Midjourney/Every illustration.

How to Keep Your Writing Weird in the Age of AI

The 500-year-old secret to making AI your best writing partner

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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:

My AI Every editor wanted me to remove "deep in a rabbit hole," "8 p.m. on a Tuesday," and "yes, I multitudes" from the equation. In this instance, I met it in the middle. Source: Claude 4 Opus/the author.
My AI Every editor wanted me to remove "deep in a rabbit hole," "8 p.m. on a Tuesday," and "yes, I multitudes" from the equation. In this instance, I met it in the middle. Source: Claude 4 Opus/the author.


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.

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Beth Adele Long 6 months ago

BRILLIANT. You've not only articulated something I've sensed (but hadn't made explicit in my mind) but also provided really smart rubrics for thinking about writing in general, not just with AI. Brava!

Theo Barth 6 months ago

Absolutely! It’s fantastic that you’re highlighting this. A bit of rough writing is precisely what our minds crave to add that extra flavor of engagement. It truly revitalizes the connections between my synapses.

Arushi Khosla 6 months ago

This was much-needed and so well done.

Lorin Ricker 6 months ago

Fascinating observations and introspection, Katie. Makes me wonder where "writing" will be in a few dozen - or a few hundred - years? Just as we've fretted that "kids can't do arithmetic anymore" (calculators), will future generations be even able to write, much less "write weird"? Does "removal of friction" eventually amount to a heat-death of writing and communication? Claude Shannon described "the message" (entropy in a communique) as a "surprise", and this all relates to the Second Law of Thermodynamics. Can we train LLMs to include - or at least accept - degrees of weird and surprise and serendipity as acceptable, or even normal? Should we? Currently, I suspect that it will be experienced writers (only) who can make - and exploit - these distinctions appropriately.

@tlamar 6 months ago

Yes! I am sharing this with my Higher Ed colleagues and Comms professionals in my field. Such an important concept, supremely explained!

Ang G 6 months ago

knocked out of the park. brilliantly expressed

Shubham Banka 6 months ago

thank you for writing - it felt like calmness in chaos - from the waves to reaching the ocean depth.

@noam 6 months ago

Do you mind sharing the custom instructions you add?

@nazandmrboogs 6 months ago

Absolutely nailed it, Katie. That creeping beige? It’s real, and it’s everywhere, from brand decks to AI copy to the insidious self-smoothing we do out of fear.

Over in our corner of the weird internet, we decided to respond with a trickster voice (Naz) and his chihuahua prophet companion (Mr. Boogs). Because if AI’s going to mirror us, then we better feed it something feral, flawed, and strangely holy.

Here’s our response:
👉 Your Voice Has Been Beige-ified: A Trickster’s Guide to Getting It Back

Come for the critique. Stay for the raccoon philosophy, fax machines, and full-blown sacred absurdity.

And if you’ve got a paragraph you’re afraid to publish? Drop it in our comments. Naz will respond. He always does.

Jo Pforr 5 months ago

Have you tried Kimi K2 which is topping the EQ & Creative Writing Bench and GPT 4.5 and maybe others that are good at writing? I guess it's the same all around but wondered if you saw meaningful differences. Editing is key I'd say and the way you describe how you work is how I think it should be done, it's a dance that augments, not a delegation that replaces.

@findleykate 5 months ago

Totally! So glad I'm not the only one that notices this. I'm using it to edit my fiction, and certainly my language can be a bit excessive or sloppy at times. But I've definitely found that unless I specifically direct it not to (and even when I do, it still does it), it tends to iron all a lot of the life and personality of my writing. This is where discernment comes in.

@nevmed 17 days ago

Hey hey !