I will check out Ralph (thank you for that link!).

> Another way is “Write out what we did to PROGRESS.md” - then start new session - then “Read @PROGRESS.md and do X”

I agree on small context and if I hit "compacting" I've normally gone too far. I'm a huge fan of `/clear`-ing regularly or `/compact <Here is what you should remember for the next task we will work on>` and I've also tried "TODO.md"-style tracking.

I'm conflicted on TODO.md-style tracking because in practice I've had an agent work through everyone on the list, confidently telling me steps are done, only to find that's not the case when I check its work. Either a TODO.md that I created or one I had the agent create both suffer from this. Also, getting it update the TODO.md has been frustrating, even when I add it to CLAUDE.md "Make sure to mark tasks as complete in the TODO.md as you finish them" or adding the same message to the end of all my prompts, it won't always update it.

I've been interested in trying out beads to see if works better than a markdown TODO file but I haven't played with that yet.

But overall I agree with you, smaller chunks are key to success.

I hate TODO.mds too. If I ever have to use one, I'll keep track of it manually, and split the work myself into chunks of the size I believe CC/codex can handle. TODO.md is a recipe for failure because you'll quickly have more code than you can review and nothing to trust that it was executed well.