford to Ignore

The gap between employer confidence and employee readiness is wider than most HR leaders realize.

According to the 2025 TriNet workforce research, 44% of employers report offering formal AI upskilling programs, but only 33% of employees confirm they actually have access to one. That 11-point disconnect has grown year over year. Employers are investing in training that employees either cannot find, do not trust, or do not find relevant to their actual work.

The SHRM 2025 Talent Trends report found that two-thirds of employees, 67%, disagree or strongly disagree that their organization has been proactive in training them to work alongside AI. SHRM research also found that U.S. workers dissatisfied with AI upskilling cited three main reasons: training was not relevant to their current role (33%), sessions were poorly scheduled (39%), and they simply did not have enough time to participate (50%).

PwC’s 2025 Global AI Jobs Barometer, which analyzed close to a billion job postings across six continents, found that the skills sought by employers are changing 66% faster in roles most exposed to AI. In practical terms, what it takes to succeed in an AI-exposed job is shifting faster than annual training cycles can keep up with. Workers with advanced AI skills are now commanding a 56% wage premium over peers in similar roles without those skills.

The organizational cost of standing still is not limited to wage competition. Organizations in industries most exposed to AI have seen revenue per employee grow at three times the rate of less AI-ready sectors. When employees cannot use AI effectively, those productivity gains evaporate. HR teams that understand the pros and cons of AI in the workplace can frame upskilling not as a training line item but as a direct driver of business performance.

Sixty-four percent of HR leaders now consider the AI skills gap an urgent problem, according to Leapsome’s 2026 research. That urgency is not abstract. Missed automation opportunities, slower decision-making, and weak return on AI tool investments are the concrete outcomes when employees lack applied AI skills.

The Skills to Prioritize First: A Three-Tier Framework

Not all AI skills are equal, and not every employee needs the same training. The most effective AI upskilling programs for employees build from a common foundation and then deepen by role and function.

Tier 1: AI Literacy for Every Employee

AI literacy is the non-negotiable starting point. Every person in an organization, from frontline staff to executives, needs a baseline understanding of what AI tools can and cannot do. This is not about technical depth. It is about dispelling both over-optimism and unfounded fear.

At this tier, employees learn that AI tools hallucinate, have knowledge cutoffs, and reflect biases embedded in their training data. They learn when AI output needs verification. They learn the difference between AI that augments judgment and AI that replaces a task. This foundational layer is also where digital literacy intersects with AI fluency: employees who already use data tools and digital workflows adapt faster.

Delivery at this tier works best through short, accessible formats: explainer videos, “AI office hours” where employees can ask questions, and structured onboarding modules when new tools are introduced. The goal is comfort and clarity, not certification.

Tier 2: Prompt Engineering and Workflow Integration

Prompt engineering has become a practical skill for any employee using generative AI tools. It refers to the ability to structure inputs, queries, and instructions in ways that produce useful, accurate, and appropriately scoped outputs.

This is not a specialist skill. A manager who learns to write a structured prompt gets better summaries, faster analysis, and fewer errors from AI tools. A recruiter who prompts well reduces screening time without sacrificing quality. A content team that understands how to constrain and direct AI output produces work faster and with more control.

At Tier 2, L&D teams should map this training directly to the workflows employees already own. The highest-leverage AI use cases per team are typically repetitive, time-consuming, or easily templated tasks. For customer support, that might be drafting responses or summarizing tickets. For HR itself, it might be first-pass drafting of job descriptions or synthesizing engagement survey data. For operations, it might be automating routine reports.

Role-specific training at this level lands better than generic AI awareness content. Generic content is the primary reason employees report that AI training does not feel relevant to their work.

Tier 3: Applied AI Judgment for Managers and Analysts

The third tier targets employees who make decisions, not just execute tasks. Managers, analysts, HR business partners, and team leads need to develop applied AI judgment: knowing how to interpret AI-generated recommendations, when to push back, and how to explain AI-assisted decisions to others.

This includes data interpretation skills, which are not the same as data science. A manager does not need to build a model. They need to read an AI-generated workforce analytics report and ask the right questions about it. They need to know what the model cannot see. They need to apply ethical AI principles when AI tools are used in processes that affect employees, like performance evaluation, scheduling, or promotion decisions.

The World Economic Forum’s Future of Jobs Report 2025 lists analytical thinking as the most sought-after core skill among employers, with seven in ten companies ranking it as essential. That demand is rising precisely because AI handles the pattern recognition while humans are expected to handle the judgment. Building that capability in your mid-level leaders is a competitive differentiator.

How to Build a Role-Specific AI Training Program That Sticks

The framework above tells you what to build. This section covers how.

• Start with a skills gap analysis. Before designing any program, survey your workforce to understand current AI literacy, tool access, comfort level, and daily workflow friction points. This does not need to be a lengthy assessment. A 10-question pulse survey by department surfaces enough to prioritize. The goal is to stop guessing where the gaps are and start targeting training where it will produce the fastest visible return.
• Map high-leverage workflows before choosing content. For each team, identify three to five workflows where AI could reduce time spent on low-value tasks right now. Then build or source training that maps directly to those workflows. An account management team that drafts client recaps every week has a clear AI use case. Train them on it specifically. This approach means employees see the relevance immediately, which is the biggest predictor of whether they will actually complete and apply the training.
• Choose delivery formats that work inside the working day. The top barrier employees cite for not completing training is time, at 50% in SHRM research. Microlearning, short bursts of five minutes or less, timed nudges in productivity tools, and learning embedded in daily workflows address this directly. Organizations that deliver training outside the flow of work see lower completion rates and faster knowledge decay.
• Assign managers as models, not just supervisors. Employees look to their direct managers to understand what the organization actually values. If managers are not using AI tools and cannot coach others on them, no program will gain traction. Manager-first training, where leaders build applied skills before their teams, accelerates adoption at scale. It also signals that AI fluency is a performance expectation, not a personal development optional extra. Boosting productivity in the workplace with AI starts with leaders who model the behavior.
• Build accountability into the program. Completion rates are a lagging indicator of engagement, not competence. Design programs that include skill verification: short applied exercises, role-specific simulations, or project-based checkpoints that show whether employees can use what they learned. Organizations that link L&D metrics to business outcomes, not just training hours, are better positioned to secure continued investment.

Common Mistakes HR Teams Make When Rolling Out AI Upskilling

Even well-resourced programs stall. These are the patterns that cause them to.

• Treating AI upskilling as a one-time event. AI tools evolve continuously. A workshop held in Q1 becomes outdated by Q3. Effective AI upskilling for employees builds a continuous learning cadence: quarterly refreshers, curated content as tools change, and a culture where embracing change in the workplace is reinforced by visible leadership behavior, not just HR messaging.
• Ignoring change management entirely. Nearly 25% of workers worry that AI will make their jobs obsolete, according to Gallup research. If HR does not address that fear directly, employees will resist or avoid AI tools regardless of training quality. The most effective programs open with an honest conversation about what AI changes, what it does not, and how the organization plans to use it. Employees who understand the why are more likely to engage with the what.
• Skipping the ethical AI conversation. The EU AI Act now classifies certain workplace AI uses, including performance evaluation and recruitment screening, as high-risk, requiring transparency, human oversight, and worker notification. Similar frameworks are emerging globally. HR teams that do not include responsible use, data privacy, and algorithmic fairness as part of their AI upskilling programs are exposing the organization to compliance risk and eroding employee trust.
• Only training individual contributors. Two-thirds of organizations lack a formal AI reskilling strategy for managers and leaders, according to HR.com’s 2025 research. When only junior staff receive AI training, the tools get used inconsistently, without strategic direction, and often in ways that do not connect back to business priorities. Leadership AI literacy is not optional. It is the connective tissue between AI investment and AI return.
• Measuring completion rather than capability. A 90% course completion rate means very little if employees are not applying what they learned. Skill assessments, manager observation, and productivity data are more useful measures. The most effective L&D teams are moving from activity-based metrics to capability-driven impact models that connect directly to workforce performance and business outcomes.

Measuring the ROI of AI Upskilling for Employees

HR and L&D teams increasingly need to quantify the return on workforce AI training, not just report completion numbers. Here is how to build a measurement approach that holds up.

• Track before and after workflow time. If you are training a team on AI-assisted report generation, measure how long that task took before and after. Time-to-completion data is concrete and easy to communicate to business leaders who are sceptical about training investment.
• Monitor employee confidence metrics over time. The TriNet 2025 research found that only 49% of employees feel equipped for their roles, down from 59% the year before. Running a simple confidence pulse before and after each training phase shows whether the program is actually closing the gap, not just filling calendar slots.
• Connect to internal mobility and retention. Salesforce’s internal AI upskilling program, Career Connect, produced a measurable outcome: by the first quarter of 2025, half of all open positions were filled by existing employees. That is a retention and mobility data point that connects directly to cost savings on external recruitment. HR teams can track internal application rates, promotion rates, and voluntary turnover as downstream indicators of effective upskilling investment.
• Build the business case incrementally. A 2025 Pluralsight report found that 89% of organizations say upskilling is more cost-effective than hiring new talent. Gallup research suggests that organizations which double the proportion of employees who feel they have opportunities to learn and grow can see a 14% increase in productivity and an 18% increase in profit. These benchmarks give HR leaders the language to frame AI upskilling not as a cost center but as a strategic investment with measurable returns.

The Role of HR in Leading the AI Transition

AI upskilling is not purely an L&D function. It is a change management challenge, a culture question, and a strategic planning exercise rolled into one. HR teams that take ownership of this transition, rather than waiting for business leaders to drive it, are better positioned to shape how AI lands across the organization.

That means partnering with department heads to identify where AI is already being used, even informally. Research from Microsoft and LinkedIn found that 78% of AI users are bringing their own tools to work, downloading and using generative AI independently without formal guidance. That behavior is already happening. The question is whether HR is building structure around it or letting it develop without guardrails.

It also means advocating for the conditions that make training stick. Gallup found that 41% of employees cite lack of time for training as their biggest L&D obstacle. HR teams that negotiate protected learning time with senior leadership, even 30 minutes per week, remove the structural barrier that undermines every other training investment.

Workforce readiness for AI is not a technical problem. It is a people problem. And HR is the function best equipped to solve it.

Build AI Capability Before the Skills Gap Widens

AI upskilling for employees works best when it is practical, role-specific, and tied to the way people already work. HR teams do not need to turn every employee into a technical expert. They need to help employees understand AI, use it responsibly, and apply it with sound judgment in their daily roles.

The first priorities are clear: build baseline AI literacy across the workforce, train teams on the prompts and workflows most relevant to their jobs, and equip managers to interpret AI outputs with care. From there, HR leaders can measure what matters: confidence, capability, productivity, mobility, and retention.

The organizations that move first will not simply have better tools. They will have employees who know how to use those tools well, managers who model responsible adoption, and HR teams that make learning part of the operating rhythm of the business.

Help Your Workforce Build AI-Ready Skills With Pathwise

Pathwise helps organizations strengthen employee development, career growth, and workforce readiness through practical learning and coaching solutions.

• For HR teams building workforce development programs:
  Explore Pathwise support for organizations and HR professionals to help employees build skills, stay engaged, and navigate workplace change.
• For scalable employee learning:
  Use Pathwise career courses to support structured development across teams, including the durable skills employees need as AI changes how work gets done.
• For manager and employee coaching:
  Pathwise coaching can help employees, managers, and rising leaders build confidence, clarify goals, and apply new skills in real workplace situations.
• For broader career development support:
  Pathwise career services give employees practical guidance for career planning, skill growth, and professional development.

Make AI Upskilling a Workforce Advantage

AI will keep changing roles, workflows, and expectations. HR teams that invest in employees now can reduce uncertainty, improve adoption, and turn AI upskilling into a long-term performance advantage.

To build a stronger, more future-ready workforce, start with Pathwise’s solutions for organizations and HR professionals.

TL;DR

Organizations rarely pay the full price of tolerated arrogance immediately. The damage builds slowly through silence, disengagement, talent loss, poor decisions, and culture erosion. When arrogance gets a pass because the person produces results or holds seniority, the downstream cost to teams grows far beyond what most leaders anticipate. This article explains what organizations lose when arrogant behavior goes unchallenged and what leaders should do before the damage becomes irreversible.

Every organization has at least one: the person whose results shield them from accountability. Their numbers look right on paper. Their title carries weight. So when the complaints surface about dismissiveness, credit-hoarding, or shutting people down in meetings, leadership hesitates. The thinking goes: we cannot afford to disrupt what is working.

What leaders consistently underestimate is how much that hesitation costs. Tolerating arrogance in the workplace is not a neutral choice. It is a decision with compounding consequences, most of which do not appear on any immediate performance report. 

The damage accumulates through quieter channels: teams that stop speaking candidly, top performers who disengage before they resign, decisions made without honest input, and a culture that learns, over time, what behavior actually gets rewarded.

This article is not a primer on what arrogance looks like or how to survive an arrogant colleague. The existing PathWise piece on arrogance in the workplace covers those topics thoroughly. 

What this article addresses is the organizational cost of tolerance: what companies lose when arrogant behavior goes unchallenged because the person seems too valuable, too senior, or too politically protected to confront.

Why Organizations Tolerate Arrogance Longer Than They Should

The most common reason arrogance survives in organizations is a straightforward but costly trade-off: short-term output versus long-term culture health. When a high-performing employee delivers results, it becomes easy to rationalize the behavior that surrounds those results.

Leaders tell themselves that brilliant jerks are simply demanding. HR teams coach and reassign rather than act decisively. Peers learn to route around the person rather than confront the pattern.

Research from SHRM’s 2024 workplace challenge survey found that one in three U.S. workers reported poor management and ineffective senior leadership in their organizations. That number is significant because it reflects a systematic tendency to prioritize visible output over behavioral accountability, not just an occasional lapse in judgment.

Three conditions tend to make tolerance most predictable.

Star culture protection is the first. In industries like finance, professional services, and entertainment, high producers often receive implicit immunity. Their behavior gets framed as high standards or intensity rather than what it is: arrogance.

Fear of disruption is the second. Confronting an arrogant person who controls key accounts, institutional knowledge, or executive relationships feels risky. Leaders weigh the cost of the conflict against the perceived cost of losing the person, and they almost always underestimate the second figure.

Short-term output bias is the third and most persistent. Quarterly targets are easy to measure. Culture erosion is not. Because the damage from tolerated arrogance is mostly invisible in the near term, it rarely registers as a crisis until the costs are already significant.

Hidden Cost 1: People Stop Speaking Honestly

The first thing that goes quiet when arrogance is tolerated is candor. When team members watch a colleague dismiss ideas, talk over peers, or respond to feedback with contempt, they draw a logical conclusion: speaking up has a cost. So they stop.

This loss of candor does not announce itself. It appears gradually in meetings that feel smooth but produce no real debate. It surfaces in project post-mortems where problems are listed that everyone apparently knew about but no one raised during execution. It shows up in leaders who believe their teams are aligned but are actually receiving filtered information.

Harvard Business School professor Amy Edmondson, speaking at Harvard Business Impact’s 2025 Partners’ Meeting, made the mechanism clear: interpersonal risk translates directly into business risk. When employees face consequences for speaking up, organizations miss insights, preventable mistakes go unchecked, and opportunities for innovation are lost. Foster workplace inclusion and candor disappear together because arrogance suppresses contribution and belonging at the same time.

Arrogant leadership does not need to be extreme to suppress candor. Consistent dismissiveness, visible impatience with alternative views, or public ridicule of mistakes is enough to teach a team that silence is the safest strategy.

Hidden Cost 2: Decision Quality Erodes

When candor disappears, decision quality follows. Good decisions depend on honest input from people who know the details, not just from people who hold the title. Arrogant leaders who dismiss input and over-rely on their own judgment remove the corrective feedback loop that organizations depend on.

The Mitchell, Boyle, and O’Gorman 2024 systematic review, published in the International Journal of Management Reviews and analyzing 42 scholarly articles, found that subordinates of arrogant leaders show measurably reduced feedback-seeking behavior. That is not only a cultural observation. It is a structural problem: organizations where arrogance is tolerated will make progressively worse decisions over time, even when the arrogant individuals are technically capable.

The practical consequences include slower error correction, fewer alternative ideas reaching decision-makers, and a pattern of strategic blind spots that compound across months and quarters. By the time a bad decision becomes visible and costly, the culture that enabled it is already entrenched.

Hidden Cost 3: Engagement Drops Across the Whole Organization

Arrogance does not stay contained to the people who interact with one individual directly. The effect spreads through teams and peer networks.

Gallup’s 2025 State of the Global Workplace report found that global employee engagement dropped to 21% in 2024, representing an estimated $438 billion in lost productivity. The same research made clear that at least 70% of the variance in team-level engagement is attributable to management quality.

A single arrogant manager can reduce engagement not only for direct reports but across every team that observes how that person’s behavior is handled, or not handled, by senior leadership.

Engaged employees are the ones who bring discretionary effort, share ideas without being prompted, and stay through difficult periods. When arrogance chips away at engagement, what organizations lose first is exactly that kind of voluntary contribution. People meet their targets, but they stop going beyond them. The work gets done, but the energy that used to make it better is no longer there.

Effective employee engagement strategies are built on trust, candor, and consistent behavioral standards. Tolerated arrogance undermines all three simultaneously.

Hidden Cost 4: High Performers Exit Before Anyone Notices

The employees most likely to leave a culture that tolerates arrogance are the ones the organization can least afford to lose. High performers have options. They do not remain in environments where their contributions are dismissed or where arrogant colleagues receive implicit protection from consequences. They begin exploring alternatives quietly, long before a resignation surfaces.

Research from Second Talent’s 2025 retention analysis found that voluntary turnover costs U.S. businesses an estimated $2.9 trillion annually. The cost of replacing a manager or senior professional runs approximately 200% of their annual salary, once recruitment, ramp-up time, lost institutional knowledge, and team disruption are factored in.

Gallup data adds further context: it takes more than a 20% pay raise to retain most employees who work under a manager who genuinely engages them. But it takes very little to lose a disengaged employee. When arrogance makes meaningful engagement impossible, attrition follows.

There is also a succession dimension that organizations frequently overlook. The people who leave because of a tolerated arrogant person are often the ones being developed for leadership roles. Their exit does not just create a vacancy. It damages the pipeline that the organization depends on for its next generation of leaders.

Hidden Cost 5: Trust in Leadership Erodes Faster Than Leaders Realize

Every time arrogant behavior is excused, employees revise their understanding of what leadership actually values. The stated values on the company’s careers page say one thing. The protected behavior of a star performer says another. People pay attention to the second signal.

Trust in leadership does not disappear suddenly. It drains gradually through a series of small signals: the complaint that did not lead to action, the feedback that was acknowledged but not addressed, the pattern that everyone can see but no one in a position of authority is naming. Over time, this produces organizational cynicism that is genuinely difficult to reverse.

When employees stop trusting that leadership will hold people to consistent standards, they also stop investing in the belief that good behavior is rewarded. That shift is expensive, and it happens well before turnover or disengagement becomes visible on any performance dashboard.

Hidden Cost 6: The Culture Begins Replicating the Wrong Behavior

One of the most underestimated costs of tolerated arrogance is what it teaches the people who are watching. When an arrogant leader advances, receives public credit, or gets protected from consequences, the organization sends a message to every rising manager and ambitious individual contributor: this approach produces results.

Over time, the behavior gets replicated. Younger managers adopt dismissiveness as a leadership style. Collaboration becomes conditional. Candor becomes a liability. The organization ends up with a culture shaped by the behavior it originally permitted at the top, and the problem is no longer one person. It is the norm.

Addressing this form of cultural debt is significantly harder than addressing a single individual’s behavior. It requires rebuilding trust, re-establishing behavioral standards, and often replacing leaders who were shaped by the original tolerance. The cleanup cost dwarfs what early intervention would have required.

Hidden Cost 7: Delayed Intervention Creates a Bigger and More Expensive Problem

Research consistently shows that the longer arrogant behavior is excused, the harder and more expensive the correction becomes. HR teams that attempt coaching after months or years of tolerance are working against an established culture pattern, not a single behavioral issue. 

The Mitchell 2024 systematic review noted that interventions focused on developmental feedback and action planning can reduce the harmful effects of arrogance, but they require willingness to change and accountability mechanisms that are rarely present when tolerance has been the default response for too long.

Delayed intervention also tends to compound legal, reputational, and operational risk. What begins as a performance management gap can escalate into formal investigations, exits that damage employer brand, or leadership failures that become visible to clients, partners, or the press.

Understanding abuse of power in the workplace matters here because arrogance, when protected by title or political status, frequently crosses from interpersonal difficulty into misuse of authority. 

Early Warning Signals Organizations Can Act On

The warning signs of a tolerated arrogance problem appear well before a turnover spike or a formal complaint. They are easy to miss because they rarely look dramatic at first.

Meetings grow quieter over time, especially in the presence of specific individuals. Rework increases because honest challenge is absent from the process. Fewer people volunteer ideas without being asked directly. Backchannel complaints and informal conversations replace structured feedback. Team members describe feeling like they need to be careful about what they say around certain people.

Skip-level feedback sessions often surface these patterns before direct management reports do. Exit interview data, when analyzed by team and by manager, frequently reveals connections that aggregate numbers hide. Engagement survey results that show consistent drops in specific pockets of the organization are worth examining by leadership relationship, not just by department or role.

Addressing manager mistakes early, before they calcify into culture, is one of the most effective things a leader or HR team can do to prevent arrogance from becoming a structural cost.

What Organizations Should Do Before the Damage Compounds

The earlier an organization addresses arrogant behavior, the lower the cost. Waiting for a crisis, a formal complaint, or a visible wave of departures before acting means the damage is already significant.

Hold star performers to the same behavioral standards as everyone else. Output does not exempt anyone from accountability for how they treat colleagues. When organizations make that exception for high earners or high titles, they signal to the entire workforce that the stated behavioral standards are not real.

Measure what the behavior is actually costing. Engagement data, retention trends on high-performing teams, skip-level feedback, and exit interview themes frequently surface the organizational impact of a specific leader or colleague long before the situation requires a formal response. Leaders who track these signals have the information they need to act early.

Intervene with coaching that is specific and time-bound. Vague coaching conversations without clear behavioral expectations and accountability timelines rarely produce change. Effective intervention names the specific behaviors, identifies the measurable business impact, and establishes clear consequences if the behavior continues.

Resist the rationalization that the behavior is manageable because results are still good. This is the most common leadership error. An individual’s output and the culture cost of their behavior are separate calculations. Organizations that conflate them consistently underestimate the second figure until it becomes a crisis.

Building the skills to improve leadership skills at every level is part of what prevents arrogant behavior from becoming a structural problem. Leaders who understand the direct connection between their behavior and organizational outcomes are better positioned to hold others to the same standard without hesitation. And empowering people at work through strong, humble leadership is the most effective counterforce to the culture conditions that let arrogance take root.

If arrogant leadership or destructive management behavior is creating measurable costs in your organization, structured coaching can help leaders build the accountability and self-awareness that strong culture requires. 

Visit PathWise Coaching to learn how our coaches work with individuals and teams to develop the leadership behaviors that protect culture and drive long-term results

Career coaching improves employee retention by giving workers a visible path forward inside the organization. When employees can see how their skills are growing and where their careers are headed, they are far less likely to look elsewhere. HR professionals and people leaders who invest in structured coaching programs consistently outperform those who do not on nearly every retention metric that matters.

This guide explains how to build and implement career coaching programs that reduce avoidable turnover, what the latest research says about coaching’s direct impact on retention, and how managers can use regular coaching conversations to keep their best people from walking out the door.

