What if you achieve everything you thought you wanted in your career, and still find yourself wondering if that’s really all there is? Former Vertex CEO Jeff Westphal joins host J.R. Lowry to discuss how you can build a Work Life Worth Living when traditional status isn’t enough. Jeff Westphal spent two decades as CEO of Vertex, helping grow the company from roughly 75 employees to more than 1,000 and increasing its value fortyfold. Along the way, he started asking deeper questions about purpose and why listening can be far more powerful than having all the answers. He shares how an intense focus on reflection transformed his leadership and helped him create an environment where employees felt truly invested. They also examine how rapid changes in AI mean distinctly human qualities like empathy, judgment, and connection will define our professional future. Whether you’re rethinking your path or leading a team, this conversation will help you reflect on what truly makes your career meaningful.

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/jeff-westphal/.

—

Watch the episode here

Listen to the podcast here

Success Isn’t Enough: Building a Work Life Worth Living, with Jeff Westphal

When people think about career success, what usually comes to mind are things like promotions, bigger paychecks, and impressive titles and maybe building a company. Those things certainly matter. I would imagine that some of you have reached goals that you’ve probably worked hard to achieve, only then to find yourself asking afterwards, “Was that it?” My guest believes that’s one of the most important questions that any of us can ask. Jeff Westphal spent two decades as the CEO of Vertex and led the company through a 40X growth in value and from 75 employees to more than a thousand by the time of his retirement.

By almost any measure, he’d achieved extraordinary professional success but along the way, he also began asking himself deeper questions about meaning, purpose, fulfillment and what truly makes a work life worth living. Those reflections became the foundation for his new book, which is called A Work Life Worth Living.

In our conversation, we’re going to explore why achievement alone isn’t always satisfying and how to build a career that’s both successful and meaningful, what leaders can do to create workplaces where people thrive, and why these questions are becoming even more important as AI transforms the future of work. Whether you’re just starting your career or questioning your next move or wondering how to make your work more fulfilling, you’re going to find a lot to reflect on in this conversation. Ironically, Jeff is very big on reflection. Here’s my discussion with Jeff.

—

Jeff, welcome and thanks for joining me.

Good to be here.

I’m glad to have you on as well. Let’s dive right in. I know you’ve got this view and you write about it in your book that a lot of people feel successful on paper, but still feel like something is missing. You experienced a bit of that yourself. It would be great to hear your own experience when you had that first clue that success alone wasn’t everything for you. It wasn’t enough.

It’s interesting. It’s not like it wasn’t enough. I wasn’t looking for more. I was succeeding to the extent that on paper, at a cocktail party at 28 years old, I would have felt like, “I’m doing as well as anybody here.” I had multiple promotions. I started at my father’s company and sales were doubling twice. I was leading sales and marketing. Not all due to me, but still I felt like I was contributing meaningfully. I was introduced by one of our salesman’s father-in-law’s colleagues who had become a certified seven habits facilitator. Covey’s 7 Habits of Highly Effective People.

Questioning The True Purpose Behind Your Hard Work

I meet this very poised gentleman who was a former executive at DuPont, the big chemical corporation. He says very nicely, “Why are you working so hard?” I was like, “Is that a trick question? To have more sales?” He’s like, “Why are you wanting more sales?” I’m like, “This guy can’t be serious. What do you mean? Of course you want more sales.” He goes, “I get that, but why do you want more sales?” I’m like, “What is this?” I was literally confused. This man is so calm and smiling at me then he says, “How do you intend to contribute to the greater whole?” I’m thinking, “What is he talking about? Greater whole of what?” I’m like, “I got to know what this guy knows.”

Why Seeking First To Understand Changes Everything

He just helped me realize for the first time that my assumption that I basically knew what I needed to know was completely off base. He gave me the 7 Habits book. In it, I learned about seeking to understand, then I tried that with my wife when we were debating going away for the weekend. I’m like, “I wonder what she’s thinking.” I’m leaning over the chopping block in our kitchen. I’m like, “What is she thinking? Don’t try to convince her.”

