Back to all writing
Aug 2026 · Short, 1:12

I let an agent run my calendar for 30 days

Thirty days of handing scheduling to an agent, and what it got wrong before it got useful.


1:12

For a month I stopped touching my own calendar. An agent took every meeting request, checked it against how I actually want my week to look, and either booked it, pushed back, or asked me one question. Week one it got things wrong constantly — booking calls back to back, ignoring focus blocks I'd never told it about explicitly.

By week three it wasn't guessing anymore, because I'd finally written down the rules I'd been enforcing in my head for years. That was the real output of the experiment: not the automation, but being forced to say out loud what "a good week" actually means to me.

Gianfranco OlofernesGianfranco OlofernesWrites it, sends it, reads the replies.Join the list