Why Most Voluntary Turnover Is Preventable

Turnover is expensive. Replacing a single employee costs roughly 33% of that person’s annual salary, according to a 2025 analysis from Capital Analytics Associates. For an employee earning $50,000, that number exceeds $16,500 once you factor in recruiting, onboarding, and the productivity gap while the new hire ramps up.

What makes this particularly frustrating for HR teams is how much of it could be stopped. The Work Institute’s 2025 Retention Report found that preventable turnover accounted for 63% of all exits in 2024. The most common reasons were career stagnation and weak management support, not pay, not commute, not benefits.

Amazon and Workplace Intelligence data shows 74% of Millennial and Gen Z employees would leave a job that does not give them enough skills development. SHRM’s 2025 State of the Workplace report identified career development programs as the top way HR professionals are strengthening organizational competitiveness. The pattern is consistent across every major workforce study published recently: employees leave when they stop growing.

That is exactly the gap career coaching is designed to close.

What Career Coaching for Employees Actually Means

Career coaching for employees is a structured, ongoing process where someone, whether a trained coach, a manager, or a career development partner, helps an individual clarify their goals, identify skill gaps, and build a concrete plan to move forward professionally.

It is different from a performance review. A performance review evaluates past output against a set standard. Career coaching is forward-looking. The focus is on where the employee wants to go and what they need to get there.

It is also different from general manager feedback. Coaching involves dedicated time, a structured format, and consistent follow-through. The Human Capital Institute’s 2025 Talent Pulse report found that 83% of organizations now report active coaching programs, with career development cited as the most common objective, ahead of leadership development and personal growth.

The format varies. Some organizations use external certified coaches for senior employees and high-potential talent. Others train managers to hold regular coaching conversations. Many use a combination. What matters is not the delivery method but whether employees leave each session with clarity about their path and confidence that the organization is invested in their growth.

For more on what effective working with a career coach looks like from the employee’s perspective, PathWise covers the full dynamic in depth.

How Career Coaching Improves Employee Retention

The connection between career coaching and employee retention is direct and well-documented. LinkedIn research shows 94% of employees would stay at a company longer if it invested in their career development. Companies with strong learning cultures retain employees at a 57% rate, compared to 27% at organizations with moderate learning investment, according to LinkedIn’s 2024 Workplace Learning Report.

The Forrester Future of Work Survey from October 2025 found that employees with a coaching manager are 1.7 times more likely to say they plan to stay at their current company for the next 12 months. The study also noted that 54% of workers now describe their manager as a coach, up from 50% in 2024.

HR.com’s State of Employee Retention 2025-2026 report puts the gap between high- and low-performing organizations in sharp focus: retention leaders are four times more likely than laggards to use effective learning and development to improve retention. Those same leaders are nearly four times more likely to have well-trained people managers.

Coaching works on retention through several mechanisms:

• Career path visibility. Employees who can see where they are headed inside the organization have a concrete reason to stay. Coaching creates that visibility. Without it, employees default to external job searches to find opportunities that feel out of reach where they are.
• Manager relationships. Research consistently shows that people leave managers, not companies. Gallup data indicates that 71% of voluntary exits trace back to poor management. Coaching changes the manager-employee dynamic. Instead of a transactional check-in, it becomes a development conversation. That shift builds loyalty.
• Skill investment. When an organization puts time and resources into someone’s growth, that person feels valued. Employees who feel undervalued disengage before they leave. Coaching shortens that gap between disengagement and departure.
• Internal mobility. Career coaching helps employees identify lateral moves, stretch assignments, and paths to promotion they might not have seen on their own. Employees who move internally are significantly less likely to leave than those who feel stuck in the same role indefinitely.

The PathWise guide on employee engagement strategies outlines how development investment links directly to engagement and long-term retention for HR teams building a broader strategy.

Four Types of Career Coaching Programs That Reduce Turnover

Not all coaching programs are built the same, and the right structure depends on the size of the organization, the audience, and the retention risks the HR team is trying to address.

1. Manager-as-Coach Programs

The most scalable approach is training managers to hold structured career conversations with their direct reports. This does not mean making every manager a certified professional coach. It means giving people leaders the questions, frameworks, and habits to have developmental one-on-ones that go beyond status updates.

When managers coach, the impact ripples across the entire team. Targeted coaching conversations can reduce preventable turnover by nearly half, according to a Gallup study cited by Chronus in a 2025 report on workplace coaching types. The PathWise resource on how to improve leadership skills provides a practical starting point for people leaders developing this capability.

2. Career Pathing Conversations

These are structured sessions focused entirely on where the employee wants to go in two, three, or five years, and what the organization can do to support that. HR leads the framework; managers deliver it. The goal is to map the employee’s ambitions against internal opportunities before they start mapping them against LinkedIn job postings.

SHRM’s 2025 Employee Benefits Survey found that 65% of employers now rate professional and career development benefits as “very” or “extremely” important. Career pathing conversations are one of the most direct ways to activate that investment.

3. High-Potential Coaching Programs

Organizations at risk of losing future leaders should invest in dedicated coaching for high-potential employees. This typically involves external or senior internal coaches working with individuals who have been identified as succession candidates. 

The International Coaching Federation data shows executive coaching delivers a return on investment of 788%, accounting for the value of retention alongside performance improvements.

4. Career Transition Support

Employees at inflection points, whether they are considering a promotion, a role change, or a move to a different function, are high flight risks. A structured career transition coaching program gives them a place to work through those decisions internally instead of externally. 

This is where organizations have the most to gain from professional coaching resources, since these moments are exactly when employees decide whether their future is inside or outside the company.

How to Build a Career Coaching Program HR Can Scale

Most HR leaders understand the value of coaching but get stuck on implementation. Here is a practical approach to building a program that grows with the organization.

• Start with manager enablement. Train your existing people managers to hold quarterly career conversations. Give them a simple coaching framework, three or four open questions designed to surface ambitions, blockers, and development needs. This costs relatively little compared to external coaching programs and reaches every employee through their direct manager.
• Identify your highest-risk segments. Not all employees have equal retention risk. Analyze your turnover data by tenure, manager, department, and level. Use that data to target coaching resources where the departure risk is highest. Two-to-five-year employees are often the most overlooked and the most likely to leave without a clear signal beforehand.
• Build in accountability structures. Coaching conversations that happen once a year are not coaching programs. Set a minimum cadence, monthly or quarterly depending on level, and make career development a standing item in one-on-one meetings. Managers who track their direct reports’ development goals on paper are far more likely to follow through.
• Connect coaching to internal mobility. For career coaching to reduce turnover, employees need to see that the conversations lead somewhere real. HR should actively communicate internal opportunities, cross-functional stretch assignments, and promotion timelines. When employees know that career coaching is connected to actual paths forward, they stay in the conversation instead of exiting it.

The PathWise guide on skill development covers how to build competency frameworks that make internal mobility legible to employees and managers alike.

How Managers Use Coaching Conversations to Prevent Exits

Most managers know they should be developing their people. Fewer know how to do it in a way that actually keeps employees from leaving.

The first shift is from evaluation to exploration. A coaching conversation is not a review. It starts with curiosity, not judgment. Useful openers include: “What part of your work feels most energizing right now?” or “Where do you feel like you are growing, and where do you feel stuck?” These questions create a different dynamic than “how are you tracking against your goals?”

The second shift is from reacting to planning. Most manager-employee conversations are reactive, focused on what is happening now. Retention-focused coaching is proactive. It asks about six months from now, a year from now. Employees who have a clear picture of where they are headed do not need to look for that picture somewhere else.

The third shift is from advice to accountability. Coaches do not just tell employees what to do. They help employees identify what they want to do and then hold them to it. When a manager asks “what did you accomplish from what you committed to last month?” it signals that the employee’s development actually matters, not just their output.

The PathWise article on feedback for professional development goes deeper on how to structure feedback within a coaching-oriented relationship so it builds capacity instead of creating friction.

Measuring the ROI of Career Coaching on Employee Retention

HR teams often struggle to quantify coaching’s impact. That problem has a practical solution: track the right metrics from the start.

• Retention rate by coaching participation. Compare 12-month retention rates for employees who participated in a structured coaching program against those who did not. This is the clearest signal available. If coached employees stay longer, the program is working.
• Internal mobility rate. Track how many employees in coaching programs move into new roles internally. Internal mobility is one of the strongest leading indicators of long-term retention.
• Manager effectiveness scores. If you have rolled out manager-as-coach training, measure changes in employee satisfaction scores for managers who completed the program. Managers rated higher on “supports my development” consistently produce better retention outcomes.
• Cost per retained employee. Calculate what you spend on coaching per participant, then compare it against the cost of replacing one employee at each level. For most organizations, even a modest improvement in retention among high-potential or high-tenure employees produces a clear return.

HR.com’s 2025 research notes that only 16% of organizations track the cost of turnover at all. That is a missed opportunity. Organizations that make this calculation tend to fund coaching programs more consistently because the math is straightforward once you do it.

What Retention-Focused Coaching Looks Like When It Works

The organizations that get the most retention value from coaching share a few consistent practices that most competitors miss.

• They treat coaching as a retention tool, not just a development tool. The framing matters. When career development budgets are positioned as “turnover prevention spend,” they get funded and protected differently than when they sit under a general L&D line item.
• They coach across levels, not just at the top. Executive coaching is well-established. What separates retention leaders is extending coaching to mid-level managers, individual contributors at risk of stagnation, and employees in their second or third year, the window when voluntary exits spike.
• They involve HR as a strategic partner in coaching conversations. HR does not just administer the program. HR reviews career path data, identifies patterns in who is leaving and when, and uses that intelligence to refine the coaching framework and focus manager attention where it matters most.
• They connect coaching outcomes to organizational strategy. Employees stay longer when they can see how their own growth aligns with where the company is going. Coaching sessions that link individual development to business goals create a sense of shared direction that generic training programs cannot replicate.

The difference between organizations that retain talent and those that do not is rarely about pay. It is about whether employees believe the organization sees them as more than a body in a seat. Career coaching is how that belief gets built, one conversation at a time.

Conclusion: Career Coaching Is a Retention Strategy, Not Just a Development Benefit

Employees are more likely to stay when they can see a future for themselves inside the organization. Career coaching gives them that visibility. It helps employees clarify where they want to go, identify the skills they need to build, and connect their personal growth to real internal opportunities.

For HR leaders, that makes coaching one of the most practical ways to reduce preventable turnover. It strengthens manager-employee relationships, supports internal mobility, improves engagement, and shows employees that the organization is invested in their long-term success.

Retention does not improve because employees are told they matter. It improves when they experience that investment through meaningful development conversations, clear career paths, and consistent support.

Help Employees See a Future With Your Organization

Pathwise helps organizations, HR teams, and people leaders build career development programs that support employee growth, engagement, and retention.

For HR Teams and Organizations

If your organization wants to reduce turnover by giving employees clearer development pathways, explore Pathwise’s resources for organizations and HR professionals.

Through career development support, coaching resources, and employee growth solutions, Pathwise helps HR teams create the kind of workplace where employees can see what comes next without needing to leave to find it.

For Coaching and Personalized Development

Career coaching gives employees dedicated space to clarify goals, navigate career decisions, and build confidence in their next steps. Pathwise Coaching can support employees, managers, rising leaders, and professionals at key transition points in their careers.

This is especially valuable for employees who feel stuck, high-potential talent considering their next move, and managers who need stronger coaching skills to support their teams.

For Career Services and Employee Growth Support

Retention improves when employees have access to practical tools that help them manage their careers. Pathwise Career Services can help employees strengthen their career plans, prepare for internal opportunities, and take more ownership of their professional development.

These services can support individual contributors, new managers, career changers, rising leaders, and HR professionals, all of whom are included among Pathwise’s audience segments.

For Structured Learning and Skill Development

Coaching is most effective when paired with skill-building. Pathwise Career Courses help employees build durable career capabilities that support internal mobility, leadership readiness, communication, and long-term professional growth.

For HR teams, this creates a scalable way to reinforce coaching conversations with practical learning resources employees can use between check-ins.

Explore Pathwise Solutions

Whether your organization is trying to reduce preventable turnover, strengthen manager-as-coach capabilities, improve employee engagement, or create clearer career pathways, Pathwise can help.

Start by exploring Pathwise Solutions or reviewing the full range of Pathwise Offerings.

Build a Workplace People Want to Stay In

Career coaching helps employees answer one of the most important retention questions: “Do I have a future here?”

When the answer is clear, supported, and credible, employees are more likely to stay, grow, and contribute at a higher level.

Pathwise can help your organization make that future visible. Explore our services for organizations and HR professionals to start building a stronger career development and retention strategy today.

TL;DR An arrogant boss can quietly damage your confidence, visibility, and career trajectory if you respond emotionally or too passively. The right approach is to stay professional, document patterns, set calm boundaries, focus on business impact, and escalate carefully when needed. This guide covers how to respond in meetings, private conversations, and written communication while protecting your reputation, your performance review, and your next move.

Most employees can work through a demanding manager, a blunt communicator, or a leader who sets high expectations. The arrogant boss is different. Arrogance at the management level follows predictable patterns: dismissing ideas in meetings, taking credit for team work, humiliating employees publicly, and resisting any feedback that challenges their authority. 

These behaviors do not just create discomfort. They reduce your visibility, distort your performance record, and erode the psychological safety your career depends on.

This article is not a definition of arrogance. If you need that framing, the broader topic of arrogance in the workplace covers the research, the warning signs across all relationships, and the cultural damage it causes. 

This guide focuses on a narrower and more urgent question: what do you do next when the arrogant person is your boss and you need to stay effective without damaging your career?

How to Tell If Your Boss Is Arrogant, Demanding, or Abusive

Before you choose a response strategy, the distinction matters. Treating a demanding boss as an arrogant one leads to unnecessary conflict. Treating an abusive boss as merely arrogant leads to legal exposure and personal harm.

• An arrogant boss operates from a belief in their own superiority. They dismiss contributions without engaging with the substance. They hoard credit, rewrite outcomes in their favor, and treat disagreement as a personal affront. Their behavior is consistent and directional: it flows downward and diminishes those around them.
• A demanding boss sets high standards and applies pressure to meet them. They may be blunt, fast-paced, and intolerant of missed deadlines. That pressure is unpleasant but rarely contemptuous. The key difference is intent. A demanding boss wants results. An arrogant boss wants deference.
• An abusive boss crosses into coercion, threats, discrimination based on protected characteristics, or retaliation for raising concerns. Federal employment laws enforced by the U.S. Equal Employment Opportunity Commission prohibit discrimination and retaliation regardless of who is in charge. The EEOC confirmed in early 2026 that rescinding its 2024 harassment guidance does not alter underlying federal statutes or Supreme Court precedent, employees retain the right to file charges and pursue claims for harassment based on any protected characteristic.

Understanding which category applies shapes every decision that follows.

What an Arrogant Boss Can Do to Your Career

The damage is specific and compounding. It does not always feel like a crisis at the moment, but the pattern accumulates.

• Credit erosion is one of the earliest and most career-limiting consequences. When your manager consistently presents team output as their own, you lose the visibility that drives promotions and internal reputation. Stakeholders form impressions based on what they see attributed. If your name does not appear attached to your work, your contributions disappear from the record.
• Confidence damage is harder to measure but equally real. Working under someone who publicly dismisses your ideas, interrupts you in meetings, or gives condescending feedback activates a chronic stress response. Over time, many employees begin to self-censor, present fewer ideas, and take fewer professional risks — not because they lack capability, but because the cost of speaking up feels too high.
• Performance review risk is where the damage becomes tangible. An arrogant manager who controls your review has full power to minimize your contributions, inflate obstacles you faced, or frame your strongest work as a team effort that they guided. Without documented wins and a network of stakeholders who know your output, your annual review becomes a story they tell about you.
• Psychological safety collapse affects the whole team. Gallup’s 2026 State of the Global Workplace report found that global employee engagement fell to 20% in 2025, costing the world economy an estimated $10 trillion in lost productivity. The same research found that 70% of the variance in team engagement is determined by the manager alone. An arrogant manager, operating with contempt and entitlement, hits every dimension of that variance.

How to Respond in the Moment Without Looking Defensive

The single most effective principle for in-the-moment response is this: react to facts, not to provocations. Arrogant managers often create situations designed to provoke an emotional response. That response, visible frustration, a sharp reply, a defensive interruption — becomes the story rather than the underlying behavior.

In meetings, when your idea is dismissed without engagement, the effective move is to pause and redirect to substance. Phrases that work:

• “I want to make sure the idea gets a fair look. Can we walk through the business case for sixty seconds?”
• “Can we align on the decision criteria before we move on?”
• “I want to note for the record that the approach I outlined is still available if we want to revisit.”

These responses are neutral, professional, and create a paper trail of the moment without escalating the conflict.

• In private conversations, address behavior in terms of its business impact rather than your emotional experience. “When feedback is given in front of the team, it makes it harder for the team to stay focused on the task” is more durable than “When you criticize me in meetings, I feel belittled.” The first framing invites a problem-solving response. The second invites denial.
• In written communication, the principle of respond, not react applies directly. Do not send emails in the hour following a frustrating meeting. Write a response, save it as a draft, and review it the next morning. What feels assertive at 4pm often reads as reactive at 9am.
• What not to say: Do not use the word “arrogant” with your boss or in any conversation that could be repeated. Do not threaten escalation at the moment. Do not say you feel disrespected. All three invite defensiveness rather than change, and none of them move your actual objective forward.

How to Set Professional Boundaries Without Escalating Conflict

A boundary in a boss relationship is not an ultimatum. It is a calm, professional statement of how effective work gets done. The distinction matters because ultimatums create adversaries. Calm standards create clarity.

• For public interruptions, a low-conflict phrase used in real time: “I want to finish this point and then I’ll hand it over.” Said steadily and once, this lands as professional rather than confrontational. In a follow-up one-on-one, you can add: “I’ve found I think more clearly when I can get through a full thought in the meeting — it helps me represent the team better.”
• For condescending feedback, the aim is to acknowledge and redirect rather than push back directly. “I hear the concern. Can you help me understand what a successful version of this looks like? I want to close the gap.” This response signals maturity without absorbing the insult.
• For after-hours demands, set expectations through behavior, not declarations. Respond to one off-hours message during business hours the next day with a note like: “Got this last night, looping back now. Here is where things stand.” Over several repetitions, the pattern establishes your norms without a confrontational conversation about boundaries.
• When boundary-setting stops working: If calm, consistent boundary-setting is met with retaliation, new criticism appearing in performance notes, sudden reassignments, or public undermining, document the sequence and move toward escalation. Retaliation for raising professional concerns is a separate and more serious category than general arrogance.

How to Document Your Boss’s Behavior Without Seeming Political

Documentation is the single most underused tool available to employees in difficult management situations. Most people avoid it because it feels formal, confrontational, or paranoid. Done correctly, it is none of those things. It is how you tell a credible story when the stakes are high.

• What to record: Date, the specific words or actions, who was present, what the business impact was, and how you responded. Write facts, not interpretations. “October 3rd: In the 9am team call, [manager] attributed the Q3 savings analysis to the team without naming contributors. I had completed 80% of that analysis. Present: myself, [name], [name]” is far more useful than “manager takes all the credit again.”
• How to preserve records: After any significant conversation, send a follow-up email that summarizes what was discussed and what was decided. “Just recapping our conversation from this morning: we agreed to X, I’ll have Y delivered by Friday, and you’ll share the client timeline by end of week.” This creates a timestamped record without appearing adversarial. The email is a professional norm, not a gotcha.
• What to track: Focus on patterns that affect performance, deadlines, client relationships, team morale, or review outcomes. A single dismissive comment does not create a case. Twelve documented instances across eight weeks tell a different story.
• Keeping it in perspective: Documentation protects you. It is not a strategy for getting someone fired. Its primary purpose is to give you clarity, protect your performance record, and provide substance if the situation escalates.

When to Involve HR, Skip HR, or Escalate to Your Boss’s Boss

The decision to escalate should be driven by pattern and severity, not by frustration alone. Going to HR too early and without documentation reduces your credibility. Going too late can mean the damage to your record is already done.

• When HR may help: Patterns that affect your employment status (skipped for promotion repeatedly, sudden downgrade in performance ratings after raising a concern), behavior that affects multiple team members, or conduct that crosses into discrimination or retaliation under federal law. Bring your documentation and frame the conversation around business impact and observable behavior, not personality labels.
• When HR may not help: General interpersonal friction, a difficult management style, or situations where the arrogant manager is also a high performer the organization wants to protect. Gallup’s research confirms that manager behavior is the largest single driver of team engagement, but organizations still protect revenue generators disproportionately. Going to HR without documentation, corroboration, or a clear business impact narrative often produces no outcome.
• When to escalate to your boss’s boss: This works best when your skip-level has direct knowledge of your contributions and when the specific concern is about business process or client outcomes rather than personality. Frame the conversation as seeking alignment: “I want to make sure I’m clear on how to prioritize X given Y. Can we find fifteen minutes?” A skip-level meeting framed as professional alignment is less fraught than one framed as a complaint.
• Retaliation red flags: If after raising a concern you notice increased criticism in writing, removal from projects, exclusion from meetings you previously attended, or sudden changes to your role or assignments document those changes with dates and context. Retaliation for protected activity under federal law is actionable regardless of the EEOC’s recent guidance changes. Federal statutes prohibiting retaliation remain fully in effect.

If you believe you may be facing abuse of power in the workplace that crosses into legal territory, consult an employment attorney before proceeding.

How to Protect Your Performance Review and Internal Reputation

Your arrogant boss is not the only person who will assess your work. Your job is to make sure that is structurally true, not just theoretically true.

• Recap emails create a paper trail of wins. After completing a significant project, send a brief note to your manager summarizing what was delivered, by whom, and what the business outcome was. Copy in relevant stakeholders where appropriate. The goal is not to be defensive. It is to be visible.
• Stakeholder relationships expand your narrator pool. When your boss is the only person in the organization who sees your work, they are also the only person who can describe it. Build relationships across functions and levels so that other people in the organization have direct experience of what you bring. Internal transfers, cross-functional projects, and company-wide initiatives all create these opportunities.
• Find sponsors, not just mentors. A mentor offers advice. A sponsor advocates for you in rooms you are not in. If you are working under a manager who consistently minimizes your contributions, a sponsor at a higher level who speaks up for you in talent reviews can change your career trajectory faster than any conversation with your manager.
• Managing up effectively: When presenting to your boss, frame your contributions in terms of outcomes. They care about their team’s visibility, the department’s metrics, the client’s satisfaction. Arrogant managers respond to arguments that benefit them. A business case that benefits the team and happens to benefit you lands better than one that centers your recognition.

For anyone navigating a difficult boss while also thinking about promotion, the guide on how to get promoted covers visibility strategies that complement the documentation and stakeholder-building work described here.

When to Stay, Transfer, or Leave

The test is not whether your boss is difficult. It is whether the pattern is entrenched, whether the cost is compounding, and whether anything is likely to change.

• Stay if: The behavior is bounded and occasional, you are building skills or credentials you need, the rest of the culture is healthy, or the manager’s tenure is visibly limited by organizational dynamics.
• Request an internal transfer if: You have built relationships across the organization, the behavior is persistent but the company itself is worth staying in, and a transfer does not require your manager’s approval. Time a transfer request to a natural organizational moment, a restructure, a new project launch, a budget cycle, so it reads as a career move rather than a flight from conflict.
• Leave if: The arrogant manager is protected by senior leadership, the culture rewards the behavior, the documentation goes nowhere, and the cost to your confidence and professional growth is real. Leaving is not failure. As the guide on working with a new boss notes, every new management relationship is an opportunity to reset the dynamic. Sometimes the healthiest version of that reset is in a different organization.
• Before leaving: Update your resume and LinkedIn with quantified contributions. Secure references from stakeholders who know your work directly, not only from your manager. Keep your exit clean, no disclosure of documentation, no expressions of grievance in exit interviews unless HR specifically asks and you have counsel. Leave the door open.

