How to be Great at Worrying

In 1994, my brain started thinking about my startup 24×7. It hasn’t stopped since.
It’s not awesome.

I know the “grind hard” startup narrative is that we should always be thinking about our startup and marry every thought to that commitment. And honestly, I get it. That sounds really committed.

But when does that break? When do we hit a point where our startup is consuming all of our thoughts and emotions and isn’t productive anymore? How do we balance the drive that fuels us with the guilt that prevents us from separating our jobs from our lives?

Why We Can’t Stop

I think a lot about why my brain won’t stop thinking about my startup. I mainly think about that at 3 a.m. when I’m staring at the ceiling trying to tell my stupid startup brain to STFU and just sleep!

My answer is simple — it’s fear.

I’m staring at the ceiling at 3 a.m. because I’m afraid of what happens if I don’t. I’m afraid that if I take my foot off the gas for even a moment, my entire startup will implode. As if when I just shut my eyes and think of literally anything else, some detonator will go off in our AWS server and wipe us off the map forever.

Does that sound crazy? It is. It’s crazy. But that’s what is running through my mind all the time. For many Founders, we might think that we’re the only ones, but I have the great pleasure of talking to thousands of Founders, and I’m 100% sure I’m far from alone on this one. In fact, I’m sure I’m in the vast majority, sadly.

When it Stops Being Useful

For over 3 decades, I’ve spent countless hours awake in bed at night pondering that one problem with my startup that I need to go solve tomorrow. Let’s say I spend about 2 hours per night in that mode. That means I’ve sent over 20,000 hours (holy hell!) working out my startup problems in the middle of the night.

You know how many problems I’ve worked out? Zero. None.

I’ve never worked out a problem at 3 a.m. All I’ve done is worry about them. There’s a point where all of this worry, all of this attention, stops being useful. It’s right around the time when we start making “worrying” the action, which is a total waste.

I find myself having to police myself constantly to say, “You’re not solving this problem right now, you’re worrying about it, which is taking away from the important steps.”
Worrying is not working. Worrying is useful energy being set on fire for no reason.

Convert Energy into Output

Now here’s what’s interesting, though. All that manic energy is really powerful, but if channeled appropriately, it makes us superhuman. The trick is knowing where and how that energy is being used.

For example, if I’m super anxious about something that’s happening in my startup, and I know there’s nothing I can do about it at this moment, I ask myself, “Where can I put this energy?” Sometimes that answer is “Go clean a room” (my woodworking shop is perpetually dirty, so this works out great). Not world-changing, but better than just worrying.

Other times, I sit down and just start writing out requirements docs for new products, or nowadays, just write as much code as Claude will churn out. I realize that my nonstop, relentless pattern of thought can be used for good or evil. The difference is when I recognize the pattern and harness the opportunity.

As it happens, most of my greatest output came from when I was by far the most stressed. Not how I wanted it to happen, but there it is…

There’s No “Just don’t Worry”

I love when people, almost exclusively not startup Founders, say “Well, maybe you should just work on worrying less!” as if that’s the solution. Yes, that does sound incredible. And if our jobs weren’t to literally have to worry about everything that could go wrong, that might be an option.

But our job is to worry. It’s what makes us effective: we spot the things others overlook because they aren’t worried about them the way we are.

What we need to do is transform that nervous energy into incredible output. We need to actively train our brains to recognize the difference between solving real problems and “just worrying about them.”

When we make that transformation, something beautiful happens — we actually solve the very problems we were worried about!

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