2018 Year in Review

It often feels like you’re waiting to win an existential career lottery. You walk through life hoping to find a million dollars lying on the side of the road. You know you’re smart — something good has got to come along sooner or later!

The thing that reveals the incoherence of this mentality is writing down what some potential jackpots might even look like. What exactly are you hoping will happen?

Asking this question reveals that you’re not looking for a specific project, you’re looking for an outcome. You’re dreaming of a project that will make you be understood. Something that will make you belong, be valued, and not wake up with terror in your stomach. Concretely writing down the absolute best case scenario you can dream up makes you realize such a project doesn’t exist. It can’t exist, and never will.

There is a feeling that if a project were “true” it would convey your whole self. It would contain your totality. You wouldn’t become That Guy Who Did X, or That Gal Who Did Y. And you wouldn’t have people who disliked your work because it would be so genuine that no one could deny your humanity. But when you look at anyone who make things, none of them reach that ideal. What makes you think you’d be the first person on earth to avoid that?

Avoiding the reality that a perfect project doesn’t exist is the source of a lot of self-sabotaging behavior. When something starts going well you think “well, this can’t be it! I don’t want this to be the thing I’m known for! I have so much more to offer you don’t understand!” So instead of finishing whatever is going well you blow it up. Or you never get started in the first place. Action is always failure.

Setting goals explicitly destroys the false hope of project-nirvana. It’s ripping up the lottery tickets and putting your lottery-ticket-money in a savings account.

And as absurd as it sounds, that can feel crushing! Especially if you’re someone who lives in their head and has an overactive imagination.

So at the end of 2018 I took time to actually write down my current understanding of what I want. 25 years from now, what would be a situation where I would feel the least regret?

Taking the time to write down what you’d like your life to look like feels 1) corny 2) terrifying. Even the most implausibly fantastic scenarios you dream up are disappointing compared to the hazy dreaming they replace.

And worst of all, writing down the absolute best-case shoot-for-the-moon scenario makes you realize it’s exactly the sort of outcome that won’t show up at your doorstep. Anything you can dream up is exactly the sort of place that requires years of hard work and showing up every day. Reality requires a million little steps forward, not some godsent coincidence.

Happy New Year, and I hope you have a great 2019!