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.

When Townsend Wardlaw agreed to be part of my event, “The Other Side of the Exit,” he confessed that his own exit had been “less than spectacular.”

But that didn’t stop him from trying.

And it didn’t stop him from trying again.

And it didn’t stop him from building a business where today, he advises other founders on how to do better in their exit than he did.

You see, Townsend sees that the first million of revenue can seem impossible. That the second million can make the plan seem workable.

But then, you have to start thinking differently. You have to start building a team that can scale what you simply can’t do on your own.

On the other side of that is magic.

Townsend is creating a community for founders who are, in his words, “crazy enough to start something.”

It could include you. And you would get access to a group of people who have been at every step of that founder journey — start-up to sale and beyond.

Let me know and I can arrange an introduction.

Recently, I had the honor of moderating a roundtable discussion with a group of experienced founders who have each been through the life-changing process of selling their businesses. Many assume that selling a company is mostly a financial transaction, but this conversation revealed a much richer reality. Founders grapple not only with negotiations but, perhaps even more, with the emotional journey of letting go of something they’ve built over years or even decades.

Below are some of the most profound takeaways from the discussion.

1. The Emotional Rollercoaster: “It’s not just a company—it’s part of you.”

One of the recurring themes was the emotional toll of selling a business. As one founder put it, “Selling isn’t just handing over the keys; you’re letting go of a piece of yourself. It feels like losing part of your identity.”

Another shared his own experience of selling his company after 15 years. “You think you’re prepared,” he said, “but once the ink is dry, you realize you’re not just walking away from a business; you’re walking away from the community, the daily problems, and the wins that kept you going. That’s tough.”

Another founder compared the experience to raising a child. “You nurture it, watch it grow, and then, at some point, you have to let it go into the world, hoping you’ve done enough to ensure it thrives without you.”

2. Planning for Life After the Sale: “I didn’t think I’d feel so lost.”

The emotional void after selling a business can catch founders by surprise. One founder shared a cautionary tale about not planning for what came next: “I thought selling the company would be the happiest day of my life. But within a few months, I found myself feeling aimless, almost like I was grieving.”

Another added, “It’s essential to have something lined up after the sale. Whether it’s another project, time with family, or even just travel—anything to fill that gap. Because if you don’t, it can leave you feeling lost.”

One founder turned the post-sale uncertainty into an opportunity for growth. “I threw myself into advising other entrepreneurs and started speaking at events. It gave me a new sense of purpose, and honestly, it kept me from falling into that post-sale slump.”

3. Choosing the Right Buyer: “It’s not just about the money.”

The founders agreed that it is crucial to find a buyer who aligns with your vision. One recounted his experience of turning down a higher offer because it didn’t feel right. “We had an offer that was above what we expected,” he said, “but the buyer’s culture didn’t match ours. I couldn’t shake the feeling that they would dismantle everything we built, and I didn’t want my team to go through that.”

This was echoed by several founders, and I reflected on my experience in coaching several founders through this process.

“You’re not just selling a company—you’re handing over your legacy. It’s important that the buyer not only sees the financial value but also respects the culture, people, and mission you’ve worked so hard to build.”

One advisor described a founder who regretted selling to a buyer who prioritized profits over people. “A friend of mine sold his company, thinking the new owners would maintain the culture. Instead, they stripped it down, cut staff, and turned it into something unrecognizable. It left him with a sense of regret that the money couldn’t erase.”

4. The Art of Letting Go: “I wanted to hold on to the reins forever.”

One of the hardest parts of the process for many founders is learning to trust the new leadership team. Townsend summed it up well: “You can’t keep your hands on the wheel forever. There comes a point where you have to trust someone else to drive.”

Letting go can be particularly hard for founders who have been involved in every detail of the business. One confessed, “I stayed on as an advisor after the sale, but I found myself micromanaging the new team. At some point, I realized I was holding them back. They needed the space to make decisions without me constantly looking over their shoulder.”

The consensus was that transitioning out of leadership requires founders to step back and allow the new owners to take control. “It’s about setting boundaries,” said one. “I told myself that I would give advice if they asked, but I wouldn’t interfere unless it was absolutely necessary.”

5. Learning from Mistakes: “Surround yourself with people who’ve done this before.”

Throughout the discussion, founders reflected on the missteps they made during their exits, offering invaluable advice for others contemplating the sale process. One founder admitted to rushing into a sale without fully understanding the tax implications. “I was so eager to close the deal that I didn’t take the time to consult the right advisors. It cost me millions in taxes.”

Greg Head emphasized the importance of building a trusted team early on. “Surround yourself with people who’ve done this before—lawyers, financial advisors, even other founders who have sold their companies. Their experience will help you avoid costly mistakes.”

Several founders agreed that rushing the process is one of the biggest mistakes you can make. “It’s easy to get caught up in the excitement and pressure of selling,” Townsend noted, “but you have to take your time. Don’t let anyone rush you into a decision you’re not 100% comfortable with.”

Going Deeper

Selling a company is about far more than dollars and cents. It’s a deeply emotional and complex experience that requires careful planning, both financially and emotionally. Whether you’re choosing the right buyer, planning for life after the sale, or learning to let go, it’s essential to surround yourself with people who can guide you through the process.

These founders’ stories serve as a powerful reminder: selling your company is the end of one chapter, but it’s also the beginning of a new one. The more intentional you are about the process, the better you’ll be prepared to navigate the journey ahead.

I’ll be posting clips from my event, “The Other Side of the Exit: Is There Happiness Beyond the Deal?” over the next few weeks. Keep an eye out for them on LinkedIn and other platforms.

And if you would like a copy of the full recording, or to be considered for the next event, be sure to DM me or make a comment below.