The Observer's Notebook

Why Smart Founders Stay Stuck Longer Than Average Ones I am about to say something that is going to sting a little, and I want you to know I'm saying it with love. The smarter you are, the longer you can stay stuck. Not because intelligence makes you slow. Because intelligence makes you exquisite at building airtight cases for why the wrong answer is actually correct. Average founders don't have that capacity, so they get bored and try something else. You don't get bored. You analyze. You synthesize. You write a Threads post about it. And the situation does not change. This is the post where we talk about that. I am going to walk you through the closed loop, the five tells you're inside one, why intelligence makes the loop more durable, what actually breaks it, and what to do about it. I am also going to be honest that I have personally been stuck inside every one of these tells, sometimes more than once, sometimes for over a year at a time. So if any of this feels like...

  The Symptom You Keep Treating Isn't the Problem There is a problem in your business that has been broken for at least nine months. By my count, you have treated it five different ways. You have rewritten the page. You have changed the price. You have hired a person, fired a person, hired a different person. You have bought the course about it. You have built a Notion doc about it that you are quietly proud of. And the problem is still there. If that opening landed, this post is for you. The reason the problem keeps coming back is not that you're undisciplined or under-skilled. It's that you are treating the wrong layer. You are working on the visible thing, the thing waking you up at 2 a.m., the thing you can describe in one tense sentence to a friend at brunch. But the visible thing is not the problem. It's the symptom of the problem. The actual problem is somewhere underneath. Almost always, it's a structural decision you made early in the business that is now s...