◇ Could this help me?
Yes, and it is the single highest-value habit on this list for anyone paying per token. The explanation is mechanically correct: history is resent with each turn, so an unbroken session makes every later prompt progressively more expensive, and the cost curve looks nothing like the difficulty curve of the work. Clearing at task boundaries also improves output quality for the same reason, since a long session carries dead ends and abandoned assumptions forward alongside the useful parts. General practice, with the one caveat the video omits: clearing discards context, so anything worth keeping should be written to a file before the clear rather than trusted to memory.
Help me build the habit of clearing sessions at task boundaries without losing anything I need. For the kind of work I describe below, tell me where the natural boundaries are, meaning the points where the conversation so far genuinely has no value to what comes next. Then give me a short routine to run at each boundary: what to write down before clearing, where to write it so the next session can pick it up, and how to verify the next session actually has what it needs. Also tell me which situations are the exception, where continuing in the same session is genuinely cheaper than starting over.