Why Founders Can't Retire

There’s no such thing as a “retired Founder.”

Just one who hasn’t started their next company yet.

I love hearing about Founders that exit, but what I always find kind of entertaining is their story about how they will now finally retire. It’s always something like “I can finally put the stress of running this startup behind me and spend the rest of my days basking in the sun and enjoying life!”

My response is always the same: “That sounds awesome… call me when you want to talk about your next startup!”

They assume I’m being sarcastic. The idea of starting another startup after just finally selling one and prepping for retirement sounds ludicrous!

And yet, inevitably, I get the call. “You know, retirement actually sucks, so I’m thinking about this one thing…”

Of course you are. That’s because Founders aren’t built for retirement. We’re built to build.

The Dream

So if this is so inevitable, why do we spend so much time dreaming and building toward this fake retirement?

It’s because in our minds, we’re not really dreaming of retirement, we’re dreaming of relief. Relief from a decade of nonstop worrying. Relief from never knowing if we’re going to be safe. Relief from just being able to breathe easy for the first time in as long as we can remember.

But that’s not retirement. That’s called taking a break, and the only way we can ever really see doing that is when work is not even an option.

Don’t get me wrong — we definitely need that break! There’s no way you can compact that much stress into such a short period of time and not need some sort of relief.

That shit is real.

But that’s not retirement. That’s a stress relief valve when we feel trapped.

At some point, we lose sight of all the amazing things building a startup provides us in exchange for a sole focus on what it takes away.

No Substitute

That is, of course, until the startup goes away. Then we’re bored AF.

But think about it — there is no substitute for building a startup. I think people make the mistake of comparing building a startup to just having a job. It’s not even remotely close. Yes, both pay you (well, ours doesn’t always…), but that’s about as close as they get.

Building a startup isn’t a job — it’s a mission.

A mission is something you feel innately compelled to do. It draws on some magical inspiration from inside that forces us to bear an ungodly amount of weight, to perform well beyond our requirements, and to develop ourselves at a pace nothing else can touch.

Many of you reading this are in it right now. Yes, it’s painful. Yes, it’s hard. But goddamn it ain’t boring!

The excitement of what we do has no substitute. Creation has no substitute. It is the fundamental gift of humanity that is on display when we build a startup. That’s why putting our toes in the sand may provide relief, but it’s no substitute for the excitement, challenge, and thrill of creation.

Do Not Deny the Calling

Now, we can deny that calling for a bit. We can fantasize about a different life that removes all the stressors, and by all means, we should. But when removing those stressors also comes at the cost of removing our calling, we feel empty.

I always tell Founders, “You didn’t get to where you are by being the kind of person that spends day and night thinking about sitting on a beach.”

As Founders, we are simply built differently. We need to embrace that.

When I’m on vacation, watching my family frolic in the pool, and taking one of the very few true rests I ever get, you know what I’m thinking about? Building stuff. I used to do everything in my power to stop thinking about it. I’d bring books, schedule outings, and deliberately try to distract myself for the entire trip.

But you know what? That’s not what I was built for. And you probably aren’t either.
We, builders, gotta build. That’s our calling, and there’s no point in denying it.

Seriously, No Retirement?

I think we need to reframe retirement. For everyone else, it’s the absence of being accountable to a job, and that goal seems perfectly reasonable.

But for us, retirement removes us from our calling, the very spirit of why we do what we do.

Instead of retirement, we should be thinking about “reframing.” We should think about creating a situation where this next milestone, being an exit or whatever we want to call it, is just a way for us to reframe how we do our next startup.

Maybe we reframe this next one so it has no investors (the most popular option!) Maybe we have a smaller team we feel closer to. Maybe we can build something that feels more like fun and less like work. Maybe all of the above.

So let’s not pretend we don’t want to build anymore. We never wanted to retire from that.

Retirement should be about doing more of what we love — and building is what we love.

In Case You Missed It

Retiring Early is a Broken Concept Have you planned your retirement? Ryan Rutan and Wil Schroter discuss why retirement goals should start now, how early testing changes your plans, and what objectives to set immediately.

The Lies Founders Tell About Retirement What is the real definition of retirement for Founders? Whatever it may be, what matters the most is we get to do what we love doing but this time with less stress, less pressure, and time isn’t measured.

What We "Lose" When We Sell Our Startup (podcast) Let’s talk about the emotional toll it takes on Founders when they sell their business, how to spend time when the Startup is gone, losing authority & level of importance, and if there’s a way to prepare to become an ‘exited’ Founder.