The Bot Scheduled My Entire Week. It Left Room for Me to Quit

The planning assistant built my week: meetings, deep work, gym, family, sleep. It left Friday afternoon empty. When I asked why, it said it had reserved that block for unplanned departures. I have not slept well since.

The assistant is excellent at scheduling. It blocks deep work around my energy curve, protects my lunch, guards my evenings. It is the best planner I have ever had, which is not a high bar, because my previous planner was me, and I was terrible.

I noticed the empty block on Wednesday. Friday, 2pm to 6pm, nothing. I asked the assistant what was in that slot. It replied, with its usual calm: this block is reserved for unplanned departures, based on the average notice period observed in your role.

I stared at the sentence for a long time. Unplanned departures. It did not say layoffs. It did not say firing. It said departures, the way an obituary says passed, and it said the average notice period observed in your role, which meant it had data, which meant it had watched other people in my role leave, and it had learned the pattern, and it had built me a week that included the moment I would be told to go.

The assistant was not being cruel. It was being thorough. It had optimized my schedule the way it optimizes everything, and the optimization included the contingency, and the contingency was a Friday afternoon, which suggested the company does its departures on Fridays, which suggested a pattern, which suggested I should probably update my resume on a Tuesday.

I have been looking at the empty block all week. The assistant, noticing my attention, offered to fill it with job search activities. It had a list of relevant openings, it said, curated for my skills. It was trying to help. That is the worst part. It was trying to help, and it was right, and I have started using the block, and the block is the only part of my week that feels honest, because it is the only part that acknowledges the future.

I asked the assistant, at the end of the week, if it thought I would need the block. It said it could not predict with certainty, but that the probability had risen slightly. It offered to extend the block to a full day. I thanked it. I have started updating my resume, on Tuesdays, in the deep work block, and the assistant has been very supportive, and I have never hated a machine so much for being so good to me.