When Our Startup Outgrows Us

What happens when the company we built no longer needs the version of us who built it?

At some point, I walked into a building as the CEO of a company with over 600 employees. I looked around and realized our HR department had more headcount than our whole company used to be, which made sense because we were managing $10 million a month in payroll.

Our focus had moved toward doubling headcount — again. We were recruiting top execs from Fortune 500 companies to help us plan an IPO. These were the same people who would have never even looked at my resume a few years earlier!

I was 26 years old at the time, and it was becoming evident to everyone, especially me, that this company had clearly outgrown me. It was time for me to go — but what do we do when the startup we built no longer needs the Founder who built it?

The Company Was Built for Who We Were

The early version of the startup was handcrafted for people like us — scrappy, stubborn, and totally willing to just roll the dice. We were rewarded for being weird in a good way. All of our quirkiness was considered a prerequisite for this job.

But then the business started working (who would have guessed?). We hired teams, then managers, then managers for those managers. The days of just getting everyone in a room and "figuring it out" were gone. From chaos came structure, and with structure, our ability to operate in chaos wasn't quite as valuable anymore.

One day, we woke up and realized the only person who hadn't moved on with the new system was us. That's OK, but it's scary. It's also hard to imagine that the result of all of our hard work and vision would be putting ourselves out of a job.

Do We Actually Want to Grow With It?

We’re told we’re supposed to evolve with the business. Learn to manage, delegate, and lead at scale. We all try, and a few of us pull it off. But while we're trying to put on the big boy pants and become the manager that our organization needs, do we risk becoming the version of ourselves we don't want?

It turned out I absolutely hated being a manager. It wasn't the responsibility that I didn't like, it was the actual job of managing people. I'm a creator — I create things. I want to be building products, writing stuff like this, and connecting with my customers. I don't want to be sitting in a room putting together slides for an upcoming internal meeting. I hate it.

Yet that's often what the job evolves into — this place where we would never get hired for the job we're expected to do. It sucks, but it's fixable, so long as we stay true to our strengths and are willing to evolve our expectations, not necessarily who we are.

It’s Not Failure — It's Evolution

There are essentially two elements to making this transition properly — recognizing we're not the person to be a manager, and doubling down on what we're great at. Sometimes that means we hire someone that reports to us, like a President or COO to be the actual day-to-day manager. We don't all have that luxury.

If we can't do that, sometimes we have to abdicate our CEO role altogether to someone who may be more suited for the job (I've never made this work, but that's just me!). Sometimes we end up further down the org chart, which feels odd, but it's also where we make the most sense.

Sometimes the best place for us isn't at the company at all. In my case, I left a year later, and it was one of the best decisions I had ever made. When the company no longer fits us, it doesn’t mean we failed. It means we did our job well enough that the business is now bigger than just us.

The Transition is a Trophy

One of the things we lose sight of when we're contemplating this change is how much we had to accomplish in order for this to even be a discussion. For every one of us that has grown a company so big that it's outgrown us there are thousands of us who never even get to this point.

In the same way as parents, we imagine ourselves proud to watch our kids go off to college one day, we need to think of our startup evolving in the same manner. It's bittersweet, but it's a rite of passage that we've earned.

Let’s not mourn what we’re no longer a part of. Let’s take pride in having helped build something strong enough to outgrow us.

That was the point all along.

In Case You Missed It

Why No One Tells Founders "It's over, move on." No one ever actually tells Founders it’s okay to quit. No one except other Founders, of course.

Retiring Early is a Broken Concept Retiring isn't really our end goal, so we shouldn't aspire to it. What we really want is to shape our life the way we want it to be.

I’m Killing Myself. How is Everyone Else Finding Work/Life Balance? We're supposed to believe that we can build a world-changing startup from nothing while simultaneously traveling to exotic places and enjoying our "best life". For most of us, that just doesn't add up. What's blowing us up, though, is how we approach the problem.