All of a sudden, I’m like, “She’s worried about the children. She’s thinking, “How are they going to eat?” I’m like, “We’ll figure it out but she’s worried.” At the time, we had a 4-year-old, a 2-year-old, and an infant. I want to go camping for the weekend. I’m thinking no problem just like when we were dating. That was a huge epiphany. Between 28 and 30, between experiences like that at home and the questions this man was asking me, my whole world got turned upside down, basically. I started realizing that instead of knowing a lot, I knew almost nothing.

I wouldn’t call myself a 7 Habits disciple. The book kicks around this house somewhere, but certainly that point about seeking first to understand, then to be understood is very simple, which is the whole of that book. It’s also very powerful because we spend so much time thinking we know the answer or wanting to get our point across that we stop listening. We stop observing. That’s what that point is about. You are getting it in both those ways.

He was pushing you to observe more deeply about why you were doing work. Not just for the goals, but what was the real reason. Your conversation with your wife and stepping back and making sure that you understood where she was coming from, which you clearly needed to step back and give thought to.

It’s like a 2X4. What was shocking wasn’t so much what she cared about. That was obvious once I saw it. It was an instant recognition that I never realized before. Ostensibly, I’m a successful guy growing and doing all these things. I had no idea. My next thought was, “What do the employees think? I wonder what they care about.” I was literally a different person at work on Monday morning.

How so?

Building Investment By Giving Up Easy Answers

I went from being decisions while you wait to thinking the measure of my success was how hard I could work to help people by giving them the answers they’re looking for, because I was in a line leadership role at the time. I just realized I don’t even know why they’re asking. The line outside my door was there just like it was most days. Not all day long, but during the day, 2 or 3 people would be coming by. Instead of saying, “Go do this.” I was like, “Why do you ask?” They’re like, “It’s because of so-and-so.” I’m like, “Why is that?” I was genuinely curious, like, “What is bringing you here?”

When they started sharing, it was like, “I’ve been making decisions with practically no information needed to make the decision and the notion that they should have any say in the decision that they were going to implement was a couple of years in the future.” With the help of my mentor, I had that epiphany. He says, “How do you plan to build spirit and willfulness among the stakeholders? He’s using an ancient esoteric technique.

Basically, stretching my consciousness by giving me challenges and questions that aren’t in my current paradigm to help me search for understanding. What I came to realize was, “If you’re not a party to the decision, why would you be deeply invested in the decision?” We then moved into a phase where we became intensely collaborative in the business and it worked out quite well.

I have to imagine that first Monday morning, when you were starting to ask these deeper questions of your staff. They probably didn’t open up just right away. They’re probably like, “What the hell’s going on here?”

Using Intentional Pauses To Foster Creative Solutions

There were times. I said to my mentor, “I’ll ask a question to the group.” There’s silence or they give an answer then they look at me like, “What do you think?” I’m like, “It’s like they want me to dive in and answer for them.” He said, “Yes.” He taught me the trick of just looking at my watch to remind me to not answer, and I wouldn’t answer. It took a while. After a while, they came to realize I’m not just going to come in and give the answer that then they can go execute.

Which keeps all the responsibility and risk on me and no real commitment on them but we’re going to do this together. What emerged were insights about the decisions we were making that none of us had anticipated. Creative solutions that emerge from the intensity of the understanding that was forged that none of us had anticipated but were clearly superior answers than what any of us would have predicted the right answer was going to be. To the point where we knew going into any of these collaborations that there’s a better answer than any of us realize. It’s here to be found and we can do it together. That was ultimately what we developed over a five-year period.

That’s pretty powerful learning for a group to have that realization that they can embrace the uncertainty of a situation and know that they’re going to figure it out. A lot of groups never get to that point.

We never would have if it wasn’t for Jim Patton who was a senior executive at DuPont. He had a heart attack that moved him off the fast track, and he became a certified Covey 7 Habits facilitator at DuPont, among one of the first corporations to ever invest in actual on-staff people to help have more effective meetings. This is back in the ’70s where they started this, but they had a cyclical downturn. They cut all the soft skill people. He was then basically my age at the time. I thought he was ancient. He was 64. He became available as a consultant.

These are highlights of the journey I was on. I’m hitting the good highlights. There were more than a few hard moments where you’re brought face to face with the limits of whatever wisdom you’ve been able to scrabble together at that point. The words experience is the greatest teacher are proven true. When there’s a new product introduction that you believe in and it fails miserably, you have to withdraw it from the market.

