Less logic please

Saving the overthinking founder

Hi all —

This week, I chose violence. And by violence, I mean “starting to post sarcastically on LinkedIn.”

Does it work? Who knows. It does seem to filter for cerebral founders. And they’re the topic of today’s post.

Ode to Overthinkers

This week I realized that the founders I tend to work best with aren’t just ex-consultants or ex-MBAs.

They’re overthinkers.

If you read this, you’re probably an overthinker.

A worrier.

A deliberator.

You want to think your way through problems in order to get to the right answer.

And usually, overthinkers find themselves stuck. Indecisive. Struggling to get to the “right” answer when you don’t have much data.

They also find themselves overcomplicating things. Trying to find the best solution. Accounting for all the important variables. Making complicated “if-then” roadmaps and plans.

Worst of all, overthinkers rely on logic. They believe the right answer is just some thinking and logic away.

I am an overthinker too, and I’ve had to abandon these ways.

Overthinking and logic

One thing I tell my overthinking founder friends is that logic is a one-way mirror. Look into the future, and you can’t see anything. Look back in the past, and you can occasionally see something.

But that one-way mirror happens to be a funhouse mirror. Even if you see through it, the image is warped. It’s easy for smart people to use logic to delude themselves into seeing what’s not there. You’ll see what you want to see in the advice you get, in the data you look at, and the arguments you don’t make.

What do you do with this?

Make decisions. Choose your target customer and try like hell to sell to them, rather than sitting around and theorizing if there might be a better fit. Don’t wait for more data - lean into what feels like it’s most likely to be right. Be rigorous with your thinking, I guess. Or don’t, and just ship things fast and see how the chips fall.

People far less intelligent than you are successful because they do things imperfectly, then improve. They don’t need to “understand” or “have a mental model.” They sleep better at night when the only thing they need to worry about is, “how am I going to make more money tomorrow?” Anti-intellectualism is against our Ivy League sensibilities, but who cares? I’d rather be a simpleminded millionaire than shop at Trader Joes.

Take yourself less seriously, overthinker. Your stress levels and business will be all the better for it.