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
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