When there’s a cyclical downturn like the Y2K collapse and what was 35% year over year sales growth goes to eight. Which was fortunate, but still now you’re looking at laying off 7% of the workforce. Hard stuff. A lot of these difficult lessons from the hard things, including my own mistakes, are in the book, A Work Life Worth Living, because they all ultimately served a deeper understanding of what matters about my work life. It’s not all just the rainbows and unicorns.

It would be helpful to hear you talk more about some of the bad moments that you’ve just referenced, particularly just thinking about how pre-28-year-old Jeff might have handled some of those situations and how post-enlightened Jeff handled those situations.

I wouldn’t say enlightened. I’d say on a path of growth, Jeff, as opposed to unconscious, clueless Jeff. The biggest difference between Jeff graduate, succeeding was only to find out because my mentor asked me that the reason I was working so hard was to prove something to my father. That was an epiphany when I realized, “That’s what I’m doing?” I was like, “That can’t be the basis of a career.” I had to work harder to figure out, “What then is a basis for a career?”

The big difference in what’s in the book is having someone you can talk to who’s not your best friend, a guy you know from the bar, somebody you played rugby with, or your uncle. Everybody has somebody at arm’s length who has a certain level of maturity and wisdom that you just know is there. It’s such a compliment to anyone to ask them, “Could I talk to you about some things that are not going the way I want in my work life?”

You’d be amazed how much clarity you can get when faced with a fork in the road, some surprise of whatever kind to just say, “I’m going to step aside for a second.” Unless the building is on fire, there’s very few decisions that need to be made tomorrow and to talk to somebody who has no dog in the hunt. The most powerful thing I ever realized. It’s not advice, but something to consider if you face that unexpected fork in the road.

Your book emphasizes this importance of reflection. Why do you think so many people avoid it?

That’s a great question. Honestly, first of all, I was never asked to reflect on the quality of my experience when I was in school. From 4 years old to 22, it was just, what’s next? Everything was laid out for me. I had some choice of courses and things, but it’s like, you’re going to take the next step. You’re going through the motions, pause and say, “How was this experience for you?” That begs the question of, “Would you like a different experience?” I can’t give you a different experience because you got to do what you’re supposed to do next. There’s no reflection in all that.

Making Reflection Your Team’s Secret Competitive Advantage

Secondly, when you get to a certain point, you invested a lot of time and energy and where you are and what you’ve done, then somebody says, “Let’s reflect on how this went.” That brings you face to face with the possibility of getting in touch with how much regret you might feel or shame or angst or fear or whatever about how it went or blame or anger. It’s like, “Don’t open that box. Let’s just move on.” That’s what it was like when Jim first introduced the idea of like, “At the end of a meeting, let’s take a few minutes to reflect on the quality of the meeting.” We’re like, “What?”

It became so powerful because we iteratively kept tweaking our process the way we met based upon the feedback people had. It started out like, “I’ll give you a reflection. This sucked.” That’s what it was like at the beginning and he’d say, “I appreciate the honesty that was shared in the room.” We’ll be like, “What are you talking about? Was there something good about this meeting?” Slowly but surely we realized that appreciation fed appreciation and when people felt appreciated, you could then have a better meeting and we were getting better outcomes because it was less of a battle.

It was more of a dance and you realize, “We’re different. I’m in sales and you’re a hardcore research guy but I can talk your language. I can hear you. Can you hear me?” The next thing, it’s like, “He does think that I have some merit even though I’m just a salesman.” Now we can talk about, “I can’t just bring the product specs in and put them in front of a guy and put a price on it and say ‘Buy it or not.’ It’s just not going to work. Do you want to learn more about salesmanship?” This is just so powerful. When you get in a habit of reflection, you can learn from your past experience and apply it to your future experience. When you do it together, it builds on itself and it becomes a positive flywheel.

For a lot of people, they’re intimidated by it for all the reasons that you mentioned a minute ago, like shame, embarrassment, or whatever. It’s a liberating thing to get to the point where you’re willing to accept all of your imperfections and your bad reactions to things and everything else and move on anyway.

