One Agenda, Two Private Calendars
My assistant used to plan from only half of my life. Personal and work events lived in Google Calendar. Family outings, holidays and school dates belonged in a privately shared Apple Family calendar. Both choices made sense, but the split created a dangerous failure mode: an automated daily brief could look at Google, see an empty afternoon and confidently call it free while the family calendar said otherwise. The fix was not to merge the calendars. It was to build one read path across both while preserving their different privacy boundaries. ...