In the autumn of 2025, when the Atlanta leaves had gone auburn, Michael's external monitor mysteriously stopped connecting to his MacBook Pro.

The timing was suspicious. macOS had updated three days prior, and the monitor — which had performed without complaint for years — now refused to be recognized. Cables were swapped. Ports were tested. Settings were reset, and then reset again. None of it mattered. After a weekend of escalating sighs, Michael did what he had been putting off and opened a chat with Apple Support.

The agents were, to a person, lovely. They were also out of their depth. Michael cycled through several of them over the course of a week, each one polite yet utterly stumped. Eventually, regretfully, he was escalated.

Being escalated has a certain aristocratic ring to it. Not everyone gets escalated. Michael allowed himself a small and fleeting feeling of importance before remembering that he just wanted his monitor to connect to his laptop again. The senior team did not deliver this. What they delivered, after several more sessions, was the following:

"Something happened during the update. We don't know what. You'll have to reinstall the OS from scratch."

Michael was afraid of this. He was afraid he would screw it up.

And he did.

Before the reinstall, Michael decided—for reasons since lost to history—that he wanted to add a new partition to his external hard drive. This was the same external hard drive that contained the only backup of every digital thing he had ever owned. Photos. Documents. Years of work. A complete record of a life lived increasingly online.

He did not know how to safely partition it. So he asked ChatGPT.

The instructions seemed straightforward. Michael followed them with the trusting heart of a man who has been told, again and again, that the future is here and the future is helpful. The future, as it turned out, will piss on your leg and tell you it’s raining.

What followed was a string of expletives long enough and colorful enough to wallpaper a 2,500 square foot four-bedroom home.

Michael did solve the monitor mystery. He was also 500 gigabytes lighter. However unfortunate this tale of sufficient consequence may be, Michael learned a very simple yet valuable lesson: Back up your backup. Then backup that back. And maybe consult “how to” articles written by real humans when it comes to life’s more delicate matters.