How to Keep Your Writing Weird in the Age of AI

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I was deep in a rabbit hole about textual criticism and the Bible when my ChatGPT tutor pointed me toward a concept that completely changed how I think about writing with AI.

Lectio difficilior potior. The harder reading is stronger.

It's a principle scholars have used for centuries. When faced with two versions of an ancient text and asked which is the original, they choose the one that's more difficult to understand. The thinking is that somewhere along the way, some well-meaning copyist, intentionally or otherwise, tweaked the original to make it clearer or more sensible according to their understanding. I'm going to call this cautious copyist a “timid scribe.”

The moment I read about this concept, I saw AI playing the role of timid scribe everywhere in my own writing. Where I might write "altar-call energy," AI defaults to "enthusiasm." Where I talk about "collecting screenshots like a doomsday prepper," it recommends "documenting examples." I fed this very essay to the AI editor I’ve tailored for my Every writing, and Claude Opus 4 pruned away the spiky edges of my opening sentence in the name of editorial efficiency:

AI takes what's specific and makes it general. It takes what's wrinkly and makes it smooth. The consequences are already visible: Scroll through any business blog, marketing newsletter, or LinkedIn feed, and you'll see the smoothing happening at scale.

AI hasn't created this problem, but it's accelerating it quite a bit. When everyone has access to the same polishing tool, we risk a kind of digital invisibility—millions of pieces of content, all professionally adequate, none memorable.

As I talked to ChatGPT about this classic principle of textual criticism, I gained language for something I'd been noticing but couldn't quite name: AI is our era's timid scribe. It’s a well-meaning assistant that takes your weird original and makes it sound like everything else. And learning to work with it, not against it, might be the most important writing skill of our time.

The smoothing engine at work

Last week, I was writing a social media post about Every's value proposition and started with this:

"Most Every subscribers don't know what they're paying for."

I asked LinkedIn's built-in AI to refine it. The suggestion:

"Most Every subscribers may not be fully aware of what they're paying for."

Look at what happened there. The AI version added hedges ("may not be"), softened the language ("fully aware" versus "don't know"), and became considerably more professional. It also became bland, beige, and forgettable.

This is AI being very good at producing the statistical average of all business writing ever created. It knows that professional communication typically includes qualifiers. It's doing exactly what it was trained to do: Produce text that fits the pattern.

The rough version has a bluntness that might make readers pause: ”Wait, do I know what I'm paying for?” The smooth version slides by without friction. The voice that might lodge in someone's brain gets traded for clarity that evaporates on contact.

Sometimes that trade is worth it! Not every weird metaphor deserves to live. The trick is recognizing when you're smoothing away confusion versus character.

When it’s producing text, AI pulls everything toward the statistical center. Sometimes the center is exactly where you want to be. But sometimes the edges are where the interesting stuff lives.

Learning to work with your timid scribe

Your timid scribe is not your enemy; you just need to learn to work with it. I'm still very much in the process of figuring this out, but here’s what I’ve learned, and how I go about it...

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1. Katie's exact method for integrating AI when writing her personal newsletter, her Every column, and for brands
2. Texture as a strategic choice, not an accident
3. Cultivating productive friction in an AI-smoothed world