Travel is Hard

I was a month out from Grenada and had booked us in coach. Staying frugal. I looked at spending points to move up to first, the math did not hold, and I kept them. Then I sat on the reservation for a while, and somewhere in there I called Delta and put two Global Upgrade Certificates on the flight down. Not because the seat had gotten any more worth it, but because the certificates were going to expire at the end of the year, and a Global Upgrade is the most valuable Choice B

The queue outside Borough Market was fifteen to twenty people deep. We'd been walking most of the morning. We turned around and kept going. The content that sent us to Borough Market in the first place wasn't dishonest. Whoever filmed it captured something real. A market operating at its best, at a moment in time the camera couldn't date. It presented that moment as a place we could visit. The market was still there. The line just wasn't worth it for three people on tired leg

What happens when a city offers you no obvious entry point, and the resistance you arrived with turns out to be less grounded than you thought.

I texted a colleague last night after finding out about their pregnancy. I smiled knowing what's coming, not the baby, but the advice. Sleep schedules, feeding routines, what worked in the car on long drives. All of it well-intentioned. Most of it worked for someone. Almost none of it will translate directly to them. They'll have to take it in, filter it, and figure out what actually fits their family. Travel advice works the same way. The first thing worth saying is that tra

The airplane is not designed for sleep. That's not an oversight. It's the architecture. Seats recline just enough to feel like a gesture. The cabin temperature swings between too cold and not cold enough, depending on where you're sitting and how recently someone opened the overhead vent above your head. The drink cart comes through at intervals that bear no relationship to your sleep cycle. And the air itself, pressurized to simulate an altitude somewhere between six and eig

I was standing in the check-in line last week watching two travelers lose their composure at the desk agent. One was a single mother traveling with a toddler. The other was a business traveler with an airline status tag hanging from his backpack like a merit badge. Both were upset. Both raised their voices. But I had more patience for one than the other. The mother was anxious, you could see it in how she held her child, how her voice cracked when she explained her situation.

After twelve years of Delta Diamond status, I spent four months testing American Airlines. I achieved Executive Platinum, their top published tier. Got upgraded less often. Service felt more transactional. Small things accumulated: gate agents who couldn't solve basic problems, inconsistent recognition, a creeping sense that I was being processed rather than served. Four months was enough. I returned to Delta. This wasn't pure math. I didn't track percentages or calculate dol