I’m not focused on helping leaders because most leaders have some budget for their self-development and there’s coaches. That a custom support system is powerful. I had it and it’s great. That already exists for most people if they want it. What I’m focused on is the people who don’t have that development budget and particularly when it comes to these deeper issues of feelings and purpose. My experience is, even when the leader is a complete zealot for this stuff, a deep believer and everybody knows. It doesn’t mean they trust them because they work for you. Their job security is at stake.

Their pay is at stake and you’ve got a big economic interest in how they contribute. It’s like, “Do you care about what matters to me?” Understandable skepticism in our corporate world. I don’t begrudge folks who didn’t buy into my most gentle invitations to consider what mattered to them. I never asked them to tell me, ever. That would just be way too unsafe.

Point simply being that it’s a delicate road that we tread when we get into deeper personal issues. When we reflect, we open ourselves up to the possibility of realizing that, hey, maybe we made a mistake. Maybe we’re on the wrong path. If you’re on the wrong path and going up the wrong mountain or down the wrong ravine, the sooner it, the better. Emotionally, there’s still a sense of, “Can I afford to acknowledge that I shouldn’t have become a doctor?” We carry a lot.

People are carrying a lot. What I’m trying to do with the book and with the platform, MeaningSphere.com, is create a safe place for people to explore these issues, provide some simple guidance about how to get the support you need to sort through this before you go jump in jobs or worse, jumping off a bridge. People do that too and it’s terrible in the law and in medicine. The amount of mental health issues is in some ways wrapped up in our lack of self-awareness about the work we do.

Yet for most people, there’s very little in the way of resources to help with that aspect of their mental and emotional well-being. I’m attempting to provide people easy access to affordable and carefully curated resources to help because I’m like the luckiest guy in the world. This is my life’s work to see if I can’t pay it forward because I was given so freely these great gifts. None of this is my idea. There is nothing I’m doing that was my idea. My idea was MeaningSphere, to create a platform where people can do this together. But that’s not even a new idea.

Philosophically, certainly what you’re talking about is well aligned with why I started PathWise, the business that I run, because I too have benefited tremendously from the professional development that I’ve gotten over the years. I wanted to be able to give back and democratize some of that for people in a way that was accessible and affordable. It’s rewarding and challenging all at the same time.

I’m curious to get your experience because one of the challenges is that getting people to come to this content and these kinds of resources, a lot of people are happier complaining than they are doing something about what’s bringing them down. That’s a sad statement, but it’s a truism that I’ve discovered the hard way.

For most people, the systems that they exist within, educational and employment, all they’ve got agency to do is complain when they’re not there. Because it’s too risky to complain when you’re there. Where are they? Ever seen an example where something could change or that they could change their situation? I don’t blame people for complaining. At least they’re vending and they’re getting some of it off their chest.

I never thought about any of this stuff. I discovered I had no idea about right. If it wasn’t for both some shocking disappointments and some unplanned and unsought experiences, I wouldn’t know what I know now. No judgment about people who might be stuck or might be feeling like they’re a victim of their career. It’s understandable. What’s evident is, if you’re waiting for the world to change before you can feel better, you’ve got to be waiting a long time.

Come back to your own company and your experience and the journey that you went on with your employee base. The point you made earlier about the fact that a lot of people are hesitant to speak their minds, to reveal their true selves, to do all the things that you’ve mentioned that come with this territory. Their economic livelihood depends on keeping that job and making sure that boss or that CEO or whoever thinks well enough of them to keep them within that organization.

Even if you’re not managing by fear, people carry that fear because you are in a position of power. How did you change the dynamic? What were some of the signals that you got from employees that they were having their own epiphanies, their own wake-up moments about how different life could be?

In addition to forcing myself to not answer my own question, and when you trust people, you are committed to inviting people to share their true perspective, strap on. It is shocking to find out how much people are telling you what they think you want to hear. When they tell you what they think, you’re like, “Are you working in the same company I am? It is amazing.” Yet it is indicative of how little support people get to be able to build a frame of reference around why they’re there.