How to Stay Grounded Through the Process

Working under an arrogant boss is emotionally expensive. Over months, the pattern can erode your sense of your own capabilities if you do not actively counteract it.

Maintain a document of your own wins — not for HR, just for yourself. Read it weekly. Peer relationships outside your immediate team are not just politically useful; they are the corrective to the distorted feedback you may be receiving from above.

Professional coaching or mentorship serves a specific function here: it gives you a relationship with someone whose incentive is your growth, not your compliance. That perspective recalibrates judgment that has been shaped by a difficult environment.

The goal is not just to survive the situation. It is to emerge from it with your judgment, confidence, and professional reputation intact. That requires active management, not just patience.

Conclusion

An arrogant boss is not just a personality problem. Without a response strategy, the impact compounds: your contributions become invisible, your confidence erodes, and your performance record becomes their narrative of you.

The correction is methodical. Stay professional at the moment. Document facts, not feelings. Make your work visible to stakeholders beyond your manager. Set calm, consistent boundaries. Escalate based on pattern and severity, not emotion. And when the situation is entrenched and costly, treat moving on as what it is: a strategic decision made in your own career interest.

If you are navigating a difficult management dynamic and want structured support, explore PathWise’s coaching options to work through your situation with a professional, or visit PathWise Career Services to build the resume and LinkedIn presence that protects your reputation regardless of what any single boss says about you.

Employee career development programs are structured systems that help workers build skills, set career goals, and advance within an organization. For HR teams, these programs connect talent development directly to business outcomes: lower turnover, stronger workforce engagement, and a reliable pipeline for internal promotion.

This guide covers what effective programs look like, how to build one from scratch, and how to measure whether it is working.

What Are Employee Career Development Programs?

An employee career development program is a coordinated set of activities designed to help workers grow professionally over time. It goes beyond one-time training events. A proper program includes career pathing, Individual Development Plans (IDPs), mentorship, skills assessments, and learning opportunities tied to defined career goals.

The distinction between a training program and a career development program is worth making clear. Training addresses a specific skill for a current role. Career development is broader. It prepares employees for future roles, lateral moves, and long-term professional growth. Organizations that conflate the two often end up with a learning catalog but no development culture, which is a different problem entirely.

HR teams are well-positioned to design these programs because they sit at the intersection of people strategy and business goals. The challenge is moving from intent to a system that managers actually use and employees actually want.

Why Career Development Programs Matter for Retention and Engagement

Career-related reasons were the leading cause of turnover in 2024, ahead of management issues and pay, according to Work Institute’s annual analysis of exit interview data from tens of thousands of employees across multiple industries. Employees who saw no path forward left. That pattern held across industries and role levels.

The cost of that departure is measurable. Replacing an employee costs an average of 33.3% of their base salary. Multiply that across several voluntary exits in a year and the financial case for structured employee career development programs becomes hard to dismiss in any leadership conversation.

The upside is equally clear. According to LinkedIn’s 2024 Workplace Learning Report, companies with strong learning cultures achieve a 57% employee retention rate, compared to just 27% at organizations with moderate learning cultures. The same research found that those organizations also experience 23% higher internal mobility, which reduces the cost and time required to fill open positions from outside. Connecting employee engagement strategies to development programming is not just good people practice. It is measurable risk reduction.

Employees with access to career development options show 34% higher retention rates than those without. Only 31% of U.S. employees were engaged at work in 2024, the lowest figure in a decade. Development opportunity is one of the strongest levers HR has to address that number, and it is cheaper than compensation increases.

Core Components of an Effective Employee Career Development Program

Strong programs share several common elements. Not every organization needs all of them at launch, but HR teams should understand what each one does before deciding what to prioritize.

Individual Development Plans

An Individual Development Plan (IDP) is a written agreement between an employee and their manager that documents the employee’s professional goals, identified skill gaps, and the specific steps they will take over a defined time period. IDPs create accountability on both sides. The employee commits to specific actions. The manager commits to providing support, access to learning resources, and regular check-ins.

Effective IDPs connect personal goals to organizational needs. An employee who wants to move into people management in two years should have an IDP that includes team leadership exposure, formal communication skills training, and experience with performance feedback processes.

Career Pathing and Internal Mobility

Career pathing gives employees a clear picture of how they can move within an organization, both vertically and laterally. Career mapping tools help employees understand what different roles require and how their current experience connects to future opportunities. When people can see a route forward, they are less likely to look for it elsewhere.

Internal mobility programs extend this by creating structured pathways for employees to apply for open roles, take on stretch assignments, or rotate between departments. Organizations with strong internal mobility programs fill roles faster, at lower cost, and with employees who already understand the business.

Mentorship and Coaching

Mentorship pairs employees with more experienced colleagues who can offer guidance on career navigation, organizational dynamics, and professional growth. Coaching is more structured and goal-focused, often delivered by certified coaches who help employees work through specific challenges.

Both formats work. The key is making them available to a broad employee population, not just high-potential employees identified by HR. When mentorship and coaching are reserved for a select few, the rest of the workforce receives a clear signal about who the organization values, and retention suffers accordingly.

Skill Development

Formal training, online courses, certifications, and on-the-job experiences all fall under skill development. The most effective programs blend formats. Formal coursework builds structured knowledge. Job experiences accelerate application. Interpersonal relationships through mentoring or peer learning fill in the gaps that formal programs miss.

One finding from recent research is worth flagging here. McKinsey found that nearly half of employees want more formal training, particularly as new technologies reshape job requirements. Yet only 46% of employees report that their employer provides adequate opportunity to learn new skills. That gap is a direct recruitment and retention risk for organizations that have not addressed it.

Manager Involvement

Managers are the most critical variable in whether career development programs succeed or fail. Research from Gallup puts it plainly: managers account for 70% of the variance in team engagement. A strong program that managers do not actively support will underperform regardless of its design quality.

HR teams should treat managers as partners in career development. That means training managers on how to improve leadership skills related to coaching and career conversations, holding them accountable for development discussions during performance reviews, and giving them structured frameworks they can use with their direct reports.

How to Build an Employee Career Development Program: A Step-by-Step Approach

Building a program from scratch is manageable when you start with structure rather than content. Here is a practical sequence for HR teams working within typical organizational constraints.

Step 1: Conduct a Skills Gap Assessment

Before designing anything, find out where employees are now and where the organization needs them to be. A skills gap assessment surfaces the distance between current capabilities and future role requirements. HR teams can gather this data through performance review records, manager surveys, or structured self-assessments.

This step also informs workforce planning. Knowing which skills are scarce internally helps HR decide where to invest in upskilling versus where external hiring makes more sense.

Step 2: Align the Program to Business Strategy

Career development programs that operate separately from business strategy tend to become benefits-focused rather than performance-focused. They feel good but produce limited organizational impact, which makes them vulnerable in budget discussions.

The goal is to connect what employees want to develop with what the business needs to succeed. If the organization is moving into new service areas, the skills it builds should reflect that. If leadership succession is a near-term concern, leadership development should sit at the center of program design.

Step 3: Design Learning Paths by Role and Level

Rather than offering a generic catalog of courses, effective programs map learning opportunities to specific roles and career stages. A learning path for an individual contributor targeting a people management role looks different from one built for a senior manager preparing for a director position.

Learning paths should include multiple formats: formal coursework, on-the-job projects, mentorship connections, and peer learning opportunities. People learn differently. A blended approach reaches more employees and produces better application of skills over time.

Step 4: Build Manager Capability for Career Conversations

Most managers were not trained to have structured career development conversations. Many avoid them because they are uncertain about what they can realistically promise around promotions or role availability.

A simple framework helps. Career conversations should cover three areas: where the employee is now, where they want to go, and what they need to get there. Managers who can navigate these conversations honestly keep their teams more engaged and retain talent at higher rates.

Step 5: Use Technology to Track Progress

Learning management systems, performance management platforms, and skills tracking tools reduce administrative burden on HR and give leaders visibility into development activity across the organization. Over half of organizations now use an LMS and performance management systems to support employee development, according to HR.com and PeopleFluent research.

The data these systems generate also enables measurement. If employees with active IDPs are being promoted more often or leaving less frequently, that data is worth sharing with senior leadership when program budgets come up for review.

Step 6: Promote the Program and Make It Easy to Find

A program employees do not know about or cannot easily access will not produce results. HR teams need to build awareness through onboarding, manager communications, and ongoing internal visibility. Framing the program as a meaningful benefit of employment, rather than a compliance requirement, changes how employees perceive and use it.

Visible sponsorship from senior leaders signals organizational commitment. When leaders reference career development in public conversations and back it with resources and time, employees take it more seriously.

How to Measure Career Development Program Success

Measurement is where many HR programs fall short. Without clear metrics, it is difficult to demonstrate value, justify budget, or identify what needs to change.

The most useful indicators for employee career development programs fall into four areas.

• Retention and turnover data tracks whether program participation correlates with longer tenure. Compare voluntary turnover rates between employees actively enrolled in development programming and those who are not. Even directional data here is useful.
• Internal mobility rates measure how often open roles are filled by internal candidates. Rising internal mobility suggests the program is building capabilities the organization can actually use.
• Engagement and satisfaction data captures whether employees feel supported in their growth. Pulse surveys and annual engagement scores provide a before-and-after view as the program matures.
• Promotion and progression rates show whether employees with development plans advance at a higher rate than those without them. This is the most direct evidence of program effectiveness and the most compelling data point for leadership audiences.

Using feedback for professional development as a regular practice, not just an annual event, also strengthens the measurement loop. Employees who receive consistent development feedback have clearer visibility into their progress and are more likely to stay engaged with their development plans.

Training programs to support career progression were cited as HR professionals’ top way to strengthen organizational competitiveness in the 2025 SHRM State of the Workplace report. Organizations that measure program effectiveness are also significantly more likely to increase their investment in development over time, creating a compounding advantage over those that do not.

Common Mistakes HR Teams Make with Career Development Programs

A few patterns show up consistently in programs that underperform.

• Treating career development as a perk rather than a strategy. Programs that exist primarily for employer branding or engagement survey results rarely produce meaningful outcomes. Development needs to connect to business goals and manager accountability structures.
• Building one-size-fits-all programs. A new employee at 26 and a manager at 44 have different development needs, different timelines, and different definitions of career growth. Programs designed around a single template fail both.
• Not involving managers in program design or delivery. HR can design a strong program, but managers are the ones who give employees time, permission, and encouragement to use it. Without their active participation, participation rates stay low and the program stalls.
• Skipping measurement. Programs without metrics cannot improve and cannot justify their existence in a budget conversation. Even basic tracking, such as IDP completion rates and internal promotion data, provides enough signal to make meaningful program adjustments.
• Making promises the organization cannot keep. Career development conversations can raise expectations around promotion timelines and role availability. HR teams should train managers to be honest about what the organization controls and what falls outside the program’s scope.

Build Career Development Into the Way Your Organization Works

Employee career development programs are most effective when they are treated as part of the organization’s talent strategy, not as a stand-alone HR initiative. A strong program gives employees clarity about where they can grow, helps managers have better development conversations, and gives the organization a stronger internal pipeline for future roles.

For HR teams, the opportunity is practical and measurable. Career development can reduce turnover, improve engagement, strengthen manager effectiveness, and make workforce planning more resilient. But the program has to be structured, visible, and connected to real business needs.

The best career development programs do not simply offer employees more training. They give people a path forward.

Help Your Employees Grow With Pathwise

Pathwise helps organizations, HR teams, and individuals build stronger career development systems through coaching, courses, and practical career support.

For HR Teams and Organizations

If your organization wants to improve employee development, career engagement, retention, or internal mobility, explore Pathwise’s resources for Organizations and HR Professionals.

Pathwise can support HR teams looking to create a more intentional approach to career growth, manager development, and employee engagement.

For Employee Learning and Skill Development

Career development programs work best when employees have access to structured learning opportunities. Pathwise Career Courses can help employees build practical skills, strengthen career readiness, and take ownership of their professional growth.

These courses can complement internal learning paths, Individual Development Plans, and broader talent development initiatives.

For Coaching and Personalized Growth

Some employees need more than a learning path. They need focused guidance, reflection, and accountability. Pathwise Coaching gives employees, managers, and rising leaders personalized support as they navigate career decisions, leadership challenges, and professional transitions.

Coaching can be especially valuable for high-potential employees, new managers, career changers, and employees preparing for internal advancement.

For Broader Career Support

Pathwise Career Services provide practical support for individuals who want to clarify their goals, strengthen their professional presence, and take the next step in their career.

For organizations, these services can help reinforce a culture where employees feel supported in their growth rather than left to manage career development on their own.

Explore the Full Pathwise Offering

To see all available development solutions, visit the Pathwise Offerings page.

Turn Career Development Into a Retention Advantage

Employees are more likely to stay when they can see a future inside the organization. A well-designed career development program gives them that visibility and gives HR teams a stronger foundation for engagement, succession planning, and workforce growth.

Pathwise can help your organization build that foundation. Start by exploring our solutions for Organizations and HR Professionals.

Building an AI-ready workforce is not primarily a technology challenge. It is a people challenge, and that distinction changes everything about how HR leaders should approach it.

An AI-ready workforce is one where employees understand how to work alongside artificial intelligence tools, feel confident using them, and trust that their organization is managing the transition responsibly. 

HR sits at the center of that transformation. Not IT. Not the C-suite. HR. This guide gives HR professionals a practical framework for developing AI workforce readiness across their organizations, with the human element intact at every step.

What an AI-Ready Workforce Actually Means

An AI-ready workforce is not one where employees have completed a single training module on a generative AI tool. It is a workforce where people at every level can apply AI tools competently to their role, adapt as those tools evolve, and exercise judgment about when to use them and when not to.

The World Economic Forum’s 2025 Future of Jobs Report found that 39% of workers’ core skills are projected to be transformed or outdated between 2025 and 2030. Skills-based organizations are already responding: 81% of employers now use skills-based hiring compared to just 57% in 2022. These figures signal a fundamental shift. The workplace is being restructured around capability rather than credentials, and AI is accelerating that restructuring faster than most training programs can keep pace with.

For HR leaders, AI workforce readiness means three things. First, employees need functional AI literacy: the ability to prompt effectively, interpret outputs critically, and identify where AI judgment stops and human judgment must begin. Second, organizations need structural readiness: clear governance policies, defined roles, and ethical guardrails embedded before problems arise. Third, and most critical to long-term success, organizations need cultural readiness. A workforce that trusts the process, understands the purpose, and feels safe enough to raise concerns when something feels wrong is far more resilient than one that simply has access to the latest tools.

Why HR Holds the Keys to AI Adoption Success

SHRM’s 2026 State of AI in HR report found that 92% of CHROs anticipate AI will be further integrated into the workforce this year, with 87% forecasting greater adoption within HR processes specifically. That makes HR digital transformation a present responsibility, not a future planning item.

HR leaders are not just implementing AI within their own function. They are shaping how every employee across the organization experiences this transition. They design the reskilling programs. They set the communication tone. They build or break the learning culture. They determine whether AI adoption feels like an opportunity or a threat.

Gartner research adds important context: by 2030, 60% of HR work tasks will be completed through intelligent agents or large language model interfaces. That frees HR professionals from transactional work and positions them for strategic territory, including workforce planning, organizational redesign, and talent pipeline development. But none of that shift happens automatically. HR leaders who treat AI adoption as a compliance task rather than a cultural initiative will find their organizations stuck in the gap between buying AI tools and actually using them well.

The Human Risk No One Is Talking About

The data on AI anxiety is significant and cannot be ignored by anyone designing a workforce development program. A 2025 Frontline Workforce Study found that 85% of frontline employees think it would be “a huge mistake” to replace humans with AI, and 64% worry AI could take their jobs. 

A separate Harris Poll found that 34% of employees feel unprepared for AI-driven changes, and 42% say their employer expects them to learn AI entirely on their own.

That last figure deserves attention. When employees feel left to figure out AI by themselves, organizational trust erodes. Engagement drops. Turnover risk rises. The organization ends up with inconsistent, ungoverned AI use that creates more liability than value. Understanding the full pros and cons of AI in the workplace is essential for HR leaders who want to communicate honestly and build informed buy-in across all levels.

The perception gap compounds the problem further. According to TriNet’s State of the Workplace 2025 research, only 49% of employees feel equipped for their roles, down from 59% in 2024. Among Gen Z workers, that number fell 20 points to just 39%. Employers, meanwhile, have grown more confident: 46% believe their workforce has the skills it needs, up from 40% the year before.

This divergence between how prepared leadership believes the workforce is and how prepared employees actually feel is where AI readiness programs collapse. The gap is not primarily about skills. It is about trust, communication quality, and how supported employees feel during change.

PwC’s Hopes and Fears Survey 2025 found that workers who feel supported to upskill are 73% more motivated than those who feel the least support. That connection between learning support and employee motivation makes workforce development a direct performance lever, not a training department checkbox.

How to Reskill Employees for AI Without Overwhelming Them

Effective skill development for AI requires a different design philosophy than traditional corporate training. SHRM research shows that while 53% of organizations say they prioritize upskilling, only 21% believe they do it effectively. The gap is not budget or intent. It is execution.

The most common complaints from employees who are dissatisfied with their current AI upskilling opportunities are that training is not relevant to their specific role (33%), is difficult to attend due to scheduling constraints (39%), and competes with time they simply do not have (50%). These are solvable design problems.

Effective reskilling starts with role segmentation. A customer service manager needs different AI fluency than a financial analyst or a supply chain coordinator. Building role-specific learning paths ensures training reaches people where they actually work rather than landing as generic information they cannot apply.

The second step is making learning continuous rather than event-based. LinkedIn’s 2025 Workplace Learning Report found that 91% of L&D professionals say continuous learning is more important than ever for career success. Static training events do not build lasting AI readiness. Embedded micro-learning, peer learning groups, and daily workflow integration do.

A proven model is the phased “crawl, walk, run” approach. Start with AI awareness for the full workforce: what the technology does, what it cannot do, and how the organization will use it responsibly. Move to tool-specific training for functional groups where AI will change how work gets done. Build advanced AI fluency for roles where automation will fundamentally reshape day-to-day responsibilities. This progression reduces overwhelm, generates quick wins that build confidence across teams, and creates visible proof points that the organization is investing in its people.

Third, connect visible learning pathways to career progression. PwC’s research found that 92% of employers say career paths are clear, but only 77% of employees agree. That gap signals a communication failure, not a lack of opportunity. HR leaders who map what AI learning milestones mean for an employee’s next role, next promotion, or next project assignment turn reskilling from a mandate into a meaningful offer.

Building AI Literacy That Sticks: A Practical HR Framework

AI literacy and AI proficiency are not the same capability. Literacy means understanding what AI can and cannot do, knowing how to engage with it responsibly, and being able to evaluate its outputs critically. Proficiency means using specific tools effectively for specific tasks. HR leaders need to build both, in that order.

• A practical AI literacy framework starts with shared vocabulary. When people across an organization use the same terminology for concepts like generative AI, algorithmic outputs, prompt engineering, and human oversight, conversations about governance, risk, and opportunity become clearer at every level.
• Next, identify and empower AI champions. These are employees at every level who adopt AI tools early, experiment openly, and help colleagues navigate the learning curve. AI champions normalize AI fluency as a core competency rather than a specialist skill reserved for the technology team. Employees are more likely to trust a peer’s honest experience with AI than a directive from senior leadership.
• Then, connect AI literacy to performance management and career development. Organizations that align AI competencies with career paths and performance metrics see significantly faster adoption rates. When employees understand that AI fluency is directly relevant to their professional growth and advancement, the motivation to learn becomes intrinsic rather than compelled.
• Finally, build governance frameworks alongside literacy programs, not after them. Employees need to understand not just how to use AI tools but what the rules are. Clear policies on data privacy, algorithmic fairness, and the boundaries of AI-assisted decisions are not just ethical requirements. They are trust signals that demonstrate the organization is managing AI responsibly on behalf of its people.

SHRM recommends establishing a shared vocabulary and role-based upskilling paths before tying AI competencies to performance metrics. The sequence matters because it builds psychological safety before accountability.

Preserving the Human Touch as AI Scales

Strong employee engagement strategies become more important, not less, as AI tools take on more routine work. When automation absorbs transactional tasks, the human interactions that remain carry more weight. Coaching conversations, performance feedback, career guidance, and conflict resolution must stay human-led, and the people responsible for those interactions need to be better equipped than ever.

Human-centered AI, in practice, means that when AI surfaces an insight, a human decides what to do with it. It means managers are equipped not just to use AI tools but to apply those tools in ways that deepen their connection to their teams. An AI platform that flags an employee as a flight risk is useful data. A manager who responds to that flag with empathy, curiosity, and a genuine conversation is what makes the difference between retention and resignation.

At UNLEASH World 2025, senior HR leaders described the emerging goal as developing “super managers”: leaders who use AI-generated insights to enhance human connection rather than substitute for it. This requires a specific type of manager readiness that most organizations are currently underinvesting in. Improving leadership skills for the AI era means teaching managers to interpret algorithmic outputs with humility, communicate transparently about how AI is used in decisions that affect their teams, and lead with more empathy precisely because their schedules have been freed from administrative tasks.

This is also where employee experience becomes a strategic variable in AI adoption. When employees believe that AI is being used to monitor, score, or manage them rather than support their growth, trust collapses and engagement follows. Transparent communication about what data the organization collects, how it is used, and what human oversight exists is not optional. It is the foundation of a workforce that embraces AI rather than quietly resists it.

Career Development as a Core Pillar of AI Readiness

One of the most underused levers in building an AI-ready workforce is intentional career development. When employees see a clear path from where they are today to where AI skills can take them tomorrow, the threat narrative around artificial intelligence weakens considerably. Career development programs that integrate AI literacy as a growth dimension rather than a compliance requirement change how employees relate to the technology entirely.

Bright Horizons’ 2026 Workforce Outlook, conducted by Harris Poll, found that 79% of workers feel they must learn new skills to remain competitive, and 32% say AI has increased that pressure, up from 26% the prior year. That pressure is an opening for HR leaders, not just a problem to manage. Employees who feel that urgency and see a credible, supported pathway forward are far more likely to invest in their own development and remain loyal to the organizations that help them do it.

Future-proofing your career in an AI-driven environment increasingly depends on developing skills that sit at the intersection of technical fluency and human capability: critical thinking, cross-functional collaboration, ethical reasoning, and the ability to challenge AI outputs rather than accept them passively. HR leaders who surface those intersections clearly, and provide the structured programs that develop them, retain employees who might otherwise see job transformation as a personal threat.

Internal mobility programs, coaching resources, and structured career conversations all signal that the organization sees its people as capable of growth and adaptation. That signal matters enormously to employees who are navigating a period of rapid, uncertain change.

The World Economic Forum’s 2025 Future of Jobs Report estimates that 59% of the workforce will need some form of training by 2030. Organizations that act now, by developing their existing workforce with structured learning, coaching, and career development programs, will have a performance and loyalty advantage that external hiring cannot replicate. 

Upskilling existing employees costs meaningfully less than replacing them: a 2025 Pluralsight report found that 89% of organizations say upskilling is more cost-effective than external hiring.

