Exiting a business is a significant event for any entrepreneur, but what surprises many is not the money, but the personal transformation that often accompanies it. My recent conversation with Michael Showalter provided an eye-opening perspective on the lessons learned from navigating an exit. Here are a few key takeaways from his exit:

1. Letting Go Can Bring You More

One of the most powerful lessons from Michael’s story is the counterintuitive reality that letting go can open doors. Michael shared how, once he stopped striving for titles and accolades, opportunities seemed to come his way naturally. In 2015, he aggressively pursued a CEO role and didn’t get it. His frustration led to a lot of soul-searching, and the realization that his actual enjoyment came from the work that he was doing and not the title he had while doing it.

That led him to seek a role that offered him more fulfillment. And when he truly let go of needing more recognition, he was offered the CEO position at his next company. It was a vote of confidence from the outgoing CEO, the founder of the company. He knew that Michael would be the best steward going forward, because he was focused on the company and not his own needs.

2. Success Without Stress

Michael’s story also illustrates that success doesn’t have to be fraught with stress. The company’s exit wasn’t a result of cutthroat tactics but a series of thoughtful, strategic decisions. They kept investing in technology when their competitors didn’t, leading to a four-year advantage. The team did the hard work without attaching undue stress to the outcome, resulting in a smoother exit and a more successful outcome.

3. The “Why” Behind the Exit

Michael spent a lot of time reflecting on the “why” behind his desire for an exit. Many founders pursue an exit thinking it will fill some personal void—whether it’s proving themselves, achieving financial security, or gaining respect. Yet, Michael emphasized that any feelings of fulfillment you’re seeking through an exit are already available to you now. The satisfaction isn’t in the exit itself but in running a business you love and doing meaningful work each day.

For Michael, the exit emerged as simply the best thing to do for the business, not as a personal or financial goal for him. In fact, he pointed out that there were several people at the firm who got more financially than he did.

4. The Fallacy of External Happiness

One of Michael’s biggest realizations came from his first attempt to become CEO. When he failed, it hit him that the role itself was not going to make him happy, and that nothing outside of him—a role, an amount of money, or any other kind of achievement—could do that. He was making himself a victim of his circumstances. He could choose a different internal experience no matter the outer situation.

Many of us believe that once we hit certain financial milestones, we’ll feel fulfilled. Yet, Michael realized that lasting happiness isn’t tied to a financial number or professional status—it’s an internal state. You don’t need an exit to feel successful; but feeling successful in and of itself can lead to a better result.

5. A Change in Perspective

Ultimately, the biggest shift Michael experienced preceded the financial reward of the exit. He discovered that his self-worth wasn’t tied to professional achievement. This allowed him to lead more effectively, as he no longer needed external validation. He could focus on the needs of the business, even when it was difficult personally.

It’s a reminder to all of us that our external circumstances—be it an exit or a promotion—don’t define us. It’s how we view ourselves and our circumstances that really matters.

Final Thoughts

An exit is more than a financial or business transaction. It’s a personal transformation. Whether you’re building towards an exit or simply growing your business, consider this: Are you chasing an external event for fulfillment? Or are you already fulfilled in the work you’re doing now?

I’ll be posting clips from my interview with Michael. Be sure to check them out on LinkedIn and YouTube.

What insights resonate with you as you think about your own business journey? Let me know in the comments. And if you’d like to be included in my event for founders who are within three years of an exit, send me a message or comment “Invite” below.

#founder #entrepreneur #leadership #exit #transformation #ceo

Three of my clients have had exits in the last year.

All of them got checks in the range of $20-50 million. Combined enterprise value is north of $400 million.

But they had very different experiences. Before, during, and after.

That started me asking some questions—

What makes for a good exit? What would each of these folks have done differently? How is life post-exit better or worse than what they envisioned? What will they do differently NEXT TIME—and they all are working toward another exit.

The more I talked to my network of founders and advisors, the more I found that founders had no one to talk to about this.

So I found some top notch people to put in a virtual room to offer their perspectives to founders within three years of an exit.

Founders like you.

A Stellar Panel of Experts on All Things Exit

Townsend Wardlaw first had his own less than glamorous exit and has since coached and advised over three dozen founders to the point of exit and beyond.

Greg Head likes to say that he had “1-1/2 exits” in the SaaS space and today helps bootstrapped SasS companies build and sell in a way that brings purpose and freedom without buying into the VC game that works for so few founders.

Michael McAllister had his own life-changing exit in early 2024 and has seen that the entrepreneurial journey is about the founder facing both their strengths and their fears. He continues that journey today as he builds a renewed and healthier sense of purpose.

Anastasia Koroleva(invited) had her own 9-figure exit and then built and sold three more companies. Her own struggles with meaning and purpose on the other side of the exit led her to start a community and a podcast, “Exit Paradox” that focused on the lessons, personal and otherwise, that founders learn during and after exit.

Virtual Invitation-Only Event on September 17

On September 17 at noon Eastern time, you can have access to all of us—to hear about the experiences we have had, the lessons we’ve learned, and the questions we still have.

