You're totally right — fine-grained “what I’m working on” tracking is usually not worth the overhead unless it’s tied to billing or some hard accountability.

One direction I’m exploring is to stop treating context as a single ground-truth stream and instead use cheap, probabilistic hints: a small “active projects” list (explicit but constrained), plus weak signals (recent files, open tabs, issue activity), and then ask for confirmation only when confidence is low. Calendars are a great example of why “seems firm” isn’t actually firm.

If you were designing this, which would you rather tolerate: (a) fewer suggestions but higher precision, or (b) more coverage with lightweight confirmation prompts?

And yes — this is exactly the problem I’m outlining in my HN bio/profile if you want the longer version.