The Chonkerton

There are no lossless transformations of natural-language text

ai

Per Simon Willison's Weblog, engineer Sophie Alpert has established a policy on using AI to help with writing: you must stand behind every sentence in your documentation. If someone questions a line, you can't say 'the AI wrote that, ignore it'—that approach confuses readers and wastes their time. Alpert's reasoning is that there are no truly lossless transformations of natural-language text. Every rewrite changes meaning slightly, and when an AI does the rewriting, it lacks the writer's full context, so information gets lost. The upshot: if you're using an LLM to help with docs, you fully own the result.

Source: https://simonwillison.net/2026/Aug/11/there-are-no-lossle...

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