Jen and Ido explore “Work MotivAItor,” a kinder focus assistant that checks in without shaming. They sketch a 20‑second micro‑journal, scene detection, and a glowing “lantern” UI that blinks instead of beeps—backed by local‑first privacy and a big pause button. Two live simulations (Ido’s slide deck, Jen’s tax dread) show how tone, timing, and tiny prompts beat nagging. They weigh body‑doubling, variable intervals, and pitfalls like surveillance vibes and configuration overwhelm, then close with a humane day‑end ritual.