Observations on Writing with AI

A writer reflects on why good writing remains hard for AI, drawing on 16 years of experience with human editors and more than 10 AI writing systems.

The author has fine-tuned models to mimic a personal voice, kept embarrassing AI-assisted drafts public as proof, and tested multi-model editorial councils modeled on code review.

The experiment reveals fundamental obstacles: each AI has a stubborn voice identity—Gemini beams sunshine, Claude is languid but sharp, OpenAI Codex is dispassionate—and when asked to edit collaboratively, the models produce inconsistent, tone-deaf feedback.

One model described a draft as “500 words of intelligent observation without a single indelible sentence” and suggested picking a single angle.

The author concludes that AI’s ability to synthesize images, video, and text makes anything creatable, but authenticity comes from imperfection: the pops of vinyl, solar flare on Kodachrome, imperfect analogies, and punctuation quirks.

AI may eventually parrot authentic writing, but the imperfections are what make writing good.

Observations on Writing with AI

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