Michael Lopp (aka @rands) and I ran a session at #foocamp this year titled “Regret at Scale.” We’d been having an ongoing conversation about how it’s au courant to be supportive of failing entrepreneurs, product teams and businesses (failure is learning!), but that there isn’t enough discussion of that related but more personal emotion, regret. In the unconference scrum of foo we figured a session titled “Regrets” would be too much of a downer to attract any campers, so we added the “at scale” modifier in order to up its nerd appeal.

The session was off the record, so I won’t reshare any regrets. But given the headline of the day, I thought it would be worthwhile to share how Michael and I defined “regret” at the top of the session, in order to distinguish it from its close cousin “failure.”

“Failure” is easy. You didn’t execute well, you made bad decisions, your timing was off, competitors ate your lunch. You pick yourself up, you dust yourself off, you (hopefully) learn from your mistakes, you move on.

“Regret,” we argued, is different. We defined regret as remorse around a decision you made or action you took, that you hope to never do again. Not because it was exogenously the wrong choice (even if it might have been) but because the choice you made or the thing you did went against your own values, and contradicted how you like to think of yourself. The things you regret are the things that sting, the things you wish you could take back, the things you for which you seek repentance.

Apologies if you thought this was going somewhere other than this:

You can argue that Marco should have anticipated not feeling good about the success of Peace, given his background as an independent software developer and publisher. And at the same time you can use Peace as an object lesson in the ongoing debate around ad blocking, privacy and The Future of the Web. Hot takes all around! But I have to give him credit: he didn’t need to pull the app; he felt like he had to pull the app. And he did.

I just wish he had picked a better headline for his blog post.

Avid reader, long time blogger, art nerd, Swiftie. I work at Medium.

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