Cognitive Debt and the Cost of Staying Wrong

Being wrong is unavoidable. The real damage comes from allowing a bad assumption to shape everything you build on top of it.

A few years ago, we sold smpl, the coworking software company I had built with two close friends.

An acquisition gives you a tidy ending. It becomes easy to look back at the decisions you made and imagine that they must have been good ones because, eventually, things worked out.

I know better.

When I think about smpl now, I see plenty of moments when I was wrong and dug my heels in for far too long. My teammates sometimes saw things more clearly than I did. Our customers gave us signals that I dismissed or explained away. I became attached to my own ideas, and that attachment cost us time, strained important relationships, and made our product worse.

smpl was acquired despite some of my decisions, not because of all of them.

Technical debt accumulates when you take shortcuts today and leave the consequences for someone (read: you) to handle later. I have started to think there is a similar kind of debt that accumulates in our understanding.

Cognitive debt begins with an assumption. That assumption influences a decision, which shapes the next decision, until we have built an entire strategy on top of something that may never have been true.

The work can still look productive. Features ship, customers sign up, and the company moves forward. A good outcome may even hide the debt completely. But every untested assumption makes changing direction harder, especially once our reputation or identity becomes attached to it.

This problem feels particularly relevant in the age of AI, when chat can produce work faster than we can understand or validate it. AI accelerates the problem, but it did not create it. People have always been capable of confusing confidence with understanding.

The scientific method offers a useful alternative: form a hypothesis, test it, observe what happens, and change your understanding when reality disagrees.

The difficult part is remembering that a hypothesis is temporary. It should never become part of your personality.

For founders and leaders, this also means creating an environment where people can challenge ideas without paying an emotional price for it. A thoughtful disagreement is valuable evidence. If someone has to fight through your ego every time they offer it, they will eventually stop trying.

I cannot know how smpl would have turned out if I had listened sooner or changed my mind more readily. Maybe the acquisition would have been larger. Maybe the journey would simply have been healthier for the three of us and better for our customers.

Either possibility would have been worth it.

One of the most useful things a leader can say is: I was wrong about this. Here is what changed my mind, and here is what we are doing differently.

Being wrong is part of building anything new. The tiny improvement is learning to stop compounding it.