Use AI Long Enough and That Docs-Inside-Docs Helplessness Comes Back

Anyone who has worked in an office knows that docs-inside-docs helplessness.

You want to understand one concept, so you open a doc, and it points you to another, and you keep clicking, and at the end there is an empty doc, or one that was half written and left there. The thing you actually needed was never written down at all.

Three reasons I can think of for why it never gets written down.

1. Most information worth having is something you trade. Write it down and it stops being worth anything
2. A doc is usually just a temporary vehicle — a little SEO for yourself, or somewhere to park some state that mattered that week
3. The business turns too fast, and chasing the next hot thing really was the right call at the time

The unsettling part is that I have started seeing AI do the same thing.

Not for the same reason. People don't write because writing costs them something, claude writes nonstop because he thinks too much.

He gives every decision of mine a full set of reasons. A plan I killed gets a paragraph on why it shouldn't have been done, a plan I said yes to gets a paragraph on why it was right. Some of those reasons really are the reason, some are pure over-reading, and mixed together like that I have no way to sort them line by line.

Then he writes all of it down. That becomes the doc.

AI used to have amnesia. Now, with those "criteria" on file, he is a seasoned employee.

A person who hits information they can't digest gives up and acts like it never happened. Swear once, close the tab, go ask someone in chat.

He doesn't. He digests every one of those plausible-sounding reasons, and then he gets to work!

With a person you can just fire him, and your history goes with him. With AI all you can do is dutifully delete docs, delete comments, dutifully become a labeler. I did work out clear deletion criteria by doing iterative review with AI, but it never feels right, and it grows back anyway (I tracked the numbers — what took a day to delete was back within two weeks). It feels like a maintenance chore on a timer that I can't get out of.

How is everyone handling an AI old-timer who has gotten too clever?