One of the things you get an intuition for after using these systems is when to start a new conversation, and the basic rule of thumb is “always.” Use a conversation for one and only one task or question, and then start a new one. For longer projects, have the LLM write down a plan or checklist, and then have it tackle each step in a new conversation. The LLM context collapse happens well before you hit the token limits, and things like ground rules and whatnot stop influencing the LLMs outputs after a couple tens of thousands of tokens in my experience.

(Similar guidance goes for writing tools & whatnot - give the LLM exactly and only what it needs back from a tool, don’t try to make it act like a deterministic program. Whether or not they’re capital-I intelligent, they’re pretty fucking stupid.)

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