Measuring AI Workforce Readiness Without Losing Sight of People

Building an AI-ready workforce requires measurement. But the metrics that matter most are not limited to tool adoption rates or training completion percentages. HR leaders need indicators that reveal whether the human element of the transition is working as intended.

Employee confidence in AI-assisted roles, measured through regular pulse surveys, captures whether reskilling efforts are landing with the people who need them most. Internal mobility rates before and after AI upskilling programs reveal whether career development is creating real movement and not just completed modules. Manager readiness scores show whether the people closest to employees are equipped to lead through technological change with both competence and empathy.

Employee trust in how AI is being used, measurable through engagement survey questions on transparency and decision-making fairness, is arguably the most important leading indicator of long-term AI adoption success. An organization where employees trust that AI is being used in their interest rather than against it will see faster adoption, higher engagement, and stronger business outcomes across the board.

Gartner’s research makes the stakes of getting this right plain: by 2030, more than 30 million jobs per year will be redesigned by AI-driven innovation. The organizations that lead through that redesign will be those whose HR leaders acted as architects of continuous learning, trust, and human capability rather than simply administrators of technology rollouts.

Conclusion: AI Readiness Starts With Human Readiness

Building an AI-ready workforce is not about moving faster than your people can adapt. It is about helping employees build the confidence, skills, and trust they need to work effectively in a changing environment. For HR leaders, that means treating AI adoption as more than a technology rollout. It is a workforce development, leadership, communication, and career growth initiative.

The organizations that succeed will be the ones that invest in people before pressure builds. They will give employees clear learning paths, equip managers to lead through uncertainty, and create career development structures that help workers see AI as a tool for growth rather than a threat to their future.

AI may change how work gets done, but people will still determine whether that change succeeds.

Help Your Workforce Adapt With Pathwise

Pathwise supports HR teams, organizations, and professionals with career development solutions designed to help people grow through change.

• For HR leaders and organizations:
  Explore Pathwise solutions for employee development, career engagement, and workforce growth through our Organizations and HR Professionals resources.
• For structured employee learning:
  Help your teams build durable career and workplace skills with Pathwise Career Courses.
• For coaching and personalized development:
  Support employees, managers, and rising leaders with Pathwise Coaching services.
• For broader career support:
  Give employees access to practical guidance and tools through Pathwise Career Services.
• For a full view of Pathwise offerings:
  Visit our Offerings page to explore how Pathwise can help your organization strengthen career development, leadership readiness, and employee engagement.

Build AI Readiness Without Losing the Human Touch

As AI continues to reshape work, HR leaders have an opportunity to do more than manage disruption. They can build workplaces where people feel prepared, supported, and equipped to grow.

Pathwise can help your organization create that foundation. Start by exploring our solutions for organizations and HR professionals.

Electrical engineering is one of the strongest job markets in the United States right now. The Bureau of Labor Statistics projects 7% employment growth for electrical and electronics engineers from 2024 to 2034, a rate classified as “much faster than average” across all U.S. occupations. 

And that projection was made before the AI data center boom reshuffled demand for power systems engineers in ways the labor market has rarely seen at this speed.

This guide covers current employment data, salary figures for 2026, the industries doing the most hiring, the skills employers are actually prioritizing, and how to position yourself in a market where qualified candidates have genuine leverage.

How Fast Is the Electrical Engineering Job Market Growing?

The BLS projects approximately 17,500 job openings for electrical and electronics engineers each year through 2034. As of 2024, electrical engineers held about 192,000 jobs in the United States, while electronics engineers held roughly 95,900. 

A significant share of those projected openings comes from retirements rather than net-new roles, which is important for career planning: the supply pipeline is weakening at the same time structural demand is accelerating.

That combination matters. Actalent, an engineering staffing firm, projects demand for engineering skills to grow approximately 13% by 2031, but estimates that a third of new engineering roles will go unfilled due to retirements, increasing demand, and a persistent skills gap. It reflects a workforce whose average age is climbing while the industries that depend on electrical engineering are all expanding simultaneously.

One additional signal worth noting: according to Glassdoor data from April 2026, approximately 74% of electrical engineers report being content with their salary, which suggests the market is compensating talent meaningfully enough to retain it, even as competition for candidates intensifies.

Electrical Engineer Salary in 2026: What the Numbers Show

The BLS reports a median annual wage of $111,910 for electrical engineers and $127,590 for electronics engineers, based on May 2024 data. Real-time data from hiring platforms reinforces those figures: ZipRecruiter pegged the average electrical engineer salary at $111,091 as of March 2026, with the middle 50% of earners falling between $83,000 and $132,000 annually.

Glassdoor’s April 2026 survey, based on nearly 9,500 self-reported salaries, puts the average higher at $120,303, with the top 25% earning above $156,682. The gap between platforms reflects differences in methodology and the mix of specializations represented. Both figures confirm that electrical engineering comfortably clears six figures for mid-career professionals.

By experience level (Glassdoor and Coursera, October 2025):

• Entry-level (0 to 1 year): $92,000
• Junior (1 to 3 years): $102,000
• Mid-level (4 to 6 years): $113,000
• Senior (7 to 9 years): $127,000
• Engineering management: $167,740 median

In semiconductor design and AI hardware, total compensation including bonuses and equity can push well above $160,000 even at mid-career levels. According to Apollo Technical, engineers with expertise in battery technology, industrial automation, and smart energy systems are among those commanding the clearest salary premiums in 2026.

By industry (BLS, May 2024):

Glassdoor’s April 2026 employer data shows IT firms paying electrical engineers a median total of $148,879, with Meta, Apple, and Nuro among the top-paying companies. In aerospace and defense, SpaceX, Anduril, and Blue Origin lead on compensation.

For those evaluating electrical engineering as part of a broader career path, the salary data makes the case clearly: this is one of the higher-compensation technical fields available to bachelor’s degree graduates, with a long runway for growth tied to specialization.

The Demand Driver That Changed Everything in 2026

Renewable energy, EVs, and semiconductors have been the standard talking points for electrical engineering demand. They still matter. But in 2026, the biggest single accelerant in the electrical engineering job market is AI data center infrastructure, and its effects are being felt across the entire power systems engineering workforce.

The Stargate Project, a $500 billion collaboration between OpenAI, Oracle, and SoftBank announced in January 2026, is projected to create over 100,000 new U.S. jobs. Data center construction is electricity-intensive: electrical work accounts for 45% to 70% of total data center construction costs, according to the International Brotherhood of Electrical Workers. 

Power demand from data centers is expected to grow 15 to 17% annually through 2030, consuming between 6 and 12% of total U.S. electricity by 2028 according to Lawrence Berkeley National Laboratory projections.

IEEE Spectrum reported in January 2026 that data center operators are now recruiting electrical engineers from nuclear energy, the military, and aerospace because traditional talent pipelines cannot keep pace. Applied Digital, which is building data center campuses requiring 1.4 GW of power in North Dakota, told IEEE Spectrum it has had to widen its recruitment perimeter significantly. 

A 2023 Uptime Institute report found that 58% of global data center operators already faced difficulties sourcing talent for open roles, and that was before construction activity accelerated through 2025 and into 2026.

The shortage is compounding itself. Data centers require grid upgrades to support their power loads. Grid upgrades require the same power systems engineers that data centers are actively recruiting. 

Latitude Media documented this circular pressure: engineers experienced in connecting renewable generation assets, retooling gas infrastructure, and designing microgrids are now the most sought-after candidates across multiple competing industries simultaneously.

This is the kind of structural demand shift that changes career trajectories. Engineers with power systems backgrounds who might have assumed modest hiring conditions are now receiving inbound recruiter contact at rates that would have seemed implausible five years ago.

Top Industries Hiring Electrical Engineers in 2026

Renewable Energy and Smart Grids

Renewables accounted for 93% of all new U.S. power capacity additions in 2025, according to Actalent’s 2026 engineering workforce analysis, even after rollbacks in certain clean energy tax credits. Clean power surpassed 40% of global electricity generation in 2024 according to the World Economic Forum. 

Electrical engineers are central to every stage of that buildout: solar system design, wind power electronics, battery storage integration, and smart grid control systems. The clean energy transition was already a durable hiring trend before AI data centers added a second wave of grid modernization demand on top of it.

Electric Vehicles

The automotive sector is running one of the most aggressive engineering hiring campaigns in the industry’s history. EV development requires engineers who can design battery management systems, power electronics, motor control units, and charging infrastructure. 

Apollo Technical identifies EV systems engineering as one of the single fastest-growing specialization categories by absolute job count in 2026.

Semiconductor Manufacturing

The CHIPS and Science Act of 2022 allocated $280 billion to boost domestic semiconductor production, triggering a wave of new fabrication plant construction across Arizona, Ohio, and Texas. Research.com data shows nearly 15% growth in demand specifically for engineers specializing in AI-related chip design. 

Competition for VLSI and chip design engineers is intense enough that companies are running multiple competing offers simultaneously rather than waiting for candidates to decide between sequential offers.

Defense and Federal Government

Electronics engineers hold roughly 15% of their employment in the federal government. Defense programs covering radar, sonar, satellite systems, and military aircraft generate consistent hiring that is largely insulated from private-sector economic cycles. NASA, Sandia National Laboratories, and Lawrence Livermore National Laboratory are among the highest-paying government employers for electrical engineering talent.

Telecommunications

Electronics engineers account for approximately 18% of employment in telecommunications. AI-driven 5G optimization and early-stage 6G network design are creating demand for RF and communications engineers who can work at the intersection of signal processing and intelligent systems.

Consistent skill development across these sectors is what separates engineers who keep pace with evolving employer requirements from those who find their expertise becoming outdated within a specialization.

In-Demand Specializations for 2026

Most active job listings now specify a specialization rather than advertising for a generalist electrical engineer. The gap between a general EE and a candidate with a targeted specialization in a high-demand area is measurable in both time-to-hire and starting compensation.

• Power Systems and Smart Grid Engineering covers design, operation, and modernization of electrical generation and transmission infrastructure. This is the specialization most directly affected by the AI data center boom. Engineers in this area work on grid stability, load forecasting, and the integration of distributed energy resources. MATLAB and PSCAD proficiency is frequently required. Demand is intense enough that Latitude Media describes the power systems hiring market as essentially zero-sum: every hire is poached from another sector.
• Semiconductor and VLSI Design supports chip fabrication from circuit design through tape-out. CHIPS Act funding has added significant hiring volume in states with minimal prior semiconductor infrastructure. This is where AI hardware demand intersects most directly with traditional EE education.
• Embedded Systems with AI Expertise involves firmware development and hardware design for microcontrollers and microprocessors, increasingly including the integration of machine learning models for real-time decision-making in IoT and automotive applications. Python and C++ are the dominant languages; experience with real-time operating systems is a common differentiator.
• Electric Vehicle Systems Engineering spans battery management, power electronics, motor control, and charging system design. Compensation in this specialization has risen faster than the overall EE average due to sustained automaker competition for a limited candidate pool.
• AI Hardware and Chip Design is an emerging category that barely appeared in job listings three years ago. According to Research.com’s 2026 analysis, engineers in this role design and optimize chips specifically for AI workloads, combining semiconductor physics knowledge with understanding of neural network architecture. Near-15% demand growth for this profile makes it one of the fastest-accelerating specializations in the field.
• RF and Communications Engineering covers antenna design, signal processing, and wireless systems. 5G infrastructure buildout and early 6G development are the primary demand drivers.

What Employers Are Actually Looking for in 2026

Actalent’s 2026 engineering workforce analysis found that 63% of engineering firms are building or already have an AI strategy in place. That is reshaping hiring profiles. The candidate who moves fastest through the process in 2026 combines domain expertise with software fluency and comfort working alongside AI-enabled workflows.

According to O*NET employer job posting data, the most frequently mentioned tools in electrical engineering postings are AutoCAD, MATLAB, Revit, Python, and C++. Python has become a baseline requirement in embedded systems, power systems analysis, and data-driven design roles. 

Candidates who hold an electrical engineering degree but have limited programming exposure are filtered out at the resume stage with increasing frequency.

Beyond software, Actalent identifies adaptability and communication as the soft skills most consistently flagged by hiring managers in 2026. Engineers who can collaborate across multidisciplinary teams, communicate technical constraints clearly to non-technical stakeholders, and adjust as project scopes shift are consistently ranked ahead of technically equivalent candidates who cannot do the same.

A 2022 Electronic Design survey found that 76% of employers already faced difficulty finding suitable candidates. With approximately 25% of the current electrical engineering workforce aged 55 or older, retirements will widen that gap further through the end of the decade. 

The Professional Engineer (PE) license is increasingly valuable for engineers who want to lead projects, sign off on designs, or provide services directly to the public, with the path starting at the Fundamentals of Engineering (FE) exam. Membership in IEEE, which has over 400,000 members globally, supports ongoing technical learning and professional network access.

Deliberately future-proofing your career in a field changing this quickly means revisiting your skill stack every twelve to eighteen months, not just when a job search begins.

Geography: Where the Jobs Are Concentrated

California, Texas, New York, Michigan, and Massachusetts continue to lead U.S. electrical engineering employment. California employs approximately 24,690 electrical engineers, followed by Texas at 14,300 and New York at 11,170. Michigan’s concentration is driven by automotive electrification. 

Texas is increasingly a dual hub: energy and semiconductor manufacturing alongside data center infrastructure, as Virginia and Texas together account for a disproportionate share of new data center capacity additions.

Northern Virginia deserves specific mention. The region’s status as a data center hub, tied to access to subsea fiber cables and proximity to federal government clients, has made it a significant hiring market for power systems engineers and electrical engineers with mission-critical infrastructure experience.

Metro areas like Austin, Seattle, and Raleigh-Durham offer competitive salaries with lower costs of living than San Francisco or New York. Remote work remains more available in software-adjacent engineering roles than in hardware-intensive ones, where lab access and on-site commissioning are standard job requirements.

Career mapping across geography, specialization, and industry is one of the most underused planning tools for electrical engineers making decisions about where to concentrate their expertise and their job search.

How to Position Yourself in This Market

The electrical engineering job market rewards specificity and software fluency more than it ever has.

• Lead with a specialization. Generalist EE job listings are increasingly rare at mid-career. Engineers who immediately signal depth in power systems, embedded AI, EV systems, or semiconductor design cut through the noise faster. The combination of a domain specialization with Python or MATLAB proficiency is the hiring profile most companies are actively competing for in 2026.
• Take AI tools seriously. Actalent’s data shows that firms with AI strategies in place prioritize engineers comfortable using AI for simulation, design automation, and predictive modeling. This is not about replacing engineering judgment. It is about amplifying productivity in ways that make candidates more valuable per hour of billable time.
• Pursue the PE license and IEEE membership. Both open doors that remain closed without them, particularly in consulting, public infrastructure, and senior leadership roles.
• Use your leverage in negotiations. Demand for qualified electrical engineers exceeds supply in multiple sectors simultaneously. That gives candidates factual grounds to negotiate rather than simply accepting initial offers. Benchmarking against BLS wage data and Glassdoor figures, then articulating specialization value clearly, consistently produces better outcomes. Understanding how to negotiate a job offer in a candidates’ market is a skill worth developing before that conversation happens.
• Aim for high-demand intersections. The engineers with the most leverage right now sit at the intersection of two in-demand areas: power systems and data center infrastructure, or embedded systems and AI hardware, or EV design and software controls. These combinations are rare enough that employers compete for them.

The Electrical Engineering Job Market Rewards Those Who Plan Ahead

The data across every current source points in the same direction: electrical engineering offers strong salaries, durable demand, and expanding opportunity in sectors that are not going anywhere. The engineers who benefit most from this environment match their specialization to where hiring is actually concentrated, build the software and AI fluency that employers now treat as baseline, and pursue credentials that give them room to negotiate.

If you are navigating a career decision in engineering and want a structured approach to identifying your next move, explore how career coaching works at PathWise to build a plan grounded in where the market is heading.

Building multiple income streams means earning money from more than one source at the same time. You keep your primary job and add one or more additional sources of income alongside it. The result is a financial structure that is more resilient, more flexible, and less dependent on any single employer’s decisions.

This approach looks different for everyone. One professional runs a freelance consulting practice on evenings and weekends. Another sells digital products that generate passive income while they sleep. 

A third offers coaching or teaches an online course. What they share is the same core principle: spreading income across multiple sources reduces financial risk and creates new opportunities for career growth and professional satisfaction.

What Are Multiple Income Streams?

Income streams generally fall into two categories: active and passive. Active income requires your ongoing time in exchange for money. Freelance work, consulting, part-time contract roles, and coaching are all active income streams. 

Passive income requires an upfront investment of time or money, then generates returns with little ongoing effort. Digital products, online courses, investment dividends, and rental income are examples of passive income.

Here are the most common types of multiple income streams for working professionals:

• Freelance services such as writing, design, consulting, marketing, or coding
• Selling digital products like templates, guides, presets, or downloadable courses
• Part-time or contract work in your primary field
• Coaching, tutoring, or mentoring
• Affiliate marketing or sponsored content creation
• Investment income from stocks, index funds, or bonds
• A weekend side hustle built around a trade, creative skill, or hobby

Most professionals start with one additional source of income before building more. You do not need three streams on day one. Starting with one focused effort is the approach most likely to succeed.

1. Build a Financial Safety Net Beyond Your Paycheck

One paycheck creates a single point of financial failure. If you lose your job, face a salary freeze, or need to take unpaid leave, you have nothing to fall back on. An extra income source creates a meaningful buffer between you and that risk.

• According to a 2025 LendingTree survey, nearly 40% of Americans have a side hustle, and 61% of those who do say their life would be unaffordable without it. This is not a fringe response from a small segment. It reflects a real financial gap that one salary no longer fills for a large share of working adults.
• A financial safety net built from multiple income streams can do several things at once. It can cover regular living expenses during a job transition. It can accelerate debt repayment or help you build an emergency fund faster. It can fund retirement savings beyond what your employer’s match provides. And it can create room for discretionary goals without cutting every other line of your budget.
• The most important step is treating the extra income intentionally. Decide in advance what each stream is for. One might go toward building three to six months of emergency savings. Another might fund a specific goal such as a down payment or eliminating student debt. Without a clear financial target, extra income tends to disappear into general spending with little measurable impact.

For professionals thinking through their options, building a career backup plan before you need one is always a smarter move than scrambling for one after an unexpected layoff or reorganization.

2. Strengthen Your Job Security Before You Need It

Most professionals do not think seriously about job security until they face a direct threat to it. By then, their options narrow. Building an additional source of income before a layoff or company restructuring is one of the most practical ways to protect your professional stability.

• A 2025 Fiverr survey of over 12,000 global workers found that 67% of Gen Z respondents consider income stacking essential for financial security. That mindset is spreading across generations. In a separate 2025 SurveyMonkey survey, 70% of workers said people should always have income beyond their main job.
• Job security today is not only about performing well in your current role. It is also about being financially independent enough that one employer’s decisions do not control your entire career trajectory. When your side gig or freelance practice generates consistent extra income, a job loss becomes a difficult setback rather than a financial emergency. You can make deliberate choices about your next move instead of accepting the first offer out of desperation.

This financial independence also changes how you approach negotiation. Professionals who do not urgently need their next paycheck negotiate better salaries, decline misaligned opportunities, and change jobs on their own schedule. If future-proofing your career is a priority, income diversification is one of the highest-leverage moves available.

3. Test a Career Change Before You Commit

Career transitions carry real risk. Leaving a stable job to enter a new field means accepting income uncertainty, an unknown timeline, and no guarantee of fit. A side gig can reduce that uncertainty considerably before you make any formal move.

• When you build a secondary income stream in the direction you want to move, you gather real-world information before you commit. You learn whether clients will pay for your services. You find out if you actually enjoy the day-to-day work, not just the concept of it. You build a portfolio of results that a future employer or client can evaluate. All of this happens while your primary income stays intact.
• This is one of the most underused advantages of having an additional source of income. It turns a major career decision into a lower-risk experiment with real data attached. You test the market with a small offer, refine it based on actual feedback, and build confidence over months rather than making a single high-stakes leap.

If you are working through making a career change, starting a small income stream in your target field is often one of the most direct ways to gather the kind of information that research alone cannot provide.

4. Develop Transferable Skills and a Stronger Professional Profile

Running a side hustle or freelance practice builds skills that your primary job may never require. Sales, client communication, pricing strategy, project management, financial tracking, and marketing are all practical competencies that surface quickly when you operate your own income stream.

According to Deloitte’s 2025 Gen Z and Millennial Survey, nearly 70% of Gen Z and 59% of Millennials engage in skill development outside of formal employment. Employers are increasingly aware that candidates with active side projects tend to arrive with broader, more adaptable skill sets than those who rely entirely on their employer for professional development.

Skills built through a side hustle often translate directly into career advancement opportunities. A professional who has managed their own client relationships understands customer needs in a way peers without that experience rarely do. Someone who has sold a digital product understands positioning and audience fit at a practical level, not a theoretical one. Those advantages show up in performance reviews, promotion decisions, and competitive job searches.

A portfolio career does not have to be random. Build income streams that complement your primary role or point toward your next career move. That coherence makes your skill development cumulative rather than scattered, and it gives you a more compelling story to tell in interviews or advancement conversations.

5. Turn a Hobby or Interest into a Source of Extra Income

Many professionals have knowledge or skills outside their primary job that carry real market value. The gap between having that knowledge and earning income from it is usually not a skills gap. It is a structural one. They have not taken the step of packaging and offering what they know.

• Monetizing hobbies does not require a formal business plan or significant upfront investment. A professional who writes, designs, coaches, speaks a second language, teaches fitness, understands financial modeling, or has specialized industry knowledge has a skill that someone will pay for. The barrier tends to be psychological rather than practical.
• Common ways to generate extra income from a hobby or professional interest include selling digital products such as templates, guides, or presets; offering freelance services in a creative or technical skill; teaching or tutoring online or in person; and building a small consulting or coaching offer around a specific area of expertise.
• The most important step before scaling is validation. Before investing significant time building out a product or service, test whether anyone will pay for it. Offer the service to two or three people and see whether they pay. Create a minimal digital product and promote it to a small audience. Feedback from real buyers is more useful than any amount of planning done in isolation.

A weekend side hustle built around something you already do well does not feel like a second job. It feels like structured development with a financial upside attached.

6. Increase Professional Satisfaction Without Leaving Your Job

Job dissatisfaction is one of the most common reasons professionals consider leaving their current role. But not all dissatisfaction signals that the job itself is wrong. Sometimes it signals that a single role cannot meet every professional need a person has.

• Research from Side Hustle Nation found that 76% of people report loving their side hustle, while only 50% say the same about their primary job. That gap is worth examining. For many professionals, a side project provides what their primary role does not: a faster feedback loop, more direct ownership of outcomes, creative control, or work aligned with a personal interest.
• Rather than leaving a job that meets financial needs but not creative ones, a side gig can complement it. The result is a more balanced professional life where multiple sources of work fill different needs, and no single role carries the burden of satisfying everything.

Professional satisfaction spread across multiple income sources also tends to be more stable. When one source of work is difficult or frustrating, another compensates. That balance makes it easier to stay patient through challenging periods at work rather than making reactive decisions that look attractive in the short term but carry long-term costs.

What Are the Risks of Building Multiple Income Streams?

Multiple income streams offer real advantages, but they come with practical risks worth understanding before you start.

Tax and record-keeping basics

Income from freelance work, digital products, consulting, and other self-employment activities is taxable. You are responsible for tracking it, reporting it, and in most cases paying estimated quarterly taxes to the IRS. Self-employment tax covers Social Security and Medicare contributions that an employer would normally split with you as a W-2 worker.

