What I learned giving myself weird writing rules

How I've been crafting my ghostwriting workflow with surprising results.

I’ve been experimenting with short-form writing for the past few months and noticed something I didn’t expect: tighter constraints produce better results. And by “better” I don’t mean more polished or more professional. I mean more people actually read the thing.

That sounds obvious when you say it out loud. Shorter writing gets read more. Groundbreaking stuff. But the way I got there was a little unconventional, and the tools I used along the way surprised me. So I figured I’d share the whole process.

The rules

Before I started writing, I built a constraint set. Every piece I publish has to follow it:

95 words or fewer. No em dashes. No bold text. No emojis. Written in second person. Staccato rhythm. Every post ends with a reader-facing question.

That probably sounds restrictive. It is. That’s the point.

Social media is full of long, rambling posts that lose people by the third paragraph. I wanted mine to feel like a conversation at a coffee shop where you’ve only got two minutes before one of you has to leave. Short enough that someone scrolling at 7am actually finishes reading. Tight enough that every word earns its spot.

The 95-word cap alone changed how I think about writing. When you’ve only got 95 words to work with, filler evaporates. “I think it’s really important to consider the fact that...” becomes a dead sentence on arrival. You learn to get to the thing.

Where Claude fits in

I use Claude (Anthropic’s AI, for the uninitiated) as a drafting partner. And I want to be specific about what that means, because “I use AI to write” can sound like I’m hitting a button and collecting output. The actual workflow has more friction than that.

It starts with an idea. Usually something I’ve been chewing on: a news story in AI, an observation about how founders talk about their work, a pattern I keep noticing online. I bring that seed to Claude along with my constraint set and a voice document (basically a profile of how I write, my humor, my quirks, the things I’d never say).

Claude produces a draft. I read it. And honestly? The first draft is almost never ready to post. It’s close in the way that a cake with the right ingredients but the wrong proportions is close. All the pieces are there. The balance is off.

So I edit. I cut. I rearrange. Sometimes I throw the draft out and ask for a different angle entirely. The voice document helps Claude get in the neighborhood, but I’m the one who parks the car.

(That metaphor got away from me a little, but you know what I mean.)

What I’ve noticed

Two things surprised me early on.

First: certain styles of writing attract more readers. I’ve been publishing these short pieces on LinkedIn, and the posts that followed my constraints consistently outperformed the ones where I got lazy and let a post run long or broke my own rules. Turns out people are grateful when you respect their time.

Second: the writing I tuned specifically for AI executives landed well with casual readers too. I expected the opposite. I figured posts aimed at CTOs and founders would feel niche or inaccessible. They didn’t. The specificity made them more interesting. A post about how a Series B founder should think about their public narrative reads differently than generic profile tips. Even people outside that world found something useful in it.

Why I’m writing this

The short version: I’m a ghostwriter, and AI is baked into how I work. This is where I take that process apart and show you how it works.

I’m going to document the tools, the workflows, the experiments. What works, what falls flat, what I’m still figuring out. If you’re curious about AI, writing, or the weird overlap between the two, you’re in the right place.