I was still clearing the cobwebs from my brain with my first cup of coffee as I opened my inbox. Among unread newsletters, random special offers, and a daily digest of what my neighbors were arguing about on NextDoor, something caught my eye: a Delta trip confirmation.

At the time, I had a high-stress job that involved non-stop travel; every day was a blur of interchangeable hotel rooms and nondescript rental cars. Every night was spent alone at a table for one in some random city. Nothing was memorable because it was a real-life adaptation of the movie Groundhog Day—the same day every day, with slight changes.

But what was this?

It came back to me with a jolt: Scrolling through my phone late at night before bed and encountering an unbelievable deal offering roundtrip flights to Rome for just under $300.…