Keep a simple log of income and business expenses from the first month. A basic spreadsheet or bookkeeping tool handles most of what an early-stage side income requires. This is not optional. Failing to track business expenses means leaving legitimate deductions unclaimed at tax time. Note that nothing in this article constitutes tax advice. Consult a qualified tax professional for guidance specific to your situation.

Burnout and time boundaries

A 2025 survey found that 67% of side hustlers report experiencing burnout at some point. Most trace it back to a common source: not setting clear time limits before starting.

Burnout from an additional income stream is real, but it is manageable with structure. Decide in advance how many hours per week you will commit. Treat that number as a ceiling rather than a floor. 

Build in regular review points, at 30 and 90 days, to assess whether the income and professional benefit justify the time invested. If a stream is generating very little return for significant effort, treat that as data worth acting on. Scale back, pivot, or stop.

Side-hustle scams to avoid

Not every opportunity to earn extra income is legitimate. The FTC has documented a rise in task-based and job scams targeting people seeking a flexible side gig or remote work. Common warning signs include requests for upfront payment to access work, unusually high pay promised for simple tasks, job offers sent via unsolicited text or WhatsApp message, and requests for payment in cryptocurrency or gift cards. Legitimate income opportunities do not require you to pay to start working.

How to Start Building Multiple Income Streams

Starting is more straightforward than most people expect. The most common mistake is trying to launch multiple income streams at once. Start with one.

• Step 1: Identify a skill or asset you already have. Think about what you do well in your current role, what you have built or created outside of work, or what people regularly ask you to help them with. That is usually the right starting point.
• Step 2: Choose one format for offering it. Freelance services, consulting, a digital product, or an online course are all viable starting points. Choose the format that fits your current schedule and energy level rather than the one that sounds most ambitious.
• Step 3: Test before building. Offer your service or product to a small group before constructing a full system around it. The goal is one paying client or one sale before you invest more time and resources. Early real-world feedback is worth more than months of internal planning.
• Step 4: Set a time boundary and a financial target. Decide how many hours per week you are willing to commit and what monthly income would make the effort worth continuing. Without a target, it is hard to know whether the stream is working.
• Step 5: Review and decide at 90 days. After three months, you will have enough real data to decide whether to continue, refine, or stop. Most side income streams take three to six months to find consistent traction.

If you are ready to move forward but want help building a career strategy that accounts for where you want to go, working with a career coach can help you cut through the uncertainty and build a plan that fits your specific situation.

Ready to Take Control of Your Career?

Building multiple income streams is one part of a bigger picture. The other part is having a clear direction, a plan that fits where you actually are right now, and the right support to move forward with confidence.

• PathWise offers a full range of resources designed for mid-career professionals who are ready to stop drifting and start making deliberate moves.
• If you want one-on-one support, PathWise coaching connects you with an experienced career coach who can help you build a career roadmap, work through a pivot decision, or prepare for your next move.
• If you are looking for practical tools you can use on your own schedule, PathWise career courses cover everything from decision-making and personal branding to leadership and negotiation, in formats that work around a full-time job.
• If your resume, LinkedIn profile, or positioning needs work before you make a move, PathWise career services include resume reviews, LinkedIn optimization, and job search support.

For a full overview of what is available and where to start, visit the PathWise offerings page or go directly to the PathWise for individuals page to find the right entry point for your situation.

Improving productivity in the workplace means helping people produce better work with less wasted time, fewer distractions, clearer priorities, and sustainable energy. It is not about squeezing more hours out of the day. It is about making sure the hours people already work go toward the right things and that employees have the structure, clarity, and support to do their best.

This guide covers what workplace productivity actually means, why it is declining across industries, how to measure it without encouraging burnout, nine practical strategies to improve it, and what managers and HR teams can do to support their people.

What Is Productivity in the Workplace?

Workplace productivity is the ratio of valuable output to the time and effort invested in producing it. A productive employee is not simply a busy one. Busy looks like a full calendar and constant task-switching. Productive looks like meaningful work completed on time, with clarity about what matters most and enough focus to do it well.

True workplace efficiency depends on four things working together: clear priorities so people know what to focus on, protected time so they can actually focus, workload management that prevents capacity overload, and the physical and psychological energy to sustain consistent performance. When any one of those elements is missing, workplace performance suffers even when effort stays high.

Why Workplace Productivity Is Declining Right Now

The data on employee productivity paints a concerning picture. According to Gallup’s State of the Global Workplace 2026 report, global employee engagement fell to 20 percent in 2025, the lowest level since 2020, costing the world economy an estimated $10 trillion in lost productivity. 

Manager engagement is an even sharper story: it dropped from 30 percent to 22 percent between 2023 and 2025, the steepest decline Gallup has ever tracked. Since managers account for up to 70 percent of the variance in team engagement, that collapse has a direct downstream effect on how productive their teams are.

At the individual level, research from Deloitte’s 2025 Global Human Capital Trends found that 48 percent of employees describe their work as chaotic and fragmented, a feeling shared by 52 percent of leaders. The average worker is productive for only five hours and 56 minutes per day, leaving a 54-minute gap per person that compounds into billions of dollars in lost output across organizations.

The problem rarely comes from a lack of effort. It comes from how work is organized, structured, and communicated. Employees cannot produce strong results when priorities shift constantly, communication is fractured across too many tools, and support from managers is inconsistent.

How to Measure Workplace Performance Without Encouraging Burnout

Before organizations try to improve productivity, they need a meaningful way to measure it. The wrong metrics create the wrong behaviors. Counting hours worked, messages sent, or tasks logged rewards activity rather than output. That leads to productivity theater people looking busy while meaningful progress stalls.

Useful productivity metrics focus on output quality, goal completion rates, cycle time for key deliverables, and employee engagement scores. Absenteeism and presenteeism data are also valuable signals. Presenteeism, where employees show up but cannot perform effectively due to stress, exhaustion, or disengagement, costs employers ten times more than absenteeism. Tracking that gap reveals where workload management and burnout prevention need attention.

For individual contributors, regular check-ins that focus on blockers, priorities, and progress toward goals give managers the visibility they need without creating surveillance pressure. For teams, tracking the percentage of time spent on high-value work versus coordination overhead offers a practical starting point. Asana research shows that knowledge workers spend 60 percent of their time on work about work coordination, status updates, tool-switching, and meeting follow-up, leaving less than half the workday for focused, meaningful output.

9 Practical Ways to Improve Productivity in the Workplace

1. Focus on One Task at a Time

Task-switching is one of the most damaging habits in modern work. Research consistently shows it can reduce productivity by up to 40 percent because the brain needs time to rebuild context each time it moves between tasks. Single-tasking, spending dedicated time on one piece of work before moving to the next is one of the simplest and most effective productivity habits available.

Practically, this means turning off notifications during focused work periods, batching similar tasks together, and resisting the urge to check email or messages between projects. Organizations can support this by establishing norms around response times rather than expecting instant replies across all channels.

2. Use Time Blocking to Protect Deep Work

Time blocking is the practice of scheduling specific blocks of time for specific types of work. Instead of working reactively off a to-do list, employees dedicate chunks of two to three hours to their highest-priority tasks before responding to requests. This is especially useful for work that requires sustained mental clarity.

Pairing time blocking with time management training helps employees build the habits and systems needed to protect focused time consistently, not just when they feel energized. Managers can model this by treating focus blocks on their own calendars as genuinely non-negotiable.

3. Build Task Prioritization Around High-Impact Work

Not all tasks are equal, and one of the most common productivity drains is spending the day on low-impact work while higher-priority projects get pushed to the end of the week. Effective task prioritization means starting with the work that moves the most important goals forward, not the work that arrived most recently.

A simple daily habit is identifying the one to three tasks that would make the day genuinely productive before opening email or checking messages. Goal setting at the team level should reinforce this by making it clear which projects take priority when capacity gets tight.

4. Take Breaks That Restore Mental Clarity

Regular breaks improve performance rather than reduce it. Research on booster breaks shows that structured recovery time during the workday improves concentration, mood, physical health, and sustained output. Working through lunch or skipping recovery time between intense tasks depletes the mental resources needed for quality work.

Restorative breaks involve stepping away from screens, ideally moving the body or spending brief time outdoors. They are different from scrolling through a phone, which replaces one form of cognitive stimulation with another. Protecting lunchtime, taking a five-minute walk between meetings, and encouraging employees to genuinely step away rather than stay at their desks reduces the risk of burnout and keeps performance sustainable.

For more on recognizing and recovering from depletion, the PathWise guide on how to deal with burnout covers the warning signs and recovery steps in practical detail.

5. Delegate With Clear Ownership

Delegation is one of the highest-leverage tools available to managers, but it only works when it is done clearly. Handing off a task without specifying the expected outcome, the decision-making authority, the deadline, and the check-in points creates confusion and follow-up overhead that costs more time than it saves.

Effective delegation includes four elements: a clear outcome definition, a named owner who has both the responsibility and the authority to complete the work, a realistic deadline, and a process for flagging blockers before they become delays. When managers delegate this way, they free time for higher-level thinking while developing the skills and confidence of their team members.

6. Reduce Unnecessary Meetings

Harvard Business Review research estimates that knowledge workers spend between 20 and 40 percent of their total workweek in meetings. That is before preparation and follow-up time are counted. For every hour in a meeting, Atlassian research suggests employees spend an additional 30 to 45 minutes on prep, documentation, or follow-up.

A practical meeting audit asks three questions about every recurring meeting: is this meeting the best format for this information, does every attendee need to be there, and could this be handled asynchronously with a written update instead? Replacing low-value recurring meetings with structured async communication is one of the fastest ways to return productive hours to the workday.

7. Strengthen Communication Norms

Fragmented communication is a productivity tax that most organizations underestimate. When employees have to chase status updates, reconstruct context from scattered messages, or navigate unclear expectations, coordination overhead climbs and focused work suffers.

Clear communication norms reduce that friction. This includes establishing which channels are for which types of messages, setting shared expectations on response times, and using structured one-on-one meetings to align on priorities and clear blockers. Building strong effective communication skills at the individual level multiplies the benefit of structural improvements at the team level.

Managers who use one-on-one meetings will create the visibility and alignment that prevents the downstream miscommunication that wastes everyone’s time later.

8. Use AI and Productivity Tools Strategically

AI tool adoption surged to 80 percent of employees in 2025, and the organizations that used these tools well saw a five percent increase in productive employee hours even as average workday length decreased. But adoption alone does not guarantee improvement. Research consistently shows that AI tools only boost productivity when employees understand how to use them effectively and when organizations invest in building the surrounding skills and workflows.

The most valuable use cases for AI in workplace productivity are removing low-value, repetitive tasks: drafting first versions of documents, summarizing meeting notes, generating status updates, and handling routine data queries. That frees human attention for higher-order thinking, judgment calls, and relationship work that AI cannot replicate. Organizations should approach AI adoption as a workflow design challenge, not just a tool rollout.

9. Connect Productivity to Motivation and Career Growth

Employees who feel their work has meaning and that growth is possible within their role consistently outperform those who feel stagnant. The connection between motivation at work and sustained productivity is well-documented. Job satisfaction has dropped eight percent since 2019, and nearly one-third of employees say they do not feel valued at work, both of which show up directly in output quality and engagement levels.

Supporting employee productivity over the long term means connecting daily work to larger goals, recognizing contributions regularly, and creating pathways for professional development and career success. Employees who see a future in their role have stronger reasons to invest their best effort consistently.

Common Productivity Mistakes That Hurt Workplace Performance

Several patterns quietly drain workplace efficiency even when leadership is actively trying to address it. Measuring activity instead of outcomes is one of the most common. When metrics reward hours worked, messages sent, or tasks completed regardless of priority, employees optimize for looking productive rather than being productive.

Overloading top performers is another frequent mistake. The most capable employees often absorb the most work, which eventually drives burnout, disengagement, and attrition — the opposite of the intended result. Distributing work against capacity and capability, rather than defaulting to whoever said yes last time, is a more sustainable approach.

Productivity theater, where employees perform busyness to signal engagement rather than because it moves work forward, is a signal that goal setting and priority communication need attention. When people are not clear on what success looks like, they fill the uncertainty with visible activity.

How Managers and HR Teams Can Support Employee Productivity

Managers have more influence over team productivity than any other single factor. Gallup’s research confirms that managers account for up to 70 percent of the variance in team engagement, which ties directly to how productively teams perform. That makes manager effectiveness a direct business growth and performance improvement lever.

Practically, managers improve team productivity by setting clear goals and revisiting them regularly, removing blockers rather than waiting for employees to escalate, and designing workloads that match the team’s actual capacity. Recognizing strong performance and acknowledging effort explicitly are also significantly underused tools that improve both employee engagement strategies and day-to-day output.

For HR professionals and people leaders, the most impactful investments in employee productivity are manager development, structured goal-setting processes, and professional development programs that give employees visible reasons to grow within the organization. Career development is not a luxury for well-performing organizations. It is a retention and productivity strategy for every organization.

Take the Next Step With PathWise

Knowing how to improve productivity in the workplace is one thing. Having the right support to act on it is another. PathWise brings together career coaching, structured courses, career services, and a professional community so you can move forward without having to piece everything together yourself.

• For individual contributors and career-focused professionals: If you want to sharpen your focus, build stronger professional habits, and take real ownership of your career growth, start with PathWise’s offerings for individuals. You can explore career courses on topics like decision-making, goal-setting, and leadership skills, or work directly with a coach through PathWise’s coaching packages to get structured, personalized guidance on your next move.
• For managers and rising leaders: If you are responsible for team performance and want practical tools for delegation, communication, and workload management, PathWise’s career services and full offerings page give you a clear view of what is available at every level of support.
• For HR professionals and organizations: If your team is struggling with engagement, manager effectiveness, or employee development at scale, PathWise has resources built specifically for you. Visit the PathWise solutions page for a full overview of organizational options, or go directly to the HR and organizations page to explore packaged learning and development resources your people will actually use.
• For coaches: If you support clients working through productivity challenges, career transitions, or leadership growth, PathWise for coaches gives you a cost-effective library of resources, courses, and tools to amplify your client results without building everything from scratch.

Wherever you are starting from, PathWise is built to meet you there.

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

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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

• Kyle Austin Young
• The Whuffie Factor
• Career Sessions, Career Lessons on Apple Podcasts
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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
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• Critical Connections
• Sunny Workplace
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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/

—

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.

—

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.

In this episode of Career Sessions, J.R. Lowry sits down with author, speaker, and culture expert Greg Hawks to tackle one of the biggest challenges facing organizations today:

Why are so many people disengaged at work and what actually changes that?

Greg introduces the concept of the “ownership mindset,” a powerful shift in how individuals approach their work and how leaders build environments where people feel invested, accountable, and motivated.

Drawing on decades of experience working with organizations, Greg explains why most employees start with energy and intention, but often lose it over time and what both individuals and leaders can do to bring it back.

They discuss:

• What it really means to “act like an owner” (and why it has nothing to do with your title)
• The difference between owners, renters, and vandals in the workplace
• Why engagement breaks down and how culture often unintentionally discourages initiative
• The five “unlocks” that help individuals and teams build ownership and accountability
• How leaders can re-engage employees who’ve stopped investing their energy
• Why values only matter when they are consistently lived, not just stated
• How to think about ownership not just in your role, but across your entire career

Greg also shares practical tools from identifying where you’re placing blame to making small, consistent changes that compound over time to help you take greater ownership of your work and your future

If you’ve ever felt stuck, disengaged, or frustrated by your work environment, this conversation offers a clear and actionable framework for reclaiming control, finding meaning, and building a more fulfilling career.

Follow Career Sessions 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/greg-hawks/.

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Watch the episode here

Listen to the podcast here

How To Act Like An Owner: Building Engagement, Accountability, And Meaningful Work, With Greg Hawks

One of the biggest challenges that organizations face now isn’t really about strategy or technology. It’s about engagement. Seventy percent of US workers aren’t engaged. This has been true since Gallup began measuring it 25 or 30 years ago, and the numbers are even worse outside the US. This dilemma has leaders across industries and around the world asking the same question. How do you build a culture where people actually care about the work, take initiative, contribute beyond the minimum requirements of their role?

You may be thinking that this is for employers to figure out, and it is. As an individual, don’t you want to go to work feeling excited about what you’re doing, feeling like there’s a purpose to it? I’d argue that this topic matters for all of us, whether we’re running companies or staffing the front line. My guest, Greg Hawks, has spent more than two decades helping organizations with this topic, and his work focuses on what he calls an ownership mindset the idea that the most effective teams are those where people think and act like owners regardless of their job title.

He’s got a new book, Act Like an Owner: Five Unblocks for Creating Culture People Love and Results Leaders Need, that we’ll be talking about. We’ll also talk more generally about what it means to act like an owner, why culture is shaped by everyday behaviors rather than corporate slogans, and what leaders and employees can both do to create workplaces where people feel engaged and accountable and invested in the outcome. Greg, welcome.

Totally a pleasure.

The Spectrum: Owners, Renters, And Vandals

Terrific. Let’s dive right in. Let’s talk first about the ownership mindset. What does it actually mean to act like an owner at work?

The essence of it is folks who bring their heart, head, and hands, is my shorthand for it. People that still care, bring a passion, use their imagination, bring some creativity, and bring their skills because I talk about owners, renters, and vandals, and so the idea is that renters are every other person at the workplace. They’re not bad people at all.

They’ve just learned it’s not worth caring, it’s not worth using my thoughts beyond what I have to do, and they just show up with their skills. They do a job, they’re good at their job, they get the job done. That ownership element is that one that says, “I’m still fully engaged, heart and mind, and I care at a level that moves me, that makes a difference in how I make decisions.” That’s the shorthand version of it.

Why do you think that some people naturally adopt this owner mindset and others, to your point, are more renters?

Work Engagement: We are all investing our lives every day, and we’re always getting a return  financially, emotionally, relationally, or through growth and development.

My philosophy is everybody starts out day one at an organization with an owner’s mindset. They show up, they want to prove their value, they want to contribute in meaningful ways, they want to make a difference, they want to show that you made a good hire, this was a good idea, “I have something to offer.” I think people show up that way. Over the course of time, they want to contribute, and people are like, “Simmer down. We’re going to crush your spirit too. We’re going to crush your dreams too. We just need you to show up here and do the job.”

A lot of work environments create a renter’s culture where they don’t want people having a sense of autonomy or a sense of opportunity. They just want them doing the job. I was talking with a marketing VP here in Minneapolis, and it’s a company based out of here, and she said, “I don’t think they want people to act like that. I think they just want them to do the task.” Not every organization wants that, but I think people show up wanting to bring that, and then the culture of the place usually snuffs out that desire.

I have a philosophy that all of us are investing our lives daily and we’re always getting a return. No matter what you’re doing, no matter what level you’re doing it at, you’re making an investment with your life. If you’re getting a return back, whether it’s financially or emotionally or relationally or growth and development. If people learn, “When I invest my life, when I care, and when I use and I contribute ideas, and they just get shot down all the time, I don’t get the return I’m looking for.” Just like any good investor, they go, “It’s not worth investing here. I’ll show up and do the job, but I’m not going to go and extend myself because I’ve learned it’s not worth it.”

A lot of companies will say that they want their employees to act like owners, but they still want the ability to fire them at will.

That’s the beautiful thing about somebody who carries an owner’s mindset. People who are contributing with an owner’s mindset at a company generally are the most beloved, in the sense that because they care, because they’re trying to use innovative creativity and thinking to move things forward, they have a tendency to be producers.

Even when you let somebody go when you have an owner’s mindset, you’re like, “Okay, I’ll find a place that I fit better, that the skills and abilities and ways of working I bring are most fruitful, and I find a lot of joy in that environment,” whereas frustration usually happens with people who are not succeeding. You can fire an owner, but somebody with an owner’s mindset then looks at it as just the opportunity that says, “All right, where can I lead my life next? What opportunity does this create for me?”

I think you’re getting into the idea about owning your career in a broader sense because you don’t have always full control. Even if you are supposed to act like an owner within a company, you don’t always have full control over what happens. It may not be your performance that’s getting you let go, it could be layoffs, which have more to do with the bigger picture of what’s going on in the company than they do with you individually. I think what you’re saying ultimately is that you’ve got to take ownership for your broader situation and manage the whole of your career, not just blinders on in the situation you’re in, the role you’re in, and just taking ownership of that.

This is so real-time for me right now. I’ve got a great client, and they’re having to do a RIF, 10% of the whole company. When you are that person and you’re like, “I just got let go,” but it wasn’t for cause, it wasn’t because I didn’t produce, it’s because of the economy and situation with the company, then they have a sense of, “I was contributing my best,” it sets you up to be referred. Even when you bring an owner’s mindset, it does have a long-term return, even if not within that company. Even if it’s not a momentary win, people that bring the owner’s mindset always find themselves in the position to at least have a sense of optimism towards what’s next.

Yeah, I hear you say that, and yet I think there are a lot of people who are renting their way through life.

Totally. That from a personal perspective, I am grieved when you get around people and so many of them feel like life is beyond their control. It’s just like, “What am I supposed to do about it?” They feel that way, they’re conditioned that way, or they grew up in a home that way because it is a mindset, it’s a mindset that’s just like, “Well, there’s nothing I can do about it.” Totally a renter’s mindset.

Owning your thoughts is hard, owning your actions is hard. It’s much easier just to blame. It’s much easier just to blame others, the situation, the scenarios, society, the work, and feel very justified about that. I get it, I have empathy for people that feel that way, but I want to be a proponent of it’s a little bit harder but a lot more worth it to take an ownership mindset to every aspect of your being.

Let’s come back to the corporate perspective and some of the clients you work with. How do you advise your clients to spot and nurture the owners within their organization?

Honestly, the ones I’ve worked with, the challenge I have for them is, “How do you recognize the potential you see in someone? How do you nurture it out of them?” a lot of times, people that already show up as owners, they usually have a distinction about them that has a make it happen personality or a make it happen mindset that’s like, “I’m going to do what it takes, I’ll figure it out.” Those people, it’s recognizable.

I work more with like how are you looking at renters and saying, “How do you get people who have said, ‘It’s not worth it’ but they’re good people, they did care once, and maybe a season of life or a bad experience or a bad manager or difficulty with a colleague have caused them to pull back and now they’re just showing up and doing bare minimum?” How do you re-engage those folks to cause them to buy back in?”

One of my philosophies is you don’t go hire the best, you just bring the best out of those you have because hiring the best is really hard because they’re a premium, but all the people you have with you, there’s a lot of people not having the best brought out of them. I live in Minneapolis now, the great 3M is up here. Historical approach to giving people a little bit of autonomy in an area of interest. In the economy, it’s hard to do, but that idea as a leader. Do you attach a person’s individual values and mission to what they’re trying to do?

I think just across the board, leaders aren’t as effective at that as they could be, that would create a sense of fulfillment with ease, saying, “Here’s the job you have, here’s the work we’re doing, here’s the people we’re serving, here’s the product we’re making, here’s the service we provide, here’s how your role in light of our values serves what we’re trying to do, and how does that connect with you? Let’s help you find how your personal value system aligns with that.”

When people come to work and they have their own personal sense of, “I’m on a mission, what I’m doing here matters,” when they’ve concluded that for themselves, it’s a game-changer for how they approach work. Leaders being able to help people do that not a lot of people know how to do that on their own or to see, especially if there’s numerous points along the way of when a client is served from where their job is, and maybe they’re internal, they’re not customer-facing at all.

