Bootstrapped Founder #144: The Risks and Illusions of the "Post-Exit Retirement"

Dear founder,

today, we'll talk about early retirement — the Indie Hacker dream — and how it can turn into a nightmare. You'll find that many of the problems that I mention can be avoided by building your business more intentionally. From the start.

Also, I'd like to say hello to the 24 new readers this week!

Please feel free check out our (indie) sponsor, Paid Memberships Pro.

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Building and selling a business is a blessing and a curse. While it catapults founders into a very different financial situation, it also shifts what gives them purpose and passion and allows for lasting impact. Chasing these elusive virtues causes many entrepreneurs who thought they could retire to get back to work — or it can have much worse outcomes.

After selling the business, my retirement lasted exactly two weeks. I thought that now that I had reached a state of financial stability, I could just spend my life playing World of Warcraft, reading books, and doing whatever I wanted.

It turned out that this life wasn’t for me — anymore. Twenty years ago, just after finishing high school, it definitely was: I spent all day long gaming, reading as much fiction as I could get my hands on, and it was wonderful. The amount of agency I found after all these years of being told what to do was a blessing.

And I chose to fill my time with games and books. They provided structure in an unstructured time.

A decade and a half later, when I had accomplished the indie hacker’s dream of building and selling a business with my co-founder Danielle Simpson, I was looking at the dreaded unstructured life again, and I returned to what I knew worked for me: games and books.

But this time, it didn’t work. Playing World of Warcraft felt shallow, and I just couldn’t keep focusing on my books. No matter how hard I tried, I couldn’t find the same joy doing these things that I found so wonderful back in the day.

Running a Software-as-a-Service business that impacted the lives of thousands of customers ruined this for me. The passion I found in helping our customers couldn’t be replaced by doing quests in a video game. Making a material impact on other people’s lives has shown me the capacity of what an entrepreneur can do: we can make a massive difference in the reality of others. No virtual world — game or fictional narrative — can come close to this.

My source of passion was my capacity to serve our customers. My purpose was to build solutions to their problems. My actions had meaning because they made a difference.

And now, all of that was done by someone else.

The more I talked to other founders who exited their businesses, the more I saw this pattern. People cash out, buy the things they always wanted, learn that this doesn’t make them happier, and then they fall into the downward spiral of realizing that they have lost more than a business.

When your company gets acquired, it isn’t just the business that’s taken over by someone else. Your roles —particularly those that defined your identity for years— are filled by other people. Your importance for decision-making processes drops to zero. You’re not needed anymore. Those little sources of motivation, passion, and purpose dry out almost immediately. A looming void appears.

This void is real, and it yearns to be filled.

And it’s not that you’re surprised by it: founders prepare for their exits, and we all get told that the void will come over us. We just don’t comprehend how intensely it will affect us before we feel it for the first time.

Many people consider retiring at precisely that point. Yet almost every founder ends up feeling that retiring early is a mistake. It sounds so easy to stop working when you’re financially secure, but you quickly learn that the absence of work isn’t the blissful paradise you thought it would be.

Post-exit life isn’t a candy shop.

It’s a scary place. We suddenly get incredibly bored, devoid of anything to do, and because so few people go through an acquisition, we have no one to talk to. If most of our friends are employed in a job somewhere, they won’t be able to relate: no matter how crazy things get at work, someone else makes choices for and with them. But for the post-exit founder, that “next step” is nebulous at best.

There is a real risk here: if you can’t find your next source of passion and purpose in another line of work, you might start looking at less-than-desirable ways of filling the void. The moment you need a drink to get some sleep, you’re opening the doors to addiction — something that happens to a significant percentage of founders after they sell their businesses. Drugs, alcohol, gaming, sex: addiction comes in many different shapes, but it always is a fake passion.

When your identity of “being a busy entrepreneur” is hollowed out by an exit, you might fill it with anything that looks attractive.

Some founders immediately throw themselves into the next business, too. Without taking some reflection or respite, that’s an equally bad move. Just because you’ve been successful with your last business doesn’t mean you’ll have a similar experience this time around. Yet many post-exit founders think they need to do it again, and this time, even better. Their need to one-up themselves quickly derails into a destructive and depressive downward spiral when things inevitably go wrong.

You just reached the summit of a hard-to-climb mountain. You don’t need to look for the next-highest mountain to climb immediately. But if you’re defining your self-worth by your mountaineering skills, that’s what feels “right” to do, even when it’s not. It’s a mental shortcut that, in place of proper reflection, will eventually lead you to a dark place.

Without a proper plan, the void will swallow up the unprepared.

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So, how can you protect yourself from this threat as a founder?

I had an incredibly hard time preparing for this moment on my own entrepreneurial journey. I thought gaming would do it for me, but it didn’t.

But I found a surprising contender in something I had done before selling the business. I had written a long blog post that I never wanted anyone to see. I hadn’t set up a public blog; I had just written the post as a draft. It was a collection of all the mental health struggles I was dealing with at the time, and it was a cathartic essay on the best ways of coping with these sources of stress and anxiety might look like. I wrote that blog post for myself as a reflection on the burnout I could already feel coming.

I never published the post.

But I went back to read it when I was searching for purpose and passion. And when I saw that draft —all the 4.500 words— I understood that it wasn’t just a reflection opportunity for myself. It was also a guide for others to avoid falling into a similar depressive state.

It was at that moment that I decided to become a teacher. I started exploring what I wanted to teach and how and where to do it. I wrote the first blog posts that I wanted to publish. Over time, the newsletter and the podcast fell into place, and I was running a media business before I knew it.

I couldn’t resist getting back to finding my passion in helping and empowering others. Writing was the conduit I needed for that.

If I can give you advice here —and I struggle even to attempt it— it would be to reflect constantly on your sources for passion, purposes, and perceivable impact in your life. Just like finances, it pays to diversify them — or at least have something lined up in case one of these sources runs dry.

Entrepreneurs run the severe risk of over-identifying with their business. That’s a problem at any stage, not just after a sale. You are not your business, and you don’t need that particular business to have meaning or impact on other people’s lives.

Instead of looking for your purpose in a role, look for its source: is it solving problems you enjoy? Or helping people? Might it be organizing knowledge into an easy-to-consume format?

Those things will translate well into a post-exit purpose. The easier you can decouple your entrepreneurial role from your personal identity, the more you’ll be able to find passion and a means to keep having an impact on people’s lives in your “post-exit” retirement — and long before that, too.

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