07-05-2025
What to Do When Travel Goes Awry: 5 Tips I Learned From Visiting Over 100 Countries
It was a somewhat distressing situation, albeit one that many frequent travelers have faced. Years ago, after flying from Bangkok to Tokyo's Narita International Airport, I waited at the gate for my connection home. But the agent made a rather important announcement: Not everybody would be making the trip across the Pacific. At least not today, because the number of passengers exceeded the number of seats on the plane.
The flight was oversold. And everyone's minds began to whir. Who would be bumped? How was the airline going to sort this out?
I immediately saw the opportunity. Not because I consider myself particularly smart, or insightful, or forward-looking. (I'm not.) But rather, mostly because I had no immediate plans for afterward. And, at the time, had never visited Japan. Approaching the agent, I asked if there would be any remuneration for those who voluntarily gave up their seat to fly instead in a few days.
As it turned out, there was indeed. So I took the cash, which she dispensed on the spot, in yen, and made a quick booking at an affordable business hotel in Asakusa. Mere minutes later, I was thundering toward the heart of the capital on the Narita Express. And the next three days were awesome: I attended a baseball game at the Tokyo Dome, ate untold amounts of yakitori on back lanes and, ultimately, fell in love with Japan.
In the course of visiting more than 100 countries on all seven continents, travel has taught me at least two things. First: Things will (eventually) go wrong. And second: When plans go awry, it's all about how you respond. Here are three lessons I've learned on the road when everything seems to be going sideways.
Make Inconvenience an Adventure
Whether your flight is canceled, your cruise ship is heading into a big storm, or your tour guide didn't show up, the first thing to do is try and be cool. True, I can testify that it's hard not to get worked up. But after allowing yourself a brief, private scream into a pillow, take a deep breath and decide to roll with it. Try and find the adventure in it all.
I've discovered hidden and unexpected corners of airports during flight disruptions and gotten some of my best sailing stories from rough seas. Once, on a remote stretch of highway in Turkmenistan, our truck broke down. Rescue was coming, but it was going to take hours. So we pulled together all the ingredients we had left in our coolers and cooked them up on a camp stove on the side of the road. It was like an impromptu feast and party way out there in the desert. I still talk about it.
Make Friends
In a tight situation, strangers can be your best friends. So it doesn't hurt to strike up a conversation with those around you. Especially if things look like they might be going south.
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An example: I was flying to a mountain town, but my connection kept getting delayed. Everyone at the gate chatted nervously about whether the flight would actually take off that day, and what to do if it didn't.
It did. But not in time for me to catch my van shuttle to a smaller village, where I was staying at a lodge. Fortunately, in the hours of waiting, I'd talked to two fellow passengers sitting near me in the airport. We realized we were all headed to the same place. One had a car waiting. So we pooled our resources and, after our very delayed arrival, drove the rest of the way to the village. We got there much later than anticipated but truly enjoyed the conversation along the way.
When in Doubt, Turn Left
Nothing too fancy here. It just seems most people naturally turn right. So when you face an annoyingly long line where there are two options, take the one on the left. There might be fewer people (I've generally found that to be the case).
Be Nice to the Staff
If you're having a bad day, chances are the people working at the train station, hotel, or airport are having an even worse time. They've got the responsibility of working out that troublesome wrinkle while also dealing with the complaints of a whole bunch of frustrated travelers.
So, if you can, just smile. These are the people who can help you the most. Acknowledge the situation. Say something like, 'I know the hotel is currently dealing with a power outage. This is hard for everyone, especially the staff. But when you know when it will be restored, could you please let me know?' Just a little kindness can work wonders—and make you both feel a little better.
Keep Perspective (You're Still Pretty Lucky)
You know how they say, 'A bad day on the lake is still better than a good one in the office'? Try to always keep that in mind.
Once, I was on a trip to a tropical Southeast Asian island. The plans for the few days there were nothing short of fabulous: snorkeling, a sunset catamaran, maybe a surprise helicopter tour. But then, those first drops started to fall. And they didn't stop. At all. Ever, for the length of the stay.
Some sort of monsoon was moving through. It washed away all those activities. But you know what? The pool was still cool. The views remained dramatic, even more so because of the never-ending storm. The food in the restaurants? Remained delicious.
So I decided to focus on the positive—not the easiest thing—including all the loveliness of staying in a delightful hotel in a beautiful location. I decided to relax and enjoy the things that were available and to save all those fun excursions—things to look forward to—for the next trip.
Three Practical Tips to Be Best Prepared
Keep Cash on Hand
Having a little cash in the local currency is very handy in a pinch. For example—when you can't get an Uber and the subway has shut down for the night. Time to call a taxi!
Stay Connected to the Network
If you're worried about roaming charges, download an eSIM with a basic amount of data (say, enough to navigate on Google Maps and send and receive online texts).
Prepare a Backup Plan
If you have any suspicions your ride might not show up or your reservation may fall through, start putting together a rough, theoretical sketch of what you might do. That way, you can hit the ground running when things start to go off the tracks.