Connecting Individual Roles To The Broader Human Purpose

Typically, they’re hired for skills to do a job. That some boss tells them, “The goal is this. You’re responsible for that.” We’re in this business. That’s the connection they get to make. What do you think about how your contribution helps move the company forward? What’s that chain of connection between the work you do and the cup of coffee that we serve the customer at Starbucks? How does the tax process affect that experience? Who has that conversation?

Not too many people. When I started having that conversation, I realized that as people were joining the company. I’m like, “How do we do this?” Once we started realizing that transaction tax software is implicit in the entire economy and it doesn’t work without it. It’s way important to use the highly technical term “way.” We realize that talking to people doesn’t work. I would meet with people in groups of 8 or 10 after they’ve been with the company from 2 to 3 weeks to 2 or 3 months in groups and ask them, why do you think the company exists? You’d be amazed.

Not just young people coming in, but people in their mid-30s and 40s to increase shareholder value to meet the customer’s needs. Basically, they give me answers they think I want and be like, “Where’d you buy those boots?” They’d answer and I’d be like, “Why’d you buy them?’ They’ll be like, “I like the way they look or I need them to ride a horse,” or whatever it is. I’d be like, “Did you buy them to help the company increase shareholder value?” We’d start having a conversation about the chicken and the egg in terms of, does the company exist for the shareholder or does it exist for the customer?

If it exists for the customer, then what are we doing? They’d be like, “What are we doing?” I’m like, “Why’d you take the job?” They’d be like, “It had the best benefits. It was a convenient location. It was the best job I could get.” If I would listen, which I would try to do, people would open up. Usually, of the group of 8 or 10, there’d be like 2 or 3 who were like, “This is cool,” and they would get into it. That would make it safe for others. There’s always two who just sat there terrified, like, “I hope this ends quickly.”

That’s what I did for twenty years. As we grew from 70 people when I became president to about 1,000 when I was no longer CEO. I went on the board and was chairman for five years. The point is, it took constant dialogue. We held all employee sessions for full days, where we had professional artists help draw in murals what the employees were saying about why they felt that the work mattered and where the connections were, to try to give them an opportunity.

What I said to everybody was this, “I feel like I’m accountable to all stakeholders to lead the company toward the purpose that we share for it. It’s not my purpose. It’s our purpose. Based on your input and perspective, this is what it feels like, what it might seem like. Is that why we’re here? What do you think?” We spend the day talking about it and then feedback. We did continue engagement for new people

About every five years, we do an engagement program. Engagement meant listening to them, not talking to them. The proudest statistic that I have of my tenure was 4.5%. We had 4.5% total turnover every year for twenty years in technology. We didn’t overpay. We paid P60, but that was strategic. It wasn’t like we were just bribing people.

Did you see, as you were doing those sessions with 8 to 10 new employees at a time, I have to imagine you saw an evolution in how those conversations went. How did you look back and say, “This is different from where we were a year ago or two years ago?” What were those moments like for you? What were they like for your employees?

You would think that’s what I would have seen. Exactly the opposite. That’s why I had the a-ha that what’s needed is MeaningSphere. This is what I need to do with the rest of my life. For twenty years, they came in exactly the same. It didn’t change at all. I’ve been doing this for 10 or 15 years before Simon Sinek publishes Start with Why. That was another. Covey was big. No change. It wasn’t like the movement that we’re aware of that you and I are part of.

It was reaching people and they were coming in and saying, “I’m here because I understand this company stands for something more than just the bottom line.” The bottom line is here to help serve an even higher bottom line, which is, are we enabling an economy that meets the needs of the society or does this culture give me the space to be there for my coworker when they’ve had some life event? Can we be human here together? Those are the things that you’d hope that over 5 or 10 years, you’d build a reputation that people would be able to say those things, at most. You’d hear, “I heard it had a good culture.” That’s about it.

I’m sitting there thinking, with what I know, the amount of research I would do into what a company’s culture is like before switching jobs would be just way more than the product.” You think about what you’re signing up for when you change jobs or in any job. With that environment, it shapes you. It will turn you into a different person. We make those choices in such a cavalier way. It’s because we’re not aware of just what conditioning influences the workplace.

