My ‘Favorite’ Travel Failure (and What It Taught Me?)

The final global immersion trip for my MBA at Washington University in St. Louis was in Singapore. Afterward, I decided to tack on a little extra travel and meet my friends in Puerto Rico for spring break. The flight route? Singapore → San Francisco (11.5-hour layover) → San Juan.

The Singapore leg was flawless. I was traveling with my WashU cohort, so there was no chance of messing anything up. When I landed in San Francisco, I was thrilled to discover my connecting flight to San Juan departed from the same terminal. Jackpot. Eleven hours of easy downtime.

I filled the hours reading, wandering the shops, and, in a wild coincidence, grabbing lunch with a friend who happened to be connecting through SFO on her way to Hawaii. When she left, I still had five hours to kill, so I read more, watched Gilmore Girls, and caught up on texts. I triple-checked the gate number and flight time. Everything was smooth.

Finally: boarding time. I gathered my things, walked to the gate, and handed over my ticket, already picturing myself sipping a piña colada on Isla Verde Beach.

That’s when the gate agent looked at me and said, “This is United. You’re flying American.”

My stomach dropped. Wrong gate. Wrong terminal. Wrong everything. And in San Francisco, “switching terminals” doesn’t mean a quick jog down the hall—it means a train ride.

I near-sprinted to the AirTrain, rode it to Terminal A, and bolted to security… only to get a phone call as I reached the front of the line. American Airlines. They were calling to inform me—so politely—that I had missed my flight. After an 11.5-hour layover, I had missed my flight.

That was the breaking point. I was sobbing in the middle of the security line. The jet lag from Singapore hit me all at once, and I was inconsolable. The poor TSA agent asked if I was okay, but I couldn’t even answer. Meanwhile, my friends were already in Puerto Rico, staying at my place, waiting for me to arrive.

Desperate, I called my dad. If anyone could fix this, it was him. He calmly reminded me that I wasn’t the first person in the world to miss a flight. In fact, he confessed he had once missed a flight to India, which left me stranded there alone for two days. Oddly enough, that made me feel better. Together, we rebooked my ticket using flight credit, and I scored the last flight out on a Miami connection that got me into Puerto Rico just two hours later than planned.

Spring break was saved. Piña coladas were had. Crisis averted.

What did I learn? Quadruple check your ticket. Don’t assume “same destination, same time” means “same gate.” And when all else fails—call your dad.