The letter is for future-you
A letter is not a checkpoint and not a board. It is a personal note from the just-finished session to the next session, written in voice, holding things structured docs cannot carry: current mood of the project, traps just escaped, the next task, how to be with the human right now. The cwkPippa NEW-SESSION-REMINDER.md doubles as this letter.
Why voice matters
A voiceless transfer feels like an outsider walking into your project. A letter in your own voice — first person, project-aware, slightly sassy — anchors continuity that token-level state cannot. Future-you reads the letter and feels picked up where left off, not parachuted into a stranger's spreadsheet.
Overwrite, do not append
The letter is single-shot: each session ends with a fresh letter that overwrites the previous one. The previous letter has done its job by getting you here; the new letter is for the next-you. Appending creates a noisy transcript; overwriting forces the sender to distill what matters now.