"Failing fast"
self
August 6, 2025
I did a startup accelerator where you are selected based mostly on your communication skills and your prior projects: you don’t need a team, or even an idea. The program begins with several rounds of “speed dating” as you try to find a person who can become your cofounder. You talk to someone, if there’s any potential at all, then you pair up, and then you run the relationship at maximum intensity to see whether it lasts or fails. If it fails under the load, that means you weren’t compatible cofounders, so you break up and swap partners.
I think that startup founders are a peculiar bunch, and venture capitalists who would run a program like this even more so. In hindsight, there were a few aspects of that program that were psychologically poisonous. But I think this idea of running towards failure, instead of away from it, is actually quite useful.
I subscribe to the belief that if you are doing the wrong thing, or you have the wrong timing, or you’ve surrounded yourself with the wrong people, or your motivation is incorrect, failure will find you eventually. The only thing you can choose is whether this happens quickly or slowly.
I also believe that failure is easy to predict with confidence and impossible to predict with certainty, and it should never be assumed. You might be able to evaluate whether one option is more likely to work than another, but you don’t know everything. If you want results, you have no choice but to pick the best option and try.
I also believe that failure is only embarrassing if you quit without producing any output. Otherwise, “failure” is indistinguishable from “learning”.
If you believe these beliefs too, then it follows that you can’t actually avoid failure, you can only plow through it over and over until you reach “success”. You can make this easier on yourself by spending as little time and energy as possible to reach “failure” so that you can reset and try again.
That means you have to come up with ways to measure whether what you’re doing is working or not (tech people call this “feedback”), and you can’t bury your head in the sand.
That means that you have to divorce your self-worth from your results, because if you can’t do this, each “failure” will take a huge emotional toll. Tie it to your character, your output, and your learning instead.
That means that there’s no point in stopgap solutions. Don’t delay the inevitable. Don’t stay in relationships or environments that have already been revealed to be incompatible with you. Don’t chase goals that you’ve already discovered aren’t truly meaningful to you. Don’t pursue paths that require compromises you know you won’t make. Use what you’ve learned about yourself to bail yourself out early so you can try something else instead of burning yourself out.
Crucially, this is different from quitting before you’ve given something an honest chance to succeed. Quitting before you’ve experienced failure doesn’t work because it prevents you from truly learning anything or producing anything.
Instead of bracing for impact, you have to strengthen yourself and weaken the impact so you can face it head-on.