As a founder, the journey to selling your company can be exhilarating. Many entrepreneurs work tirelessly with one in mind: an exit. The vision is simple — build something valuable, sell it, and reap the financial rewards. But what happens when the deal is done, and the dust settles? What do you do when you’ve won the game you were playing?
The Reality of Post-Exit Life
I recently spent two and a half uninterrupted days with a client who had just sold his company. He had many questions about what was next. This isn’t uncommon. In fact, it’s one of the most important conversations founders face after an exit. Before the sale, you’re laser-focused on growth, impact, and the ultimate transaction. But after the sale, a new question arises: What’s the next game you want to play?
For many founders, life after an exit is very different from what they imagined. The sense of fulfillment that they expect, for example, may not come. Instead, they may feel a sense of uncertainty or even emptiness. This disconnect is compounded by others around you who may not fully understand your experience. There aren’t many people who understand the letdown a founder can feel even after a big check.
There are often feelings of disappointment with the deal or frustrations with the new role in the acquiring company (as happened with my client). The reality of post-exit life can be much more complicated than expected. The money doesn’t change everything (or at least anything of importance), and the existential questions of path and purpose become more prominent than ever.
The First New Game: Embrace the Uncertainty
For the exiting founder, the first challenge is that there is often no clarity around what comes next. Maximize the earnest? Leave now to start something new? Quit everything for good? It’s easy to rush into the next project, but I encourage founders to embrace the uncertainty and use this time to explore, experiment, and be curious.
As I told my client, this is a period where you can afford to be unsure. You don’t have to wake up every morning knowing exactly what’s next. You’ve earned the space to try new things, to test out ideas, and to see what feels right. It’s about trusting the breadcrumbs that show up along the way and seeing where they might lead.
I had been wanting to go out on my own as a coach and trusted advisor for many years, but when I was first laid off from my corporate job in 2016 I kept chasing consulting gigs, thinking that I wasn’t prepared to make a full-time living from coaching.
The universe seemed to have a different opinion. Every time I went after consulting work, I got a hard “no.” But people seemed really happy to have coaching conversations with me, even though it took awhile before people started being willing to pay me. By trusting the flow, and being patient, I created a business coaching founders, even though I had never been a founder myself. But each of my clients, like me, had a spiritual openness and a history of seeing the world differently than most of the people around them.
Be patient, be yourself, and your path will unfold.
Another Game: The Joy and Purpose Game
One of my favorite questions of an exited founder is, “What do you want when you don’t need anything?”
For most people, life is more about wants than needs but they have created it in a way that a certain amount of income, a certain position, a certain lifestyle feel like absolute needs.
But for the founder, that illusion is shattered in one transaction.
Finally, they are able to see many of the possibilities that they missed while they were missing their business. And whether it is giving back, deepening relationships, exploring hobbies, or even building another business, the founder can create what is next much more intentionally, and finally live the life of joy and purpose that they thought they might get playing the founder game.
Can You Relate?
Does this resonate?
If you’re in the same position, where you’re asking, “What now?” after your exit, know that you’re not alone. It’s a time of immense opportunity but also one of uncertainty. The key is to trust yourself and allow the space to see what evolves.
And if you’re looking for a community of like-minded founders who are navigating this same question, I’m building something for exactly that. Whether you’ve had one exit or five, this is a conversation that matters.
If this resonates with you, reach out. I’m putting together a community for founders who are in this phase of their journey — exploring, experimenting, and figuring out the next big thing. Whether we have a short conversation now or I just keep you posted on what I’m putting together, I would love to make sure that you know where you can go when the time is right.