Why I Might Never Start Another Company

As I’ve begun to look into the abyss of what might be next, I am realizing there is no way to find my way to a real answer of the work that is mine to do without casting off this identity and these assumptions.

Why I Might Never Start Another Company

Last week, my therapist and I were talking about the challenges of parenting. She told me a story that was intended to be illustrative for a challenge I’m facing on the parenting front, but it ended up being incredibly illustrative for me personally.

She told me about an experiment run in an English school. The school was designed to be an alternative school for ‘troubled’ kids, kids that were failing to succeed in mainstream schools. What was special about this alternate school was how little the schoolmaster changed from a ‘normal’ school. He made albeit major adjustment. There were no rules, save one: you use not impede on the space or rights of another student. Aside from that, students were left to their own devices.

They could  go to class when and if they liked. Roam the hallways. Hang out in the library or on the playground. Whatever struck their fancy.

The crazy and almost unbelievable outcome is within six months nearly every student was regularly attending class and excelling academically. These seemingly troubled students were crushing school.

So what made the difference? Ostensibly, at least according to my therapist, children struggle when rules and order are imposed on them. Their natural curiosity and drive is squashed out. The route back to their natural tendencies is one of space, freedom, and time.

As my therapist finished the illustrative story, I found tears welling up in my eyes. Not tears on behalf of my son (who largely is doing just great), but tears for myself. I realized 7 years running a venture-backed startup had crushed the curiosity and drive out of me.  But the tears weren’t about the loss.

The tears were tears of hope that what I’d lost might return. The story connected me with a framing that helped to cast light on the truths that much of what I’ve been experiencing around fatigue and burnout is normal and that there is a well-worn path back to my natural state. And the path that’s needed is one of freedom, space, and most likely rest.

We sold Twenty20 in April of this year. By July, I found myself beginning to tinker with new business ideas. For years, I’ve kept a backlog of all the ideas that came up over the course of my time founding and running my company and I felt excited, or so I thought, to have time and space to begin exploring those ideas.  However, whenever I sat down for a half a day to dive in, I found myself hitting an emotional wall. I’d get excited for a few hours, dive into the early exploration and validation process, then find myself overwhelmed with fatigue, depression, or despair.
A week ago, during dinner with a close friend and a conversation about this experience, I came to a realization that I needed to let go of the idea that I would start another company.

For more than a decade now, my identity has been in large part one of ‘founder,’ ‘entrepreneur,’ and ‘CEO.’ Even as I approached the sale of the company, I found myself talking with friends about what I might do next, what I would start. After all, I was an entrepreneur. Starting companies is what we do. But as I’ve begun to look into the abyss of what might be next, I  am realizing there is no way to find my way to a real answer of the work that is mine to do without casting off this identity and these assumptions.

I might start another company. I might start 10 more companies. That’s not the point. The point is that jumping to starting another company out of a sense of identity, obligation, or a need to prove that I can feels life-threatening. Maybe not in the physical sense, although perhaps that also, but definitely in the emotional sense.

So during that dinner, I decided to announce to my friend, and more importantly to myself, that I was going to let go of the belief that I will start another company. I’ve realized since I must also let go of my identify as entrepreneur, CEO, or founder.

For now, to find my way, to remember my heart and my true identity, I must be simply Matt.

For me, that line in the sand, and the step I’ve taken past it into being simply me, is the beginning of my time of freedom in this new school for troubled and recovering students. I need to be here, to rediscover what it is that makes me me. To rediscover the innate parts of me that are curious, driven, and creative. To remember that before I raised money, hired a team, went through the countless struggles to build a company that supported thousands of customers around the world, before I ran face-first into burnout and exhaustion, before we found a safe and wonderful place for our product and team to carry on beyond my tenure, before all that, I was a curious kid who liked playing with computers. Liked reading about new things. Liked thinking with friends about what might exist in the world that doesn’t yet.

So here I sit.

Just Matt.