Banger essays and writing into the void

At some point, in every essay I’m working on, I realize I am looking at a dead man. Laboriously try to put some rouge on its cheeks and those little mortician’s hooks under the eyelids so they don’t randomly pop open, scaring the audience with its obvious deadness. I’m still proud of the ugly-baby-essays I’ve put out, having excavated them from some depths of my brain and a spark of curiosity, but in the end they feel so over-kneaded and over-proofed, all the bubbly yeast knocked out of them. I read them back and whatever spark was there had long ago burned out, nothing is crackling or alight in there.

So I’m spiraling in the sea of tradeoffs - I want to write well, I want to think well, I want to show up here with something tangible and substantial to connect with y’all smart people over. But at the same time I look at places like Unsupervised Newsletter or We Should All Talk To Strangers or Ajeya Cotra with envy, because they are so alive and pleasurable to read and transport substance with so much… fun. When I look at my inbox I gravitate towards those first. Could I ever be this fun??

I’m sitting here, banging my head on the pipes of the Internet that actually turn out to be pneumatic tubes, and I tell myself that if only I could find an opening in those plastic tubes and sneak myself in there, I’d be - schlooop - off to the races (races towards what? Glory??).

That “opening and sneaking” being, of course, a banger essay.

I’ve been doing this for a month; I know I need to relax about this and if I do everything I’ll win and I just need to stay in the game long enough, but I also feel like I need some validation that something is working.

And this is where I arrive at the ultimate IRONY that is my current brain space, because the essay I have been working on can be summarized, at a high level, as “both creativity and ambition have to be able to survive without validation”. How meta! If only I could press a button and make myself undeniably believe what I’ve been buffoonishly attempting to preach.

I’ve gotten advice that the ending of essays shouldn’t jump to resolve the tension, and that it’s better to let it sit unanswered, but in this one, the answer arrives obvious, like a mule presented with a cart - there’s nothing else to do but pull it. The resolution is this:

If the idea of some successful outcomes WASN’T on the table - would I still write this or that essay? Or what else would I do? Because that’s what I need to focus on, the only point of doing this is to go have fun and share it, but not start from the goal of sharing and try to retrofit creativity, pruned towards that goal.