I wrote an essay against confidence for The Outline

He must be getting massive royalties from this quote.

One of my favorite things about The Outline is that they will publish a weird essay about an idea. Other outlets will run weird essays about pop culture or internet events, and yet others will publish personal essays or ruminations on a niche topic (model trains, karate, the president of the United States.) But The Outline is on a short list—along with Popula, the New York Times Magazine, and maybe The Baffler—of publishers who will say yes to your Montaigne-eque walking tour of a concept. I don’t know how much the promise of a “New Yorker for millennials” still guides The Outline’s editorial process, but they subscribe to the older publication’s belief that any subject can be interesting if you write about it right.

Did you know that if you play the sound of an execution-dependent idea, I unconsciously salivate? Brandy Jensen let me write this essay based on an idea I had been reminding myself not to think about for a while now: that confidence is actually bad. I hesitated to pitch it because, you know, the internet already publishes too many clickbait articles systematically unpacking a concept. Maybe I could work the angle that this time it’s a white guy doing it, I thought, but I was still unsure. Then Brandy was like “no, this idea is good,” and I’m glad she did.

I had fun writing this essay, and Brandy plugged at least two holes in my argument along the way. That kind of fireproofing is crucial to an essay of this kind, which basically erects an argument and invites the reader to knock it down. In addition to being a great way to get punched in the dick, writing an essay like this one offers a particular feeling of catharsis, the kind that comes from carefully saying something you worry you shouldn’t.

As a reader of stuff on the internet, I’m more interested in weird essays than, say, celebrity gossip or partisan news aggregation. I think I probably represent a niche population in that respect, but aren’t niches supposed to be the future of digital publishing anyway? I’m glad The Outline is out there serving its niche audience (New York media types) at all levels of production. But don’t take my word for it—read the essay, then go back and read the other essays linked above. Be sure to open each one in a separate browser, ideally from multiple IP addresses.