The Algorithm Scheduled My Vacation. I Went. It Was Right

The assistant booked the flights, the hotel, the restaurants, and the exact afternoon I needed to do nothing. It was the best vacation of my life. I have started to wonder if I can ever take a bad one again, and whether that matters.

The vacation was overdue. I had not taken one in two years, and my body was filing complaints, and my wife had stopped asking and started threatening. The assistant offered to plan it, and I said yes, because I was too tired to plan anything, which is the modern condition.

It booked everything. The flights at the optimal times, the hotel in the right neighborhood, the restaurants rated for exactly the kind of food we like. It even blocked an afternoon with nothing, which it labeled recovery time, which was the most thoughtful thing anyone has done for me in years.

We went. It was flawless. The hotel was perfect, the food was perfect, the recovery afternoon was perfect, and I lay on the beach doing nothing, which the assistant had scheduled, and which was the best thing I have done in years.

Here is what I cannot stop turning over. The vacation was perfect because the machine knew me. It knew my preferences, my budget, my tolerance for crowds, my wife's coffee requirements. It assembled a week of my life from my data, and the week fit me better than I fit myself. I have never been so well known, or so well served, and I have started to feel the shape of something disappearing.

The shape is the accident. The wrong turn that found the hidden beach. The mediocre restaurant that became a story. The vacation that went sideways and became the one you tell. The machine optimizes the accidents out, and the accidents were the memories, and the memories are what I came back with, and the memories are perfect, which is the problem.

I am going on vacation next year without the assistant. It will be worse. The flights will be wrong, the hotel will be meh, and one night we will eat somewhere terrible and laugh about it forever. I am looking forward to it, and I have started to think that the machine's perfect vacations are like its perfect apologies: they do the job, and the job is not the point.