How does that align with a mission and values that resonates with someone that then enables them to serve and go, “Here’s why what I do matters?” That’s a pretty simple idea, but it’s really hard for people on their own to calculate, and without a strong leader and a smart leader that says, “Let me show you why this is really important, and I’m not just giving you lip service, but here’s why this really matters, and I hope you find a sense of yourself in this thing we’re doing,” that’s always the first step for me. Have you helped people align their own mission, values with what we’re trying to serve in a way that they really then can sincerely go, “What I do really matters.”

The Five Unlocks: Building A Culture Of Excellence

You talk in the book about five unblocks. Do you want to walk us through your framework and how that fits into the discussion?

Sure. I love those five unblocks and those are the attributes. That idea of the first one is the Risk Bold Commitments, and so I’ll talk about like accountability and contributions. I’ve been referring to that because it’s a commitment to keep contributing when it’s not well received. It’s a commitment to be held accountable in areas as a professional because it’s really hard to acknowledge the essence of accountability is that we need help. There is no grown adult professional who’s walking around going, “I need a lot of help in my job.”

That’s not a position most people want to take, but accountability says, “I’ve recognized something in my life that is not at the level I’d like it to be. Would you help me get there?” I look at it as a nudge. Invite people to nudge you to be who you’re currently not. We drop back to mediocrity as people, which is where our natural existence is. We don’t live at a level of excellence, and so it takes people in our lives that holds us to that standard.

My philosophy is without accountability, you can’t have excellence. With that bold commitment of saying, “I’m willing to put myself and subject myself to a peer and be transparent, vulnerable in this area and I’m going to invite these people in,” that’s a big commitment. I have the reverse philosophy like if you don’t have people in your life that you’re accountable to, then you’re just committed to mediocrity.

It’s just like, how could you not recognize there’s always opportunities to grow? Even with accountability, I think of them as like progress partners. That idea of the Risking the Bold Commitment is how am I putting myself out there to let other people know that I’m self-aware enough I still have areas to grow and I want to invite you to help me, and I can acknowledge you’ll do that.

The second one, Activate Lasting Value, is really probably one of my favorites, if not my favorite of the five. It’s this idea of how do we just make things a little bit better? How as an owner am I always just mindful that I can create some little change and little adjustment and little thing that activates value that’s going to stick around and last?

In the book, one of the pushbacks I would get is like, “Well, I don’t have a budget, I don’t have authority, I don’t have decision-making power.” Again, the people in your audience whether they’re at the top of the leadership, they’re just starting out at a new job, I talk about using free words that everybody has access to free words. If you can use your free words in a specific way, it can transform literally people’s lives and your own life if you’re cognizant of being intentional with it.

In that one, just that idea of how are we creating value with the people that we’re working with, how do we value them? It could be spoken words, could be written words, could be expressions of gratitude. I always say that value lands in specificity. The human nature, the negative sticks and the positive slips. Most people carry around negative self-thoughts. People have said words to them negatively that have just landed and have never left them. That’s just the nature of the soul. Unfortunately, we all have that.

The idea of how do we use positive words in a way that really grabs hold and makes a difference to create internal motivation is through specificity, that’s the hooks in the soul, I call it. When you use specificity, it gives people identity to grab hold of. That’s why it’s this activating lasting value because my belief about motivation is it’s not an external force.

You and I are most motivated when we have an internal connection to this identity that we’re moving into. You’ve probably gotten to do this and it’s one of the great gifts of leadership. When you speak to the potential of someone and you say, “I see this in you,” they go, “I didn’t see that in myself.” All of a sudden, they go, “I love that idea that I could be that person,” then they live into it is my terminology for it. They live into that image that you see, the potential that they don’t see. That as a leader, that’s the gift, that’s the best thing about being a leader is we get to do that for others.

Nobody has to say you’re a leader. You can do that peer-to-peer. I can say, “JR, one of the things that I really appreciate about you, one of the things I really notice about you.” I can do that to anybody I work with, and it immediately makes you more valuable because you have a sense of recognition and being seen and being understood, and there’s real value to that and then the words I say also.

There’s a reciprocity that happens when I start saying these things to you and I literally would say something like, “JR, I just really like you.” There’s something that happens soul-to-soul, not in a manipulative, not in a weird way but it’s just like you’re like, “I like you too, man, I don’t know what it is.” It’s this idea that people like people who like them. You don’t have to be a likable person. You don’t even have to have an extroverted personality.

Sometimes people think, “I’ve got to have this dynamic personality.” You don’t. You just have to be a person who likes other people. If you’re that kind of person, you will be a magnet. People will be drawn to you, connect you, because there’s this reciprocity. I don’t know what it is in human nature, but it doesn’t take a lot to figure out. We’re drawn to people who like us. “You like me? I like spending time with you. Tell me the things you like about me.”

With leaders, you don’t have the right to not like the people you lead because if you don’t build some likability, you won’t have trust. Without trust, there is just no chance of effective leadership, good communication, transparent, truthful communication. With leaders, it’s not so much that everybody needs to like you so you can be buddies, it’s people don’t trust people they don’t like. You’ve got to be someone who nurtures that and says, “I really like you as someone I’m leading.”

Work Engagement: You can fire an owner, but someone with an owner’s mindset will always ask, “Where can I lead my life next?”

That creates a value on a team and in an organization that you can’t maybe put any metrics on, but when there is thick trust, people solve the right problems quickly, they’re willing to have the hard conversations right off the bat, and they’re not wasting time in dancing around things and they get right to the heart of the matter. That’s what’s so significant about that.

That’s 2 of the 5, JR. Third one. Reach for Responsibility. It’s the idea of this is what most people think ownership is going above and beyond. This is the one where I’ll talk about an E-FROG return. Emotional, financial, relational, opportunity, growth. That idea that people really matter and why would somebody go above and beyond?

Fourth one is Widen the Circle. A lot of organizations have silos and they’re location-based and they’re floor-to-floor. I’ve worked with companies that the second floor didn’t like the third floor because you know who’s up on the third floor. It’s weird separations. This idea of how do we widen the circle? What happens is people find their identity in their authority. If you are in sales and you’re like, “This is my background, this is my history, this is my experience, this is my education,” well then of course you’re like, “I’m great.”

If somebody from the HR team comes over to you and says, “We’ve been talking in HR, we got a few ideas on how sales could do this better,” they’re like, “What? Who are you?” There’s this thing. That’s why a silo exists, because it’s all built on the renter capacity the hands, the skills, the ability. That idea of how do you invite people, how do you go, “It’s not just the sales team or it’s the HR team,” but how do we take people who appreciate what we’re trying to accomplish and be strategic about invitation, incentivizing, all those things.

The fifth one is similar and it’s Think Whole House. Most people think their room’s the most important room in the house. This idea of how do you think whole house? As an owner in buying homes, I don’t like any room better than another room because the house is what gives the room value, not the room giving the house value. You’ve probably heard this, JR, where people are like, “If it wasn’t for us, this whole place would fall apart. People don’t even know what we do around here.”

It’s not true. You’re a room in the house. You’re not more significant than the house. Yet it can feel like that because people spend so much time there. That idea of how are you thinking whole house? A room outside of the house is just a box in a field with no value. What gives your room value? It’s because you’re part of a whole. When you have a thinking about the whole accurately, it enables you to serve way more effectively in the room you’re in.

Again, for leaders, that trickle-down effect of it’s not just semantics but really saying, “I value the whole, I’m here to serve the house and this is the room that I’m serving in,” instead of “I’m in this room and I got to go fight the house so everybody knows how important our room is.” it is really a lot of mindset. That’s not a skill thing. It’s not like I need you to work in every room. I just need you to care. I need you to care that when one room is hurting instead of despising them going, “How could we contribute to it?” because they’re going to affect the whole house of our value and our growth and our opportunity.

It’s totally just a mindset on those five. When you see people that think like that, the original conversation about how do you connect people to it. How are you cross-pollinating from department to department? How are you reaching beyond in ways that aren’t maybe in your job description but could be things that are fueled by your own passions and how are you thinking about the whole and being mindful of what we do here, how it affects other people? Those are those five unblocks.

Defining Culture: Beyond Static Symbols

We talked a little bit earlier about what leaders can do to foster this. How about more at the corporate level? How does a company or an organization create the environment where people feel empowered to act like owners?

JR, I love that. That is the sweet spot of my passionate self because the people at that level then are shaping the environment. They’re saying, “We’re going to utilize our values and our efforts in communication here to not just declare but model how we operate here.” I don’t know how you define culture. I’ll get asked that in these conversations. It’s usually interesting in so much that it’s like there’s not just one definition of culture because people define it in context of in their world.

When I think of culture originally, I think of it like in a broader sense of society. If you go to France, they have a language and an art and a way of thinking and a way of engaging and a food and music. They have all these things that create the culture of the French. When they are out and about in the world, they still carry that sense with them.

You come here to the United States, you just go state to state, and different states have different cultures and it’s usually around arts and maybe government policies and the way they process and function and all that. In an organization, the idea around culture is what is this environment that is shaped by the values you have? It’ll be demonstrated by whatever the place looks like, whatever the place feels like, what your branding is what all those things are the external, the art of it if you will but what is the internal?

Executive leaders get to lead the charge in creating environment built on the values. I’ve had the good fortune to work with companies that their values like really matter. They’re not just static symbols, they’re not just words, and they’re not just from 50 years ago. They’re for-profit companies that are like, “This matters, how we act around here.” Executive leaders, they don’t get to define those words, but they do get to create the opportunity for those words to be discovered.

Values are discovered, and then they’re the ones who model at the top levels and put in processes for those values to be infiltrating through the whole company, whether it’s through visual campaigns, whether it’s through every meeting we start with these things and these are our mantras and this is our three words that are critical to us and so we’re going to talk about them weekly.

When we do our town hall meetings, we’re going to have people stand up and share stories about how those values played out in their business unit or in their community.  For executive leaders, it’s the clarity of values, the reality of living them out, and then show that they are actually true, meaningful to us. Executives bear that responsibility. Once that’s in place, then they’re the perpetuators of continuing the message consistently.

I think of it as values and beliefs and behaviors. It comes back to what you were saying earlier about the fact that it’s got to be real. It can’t just be words, it’s got to be things that are actually lived in practice that are steeped into the way that things work in a company day to day. If you don’t have that, your culture is just hollow.

The Expanding Role Of The Modern Workplace

I appreciate you saying that because it’s been really fortunate. I’ve worked with some companies where it’s like not just values at the top of the organization matter, but people talk about them, they’re integrated into the language. You’re like, “This is what it really looks like when values aren’t just terms, but they’re really held in regard like these are sacred mandates for us at this place.

“How we interact with each other and how we behave and how we treat each other and how we talk to each other and how we respond to problems and how we serve clients and how we filter decisions.” It’s really rewarding to see that. Of course, I’ve worked with companies that that hasn’t been the case where it’s like “people matter” then it’s like “not really, what matters is getting the job done.” We’ll burn the people out.

Go get new ones.

Honestly. It’s like they have frustrated ones and disappointed ones, but at the end of the day, it’s like, “Oh, what really matters is.” There’s grace because it’s hard. Just like we talked about earlier, Jared, the idea of like the shifts in society and I’d love to hear some of your take on this because I’ve been working through some of this. The workplace in general has had to absorb more responsibilities for the individual than they used to.

That never used to be work’s responsibility. The spiritual life of an individual, the relational life of an individual. Now it’s like work is being asked to meet all of those needs, whereas before, society just in general, all that was exist out there. Now it’s like everything needs to come through my workplace, and if it’s not, then I’ve got an attitude. That’s a big burden to put on a company because they also have to serve the client, produce the product, get the thing out the door. The difficulty in work now is there’s a lot more expected a workplace to provide for an individual than is ever been expected before. How do you think about that?

I think you’re right and I think part of it is religion has fallen off in importance. I know you are a faithful person, but for a lot of people, they’re not in the way that they were a generation or two generations ago. Organized religion plays less of an important role, so you lose that. I think community plays less of a role for most people. We are more transient in terms of where we live and how we interact with the people who live around us.

People are looking for more from their work environments and to your point, you’re right, most workplaces are not in a position where they’re really well able to handle all of that. It falls to some degree on individual leaders to deal with some of the issues that people on their team are facing and to navigate through corporate systems that aren’t necessarily going to be really helpful to them. I just think it’s all really hard. I think there’s a lot of things that are making it really hard right now. I wish I could tell you that I had a magic answer, but I don’t. I think it’s hard both for companies and for the individuals and I’m not quite sure how it’s going to play out.

For me, because I’m an optimist also, and that’s the excitement of life. We don’t know how it’s going to work out, like there’s so many factors that are just all unknown. How will any of this work out? I don’t know. You know what I do know? If you’ll take ownership of your own life, you got the best chance for a successful, fulfilling, meaningful life in your relationships and in the work that you do and the skills you develop and in the way that you invest your time and life.

It’s hard for employees to have compassion for the corporate beast for the monster of it that is. It’s also like they’re taking on church, they’re taking on the community, they’re taking on all these aspects. It’s really difficult and I think leaders finding ways to articulate that without it sounding like making excuses, and I think employees that are engaged in a way that they’re like, “I’m getting what I can here.”

Social media, that has given inaccurate perspective about so many things about work because people are watching people quit their jobs in real time or get reprimanded. Nobody’s had exposure to that before. I think speaking about our young, the idea that they’ve seen other people quit jobs and get new jobs or they’ve seen people quit jobs and go retrofit a bus or a van and live in it and you’re like, “Is that an option for life? Okay, I didn’t know that could be done.”

It’s a convoluted work environment on both sides. This philosophy that I have that I genuinely have a passion for is that if people just take ownership, then all these meandering routes of how and why and when and where they’re unknown, but you just take the next best step. When you own that, and you don’t blame others, then you really will find yourself in a place of fulfillment.

Work Engagement: When people take ownership, the endless questions of how, why, when, and where become less important. You take the next best step, stop blaming others, and find yourself moving forward.

Conclusion: Reclaiming Agency And Ending The Blame Game

If someone reading who wants to start acting more like an owner tomorrow, what’s the first thing they should change?

Do a bit of a self-analysis on where blame exists. Who am I blaming for what? Then take back my own agency and say, “I’m going to do something about that.” I’m going to take the responsibility even though if it’s not my responsibility, even if I don’t think I should. People can talk themselves out of it. The first step is saying, “Let me just do an assessment, a blame assessment. Am I blaming anyone or anything else for a condition that I’m currently in? If so, if I reconfigured my mind to go, ‘Okay, that’s all on me. It’s 100% my responsibility,’ how would I then approach it?” That’d be the first step.

I think that’s a good way to close and thank you for doing this show with me.

Thanks, JR. It’s been a great time. I appreciate you.

All right, practical takeaways from my discussion just now with Greg. First, ownership is not about your title or whether you hold equity in the company. It’s about how you show up. Anyone can bring an ownership mindset to their role by taking initiative and solving problems and investing energy into improving the environment around them.

Second thing is that leaders play a role in this. As we talked about, it is a lot harder to be a leader in an organization nowadays because your employees are expecting you to play a greater role in their lives than I think was the case when I started my career. You’ve got to foster this owner mentality while also looking out for the whole of your people and delivering results. It’s a hard mix to get right.

The same is true at a corporate level as well. Creating a culture, living a culture, honoring that culture, delivering results, taking care of the people it is a very difficult mix. If you want your team and your organizations to be engaged and energized, you have to get that equation right. Coming back to this idea of having an owner mindset, it also means looking at it in more of the whole of your career. It’s not just within the scope of your role.

If you are working now and you are under the age of about 55, you are going to have multiple more jobs and potentially more careers in your life. Being ready to think about the fact that you always have to be managing your career direction, you don’t always have to have things figured out, but you always have to have an assumption that you are taking ownership for how things are going to play out. Whether good or bad, and you’re going to have to make the best of those situations, and that’s what taking an owner mindset looks like in the scope of your career.

Finally, it’s just this idea of little actions compounding over time. We didn’t talk about that so much, but I think it’s an important thing for this conversation. Contributing a little bit more, taking a bit more responsibility for challenge, investing more in your work, taking steps outside of your job to invest in your own growth, all of those things compound on each other in a way that will benefit you in the long run.

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Important Links

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• Act Like an Owner: Five Unblocks for Creating Culture People Love and Results Leaders Need
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About Greg Hawks

Greg Hawks is a keynote speaker, author, and corporate culture specialist who challenges leaders and teams to Act Like an Owner. For more than 25 years, he has partnered with organizations across the country to reshape culture, deepen trust, and activate ownership mindsets.

Earlier in his career, Greg spent a decade as Executive Director of a nonprofit, leading teams through complex challenges and building environments where people contributed their best. That experience became the foundation for his work with companies of every size, from ESOPs and credit unions to Fortune 500 corporations and national associations.

In his book, Act Like an Owner: Five Unlocks for Creating Culture People Love and Results Leaders Need, Greg introduces vivid metaphors and frameworks such as Owners, Renters, Vandals, the Five Unlocks, and the 3D Plan for designing culture intentionally. Known for his energetic presence, distinctive language, and practical strategies, Greg equips executives and employees alike to re-engage, increase accountability, and spark growth.

Today, his work transforms workplaces into ecosystems where an ownership culture becomes the competitive advantage.

In this episode of Career Sessions, JR Lowry sits down with coach, speaker, and bestselling author Mary Olson Menzel to explore a question many professionals wrestle with: What does it really mean to build a career that lights you up and is it realistic to do so?

Mary challenges the conventional wisdom that playing it safe is the responsible path. Drawing from both personal experience and her work with clients, she argues that ignoring what energizes you can come at a much higher cost over time.

They discuss:

• What Mary calls your “light” and why it’s a real competitive advantage
• Why employers often choose energy and authenticity over credentials
• How to balance passion with financial responsibility using the concept of Ikigai
• Practical strategies for navigating job searches in a difficult market
• How to know when it’s time to pivot and how to do it thoughtfully
• The role of storytelling and networking in standing out

Mary also shares actionable tools from building a targeted job search strategy to tracking your own “light” through daily reflection.

If you’re feeling stuck, burned out, or unsure what’s next, this conversation offers a practical and grounded path forward – one that doesn’t force you to choose between purpose and stability.

Follow Career Sessions 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/mary-olson-menzel/.

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Watch the episode here

Listen to the podcast here

What Actually Gets You Hired And Promoted, With Mary Olson Menzel

The Concept Of “Light” As Your Career Advantage

We hear so often that we should be practical about our career choices, pay the bills, be responsible, and take the safe path. In What Lights You Up, my guest Mary Olson-Menzel argues something both inspiring and unsettling, which is that playing it safe might cost us more than we realize. She shares a deeply personal story of watching her parents’ lights go out when they both gave up work that they loved to take on the responsibility of running a family business, something that was more an obligation for them than a choice.

For Mary, the realization that her parents were working out of a sense of duty more than out of a sense of passion became the defining moment that shaped her career journey. In her work and in her book, Mary challenges a belief that many of us carry, which is that credentials and resumes are what get us higher.

She makes the surprising case that employers will often choose someone with fewer qualifications, but more light, more energy, authenticity, and purpose. In this episode, we’re going to explore the tension between the sense of responsibility and our sense of fulfillment, and what it takes to build a career that doesn’t just pay the bill, but lights you up. Again, my guest is Mary Olson-Menzel, a coach, speaker, facilitator, and bestselling author.

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Mary, thank you for joining me.

Great to be here.

Let’s dive right in. In your book, What Lights You Up, you talk about light as someone’s secret sauce. How do you define that in practical terms, and how does it help you?

In my mind, and the way I describe it in the book, is that your light is the essence of who you are. It’s the spark that people see in your eyes when they’re speaking to you. It’s all of your natural gifts that you’re bringing to the table. That’s why it’s the secret sauce. You notice a person who walks into a room who is lit up from within. Those are the people who tend to get hired faster, promoted more, and have more success and happiness in their lives.

Ikigai: Finding The Intersection Of Passion, Skill, And Pay

You told a story at the beginning of the book, a pretty powerful one, about watching your parents’ lights dim. As you described it, your dad decided to take over a family business, and then your mother joined him in running that family business. It was out of a sense of duty, not what either one of them wanted to do. You were a kid, but when did you realize that that’s what had happened to your parents? More generally, what are the signs that someone’s light is dimming?

I was very young. I’m pretty perceptive and intuitive. There was a slight shift in the energy in our house. It was later, probably looking back as a young adult, when my parents ended up getting divorced that I realized that some of this stemmed from those early decisions and those decisions made out of responsibility instead of following what lights them up. That threw me into this trajectory of wanting to help people create success, joy, and happiness in their careers.

You make the point as well that you can be successful financially, but not be lit up. How do you distinguish between the two of those?

If you talk to people and they talk about those Sunday scaries or that little depression that comes in on Sundays before work, those are the people who probably are not as lit up in their work. There’s also a concept that I talk about a lot in the book and a lot in my speaking engagements, which is called Ikigai. Ikigai is a Japanese word that, translated to English, is your reason for being. It’s this wonderful, sweet spot in a Venn diagram of what you love to do, what you’re good at, what the world needs, and what you can get paid for.

When you’re in that sweet spot of Ikigai, you tend to be more lit up from within. You’re also bringing that to the workplace, whatever that is. Whether it’s a screen, an office, a hospital, or whatever it might be, you’re bringing that enthusiasm and that deeper sense of purpose to your work. Those are the people who you can tell are lit up.

Ikigai is a framework that’s one of my favorites. Anybody who tunes in to my show or reads my newsletter will know that I talk about it relatively regularly. It’s something that so perfectly captures the essence of it beyond this idea of following your passions or whatever your purpose is. There is more to it than that. You’ve got to have something that people want to buy and are willing to pay you for. When I first heard it, I was reading another friend’s book, and it completely clicked for me. It was fresh in my mind when I was reading yours.

Think about it. We all have to work. We have to work to keep the lights on in our house so that we can pay the bills. When you do discover that sweet spot, and you can love what you do and get paid for it, then you’re winning.

Let’s talk a little bit about this idea of light in the recruiting process. The job market is pretty soft. A lot of people are facing job searches that are stretching into months, sometimes six months or more. In these kinds of job markets, my experience is that a lot of recruiters play it safe. They hire for credentials because that’s what’s least likely to get them fired. You think there’s a way that you can counter that with light. Tell us how that is.

Using Energy And Authenticity To Stand Out In Interviews

When you’re coming to an interview, first of all, recruiters are busy. You may be the eighth person they’ve talked to. They’re tired. They’re burnt out. They’ve got a lot on their plates as well. The more that you can bring in that exuberance, light, and enthusiasm into the interview, the more it is going to wake up a tired recruiter. The story about Ken in the book is one of my favorite stories because he was this scrappy guy who came from the other end of town, the competitive newspaper that wasn’t quite as prestigious as the one for which he was interviewing.

What was beautiful about it was that my hiring manager, who was the CEO of the publishing division for our organization, was looking at lots of people who looked like him. Big pedigrees, great goals, resumes, and great skillsets. What happened was when Ken walked into a room, he lit up the room. You could feel the energy shift when Ken walked in. He was this big guy with this big, bright smile.

Ken is the perfect example of that Ikigai. He had the skills. He didn’t necessarily have all of the pedigree that some of the other candidates did, but he had that energy. In the book, I talk about how it was one of the best decisions that my hiring manager ever made because he was able to revitalize the entire department after the person that he replaced had retired. It was beautiful to watch.

When I was reading about him, I was thinking about situations I’ve been in when I’ve been hiring. You want to make sure, as a hiring manager, that you get the best person. Often, it’s easy to resort to looking at credentials and skills. Every now and then, you do get a person who walks in and has this aura, light, or whatever you want to call it around them.

