The Two-Calendar Problem Every developer with a day job and a personal life has two calendars. My work Outlook has team syncs, 1:1s, and planning meetings. My personal Google Calendar has doctor appointments, NICU visits for my premature twins , kid pickups, recording sessions, and the occasional oil change. The problem isn't having two calendars. The problem is that nobody at work can see the personal one. So a coworker schedules a meeting at 10 AM on Tuesday — right on top of my wife's OB appointment. I catch it at 9:45, scramble to decline, and look unprofessional. Or worse, I don't catch it. The manual fix is tedious: open Google Calendar, find the event, open Outlook, create a matching "Out of Office" block, repeat for every new event, every change, every cancellation. I was doing this three or four times a week. Then I stopped doing it because humans are bad at repetitive cross-system data entry. Then I missed more meetings. So I built a system where two AI agents handle it automatically.…