In Retrospect, That Thing I Did With My Startup Was Dumb
How to fix what’s really wrong instead of what’s just easy
About six months ago, I did something really dumb with Teaching Startup, and it’s the kind of mistake I don’t want to make again. I’m not going to color the exact mistake here — this isn’t that kind of post.
What I do want to talk about is how recognizing the dumb things we do and learning from them is something that everyone says they do, but few actually do. And there’s a reason for that. And we’re going to address that reason together, so that we not only learn from our mistakes, but potentially fix the real problem.
I’d say I do a big dumb thing every couple months. And several smaller dumb things along the way during those months. And every few years, I do a thing so stupid that I wind up costing myself tens or even hundreds of thousands of dollars, personally, either in real cash or opportunity cost.
I do these dumb things by accident — well, accident in the sense that the outcome wasn’t what I intended. But I always pull the trigger. On purpose. Because I mean to do dumb things sometimes.
The trick is for every dumb thing that blows up in your face, you have to do two dumb things that work.
