Dan Levi knows a thing or two about finding his way around an airport.

As executive vice president and chief marketing officer at Clear Channel Outdoor—the largest airport advertising company in the country, with a presence in more than 55 commercial airports nationwide—Levi applies his 38 years of experience in media and advertising to helping bring digital innovation to out-of-home (OOH) campaigns. During his nearly 10-year career at Clear Channel, he has spearheaded the company’s mission to be first to market in the OOH sector, with game-changing planning and measurement solutions going back to 2016. The company reaches 130 million Americans weekly with some 70,000 roadside and airport displays in more than 65 markets, and saw revenue in its airports segment jump 16% in 2024, on the back of record-breaking passenger volumes through U.S. airports last year.

Levi averages two trips a month, many of which take him to Clear Channel’s 30 offices across the U.S. While he’s never in one place for long, having his Kindle and iPad handy and the refuge of an airport lounge at the ready helps him maintain an even keel.

He spoke with Fortune about a singular adventure in Cambodia, the virtues of feather pillows, and the impact of travel on both work and life.

The transcript below has been condensed and lightly edited for clarity.

What’s the best trip you’ve ever taken?

My wife and I went to Antarctica last year for our 30th anniversary, which was the most amazing trip we’ve done recently. I don’t have a bucket list, but it was one of those bucket-list experiences. It’s such a different part of the planet, and unlike anything you’ve ever experienced before, no matter how much you’ve traveled.

We left on a cruise from Argentina and crossed the Drake Passage, which is legendary for being two days of seasickness and very rough seas. We were really fortunate because it was relatively calm, which the crew told us happens about 1% of the time, so we did it in a day and a half. Since we had that half-day head start, we were able to go farther south than the cruise had ever gone before. We saw parts of Antarctica that even the crew had never seen, and so many penguins, which are hysterical—they just look at you and walk right by.

My other favorite was our honeymoon in Cambodia in 1993, a few months after the U.N. peacekeeping forces—which had been there for two years to support the creation of a functioning democracy—had left. I like to say that I’ve never met anyone else who’s heard machine-gun fire on their honeymoon. Cambodia was truly independent for the first time in a very long time, and it was so spectacular not only to visit Angkor Wat and the nearby temples and other sites, but also to be there with almost no other tourists. We flew on a Russian surplus plane from Phnom Penh to Siem Reap with a pilot we were convinced was drunk, and then stayed at the nicest hotel in Siem Reap, which was basically a hostel with shared bathrooms. There are luxury hospitality brands there now, but this was a very, very different time. It’s such a wonderful memory, and marked the first time I had that kind of adventure travel experience. And it laid the foundation for much of what we’ve done since then, including moving to Southeast Asia for five years.

If you could go anywhere in the world you haven’t yet been, where would it be, and why?

I have this running joke with my wife that with all the travel we’ve done together, we still haven’t been to Ireland. I’ve suggested it so many times when we’ve talked about where we should go, but we haven’t made it there yet, so I’m going with that to keep the joke going and put a little more pressure on her. I love the U.K.–I studied abroad in England, and have spent time in Scotland, Wales, and lots of other places there. Between the nature and landscapes, and everything I’ve been told about the people, Ireland just seems like a really cool place to hang out for a week.

What’s your favorite/most memorable meal you’ve had while traveling?

I was working for MTV in the early 90s, and they asked me to move to Singapore in 1995 to help launch MTV Asia. India was a very important market for MTV to develop–I ended up living in Bangalore for three months to get the business going–but the first time I went was before we had any infrastructure there. My wife came with me to Delhi, where it was more than 120 degrees–nobody wanted to do anything but sit inside and not move. But having never been there before, we wanted to see the sites. MTV had only one person on the ground then, the daughter of a very well-known Indian author, and we dragged this poor woman along to help us see the Red Fort and all these other places. Then we went to her grandparents’ home and had the best vegetarian meal I’ve ever had in this cute little house in Delhi, with one air conditioner in the bedroom. We all sat in there on the corners of the bed and had this unbelievable meal together. I’ll never forget it. I love India.

What are a few of your favorite travel hacks?