You think, “There’s something about this person.” I always worry, though. When I’m in one of those conversations if this person going to bring the goods when the job comes, or wowing me with their charisma. How do you tell the difference between somebody who’s charismatic and somebody who’s charismatic and has the goods?

Also has the skills. You have to ask the right questions. You and I have done enough hiring in our days. You know that even if you’re blown away by somebody’s personality, you’ve got to do your due diligence. You’ve got to make sure that you’re checking the references. You’ve got to make sure that you’re asking the right questions. I have a lot of behavioral interview questions in the book as well.

Those always tend to get to the meat because they’re talking about situations, and people are getting real-life scenarios. I would not say that just because you love this person, they’re very charismatic, and they shift the energy in the room, that you should hire them. They have to have the skills, too. That’s that beautiful combination. It is when you can be intentional about making sure that they have what it takes to get the job done, but also that they’re going to bring that brightness of energy to the job, too.

Those behavioral questions are important. I’ve been using them for a long time as well. They do force people to bring their experience. If you ask them in the right way, prompt them, and ask follow-up questions. You’ll get into some of those things that highlight whether they are going to be able to bring the skills and not just the personality to the job.

Sometimes too giving them a case study to work on. With things like that, you can see how their brain works in real time.

I was a McKinsey guy, so I’ve given a lot of case studies. I’m not sure I ever want to do another case study interview of my life on either side.

I hear you, for sure.

How do you get the idea of light across on paper? When they’re looking at your resume, they’re not hearing or seeing you. You’re only getting a few seconds’ glance. How do you get it across in a way that gets you into the interview stage?

That’s why you look at people’s professional social media or professional media. A resume tells me what your skill sets are, but then when I look at you on LinkedIn or when I Google you to see what you’re doing, that’s going to give me some of a fuller picture. It’s also about how you tell the story. I say a resume tells me, but a story sells me on who you are. Being able to articulate your own special, unique story of your career path and your journey is what’s going to draw an interviewer in.

What Gets You Hired: A resume tells me what your skill sets are, but then when I look at you on LinkedIn or when I Google you to see what you’re doing, that’s going to give me some of a fuller picture. It’s also about how you tell the story. I say a resume tells me, but a story sells me on who you are.

Still, I worry for people who maybe have a non-traditional background and are applying for a role, who might not even get the benefit of that Google search or LinkedIn profile review because the recruiters are going through hundreds of resumes over 6 to 8 seconds each, or whatever the depressing statistic is.

It is depressing. It’s that short. They look at you and say yes or no, and then that’s it. That’s where referrals come in. This is a perfect segue into the intentional target list that I talk about in the book called the three Ps. What that is, is getting very intentional. People can apply to thousands of jobs in a black hole. You put your resume in a database, and you don’t know if a human being is even going to see it with AI and everything else.

You can put together a target list of companies that fall into the three categories of the Ps. That’s your usual Prospects, which is something similar to where you are. Your Pivots, which would be, for you, going from McKinsey into corporate or from corporate into consulting, and your Passions. A list of all of the organizations that you would aspire to work at, like companies or organizations that are intriguing to you in those three categories.

You can then start to back into it in a different way. It’s almost like flipping your job search upside down. You’re not waiting for the jobs to come to you. You’re starting to reach out to the people that you know at these companies or people who might have a loose connection at these companies to see if you can get an introduction.

I did my first job search many years ago. At that point, I didn’t feel like I had a lot of job search advice to draw on. This is before the era of social media and everything that has happened since then. I tell people when they ask for job search advice to have a list of ten companies. You’re always working that list of ten companies. You’re working people you know at those ten companies.

You’re working with people who know at ten companies. You’re always working on a short list. If you try to play this massive throwing-out-resumes and hoping for the best, it’s not going to work. There will be times in one of the companies, you decide, “I don’t want to work at this place. It doesn’t sound as good as I thought it was going to be.”

If there’s some other reason that it’s not going to work out for you, bounce them off the list. Put somebody else on the list. It has always worked very well for me. It forces and brings focus and discipline to the networking activities that you also talk about in the book. When you’re doing a job search, you’re going to be scattered if you don’t have that degree of focus.

A job search is almost like a full-time job in itself. If you don’t have a strategy around it and you’re not intentional about it, you’re going to be frustrating yourself. It will feel like you’re banging your head against a wall because you’re not doing it with intention and strategy around there. To your point, I read a statistic that for the average executive will take them 9 months to 1 year to find a new job in this economy. Not to depress people out there, but to give realistic numbers.

I was reading statistics as well about how the job searches are lengthening, and it’s daunting. It’s daunting because a lot of people can’t afford that financially. It’s daunting because you get up every day, and you’re like, “I’ve got to do a job search again today.” It’s emotionally exhausting.

Rejection is exhausting. You talk to a lot of people in order to get that one yes.

I describe it like a game of baseball, except you only have to get one hit. You don’t have to get a lot of at-bats. You have to get one hit. For somebody who’s thinking about this idea of following their passion, how do you suggest this idea of balancing prospects like the safe bets, with this idea of passions and dream roles?

That goes into the concept of Ikigai again because we all need to make money. To me, the ideal scenario is if you’re working in an industry or working at a company you’re passionate about. I can give you an example of a woman who worked in New York in the media industry. She went through my ten-step pivot program.

What she confessed to me at one point was that her passion was horses. She was like, “There’s never anything I could do with that and my skillset.” I said, “Why not? Let’s explore it.” She ended up getting a job at a race course as their head of media and entertainment. It can happen. You can hit that sweet spot. I have so many stories like that in the book. It’s so beautiful to see. When you see somebody falling in love with what they do, you know that they’re making the world a better place and creating a ripple effect for all of us.

Let’s talk a little bit more about pivots. All of us are going to go through pivots. Especially as lives get longer, careers get longer, and career tenures with any one firm or any one job get shorter. As an individual, how do you know when it’s time to pivot versus when it’s a bit of tough sledding?

Recognizing When It’s Time To Pivot In Your Career

It’s such a personal thing, but I think it’s when you start to feel like you don’t want to go to work anymore. That is almost the point where you maybe should have started seeing a little bit of that earlier. When you’re starting to get resentful about the things that you’re having to do, when you’re starting to get those Sunday scaries, or when you’re driving to work and you don’t feel great about it anymore. Those are the things that you need to pay attention to.

For many, you come to that realization, and then it’s like, “I’m at this realization. I want a new job tomorrow.” You have to also be patient with yourself and with the process, especially in this economy. It is about having that strategic plan. Let’s say you want to do a pivot. You’re at McKinsey, but you love photography.

That’s a long-planning pivot because you’ve got to start to build up what that looks like in photography and everything else. Maybe we can even build up a side hustle to start doing some photography on the weekends so that you can eventually pivot into it. All of it is so much planning and strategy. If you can give yourself little micro goals every week, then you can break them down, and it won’t feel so daunting and overwhelming.

I would imagine for somebody whose initial answer is, “I’ve been doing this my whole life. I don’t know what else I can do.” Some of those suggestions also apply. The idea of dipping your toe in the water and trying it as a side thing, or finding other ways to experiment with it before you take the full-on plunge.

I did it, which is why I can talk about it so easily. My background was in executive recruiting. What I realized was that, as a recruiter, I was a career coach every single day. That led to more leadership coaching, which led to more and more helping people have success in the workplace. That led me to where I am.

Everybody’s going to go through pivots. I was a Military officer when I started my career. I did my pivot by going to business schools. I left consulting, and I went into the corporate world. I left the corporate world, and I’m doing some different things like this. We’re all going to go through these things. You just have to get comfortable with the fact that there’s some freedom that comes with not doing one thing your entire life. You do have to prepare for it, and you have to be thinking about it. That’s what a lot of people struggle with because so many people are passive with their careers until they find themselves in a desperate situation.

This is why you and I do what we do. We don’t want to see people who get complacent. We want to see people who are successful and who are enjoying what they do and who are good at what they do.

I want to go back to this idea of storytelling. You said a resume tells, and a story sells. Talk a little bit more about the importance and the linkage between your light and conveying your personal brand telling your story.

The Power Of Storytelling In Showcasing Your Value

I would love to share another story that people love from the book. It’s about a guy named Pat. Pat was in finance on Wall Street. He knew that he wanted to make a pivot. He knew that he wanted to step out of Wall Street, so he worked with us, and we went through the whole program. I happened to know Pat lived one town away from me.

I happened to know that he had delivered his baby in a snowstorm on the side of 95 on his way to the hospital. We were talking about his story and how he could help people see how reliable he was and how he comes through in a clutch. I said, “Pat, you’ve got to tell the story about the baby.” He said, “No way. On Wall Street, we don’t talk about personal things like that.”

I said, “You delivering a baby on the side of the road tells me that you can come through and deliver anything for me in a pinch. You have grace under pressure. This is what companies want and need right now.” He was able to tell the story in a way that was comfortable to him, but also portrayed to the company all of these great attributes that he would bring to them. He was able to pivot into a great job that he’s still in.

Not everybody is going to have that crazy story that conveys something valuable for them. We certainly don’t need people running out and trying to deliver their baby on the side of the road to have a story to tell. If you don’t have that kind of story, how can you otherwise make the stories that you do have compelling?

Everybody has a unique story. If we’ve lived long enough, or even if we’re young, we’ve all had adversity in our lives in one way or another. It’s how you overcame that. We’ve all had things that have pushed us and caused us to grow. Those stories matter. Sometimes, people think, “My story is boring. This is what I did.” You might think it’s boring to you, but to an employer, it may be fascinating. You don’t know what’s going to resonate with somebody until you start engaging in a meaningful conversation with an interviewer.

Sometimes, it takes practice. Some people are natural storytellers. I can think of one of my friends who will have a whole room riveted with whatever story he’s telling. He can make the most mundane seem interesting. Other people struggle with that, the idea of time, place, and everything else that goes into good storytelling. How do you help people sharpen their stories so that they are as compelling for the recipient as possible?

First of all, I like them to start and go from beginning to end, so there is a story. Chronological order is important. The brain is wired to understand that. Also, it is practice. You’re right. Practice in the mirror, practice with friends, or practice in front of your dog. This starts to flow more easily off your tongue, because nobody likes to talk about them. Some people like to talk about themselves, but a lot of people don’t.

Also, bullet-pointing every experience you’ve had. Start by laying it onto a computer screen or a sheet of paper and building, “What were the biggest learnings at this job? What were the biggest wins at this job? What’s something I overcame?” Start to think of it in terms of those behavioral interview questions as well, so that you’re capturing those key learning moments and the key transition moments when you move from one job to the next and so on.

I do think testing stories. You’re writing them down as a way of testing them. You read them back and think, “I could embellish this point or highlight this a little bit more. I could bring this nuance into the story or this bit of context,” and then share it with people and get feedback. They will get better with practice. You can have a phenomenal story told badly that will not have the impact that you want it to have. My one friend that I think of can turn the mundane into the fascinating. You want to convince people that there’s something there about you. With storytelling, practicing that skill, getting good at telling your own story, and getting comfortable with a self-promotion piece of it is important.

If you’re going to apply to a specific job or a specific company, or better yet, somebody refers you to a specific company. It is making sure that you know everything about that company. Make sure you know what their values are, what their mission is, and all of that. If it’s a specific job, it is studying that job description, and then looking and saying, “Where does my skillset match here? How do I relate those stories?”

You talk about networking in the book, this idea of, “How can I help?” How do you happen to the natural generosity that people have and get over the discomfort that a lot of people have with networking so that this isn’t something you have to do by yourself?

Building Strategic Networks Through Genuine Relationships

I spoke at Kellogg, which is where I went to graduate school. One young woman raised her hand and asked a very similar question. She said, “I have been taught here at Kellogg that it’s about reciprocal relationships.” I said, “This is exactly what it is.” That’s why in the book, I talk about, “How can I help you?” You don’t want to always approach it with, “How can you help me?” It is, how can we help each other?

For the introverts out there, it’s not always easy to put yourself out there. It’s those daily micro goals of, “Can I reach out to 1, 2, or 3 people per day? Can I have five meaningful conversations?” It is always asking at the very end of the conversation, “Thank you so much. How can I return the favor? How can I help you? Is there anyone else that you think I should meet?” That’s going to expand your network exponentially, too.

That last part is important, expanding the network and asking them who else they think you should talk to or who else might be able to help them. It takes some of the pressure off them in terms of feeling like they have to necessarily do something directly for you. A lot of people aren’t going to be in an immediate position to do that for you, but they may know somebody who they think could help you. That expands your network.

Going back to my first job search, some of the people that I didn’t know at the beginning of that I’ve had lifelong relationships with since then, because somebody introduced us. This is the way that you expand the likelihood of always having help when you do need it. Whether it be when you’re in the middle of a job search or otherwise.

That abundance attitude and having the generosity of spirit is the reciprocal relationship. It is remembering these people and staying in touch with them. To your point, developing a relationship so that it’s not just you’re calling them because you need something. It’s calling in to check in and having a two-sided conversation. It unfolds a little bit more organically as well.

You’ve pulled all of this together into an equation of sorts.

It’s a ten-step program. The first thing that we do is we go very deep into who you are as a human being, not who you are as an executive or who you are as a professional. You have to look at who you are as a human being. What are all the factors? Such as family factors, relocation factors, and money factors. Then, we start to talk through what your LinkedIn profile looks like. What does your resume look like? All those things that will set you up to then create that target list of the three Ps and then reach out to your network to start having meaningful conversations.

When I think about networking for people, I tell them to say yes to every conversation. Even if that conversation doesn’t lead to a job at that moment, it can lead to a new relationship or industry research. You’re doing market research while you’re having these conversations as well, so that you can speak more intelligently to the next conversation and the next one. There’s a formula. Also, it is about remembering that you’re interviewing people as much as they’re interviewing you. Make sure that you’re being intentional about where you’re going. You’re not running away from something, but running to something that you want.

Stepping back for somebody who’s feeling stuck or overwhelmed, what’s the first step you would recommend that they take tomorrow?

Finding Clarity By Reflecting On What Truly Lights You Up

If you are feeling stuck, understand that you’re not alone out there. There are so many people who are feeling this way. The first thing to do is take a good look at where you are and then start to think about where you want to go. You don’t have to see all of it immediately. If you say, “I’m so stuck that I don’t even know where I want to go,” start to pay attention on a daily basis to the times when you feel in the flow.

Pay attention to the times when you feel happy doing whatever you’re doing, and keep logging that. I call it creating a daily light log. Look at the patterns of when you’re in the moment or when you’re in the flow, so that you can start to create more of that. That will help you decide what’s the next step, and also, where you want to go.

I had a lawyer who was working with me. His favorite thing about his day was using his French press to make coffee in the morning. We started looking at companies like Starbucks for him and places that were off-the-grid from where he was. Expand your horizons and be open to almost any conversation, and then you’ll start to get clarity. It will crystallize as you continue to have more conversations.

The journaling part of what you talked about, however you choose to do it, is important. For a lot of us, there is some time needed. You have to immerse yourself in this experience of figuring out what you want to do next, whether it’s a big pivot or maybe not even a pivot at all. Getting the ability to let things sit with you and see how they feel. Journaling helps with that because it forces you to articulate your thinking. You can come back, look at it, and say, “I’m not sure that that’s still how I feel or I feel even more strongly.” It helps you triangulate in on the kinds of things that are going to light you up and are going to get you paid. The other elements of Ikigai as well.

Also, thinking about, “Why do I do what I do?” Simon Sinek and your why. “Why am I doing what I’m doing? Is this still serving me? Is this still good for me at this juncture in my life, or do I need to be doing something different?” Also, I love asking people this question. “What did you want to be when you were little?” Go back to that. I wanted to be a professional figure skater but that ship sailed a long time ago. A lot of times, people can go back to that and still feel that resonance with what they wanted to do when they were little. It’s always fun to ask yourself that question, too.

I don’t know that I ever had a realistic thought of what I wanted to be when I was a kid until I was probably contemplating college. I know a lot of people did when they were little, and some of them stuck with it. One of my kids knew she wanted to be an architect from the time she was ten years old.

Some people do have that clear direction. Don’t beat yourself up if you don’t. Let it unfold with some of the exercises that we’ve talked about.

Thank you for doing this. It was a great conversation. I love hearing more about your book and having you bring some of the stories that were in the book to life for our audience. I appreciate your time and your being here.

Thank you. Great conversation.

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Lots to unpack from my conversation with Mary. First is this idea of light. It’s not fluff. It can be a competitive advantage. Hiring and promotion decisions are often influenced not just by credentials alone, but by energy and the authenticity that you bring to the interview process. It’s your mindset. All of that is embodied in what Mary calls light. Employers will repeatedly choose people whose presence, passion, and humanity stand out. Don’t forget that, even in a world where skills still do matter.

Ignoring your light can have real consequences. One of the most powerful themes in the book comes from Mary witnessing how her parents gave up work that they loved out of a sense of responsibility, and then realizing that their lights had gone out. Career mismanagement doesn’t affect your job satisfaction. It affects your health, your relationships, your sense of long-term fulfillment, and your identity. Third, the world of work has changed, and so have expectations. Work is not just about technical competence. Human qualities like emotional intelligence, adaptability, creativity, and presence matter more than ever. They’re not soft skills. They’re critical ones.

Fourth is the idea that clarity comes from reflection and not just reaction. Mary pushes this idea about intentional self-discovery through exercises, journaling, and pattern recognition to uncover what energizes you. This is important because so often, our career decisions are made passively or made reactively. They’re driven by inertia, fear, urgency, external pressure, or whatever the case may be. If you’re going to have success, it’s sustainable. It requires stepping back to understand what you want.

Finally, the idea that purpose and practicality don’t have to be mutually exclusive goals. A major misconception that Mary tackles in both her book and her work is that following your passion is like abandoning your bank account or your financial responsibility. You can, with creativity, find something that does light you up that also pays the bills. You don’t have to sacrifice one for the other.

Thanks for joining. I invite you to subscribe to Career Sessions, Career Lessons 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.io. You can get to that at Community.PathWise.io. Thanks.

Important Links

• Mary Olson-Menzel on LinkedIn
• Mary Olson-Menzel on Instagram
• MVP Exec
• What Lights You Up?: Illuminate Your Path and Take the Next Big Step in Your Career
• PathWise on LinkedIn
• PathWise on Facebook
• PathWise on YouTube
• PathWise on Instagram
• PathWise on TikTok
• Career Sessions, Career Lessons on Apple Podcasts
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About Mary Olson-Menzel

Mary Olson-Menzel is a renowned expert in career and workplace success. She has over 30 years of leadership experience across various industries, including media, tech, healthcare, and sports, and has worked with many global organizations. She is the Founder and CEO of MVP Executive Development, a national leadership, coaching, and organizational management consultancy with offices in New York, Connecticut, and Illinois. Her clients range from Fortune 500 companies to start-ups with a broad reach of industries, from FinTech to Football (the NFL). As a seasoned executive leadership coach, Mary works with both companies and individuals to unlock their potential, improving business performance and catalyzing growth. Her coaching methods bring a fresh lens to business and a perspective that nurtures teamwork, helping drive results through grace, empathy, and Humane Leadership.

Before starting her company in 2012, Mary was a partner at two leading global executive search firms. She also spent a decade at Tribune Company in Chicago, serving as National Managing Director of Talent, where she led a team of recruiting professionals. This is where her understanding and expertise in recruiting and coaching were honed. She worked closely with hundreds of media assets nationwide to attract and retain the best and brightest.

In her early years, Mary worked in both the tech sector and the media and entertainment industry, where she began her career as a television reporter. Her innate curiosity and ability to connect with people paved the way for her life’s work: helping leaders at all levels channel what “lights them up” and inspire them to follow more fulfilling and successful personal and professional journeys. Mary earned her MBA from Northwestern University’s Kellogg School of Business and a Bachelor’s degree in Communications and Public Relations from Illinois State University.

Mary currently lives in Westchester, NY, with her husband and family. She is a part of Marshall Goldsmith 100 Coaches, which brings together the world’s leading executive coaches, consultants, speakers, authors, iconic leaders, and entrepreneurs. Mary is a regular Guest Lecturer on career development, internships, and workplace success at the NYU School of Professional Studies, Division of Programs in Business. She also volunteers for various local charities. What Lights You Up? Illuminate Your Path and Take the Next Big Step in Your Career is her first book and is a USA Today National Bestseller. For more information, visit www.mvpexec.com and www.maryolsonmenzel.com.

In this episode of Career Sessions, JR Lowry speaks with behavioral scientist Jon Levy to explore what actually makes teams effective and why the answer isn’t what most people think.

Drawing on research across psychology, business, and even sports, Jon breaks down the hidden dynamics behind high-performing teams, including the overlooked role of “glue people” – those who quietly elevate everyone around them.

They discuss:

• Why emotional intelligence matters more than IQ on teams
• The surprising reason too much talent can hurt performance
• What “glue players” do differently and how to spot them
• How influence really works (and why it’s not about power)
• The role of trust, belonging, and feedback in team success

Jon also shares insights from his unconventional work building communities and designing experiences that foster deep human connection.

If you’re leading a team or want to become more effective within one, this conversation will challenge how you think about performance, influence, and success.

Follow Career Sessions with JR Lowry 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/jon-levy/.

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Watch the episode here

Listen to the podcast here

What Leaders Get Wrong About Performance And Teamwork, With Jon Levy

Several months ago, I was reading an article in the Wall Street Journal on people who play glue roles on teams and I thought to myself, I would really like to interview the person who was profiled. Here we are. My guest is Jon Levy, and we’re going to talk about his multifaceted work and life, covering what makes teams particularly effective, including glue people, influence, and the science behind it.

Also, Jon’s very unique Influencers community and his crazy year spent traveling the world and attending some of its most iconic events. Before we dive in, let me remind you that our episode is brought to you by PathWise.io. If you’re ready to take control of your career, like thousands of others already have, join the PathWise community at Community.PathWise.io. Okay, it’s going to be a fun conversation, so let’s get going.

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Jon, welcome. Thank you for doing the show with me.

JR, are you kidding? I’m so excited.

As I mentioned in the intro, the genesis of this was a Wall Street Journal article that you wrote back in the fall. We’re recording this in January. Before we dive into the topics that I had planned to cover, it’d be great to get just a quick background on you.

John Levy’s Secret Dining Experience (The Influencers Community)

I’m a Behavioral Scientist. I’ve spent most of my research career looking at trust, connection. I oddly did the largest study, I think, in history on dating, where we found weird things like if you have the same initials you’re 11.3% more likely to date. It’s called implicit egotism. Anything that reminds us of ourselves is more attractive and appealing. What I did with my knowledge, years ago, I created a secret dining experience. Twelve people are invited and they come to cook a terrible meal together, anonymously.

Nobody knows who’s going to be there and they’re not allowed to talk about what they do or give their last names. They cook this awful meal, they sit down, and as they’re eating, they play a game to figure out what people do professionally. That’s when they find out they’re sitting with astronauts and Olympians and Nobel laureates and the editor-in-chief of a major magazine or the guy who won an Emmy for barking on “Who Let the Dogs Out.” it’s incredibly varied. Although I don’t do research on the dinners themselves because it’s not really how it would work, it gave me insights over the years that led to actual work that was made.

Why is it a terrible meal?

Anytime you do something that’s a professional task with a group of people who are not professionals, it’s not going to work out that well. It’s not by design a terrible meal. It’s just there’s Nobel laureates are busy in a lab, they’re not busy in a kitchen. The same is true for CEOs of big companies or Academy Award winners. It’s just a different skillset. You can have a fine meal that’s edible. Nobody’s ever gotten sick. All these people can afford a much nicer meal at a very fancy restaurant if they want to go.

