How to learn from failure

I’ve always been a fan of hearing failure stories, picking apart my own to learn from it, to not repeat them. I’m even somewhat biased towards failures more than success stories. I prefer the raw, gritty, vulnerability of being honest and public about what we did wrong, over the glossy celebrations of wins.

It’s like… I see an MRR screenshot on Twitter, I almost yawn out loud. If it’s a friend, I feel a moment of gladness for them and reply with an obligatory congrats. Then move on as quickly as I came. But if I see a tweet about a failure story, man, those engagement minutes on tweet are gonna shoot way up high.

But sometimes I think the obsession with learning from mistakes can get unhealthy. For the mind.

When it goes from objective learning to self-flagellation, yes, it’s unhealthy.

James Clear summed it up well here in his latest newsletter drop:

When you tolerate an error, you rob yourself of learning.
When you ruminate on an error, you rob yourself of happiness.
Notice it, improve it, and move on from it.

That last line is the key. The last 4 words, in fact.

Move on from it.

The most interesting insight about failure though, was from Annie Duke in her book Thinking In Bets:

You’re not always right when things go your way; you’re not always wrong when they don’t.

Failures doesn’t always mean you were wrong. This is especially through in non-linear, chaotic games like entrepreneurship. Trying to learn too much from failure and potentially adding lessons where there might be none can be as harmful as narrative-shaping your win from hindsight.

So the best way to learn from failure as just improve the process where there were obvious gaps, but don’t over-analyse on the severity or outcome, because there could have been many other factors outside of our control in that failure.

And then just keep calm and carry on.

Without any additional baggage.