I had spouses come to me in tears on multiple occasions. I don’t know what you’re doing, but he’s a different person and I’m so grateful. I’m like, “It’s not me. It’s not what I’m doing. We’re doing this together.” People would go home and they’d be a little more interested in listening to their spouse. We did communications that were intended to be. Be more user friendly for the significant other about our benefits program and we started to be more conscious of relationships. I feel so very fortunate.

It’s fascinating to me that the cultural things you were doing didn’t manifest themselves in your recruitment process. People came in as uneducated in year twenty as they did in year one.

When you have people who care about the work and want to succeed and have technical knowledge, corporate tax software is a very intensely technical world. This is hard to balance. Your first thought is, “This individual better have the technical ability and skill to meet the demands of the job.” The culture is nice and everything. I love the culture too, but I’m not going to hire somebody because they love the culture.

They got to know how to program. In the hiring process, I had to walk my own talk and not do too much. Frankly, the only times I took over, we never went well. The people who had the skills were way better, even though I had “the power.” I never intervened on this, but I felt like we could have done a much more proactive job of recruiting people with skills who also wanted the culture that we were offering. I don’t know that we were ever very successful with that, honestly.

Fair enough.

Since we had such great retention, even though we were growing, we weren’t hiring as much as other companies because we were losing people.

Now, we’re in this era of AI, which is automating more and more of what we do by the day. How do you think that affects what meaningful work looks like in this new era?

The foundational primary research done in the field over twenty years, peer-reviewed, journal-published, primary research conducted by Dr. Marjolein Lips-Wiersma at the Auckland University of Technology with her partner, Sarah Wright, demonstrated that people care about mostly relationship-related issues with other people.

There’s four quadrants that the research clearly identifies, unity with others, integrity with self, service to others are 75%. This is cross-cultural. The only one that is more skill related is mastery. Mastery is very meaningful. As you develop mastery, the people’s things will become more important. With AI, it will help accelerate mastery if you’re careful and you don’t take it at its word and you do the underlying research but it will have an accelerating effect.

Will it help individuals feel like they’re working with others and in an environment where they can have integrity with themselves? That is all about relationships and the expectations that are present in the environment and your effectiveness in clarifying and negotiating those expectations. Will you feel a sense of unity with others? Do you feel unity with the machine? Maybe. Maybe some people are feeling, at least so far, some level of unity with the machine.

The jury’s out in my mind with regard to how healthy that is. We’ve got some decades of research to find out how healthy that trend might be. Count me as a skeptic. When a robot can shake my hand and I feel a pulse, I feel body warmth, I know it’s a person and I can feel the intensity of that handshake. That is different. I don’t even want to shake a hand with the robot.

Protecting Human Judgment In An Automated World

These human dimensions that build trust, that build a sense that I matter. I matter in a context of how others see me. I feel what makes being human so wonderful and also difficult and challenging. Will AI speed up all the intellectual things in dramatic ways? Absolutely. When you think an AI can decide for you what you care about, that’s where we’ve lost our way. We’re going to recognize that as a society, as a humanity and go, “This power is here to serve us and help us serve why we’re here.”

We’re not here to become subjugated to the power of this intellectual behemoth because life is richer than that. I point out in each of the action step sections of each chapter, a little bit of a hint about, is this a place where AI can be helpful? Two thirds of them, AI can be helpful but I also point out where you’ve got to own the responsibility of taking what AI is telling you and divining for yourself what matters to you. It’s the question confronting us.

It’s a key question. For some people, they will relish the ability to spend more time on deep work, deep conversation and deep interaction. Other people are going to find it terrifying and exhausting. We’re going to have to go through what that change process looks like for a lot of people, potentially. We’re obviously observing that more of the transactional aspects of work can be accomplished in an automated fashion. That’s going to leave the harder stuff and we’re going to have to rise to the challenge. The companies that do the best economically will rise to that challenge, but I hope they don’t lose their souls anymore. Most companies have already lost their souls so far.

We’re going to find out. It’s not going away. I’m an optimist, ultimately. No pain, no gain. Whether that’s working out, learning a new skill or a trade, building a company, there are going to be disappointments. There’s going to be surprises. There’s going to be difficulties, adversity. Those are all learning opportunities. AI is yet the biggest one. We’re inherently adaptable and we care. We care at a heart and soul level. Not at a, “I’m going to say words of caring because the book I just read in an instant tells me that the right word to sound caring is so-and-so,” which is basically what an LLM does.

