On Mistakes

In the past few Decembers, I’ve become increasingly hard on myself as I’ve reflected on the past year’s mistakes.

No, not the I spilled my Chipotle bowl on my girlfriend kind of mistake (though that does have dire consequences). Instead, I mean the more serious and heavy regrets, such as delayed career pivots or critical financial decisions.

I guess some human part of me wishes I could’ve prematurely had all those newfound perspectives, learnings, and skills at the start of the year. All those mistakes could’ve been avoided.

While I’m a firm believer that failures should never be fetishized, I also understand that retroactively cherrypicking past events isn’t always realistic or helpful either. Often times, the mistakes we learn from are only obvious in hindsight, since we only develop the fortitude to navigate them by making them in the first place.

Whether it be more minor mistakes, such as referencing a kinda outdated MongoDB video, or something more serious, like messing up an important business dealing, there will always be a limit to the amount of lamenting that will help. Once we’ve already effectively internalized the lesson and learnings, further regret is fruitless. Over-lamenting the past leads to neglect of future; future becomes past and the cycle repeats. Eventually I have to let go.

At a certain point I have to be okay with that more naive self from my past. That person who never actually thought through their life, try building leveraged skills like design or code, or have any intrinsic, personal aspirations beyond those arbitrated by shallow external expectations. The only reason that I am no longer that person today, is because I faced the negative consequences of making those mistakes long ago. In the next few decades of my life, I can’t even imagine how many more mistakes I will make.

Brendan, if you’re now some weird, wrinkly 80 year old prune that just finished meditating and started reading this, I apologize for all the trouble I will cause. Even before I’ve enacted any of the mistakes you’re probably cringing at, I can already tell that I’m full of personal weaknesses and have a long way to go.

This piece is a reminder to my future self, that although giving your everything is a fundamental requirement, new mistakes are the ingredients for drastic improvement, lest we never know what we don’t.