And you will have full access both to ask us any questions you have, and to connect with a group of founders just like you.

If you want to be live in the room, and you are within 3 years of an anticipated exit, please respond “INVITE” or send me a DM

I’ll ask you a couple of questions about what you want to create and then send you the invite.

Have a great week!

#founder #founders #exit #freedom

This week, I’m writing from a place that holds deep memories—visiting my 88-year-old mom in Bettendorf, Iowa, part of the Quad Cities region of Illinois and Iowa where I grew up. Every time I come here, I see more of the patterns from my childhood that shaped much of my adult life—patterns I thought I’d left behind, but that still surface in unexpected ways.

The Roots of Overachievement

I’ve often talked about my drive to overachieve, but I haven’t always shared the deeper reasons behind it. On this trip, I had a moment of clarity about how much of my childhood was spent managing my mom’s anxiety, which in turn became my anxiety. This deep-seated need to manage and control has shaped much of who I am today.

The Weight of Expectations

Growing up, I constantly felt like I wasn’t measuring up to my mom’s expectations. My dad was the epitome of success—class president, homecoming king, high school quarterback—and I was none of those things. Instead, I was a pudgy, sweaty, stressed-out kid, more into in science and Star Wars than sports. Sure, I played baseball and football passably well, and I was likable enough, but I never quite filled the shoes that my mom expected me to fill.

Coping Mechanisms: How I Adapted

To cope, I became really good at other things. I got excellent grades, always made sure to be the teacher’s pet, and figured out how to make authority figures like me by working really hard. This strategy worked well for a while—I excelled academically and professionally by showing up exactly how others wanted me to. But it came at a significant personal cost.

The Unsustainable Pursuit of Perfection

My need to manage my anxiety by being perfect was unsustainable. I had to succeed, but as a child of Midwestern parents, I couldn’t get “too big for my britches.” I had to stand out AND fit in. I needed to be good, but not too good. Successful, but not too successful. It was a psychological nightmare that became increasingly impossible to navigate. The pressure to maintain this delicate balance eventually became too much, turning into panic attacks and a lot of self-medication.

The Turning Point: Realizing the Limits

I had a lot of professional success, and I’m sure others thought I was doing great. But was never truly happy because I was always trying to be what others wanted me to be. If you had asked me at that point what I wanted, I would have had no idea beyond following a path that others had prescribed for me.

I remember driving to work one day, listening to a book on tape (a biography of Harry Truman), and having a profound realization. I was playing an unwinnable game. There would always be someone smarter, harder working, more talented, at whatever I set out to do.

It took me a while to realize what the game actually was. To be wholly myself and to find a place where I could be rewarded for that. I had no idea how to do that—it was the one thing that had never really been allowed in my house. But I was willing to try, and started exploring meditation and other practices as a way to learn. Slowly, I began to see and get comfortable with the real me, rather than the one who was performing for others all the time.

An interesting thing happened when I stopped putting so much pressure on myself. I started enjoying myself. I started connecting with people. I started getting promotions. The more I tried to just be myself, the more success I had. And I found myself wanting to share this with others. By this time I had done years of work on myself, without recognizing that it was actually job training—the job of executive coach.

Breaking Free: A New Approach to Success

When my last job was eliminated in a corporate restructuring in 2016, I decided to go out on my own as a coach. Ironically, the people who looked most like me—corporate types exhausted from showing up as they thought others wanted them to—were completely uninterested in working with me. They just weren’t ready to look there.

But then I coached a founder. And another. And over time I find that there was a very small subset of founders and business owners who understood that when they showed up more authentically, everything changed, both for them and their businesses.

Just as it had for me.

I built a very successful coaching business by knowing both myself and the people who I could help the most. And more and more, just showing up as myself. I understand now that this is all we ever need to do.

Embracing Ease and Balance

Today, I’m more financially successful than ever, working half the hours I used to. I’ve found that the more I step back from work, the more intuitive and effective I become. Life has become an experiment in seeing how little I can work while still achieving more. I’m now coaching incredible founders and companies, and making a significant impact doing so.

Health, Hobbies, and Happiness

I started playing the saxophone, and practice about an hour a day. I’m physically fit, running, lifting weights, and doing yoga regularly. If you had told me a few years ago that I could do all this, I would have guessed I’d have to give up at least half my income. But this balance hasn’t required me to sacrifice anything—instead, it’s created more ease, abundance, and financial security than I ever thought possible. I’m making significantly more than I was at my old corporate job, and having more of an impact than ever.

It’s hard to believe that working less would actually mean MORE money. But over and over again I have seen that this can be true, not only for me but for the people I coach.

Ready for a Change?

If any of this resonates with you, reach out. Let’s explore where you might be getting in your own way and how you can create a life of ease and abundance too. Connect with me on LinkedIn or join my email list. When you’re ready, let’s talk.

And if you’re a founder within 2 to 3 years of an exit, I have a special event for you on September 17. Leave a comment or DM me with “founder” and I will make sure you learn more. We’ll explore, with people who have dozens of exits among them, how to navigate the exit journey while remaining true to yourself along the way.