Who chooses the menu?

Me and my team. It’s just the same thing at this point every time because you need something that can be prepared in a certain length of time. It needs to be able to be safe for everybody. If you’re vegan or vegetarian or something like that. You have to occupy a certain number of people. It’s just fallen into a very basic routine.

I had to do something a little bit like that. I was going through an outdoor leadership training program and we had to prepare each of the meals and so none of us really knew each other. We got thrown into the kitchen and had to plan a menu. One of the guys called an audible at the very end and decided he didn’t feel like cooking pasta, so he’d gone out and brought a bunch of stuff to cook this Indian dish.

The guy who was running the program, he told us late, “I was thinking in my head, ‘This is going to be an unmitigated disaster.’ There is no way this group of you who don’t know each other are going to be able to prepare this Indian dish that half the group wasn’t familiar with and have it turn out okay. You proved me wrong. You guys did it. Nobody yelled at each other, nobody had a meltdown, it actually tasted okay, you cleaned up, it was all good.” that’s the closest I’ve come to your secret dinner experience.

The beauty of the dinner is that when it comes to connecting people, we tend to do everything wrong or backwards. In the business world, we think, “Okay, you are somebody I want to sell something to, so I’m going to take you out for an expensive business dinner.” The problem is that stuff doesn’t actually work. It’s like this. If I said, “JR, I know you don’t like my personality, but I have tickets to the Super Bowl. Do you want to hang out?” Now I have just rented your attention, hoping that it’ll convert into business. The reality is that it’s rented time. It’s not something you care about.

What causes us to care about something is called the IKEA effect, which is that we care more about our IKEA furniture because we had to assemble it. As a byproduct, anything we put effort into we care about more, whether that’s our kids, our pets, our plants, or our work. By getting you to invest the effort into making the food with each other, it caused you to feel more connected and care more about each other and the product that you made.

I literally just put together an IKEA nightstand for reasons that we don’t need to go into here, but I don’t love that nightstand any more than I would love a nightstand normally. I sat there as I was building the thing going, “This is a really bad use of my time relative to other things I could be doing. I would rather avoid the flat pack and just buy the finished-made thing.”

Here’s what’s interesting. I’m not saying you’ll even like it. I’m just saying you’ll care more about it. It was a sunk-cost effort that you will never get back and right now, if you were to say, “Which one of these items do you have the strongest emotional connection to?” It’ll probably be your IKEA side table because you’re like, “After all that effort, if we’re not using this thing I’m going to go crazy.”

Let’s dive in on some of the work you’ve been doing. I know you study teams. When you have studied high-performing teams across the various domains that you’ve looked at, what separates them from the rest?

Defining High-Performing Teams & The Role Of Emotional Intelligence

The first question we need to ask is what do we actually mean by high-performing? There’s so much jargon that’s thrown around that’s total BS out there. What we’re probably talking about is more how smart a team is. How quickly can that team solve a problem with the resources they have? If we take a bunch of different teams and give them a series of challenges, what is it about the teams that perform quickly versus those that don’t? This was originally research that came out of the failures of September 11th.

September 11th occurs. After, a report showed that the CIA knew about half of Al-Qaeda’s plan, the FBI knew the other half, but they worked so poorly together that they became collectively stupid. The government funded a bunch of research. A lot of it was led by this woman, Anita Williams Woolley. What she found is that the things that we thought predicted an effective team actually don’t. Having absolutely brilliant people on the team made no real difference. How much the team members liked each other could actually be a liability.

The single greatest predictor was unexpected. It was the number of women on the team. The more women, the better the team did. I think it’s important to understand why, because it doesn’t tell the full story. It’s not that all teams should be all women except for one man or something like that. It’s that women tend to score higher on emotional intelligence. When we look at a group’s dynamics, you could have the smartest people in the world, but if they are just butting heads constantly and can’t make progress, it doesn’t matter how smart they are.

Emotional intelligence allows us to understand when to push on a topic, when not to. Who to go to for the knowledge that you need. When to call on somebody when they’re being quiet but actually have the information. The more of it that we have on a team, the tendency is that the team does better. What Woolley and her colleagues discovered is that there’s an entire collection of characteristics that actually empower a team to succeed. A lot of it is actually underpinned by emotional intelligence.

Effective Teams: Emotional intelligence helps us know when to push a topic and when to hold back, who to turn to for the knowledge we need, and when to draw out someone who’s quiet but has valuable insight. The more emotional intelligence a team has, the better it tends to perform.

Which I guess should not surprise us. We’ve been talking for the last 30, 40 years about emotional intelligence and the way that it trumps IQ in many other things and plays such a valuable role. At the same time, we’re still having debates about bringing women into the boardroom and into the executive suite and it feels counterintuitive to what the research shows but power ultimately isn’t always the most logical.

I think one of the big mistakes we’ve made is measuring what’s easy to see versus what’s useful. I’ll give you an example in sports and then let’s get back to that boardroom that you just talked about. In basketball, there is one stat that predicts a player’s salary. Simply the number of points they score. There’s also only one stat that predicts if a coach is effective. It is not wins. It is the increased rate in passing under that coach. Now what most people don’t realize is that these two stats are actually the exact opposite of each other.

If you’re incentivized to score in order to earn a lot of money, you are going to take a lot of bad shots. That will be very bad for the team but very good for you. Let’s call it empty calories. Increased rate in passing means that you’ve stopped thinking about your own personal goals and started thinking about the team’s goals. As a byproduct, the ball ends up with the person with the highest chance of scoring. What that actually translates to is selflessness. You can see that what’s easy to see is points. It’s not the thing that’s good for us.

We have to look past the obvious. The easy to see thing right now is saying, “We need more women.” No argument there. It actually misses the point. What we need is higher levels of emotional intelligence. If we reduce people to the easy to see stuff like race, gender, orientation or anything like that, we’ve reduced them to the things that they can’t improve or get better at. Whereas if I say, “I really want JR on the team because he has really high emotional intelligence and allows us to function better,” then suddenly, you’re an asset to the team that brings value.

There’s also plenty of men with high emotional intelligence and plenty of women who don’t have any. If we focus on bringing the right variety of skills to the team, inevitably the teams will look more diverse. If I simply reduce you to these immutable characteristics, then you’re going to get backlash, and understandably.

I think the hard part in what you just said is emotional intelligence is a very subjective thing. It’s really difficult to measure it relative to a lot of other things and that probably makes it harder to do what you’re suggesting.

If these things were obvious and easy, people would be doing them. Companies aren’t stupid. The status quo is really easy to maintain and inertia is hard to overcome. If you have a general policy in place or habit that you think is working, there’s a million other fires to put out. Why would you begin there?

Interesting that you brought up NBA statistics a minute ago because the statistic that I was thinking of wasn’t scoring or passing but this idea of plus-minus. How many points does the team score when you’re in the game relative to the opponent and how much do they score when you’re not in the game? You can see whether when you’re in, do we build our lead or do we lose our lead? To me, that’s a great measure of a person who’s in a glue role.

Shane Battier is a guy I’ve always admired as a glue guy in the NBA from his time. He always embodied that idea of bringing a team together and not necessarily showing up in the obvious stats but in making his teams better and would just love to hear a little bit more about what you’ve learned about these people who play these glue roles on teams.

The Characteristics Of Glue Players

We’re so obsessed with the people who score in basketball, so the general belief is let’s just get a lot of these top performers together on the same team. It turns out that there was a research project that looked at this specifically and found that in basketball and in soccer, or European football, when you cross about the 50% mark of top talent, you actually get a reduced performance from the team. The reason is selfishness. When everybody’s only looking out for themselves, it’s not surprising that suddenly, people aren’t passing and the team isn’t coordinated.

Amusingly enough, this doesn’t actually exist in baseball because there’s no way to be selfish in baseball. If you are up at bat and you hit the ball or don’t, it doesn’t really have a direct impact on the next person. You can’t steal runs from another person. The question then becomes, how do you fix the too-much-talent problem? What’s the best composition of teams? A research group from Brigham Young University said, “Okay, we’re going to look at player stats and see are there any players that have a huge impact on the team but maybe don’t score a lot?”

What they found is that there’s an entire collection that they called spillover players, I call them glue players and these people can multiply everybody else’s results by about a factor of 1.6. The question is, so in basketball, if a player cares more about the team than they do about themselves, when it comes time to getting rebounds, they might block you, JR, and push you out really far so you can’t get the rebound, and then somebody else on the team can get it.

They’re sacrificing their own stats in exchange for the performance of the team and you get the stat instead. You could imagine that over the course of a game or a season, that begins to really add up and your stats begin to look significantly better, or whoever gets the rebound. This behavior has an outsized impact. What I mean by that is the people who tend to have these characteristics have three habits. The first is that they’re incredibly team-oriented. They put the team above themselves.

In Shane Battier’s case, he was probably one of the few players ever in NBA history to say, “Take me out, coach, so that I can be better rested when they put their best person out there.” That’s incredibly selfless. Nobody in sports does that. The second is they tend to have really high emotional intelligence, meaning that they are able to understand how to maneuver the big personalities and communicate with people to get them to be more cohesive and gel.

In Battier’s case, he was famous for being called Lego because when he’d get on the court, everybody would click into position. As a byproduct, he actually ended up speaking more than other people do on the court because he’s passing information to everybody to be aware of what’s going on. The third characteristic is that he’s incredibly forward-thinking. He takes the actions that nobody else even thinks to take.

In Battier’s case, he would memorize the opposing team’s stats, knowing that a specific player will shoot 5% worse from areas on the court and if you can just push them there over the course of a game, that has a huge impact on their scoring potential. You can begin to see that with these characteristics in place, people trust him. They know that he’s not going after their status so they’ll accept support from him. The emotional intelligence allows him to maneuver between the team members and understand how to communicate with them and he’s taken these actions that people don’t expect that improve everybody’s success.

In the corporate world, that’s like that employee who welcomes a new person onto the team and makes sure that they’re integrated quickly, so instead of taking 6 months to integrate, they integrate in 2. Suddenly, you have a massive uptick in productivity from that person. It’s the person who rewrites the slides before an important presentation because they realized they were a little messy. It’s the person that plans the group birthdays or acknowledges people for their efforts. It’s the person that calls on the quiet person in a meeting that has something to share. These people are the glue of your team. There’s no award for them, there’s no bonus for that behavior, but it literally multiplies everybody else’s performance.

If you’re a leader, how do you learn to appreciate and spot this person and these behaviors?

The first thing I would do is probably ask the people on the team, “Who’s the person you trust the most?” or “Who’s the person you go to for advice?” or “If you need a connection in another division, who do you go to?” The other thing you can go for if you want to get really technical is that there are emotional intelligence tests that you can perform and see who has a high EQ. Now the next thing you should understand is that having it on the team is really important, but you shouldn’t beat yourself up if you don’t have the highest emotional intelligence.

You can partner with people and say things like, “JR, I know you are really good at these things. I’m not. Will you signal me if I’m overspeaking? Will you let me know if I need to have a conversation with somebody from the team?” the fact is, we put too much pressure on our leaders to be great at everything and that’s just not realistic. Instead, we need to look at it from a team perspective. How do we get everybody to contribute so that the team is as smart as possible?

I think a lot of leaders miss that. Though. Would you agree?

Yeah. It’s not because they don’t care. It’s because we’re stuck in this model that in order for you to be a leader, you need to have this perfectly curated collection of skills that nobody has. The most effective leaders in our society are not well-rounded. Elon Musk is not great at creating psychological safety, neither was Steve Jobs or Bill Gates. They created incredible organizations that each changed the world in some way. We have to understand our leaders are wildly flawed. That means that you can be wildly flawed and still accomplish extraordinary things, but it’s important to understand what to focus on and what not to do.

For people who are or perceive themselves to be the glue, what’s your view? Good role to play, bad role to play? Does it ultimately help or hurt you if you’re being selfish and thinking only about its impact on your career?

I think asking the question of if it’s a good role to play or bad role to play is like saying, “You’re American. Is it good to be American or not?” the point is you were born probably in the US and you’re American, and we’re not going to change that about you at this point. Maybe you could go apply for citizenship somewhere. The point is that at this point in most people’s career, they’re probably baked in with that characteristic or not. You can try to maybe tone it down or tone it up. We’re not going to go from a 2 on emotional intelligence to a 9. It’s just not going to happen.

Now if it’s good or bad, I think is irrelevant. I think that it’s important for teams and hopefully we’re going to be in an era now where we give it more credence and value. I think the potential is that AI models will be able to notice it by you being on a Zoom call or a Teams meeting and then be able to highlight these things and show, “These people are having an outsized impact. You should promote them or you should put them in like the leadership teams because the impact they could have there is incredible.”

The second thing is that regardless of where you land on the spectrum of these skills, it’s important to understand that no one skill works by itself. A multiplier or glue player needs somebody to multiply. A team of Shane Battiers accomplishes almost nothing because they block everybody from getting the rebound and then there’s nobody there to get it. Pairing him off with a LeBron, a Chris Bosh, and a Dwyane Wade like he was with the Heat, they won back-to-back championships. It’s important to understand that we’re over-focused on the individual and under-focused on the team.

Certainly, it’s hard if you’re dependent on one person to carry you for you to do that over a sustained period. I’m curious to get your views. There’s a lot of teams in the sports domain and otherwise that have their heyday, that hit their high, have this fantastic moment, but they can’t keep the magic going. I wondered if any of your research looked into what are the behaviors ultimately that are important to creating long-term effectiveness.

Creating Long-Term Team Effectiveness

In basketball, which we keep coming back to, there’s an interesting article written about a guy named Gregg Popovich. That’s when a statistician looked at just about every team and the talent level that it had and they all win just about the number of games that they should, except for Gregg Popovich, who is the coach of the Spurs. They won over 100 games more than they should based on the level of talent. That’s because Gregg Popovich was the ultimate glue player when he was a coach. He would make people feel a greater sense of belonging to the team than probably anyone else out there.

As a result, they played team basketball. In fact, it was the Spurs that then beat the Miami Heat when they were in their heyday. I believe Popovich has, what is it, five championships or something like that, which is just an astounding career. The flip side of it is when you look at the Golden State Warriors, which had a fantastic streak, and ask what is it that changed the team’s dynamic? A lot of sports commentators would say it was when Draymond Green in a practice, I believe, punched or choked out one of his own teammates.

When you breach the social contract to that degree, it is really hard to come back from it. One of the things I keep emphasizing is, and this took me a long time to realize and learn, do you remember when you had your first kid and everybody gave you all of the unrequested advice on how to raise children? It’s like, “Read them these books and you have to play with them in these things. You’ve got to do music class, my god it helps in their development so much.”

Any parent at one point realizes, “Wait a second, there’s no number of books I can read to a child to make up for somebody verbally abusing them.” The negative impact of breaching the social contract is so much worse than the positives of, “Let’s take you to a Montessori school.” Somebody in a workplace experiencing sexual harassment cannot be made up for by giving them really great feedback in their annual reviews because the negative impact of the bad stuff is so much worse than the positive impact of the good stuff.

They say that as a manager, if you really want your constructive negative feedback to be taken in the right way, you need to have 7 to 10 times as much positive feedback that you’re conveying right alongside it so that people know that you care. You create this element of psychological safety in your feedback construct with that person that implies that, I’m doing a little bit of funny math here, but means that your negative feedback carries seven to ten times as much weight as your positive feedback.

It comes from an article by Dan Kahneman and I think Amos Tversky, who proposed Prospect Theory. The idea is that the pain of a loss is a multiple of the pleasure of the gain. Meaning like if I lose $100, that amount of pain from losing $100, to make up for it, I have to have like the joy of finding $500 or something like that. Now it’s estimated somewhere between I think 2.5 and 5 times is the ratio.

The issue is that, listen, no feedback is terrible. Negative feedback is better but it doesn’t compare to positive feedback. Positive feedback gives such a profound multiple in terms of reward and likelihood that somebody will perform the task again, that it’s just critical. Now there’s a few things you can do around these things.

One is you can just constantly catch your people doing something right and reinforce and reinforce and get like a flywheel going. You could also toughen up your people so that they become antifragile. There are certain things that when you apply pressure to them, they get stronger, and then it becomes a group activity to break everything down and improve.

Let’s shift gears and talk a little bit about influence. I know you also study that and would love to hear your thoughts on what people misunderstand about how influence actually works.

The Three Factors Of Influence

We’re used to thinking of influence these days as either a great book by Robert Cialdini or some twenty-something eating avocado toast on Instagram. I think we’ve lost focus on what actual influence is. It’s simply the ability to affect a person or an outcome. It is not power. It is not force. Me telling you that you have to go do something because I’m your boss is not influence. That’s power. Influence is me saying, “Have you considered getting this car?” and then potentially you buying it.

If we were to oversimplify things, the factors that seem to influence us consciously, let’s call it, are who we know, how much they trust us, and the sense of belonging we share. This should seem pretty obvious. If you don’t know someone, it’s pretty hard to influence us. The second factor is how much they trust us. I might know you, but you might think I’m a complete liar. If I say, “You should check out this investment opportunity,” you’d be like, “I know exactly what I’m not doing this afternoon.”

The third factor is the sense of belonging we share. Let’s say you were traveling through Southeast Asia and you hear somebody speaking English. You suddenly go, “Are you an American?” and they say “Yeah,” and you get chatting and you find out that both of you went to Duke. How do you think you feel about that person?

I’d feel certainly a sense of belonging with that person as an American, as a Duke graduate. It’s amplified and I want to get your view on this by the fact that we’re in Southeast Asia because it is a rarer thing to run into an American Duke grad there than it would be to run into one in Philadelphia or New York.

The answer is yeah, it’s amplified. That is a contextual characteristic. What it points to is also that the more common ground you share with someone, the more likely you are to feel a sense of connection. In this, what you begin to realize is that you have a disproportionate level of connection and trust to that person.

That sense of belonging amplifies it. If we could affect any of those factors, we can affect the level of influence you have. Question isn’t do you have influence? We all do. It’s over what and to what degree. Now the only question is, what do we want to be able to influence and then how do we connect with those people and build trust?

I’ve heard this idea of know, like, and trust being the three pillars. Yours is a little bit different in terms of this sense of belonging. It’d be good to get your view on that.

First of all, it’s really hard to tease out like and trust. It’s possible, but I think it’s very hard. Think of all the people you actively dislike that you trust, and you might not be able to think of anyone. Likability is often a factor of, if you actually know them, two things. People who are most likable are often people who know a lot of people and let them know why they are liked.

Meaning if I go and I say, “JR, I really respect how thoughtful you are when you interview. You do your research and you ask relevant questions. That’s appreciated because a lot of people I’ve interviewed just don’t do the work.” I’ve now given you a feeling that you are safe, you belong, and are appreciated. The tendency is you will like me as a byproduct. It’s not that I’m trying to get you to like me, it’s that I’ve told you why I like you. The people with the highest likability tend to be the ones that express to others why they are liked. I think it’s really just showing a sense of belonging to some degree. I think it’s a fair overlap. It’s just really hard to tease out likability from trust.

There’s so much more we could talk about, Jon, but I want to at least make sure we talk a little bit about some of your adventures. You spent a year having an amazing, exhausting adventure traveling the world and going to a bunch of iconic events like Burning Man and Art Basel. I’m curious what prompted that and what you took away from it.

Every year, I used to take on a crazy challenge that I didn’t know how I was going to complete. One year was go to all seven continents in the year. I did it in eight months. I had another year where I went every month to the biggest event in the world. Burning Man, Art Basel, Running of the Bulls I got crushed by a bull and almost died. I did all these things and it was fantastic. I ended up writing a book about the science of adventure called The 2 AM Principle.

I ended up meeting my wife in the process at an airport as I was collecting stories. Now we have a large family and it’s a completely different type of adventure. I stopped being able to take on those big travel adventures because I am not going to subject a poor child to getting on a plane every month. Hopefully later on when they’re older, they will be well-stamped on their passports.

Certainly, my kids who are now grown, I think would look back and say that the trips we did to other countries when they were younger and it was mostly Europe helped them see the world in a different way and gave them a love of traveling and getting out and doing unique and different things. That’s been something for me. I’d never really traveled as a kid outside the US other than to Canada and then I went traveling with some friends after college and obviously developed a lifelong case of wanderlust at that point.

My kids, now that they’re grown, I can go wherever. It gets me into trouble. I have had my share of illnesses and injuries in far-off places and you learn how to take care of yourself in lots of different circumstances, but I definitely have not come as close to death as you have when you were getting gored by that bull or run over by that bull.

That was really rough and I still have injuries to this day. I got crushed, I think it was left shoulder was where the bull landed from a jump, and I think it caused my right shoulder to tear so my back was a mess for years and years. Yeah, some crazy adventures. Everything from battling Kiefer Sutherland in drunken Jenga and winning an invitation to his family Thanksgiving that he then promptly forgot he invited us to, so when I showed up, he was like, “Who are you?” All the way through to within ten seconds of meeting the woman behind the duty-free counter in Stockholm airport, she quit her job and decided to travel with me and my friends.

That’s very funny. Coming back to your Kiefer Sutherland experience, one thing I will say is that I have a rule that I need two-factor authentication on any invitation extended when somebody is a certain amount drunk. If I don’t get confirmation later on that they really meant it, I’m not going to take it at face value.

I’m just going to show up and make it awkward.

Alright, Jon, this has been a fun conversation. I feel like we should schedule another one at some point and dive into all the other things that you’ve been up to. Certainly, I appreciate your time today. It was really interesting to hear your thoughts on teams and influence and glue people and all of that. The fact that we talked a little bit about travel is just a bit of a bonus on top. Thank you.

It was a pleasure. Thanks for having me on.

Absolutely. Take care.

—

Thanks to Jon for joining me to discuss his research, his work and his adventures. As a reminder, this episode was brought to you by PathWise.io. If you’re ready to take control of your career, join the PathWise community now. You can also sign up on the website for our newsletter and follow us on LinkedIn, Facebook, YouTube, Instagram and TikTok. Thanks.

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About Jon Levy

Jon Levy is a behavioral scientist and NY Times Best Selling author known for his work in trust, leadership, and team intelligence. When results matter, Jon gets the call.

Levy specializes in applying the latest research to transform the ways people and organizations approach the way they build trust, and work together. His clients range from Fortune 500 brands, like Microsoft, Google, AB-InBev, and Samsung, to startups.

Fifteen years ago, Levy founded The Influencers Dinner, a secret dining experience for industry leaders ranging from Nobel laureates, Olympians, celebrities, and executives, to artists, musicians, and even the Grammy-winning voice of the bark from “Who Let the Dogs Out.” Guests cook dinner together but can’t discuss their careers or give their last names. Once seated to eat, they reveal who they are. Over time, these dinners developed into a community. With thousands of members, Influencers is the largest community of its type worldwide.

Jon’s second book, You’re Invited, was released to critical acclaim, quickly rising as a New York Times, Wall Street Journal, and international best seller. In it, Levy demonstrates the value of trust, connection, and community in accomplishing what is most important to us.

His third book, Team Intelligence: How Brilliant Leaders Unlock Collective Genius, demystifies the science of leadership and the habits that make teams more than the sum of their parts.

In his free time, Jon works on outrageous projects. Among them, spending a year traveling to all 7 continents, or to the world’s greatest events (Grand Prix, Art Basel, Burning Man, Running of the Bulls, etc.) and barely surviving to tell the tale. These Adventures were chronicled in his first book: The 2 AM Principle: Discover the Science of Adventure.