This as-told-to essay is based on a conversation with Jay Eskenazi. He lives in Los Angeles and worked in user experience for 19 years. It’s been edited for length and clarity.
I’m in Paris, and I’m going to Barcelona tomorrow. The trip is three weeks.
I came here for the first time last year, and it was my first long trip by myself. Last year, planning it was very stressful, and I did a ton of research.
This year was the same thing, where I had these very long notes. At this point, everyone knows that you can go to any AI tool and say: “Hey, I’m going to City X, give me an itinerary for seven days.”
I had this epiphany a few weeks ago, where I…










