Stop Starting Over: Two Techniques for AI That Builds on Itself

Van Slyke names the two distinct ways a long working relationship with a chatbot goes wrong, which are context rot, where the model quietly stops holding what you established an hour ago, and your own inability to find which of two hundred saved chats contained the good version. He gives one technique for each: a handoff document that summarises a session so the next one resumes rather than restarts, and a memo that keeps a durable, searchable record outside the chat window. You finish able to run a project across several sessions and several weeks without re-explaining yourself each time, which is most of the difference between using a chatbot and having a workflow.

Task

Custom workflows

Time

10 min

Level

beginner

Cost

Free — Nothing to pay. A free account at most.

Tools

None in particular

Published

2026-05

Voice

Craig Van Slyke — The rare serious academic who shows his work on the affirmative side, publishing the actual output so you have something falsifiable to argue with.