Don't Schedule Anything You Haven't Run Manually Three Times

You set up a Monday-morning digest. Cowork pulls last week's closed deals, flags the stalled ones, posts a summary before you sit down. The first one lands and it's great. You stop opening the others; you trust it now.

Six weeks later someone asks about a deal that's been stuck since April. It's not in any digest. You scroll back: the summaries went thin three weeks ago, then stopped saying anything useful. The runs all show a calm green checkmark. Nothing errored. Nothing told you.

The scheduler did its job. It started a session every Monday, exactly on time. The problem is that you automated a prompt you had never watched run to completion; you promoted it to autopilot on the strength of one good morning.

A schedule doesn't make a task reliable. It makes a task invisible. That's fixable, and the fix is a habit, not a setting.

#Green means "it ran," not "it worked"