If I can bring my own pillow, I will. There’s almost always room in a suitcase for a feather pillow—I’ll squish the air out of it and shove it into a corner, or I’ll put it on top of everything I’ve packed and force the suitcase closed.

I have TSA PreCheck, Global Entry, Clear, Digital ID—and if a new program comes out that will get me through airport security faster, I’ll register for that one too.

Though I once swore I would never pay for a credit card, after getting stuck in the Dallas airport for six hours due to storms a number of years ago, I now have an American Express Platinum Card so that I can access the Centurion and Delta lounges—I’m a Delta frequent flyer. To have a place to work and not have to deal with the overall stress of the airport experience makes a huge difference.

What three things do you never travel without?

I’m a tech nerd, so this one is easy. I never travel without my Kindle, because I need to be able to read on something other than my phone.

Second is my iPad—it’s my favorite device, and gives me the ability to work as well as watch video if I want to get online.

Over the years, I’ve curated this collection of chargers and cords that’s the first thing I pull out when I start packing for a trip. It’s in its own little case, and I know that wherever I go, whatever I need is in there.

Do you have any hard and fast travel rules?

I definitely strive to carry on, but as I’ve gotten older, I’ve realized that sometimes it’s better not to spend so much time on having to pack perfectly, and I’ll check my bag. But if I can, I prefer to carry on.

I’ll only take a connecting flight if there’s no other way to get there.

I like to get to the airport early, and not have the stress of running for the gate. When I lived in Singapore, I worked for a guy whose mission was to be the last person on the plane every time. When I traveled with him, we’d be paged and I’d have to do the walk of shame to the gate, then we’d be the last people to board—they’d shut the door behind us. I don’t like being that guy.

What’s the most important life lesson you’ve learned from travel?

I think that in life, as in travel, there’s no such thing as a bad experience. You can have a good experience or a good story, and if you’re lucky, they’re one and the same. Bad travel experiences are the ones you tell friends about over drinks to lots of laughs.

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One of my favorites is when we lived in Singapore, and were meeting my brother and his wife in Chiang Mai after they’d visited us and then traveled a bit on their own. I was in Bombay for business, and the only way I could get to Chiang Mai in time to meet them was to fly overnight via Delhi, Hong Kong, and Bangkok in one journey. I don’t like taking sleeping pills, so my brother, an anesthesiologist who trained in the Air Force, gave me a sleeping pill that’s approved for pilots because it doesn’t make them groggy. He told me exactly when to take it so that I’d get the maximum amount of sleep, which I did as we took off for Hong Kong, but I couldn’t fall asleep. I went to the lounge during my two-hour layover there and started getting tired so I put my head back, then fell asleep and woke up 10 minutes before my flight was scheduled to take off. So I became that guy running through the airport, with my bag bouncing from wheel to wheel behind me and my coat hanging off. It was a bus gate, and the bus had already left, so I somehow convinced them to get another bus for me. I was barely awake, and did that walk of shame onto the plane, where everyone else who managed to get there on time was waiting. It was a bad experience, but a great story.

Are there any lessons from your own travel experiences that you’ve applied to your work at Clear Channel Outdoor?

The first pertains to our airport business. If you’ve flown through LaGuardia Airport in the last couple years, and also before it was redeveloped, you realize the difference between a great passenger experience and a horrific one. Traveling so much and passing through so many different airports, and especially having had Changi Airport in Singapore—which for many years was regarded as the best in the world—as my home airport for five years, for me has really reinforced the importance of the airport experience, and how much it matters both to travelers and to the marketers who are trying to reach them.

The bigger one is that travel is about experiencing new things—it’s about learning. I travel to our branches and to our local markets to learn. Our business isn’t driven by the people in New York and the big agencies—it’s driven by our people who work across our 30 local offices, and by our customers in those markets. If I can’t speak to what’s going on in our markets—to what our local clients’ and salespeople’s needs are, and how my team and I can support them—then I can’t effectively do my job. I think about it the same way I think about personal travel, and what I take away from these incredible trips to Antarctica and India and all these other amazing destinations: I travel to experience our business where it happens, so that I can do my job better.

The marketing executive who curates your pre-flight ads says traveling for business is crucial to his career success: ‘I travel to learn’