I spent three years writing grant proposals for a nonprofit on the south side and I got very good at a specific kind of lie. Not fraud. Nothing like that. I mean the lie of authority. The lie that says: we know. The lie that writes "research demonstrates" and "evidence suggests" as if certainty is something you can borrow from a footnote and wear like a coat.
It worked. We got the grants. And I got very good at producing sentences that felt like walls... solid, load-bearing, impossible to argue with. Which is exactly the problem.
Because you can't connect with a wall.
The truth is, I did not understand what was wrong with my writing until I started reading personal essays out of desperation. It was 2019, I was burnt out, and a friend handed me a copy of James Baldwin's Notes of a Native Son at a coffee shop on 53rd street and said "just read the first essay, you can give it back." I didn't give it back. I read it in one sitting and felt something shift, the way a joint pops back into place and you didn't even know it was wrong until the pain stopped.
Baldwin didn't argue with me. He argued with himself, on the page, in front of me. And somehow that was more convincing than anything I had written in three years of grant prose.
The Thing Formal Writing Gets Backwards
Here's what school teaches you about writing: have a thesis, support it, conclude it. The goal is to eliminate doubt. To be so airtight that no one can find a crack. The gold standard is the paper that admits no weakness, no uncertainty, no moment where the writer isn't sure.
Nobody tells you this but... that's actually the opposite of persuasion. At least the kind of persuasion that builds an audience.
Formal writing treats the reader like a judge. Like someone who will poke holes in your argument if you give them the chance. So you close off every angle. You become a fortress. And the reader, sensing this, does exactly what you'd do if someone stood across from you with their arms crossed and their jaw set... they cross their arms right back.
The personal essay treats the reader like a friend at 11pm who you're trying to work something out with. You're not delivering a verdict. You're thinking out loud, and you're inviting them to think along with you. The whole form is built around the visible mind at work. You change direction. You contradict yourself. You say "I thought I believed this, and then this happened, and now I don't know."
That uncertainty is not weakness. That uncertainty is the thing people screenshot and send to their friends.
I think about the writers I actually read. Anne Lamott admitting she is petty and jealous and still somehow teaching me about grace. Hanif Abdurraqib writing about a Carly Rae Jepsen concert in Columbus and making me feel something I didn't expect to feel. Both of them arguing with themselves, openly, in prose that moves like a conversation. Neither of them building walls. Both of them building audiences that are almost unsettlingly loyal.
Why This Matters If You're Trying to Build Something Online
Most online writing is stuck in formal mode and doesn't know it. It's trying to be authoritative and human at the same time. It opens with a confident claim, adds some data, wraps up with a call to action, and the whole thing feels... fine. Competent. Forgettable. Like the grant proposals I used to write. Technically correct. Emotionally nowhere.
The hollowness you feel reading a lot of content right now... I think that's why. It's performing certainty. It's pretending the writer already figured it out before sitting down to type. And we know. We always know. You can feel the performance in the first paragraph.
The personal essay form breaks that by forcing you to do something uncomfortable: it makes you visible. Not your brand. Not your expertise. You. Your actual confusion about the thing you're writing about. Your specific memory of the specific moment that made you want to write it in the first place.
I started a photography practice four years ago mostly because I kept showing up to shows at Sleeping Village and feeling like the energy in that room deserved to exist beyond the night. I didn't know what I was doing. I shot everything on a Fuji X-T3 I barely understood, at ISO 6400 in rooms lit like caves, and most of my early shots were garbage. But when I started writing about that process... the failure included, the not-knowing included... people responded in a way they never had to my polished grant writing. Because they recognized themselves in the confusion. Because I was arguing with my own assumptions on the page instead of presenting conclusions from behind a podium.
That's the thing nobody in marketing school tells you. People don't follow you because you know things. They follow you because watching you figure things out makes them feel less alone in their own figuring.
There's a risk here, obviously. Arguing with yourself in public requires that you have an actual self doing the arguing. That you've thought something through enough to show the seams. A lot of people skip this part. They write "I've been thinking a lot about authenticity lately" and then deliver a listicle. That's not a personal essay. That's a press release in a flannel shirt.
The difference is whether you're willing to land somewhere surprising. Not just to the reader... to yourself. The best essays I've ever read, and the best ones I've managed to write, all end somewhere the writer didn't expect to be at the start. That journey is the content. The journey is the thing people are actually paying attention to.
I think about someone I know who makes music in her apartment in Pilsen, has been making music for six years, and is genuinely one of the most gifted producers I've encountered in this city. She's not building an audience. Not because she's not good enough... she's better than half the people on streaming platforms with 100k listeners. But she can't bring herself to write about the work in a way that shows her thinking it through. Everything she puts out publicly is finished. Polished. Certain. And it slides right off people because there's no friction, no entry point, nowhere for a stranger to hook their own experience onto hers.
The personal essay would give her that. Not because it would make her seem less capable. Because it would make her seem like a person.
The truth is, the creators I've watched build something real over the last few years... they all have this in common. They write and speak like they are still mid-thought. Like they are turning the problem over in their hands, under a light, looking for the part they haven't understood yet. They don't wait until they have the answer. They document the search. And the search, it turns out, is what people want to watch.
Formal writing taught me to arrive with answers. The personal essay taught me that showing up with questions... specific, honest, hard-to-ask questions... is the braver thing and, almost always, the more effective one.
Three beers in, I'd tell you this: stop trying to sound like you know. Start writing like you're still figuring it out. Because you are. And so is everyone reading.