You’ve got this book. You’ve got MeaningSphere. For somebody who reads your book, A Work Life Worth Living, what do you want their own Monday morning experience to be like after they’ve read the book?

That’s a great question. In a perfect world, the people who read my book would go to work on Monday morning in wonder, just in wonder, “What else might I discover about myself and the world of work and this environment that might not have dawned on me before having read that book? Open your heart up to insight that you might not have had before. Why is the environment the way that it is? What are the unspoken? When you start perceiving those, you start feeling them in yourself. A whole world of new possibilities to take ownership of creating the work life of your dreams becomes possible. That’s what happened to me. I hope that’s what happens for you.

I would just add on to that. Step into the breach despite whatever misgivings or fears you may have. Because it is a bit of a courageous leap to start to look at the world in a different way, the way that you’re describing. People have got to get themselves across that chasm and be willing to move on in spite of everything that comes with it, messy or otherwise.

These old words of wisdom, “No pain, no gain,” things like that. There’s a reason we say them because they’ve been borne out as true and nothing ventured, nothing gained is one of them. It sounds trite, but if you don’t swing the bat, you cannot hit the ball.

It’s very true. Thank you. A philosophical conversation. I appreciate your time and what you’re doing now with your own movement and I wish you the best of luck with it.

You, too. It’s a pleasure. Thank you so much for having me.

Take care, Jeff.

—

To wrap up the conversation here with Jeff, I want to leave you with a few ideas that I hope stay with you. First is that success and fulfillment aren’t the same thing. We know this intuitively, but we often forget it day to day. The promotions, titles and financial rewards are important but they’re milestones. They’re not necessarily destinations. A truly rewarding career comes from aligning your work with your values, your strengths, and the impact that you want to have on others.

Second is that meaning is something that you create. It’s not something that you find. Waiting for the perfect job or the perfect organization is probably going to be a recipe for disappointment. The people who experience the most fulfilling careers are intentional about how they show up, the relationships they build, and the purpose they bring to the work they’re already doing.

Third, and you heard this in spades from Jeff, leadership is ultimately about helping other people thrive. The best leaders create environments where people can grow, contribute and find meaning in what they do. Link it to a broader purpose. That’s good not only for employees, but for organizations as well. Vertex is certainly a beneficiary of everything that Jeff did to make that real in his company. Finally, as AI changes work, our humanity is only going to become even more valuable.

Technology will reshape jobs. It will take away certain tasks that we perform. The uniquely human things like curiosity, empathy, judgment and purpose and the ability to inspire others are going to become increasingly important. Building a work life worth living isn’t just about keeping pace with change. It’s also about becoming the person that technology is not going to replace.

If you found this conversation valuable, please subscribe, leave us a review, and share this episode with somebody who’s looking to become a better leader or build a stronger career. You can also sign up for my membership community, which is called PathWise and our newsletter PathWisdom. Thanks for tuning in.

Important Links

• Jeff Westphal
• Jeff Westphal on LinkedIn
• Jeff Westphal on Facebook
• Jeff Westphal on Instagram
• MeaningSphere
• Vertex
• A Work Life Worth Living
• 7 Habits of Highly Effective People
• DuPont
• Start with Why
• PathWisdom Newsletter
• PathWise on LinkedIn
• PathWise on X
• PathWise on Facebook
• PathWise on YouTube
• PathWise on Instagram

About Jeff Westphal

In the mid-1990s, Jeff Westphal took over his father’s upstart sales tax software business and over the next two decades built it into a dominant industry leader. Under Jeff’s leadership, Vertex became an essential cog in the commerce machine, relied upon by more than ten thousand of the largest companies in the world. Behind this success story is another, more complex story of how a leader found, then lost and found again, meaning in his life and work—and how, by helping his employees create meaning in work as seemingly meaningless as sales tax software, he helped his company thrive. Today, Jeff is a seasoned corporate executive, entrepreneur, philanthropist, corporate culture enthusiast, and conservationist. In addition to leading Vertex for two decades, he has founded two new ventures—MeaningSphere® and Mosaic™—as he continues to give back and encourage others to create meaning in their learning and working lives.