The Post Exit Playbook

April 22, 2024

Selling a company, often considered the holy grail of entrepreneurship, isn’t always sunshine and rainbows. The financial windfall and newfound freedom we so desperately seek can actually become overwhelming. After selling the company, founders often find themselves facing an identity crisis, wondering who they are without the company they’ve worked so hard to build.

​(This blog post is the third of a three-part series. If you missed the first two, you can catch them here and here.)

​Having experienced my own ‘what-does-it-all-mean’ phase, or what some might call an exit-induced midlife crisis, I’ve dedicated significant time to my own healing and assisting other founders on this journey.

​Over time, I’ve crafted a 7-step framework for navigating the ‘messy middle’, a term often used to describe the post-exit period. While initially designed for post-exit founders, I’ve discovered that these steps are equally effective for any significant life transition, be it career-related or otherwise.

And so, without further ado, I present to you, the Post-Exit Playbook.

Step 1: No fast hands in the cockpit

​I admittedly lifted this saying from my time flying F-18s in the Navy, but I can’t imagine a better way to sum up the first step. Dealing with a newfound abundance of wealth and time is already a complex situation, but we compound it exponentially if we put pressure on ourselves to figure it out too quickly.

The fact is, there is plenty of time. We don’t need to rush to put our capital to work or to optimize our calendar. The more time we can put between ourselves and the exit before making any major decisions, the better.

​My advice to founders in this phase is to set aside a portion of the money to celebrate the win, such as by buying a watch, a car, or taking an extended exotic vacation. But beyond that, I wouldn’t make any major decisions at all —especially when it comes to investing.

​Which leads me to…

Step 2: Sit in stillness

​I would argue that the worst thing I see founders do is jumping immediately headfirst into founding a new company.

​I get it. We all have ideas. We’re used to living fast-paced, high-stress lives, and we all probably have a new idea that’s been burning a hole in our back pockets.

​But by the time we get to the exit, we’ve often been working a decade or more on our company, not to mention the often exhausting transaction process.

The gift of time and space (while young enough to truly enjoy it) is one that many on this planet will never get to experience. Take it. Relish it.

​Resist the temptation to say yes to all the new and exciting opportunities.

​Instead, I’d urge you to….

Step 3: Get bored.

​When asked about retirement, so many founders will immediately pontificate upon how they could never retire and simply do nothing! Why, they are driven, hard-working individuals on a mission to change the world. After all, without my work, I’d be so bored!

​And yet, this is exactly what most of us need.

​Ask yourself: what’s behind the constant need to be busy? Why is it so uncomfortable to not fill every minute of our time?

​Or perhaps… what is it we are trying to avoid feeling?

When we get quiet with ourselves, we often notice just how noisy it can be inside our own heads.

​Our societal solution?


​We self-medicate with drugs and alcohol, exercise, work, golf, or any other accepted method of filling our time. But instead of leaning on a new hobby or a new company, this newfound boredom can give us a chance to…

Step 4: Do the work.

​Remember those pesky questions from before? Those feelings of discomfort when we aren’t filling every second of every day with busyness?

Now’s your chance to answer them.

​Read books. Journal. Go to therapy. Hire a coach. Maybe all of the above.

​When we get curious with ourselves, when we are open to pulling the thread and seeing where it leads, we can finally start to find some answers.

​We may find that we were so busy because we didn’t want to feel repressed emotions or grieve losses or because we were busy proving to the world that we were worthy.

​You just never know what may be lying on the other side of door number 2.

But for those brave enough to lean in, this step can be absolutely transformative.

​And that nagging feeling of emptiness? The one you just can’t shake?

​It may start to dissipate finally. And once it does, now you can…

Step 5. Determine your values.

​Before starting any new endeavor, I like to start with the outcome in mind.

​As we start to design a new life, we really need to understand the ultimate question: What are you optimizing for?

It’s really hard to to build an intentional life without first understanding what it is that we truly want.

​I see so many founders simply choose the default: continue building. It doesn’t matter how much wealth they’ve already accumulated; the only answer to how much is enough is more.

​This is demonstrated quite clearly by the Hampton Wealth Survey, released last December. It found that regardless of net worth, individuals all believed that they needed at least 2x what they currently have to feel secure. 

I believe that we can actually come up with a number. It simply takes getting clear on how we want to spend our most valuable asset: our time.

​Once we determine how we want to spend our days, we can calculate the cost of our ideal lifestyle.

​The irony? Many of us, especially post-exit, have either met or exceeded our number.

And once we figure that out, then we can…

Step 6. Try things on.

​If we aren’t optimizing for growth at all costs, our options open up dramatically. I encourage folks to start with a list of problems that they would want to work on if money were not a consideration (because often, it isn’t—or at least not the primary consideration).

​Once they have their list, they can start comparing their ideas with the ideal lifestyle we came up with in Step 5. Some problems may be incongruent with living our ideal life, and thus, we begin the process of elimination.

The critical part here is that we don’t fall prey to the sunk cost fallacy.

​Entrepreneurs are known for their burn-the-boats, win-at-all-costs mentality.

​However, in this phase, total commitment can become a limitation. Many founders launch headfirst into their new endeavor and then wake up months later working 80-hour weeks and stuck because they raised a new round of capital.

​Continue to be curious, try things on, run experiments, and, most importantly, set performance gates and kill criteria.

​And in those kill criteria, at least one should center on whether the new role is as fun as they thought it would be.

​As long as the answer is yes, then we get to…

Step 7. Create from joy

​I’m convinced that this last part is the most critical to living a fulfilled life.

​When we build our first company, it’s often because we are trying to build a better life, to escape the circumstances that we were born into, and to create a legacy for our family.

​But once we’ve done those things, we have the opportunity to build from a new place. We get to choose how to spend our time, on the things that matter to us and, more importantly, on the people that matter to us.

​As we build our new life, we must ask ourselves: Would I continue to choose this every day? Is what I’m doing bringing me joy?

​If not, we risk the same burnout and stress and simply repeat the cycle.

​The worst part?

​This is a totally avoidable problem.

​But it means resisting our default programming. It means getting uncomfortable.

​Ultimately, it means we must grow.

And that, my friends, is the gift that many of us never knew we needed.

To sitting in stillness,


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