
Many frequent travelers revel in talking about how many miles they’ve flown, which airport lounges are best, and how they cope with jet lag. Far fewer have much to say about the people and places they encounter during their globetrotting. I can easily be lured into the posturing game of airline status and the numbers of countries visited. But I try to push myself and other travelers to engage in more meaningful reflection: What’s something that surprised you from the last place you visited? What have you learned about yourself from visiting so many places?
I sometimes wonder if those who travel less do a better job learning from international experiences than those of us who have visited dozens of countries. When we’re planning our next family adventure somewhere, my kids often ask, “Wait, Dad. Have you already been there?” In many cases, I have. But visiting a place with my family often feels like I’m seeing it for the first time. My wife and daughters notice things I miss, ask questions that don’t occur to me, and pull me out of my efficient routines to linger longer and take in the wonder of the unfamiliar.
The research is clear. International travel is one of the best ways to develop cultural intelligence. But it’s not automatic. Exposure alone doesn’t create understanding. You can easily spend 100 days a year traveling the world and learn very little.
I get it. Particularly when my kids were still at home, I wanted to get in and out of a place as quickly as possible so I could minimize time away from them. I hit the ground running, spent my days in offices and hotel conference rooms that look similar most everywhere, and headed back to the airport as quickly as possible.
The more you travel, the easier it becomes to stay inside a comfortable bubble of executive lounges, hotel restaurants, and ride shares while experiencing very little of the rich wonders lying outside. The issue is less about finding extra time for sightseeing and it’s more about how we pay attention.
Here are a few simple routines I try to use when visiting a new place or even somewhere I’ve been repeatedly.
1. Observe real life before you get down to work
Whenever possible, I go for a run before I jump into my workday, wherever I am in the world. Yes, it’s part of my fitness routine. But it’s also about getting out of my head and into the world where I am rather than shuttling straight from the hotel to a meeting room. For you, it might not be a run but perhaps it’s a walk through a residential neighborhood, sitting down to have a coffee at the corner café, or taking public transportation instead of a taxi. The point is to get into a public space where you can see real life happening.
Look for:
- Who is out early in the morning?
- What businesses are already open?
- Do strangers greet one another?
- Who seems rushed? Who seems unhurried?
A short walk or even a quick stop at a local grocery store often does more to orient me than reading a culture brief. Even if you’re somewhere you’ve been many times, try to wander the streets imagining what you would notice if you were visiting for the first time.
2. Eat at least one meal where locals eat
I’m an insufferable foodie, so I’m highly motivated to find great local food whenever I travel. But eating where locals eat is about so much more than the food. Dining outside the hotel is one of the best ways to observe a community’s rhythms and values. Go beyond the business district and tourist haunts, visit a local café and notice:
- Who eats together?
- Do people linger over meals or eat quickly?
- Do people eat alone?
- Is the atmosphere loud and animated or quiet and reserved?
- How do people interact with the servers?
Smoking sheesha pipes with a group of Saudi pilots in Jeddah, cracking into a chili crab with colleagues in Singapore, and eating smorgasbords while watching people come and go in Copenhagen have given me a taste of life in these places. None of these experiences tell the whole story of a culture, but they reveal things people may not think to tell you if you simply ask what life is like there.
3. Go Beyond Transactional Conversations
Business travel can become remarkably transactional. We check into hotels, order coffee, take ride shares, purchase meals, and move efficiently from one appointment to the next. Yet some of the most memorable insights I’ve gained while traveling have come from brief conversations with people I otherwise may have treated as part of the background.
Nicholas Epley’s research finds that most of us underestimate how much we will enjoy talking with strangers. We assume others aren’t interested in conversation, yet both parties often walk away from even brief interactions feeling more connected than expected. I don’t welcome random conversations with every stranger I encounter but a few carefully chosen ones have provided some of my richest insights about a place.
Pause for a moment to talk with the server refilling your coffee. Ask your taxi driver what the public sentiment is right now about AI. Stop to see the humanity in the people walking by you. And if a colleague or local friend invites you to their home, wedding, or another personal event, by all means go! No matter how exhausted you are, you won’t regret it!
4. Look for Surprises
We all carry expectations about the places we visit, frequent flyers in particular. Whether it’s a destination we’ve visited countless times or one we’ve been told is similar to somewhere else, we arrive with assumptions. Singapore will be clean, efficient, and rule driven. Miami and Dubai will be dripping with bling. Copenhagen will be hip, cool, and design-forward.
During a recent trip to London, I started a note on my phone labeled “Surprises.” I’ve been to London dozens of times, but creating this note prompted me to notice things I would have otherwise missed. A few of my observations included:
- The people walking the fastest up and down the Tube escalators are consistently men…in suits.
- Pedestrians are quick to apologize when they bump each other on a busy sidewalk.
- There’s a swift synchronization of umbrellas moving up and down as people walk along Oxford St in the pouring rain.
Best of all, I unexpectedly stumbled on Bansky’s newest installation, “Blinded by the Flag.” I lingered to observe the diversity of people posing for selfies.
Actively looking for surprises primed me to notice things I would have otherwise missed. And it made the time spent moving from one meeting to another far more interesting.
5. Do Something You’d Do at Home
Finally, a favorite way I try to experience a different side of a culture is to take a routine activity I do at home and do it while traveling, whether it’s getting a haircut, buying groceries, going for a bike ride, taking a yoga class, attending a concert, spending 20 minutes in a bookstore, or even scheduling a dental cleaning.
There’s something about participating in the ordinary routines of daily life that gives a much different level of insight about how a place functions. It can reveal what life is actually like in ways that landmarks and tourist sites don’t.
A few years ago, my daughter had a serious cycling accident in Ireland that required emergency surgery. At the time it happened, my attention was solely focused on her care. But once I knew she’d be okay, the time spent sitting in the hospital gave me a chance to observe Irish life that I had never encountered in previous visits. This included things as simple as medical language that was unfamiliar to me (“She’s out of the theatre now” and “The consultant is ready to see you”) as well as observing the ways patients, families, and medical staff interacted.
Some of the most meaningful insights about a place come when we temporarily stop acting like visitors and participate, however briefly, in ordinary life.
Boarding Zone 1
I understand how demanding international travel can be. Most of us don’t have the margin to squeeze more activities into an already packed itinerary. My admonition is to simply pay a bit more attention while going about the day. A walk through a neighborhood, a meal in a local restaurant, or an unexpected conversation can reveal perspectives that don’t show up in reports, guidebooks, or briefing documents.
Frequent flyers have an enormous privilege. We can learn about ourselves and others through firsthand travel experiences that many people never get. The world has a remarkable ability to teach us when we’re willing to notice. That’s good for the soul, and it’s good for business.


