Learning, Connecting, and Asking : On the Road with Derek Loudermilk

This is a traveler case study. (Read others or nominate yourself.)

A scientist turned world traveler, Derek Loudermilk has put research on hold, and discovered he loves waking up and going to work every day in a completely different country and field.

Introduce yourself!

I grew up in St. Louis, Missouri, graduated from Macalester College in Minnesota, then went on to be a professional cyclist in Boulder, Colorado. Eventually, I returned to school and did graduate work in Bozeman, Montana, where I studied the beginnings of life and discovered a new species of virus living in the hot springs of Yellowstone National Park.

But after finishing grad school, I’ve been traveling around the world. I’ve been to Vietnam, Cambodia, Laos, and Singapore. I’m currently based in Ubud, Bali.

Six months ago, I founded the Art of Adventure podcast as a teaching tool for entrepreneurs, artists, and athletes to learn what they need to start their next big project. I now wake up excited each day to rush off and do my work.

I’m passionate about connecting people and ideas, wearing bright colors (as a form of expression about being yourself), being a lifelong learner, and I ask a lot of questions.


What inspires you to continue to travel?

I love that travel allows you to have a “New Years Resolution” moment whenever you want it. Simply start the new habits you hope to cultivate anytime you arrive in a new place!

I also love immersing myself in a culture by staying somewhere for 3-12 months. It’s so cool when you get to the point when your local café knows your “usual,” when you don’t have to pull out a map, and when you can show new people around.

One of the main reasons I travel is that it gives me a beginner’s mindset. When I get to a new destination and notice all kinds of little things that are different than back at home—maybe it’s the color of mailboxes or the crazy amount of exposed telephone cables—I get to see the world differently, and new situations force me to creatively problem solve.


Tell us a story from your recent travels.

I was motorbiking down the Ho Chi Minh highway in Vietnam in the middle of monsoon season, and running out of daylight. I had two choices: take a gamble, push on and get in more miles while hoping to not get soaked, or stop early and stay dry. I gambled.

Suddenly, the heavens opened up and unleashed more rain than I have ever seen! The streets were several feet deep under water within minutes. I started getting worried I’d soon be sleeping in the (wet) streets. At the next town, I asked where the nearest hotel was. A kind women told me it was three kilometers away.


During the downpour!

Three, four, five kilometers down the road, the town ended, and I hadn’t found the hotel. I turned around to retrace my steps.

Just as I crossed the bridge back into town, the rain let up, the sun came out in time for a beautiful sunset, and a double rainbow arced across the sky. I ended up finding a hotel right next door to the woman I had asked for directions!


Just before the double rainbow broke out.

How do you pay for your travels?

I decided that to be able to travel long term, I would need to be making at least $1,000 per month. I rely on my cycle-coaching practice to provide a majority of that income, and now I am getting sponsors and patrons for the Art of Adventure podcast.

Since first reading Chris’s blog 4 years ago, I have been saving and earning miles largely through opening credit cards and manufacturing spends. My best redemptions have been first class round trip flights to Asia and flights to Alaska (which was my 50th state!)

So far I’ve earned about 400,000 miles, mostly through United/Star Alliance and Frontier.


What encounter from the road sticks out in your mind?

You remember your favorite teacher or your college roommate vividly because of the time you spent with them and the impression they made on you. I have a similar feeling about a man I met in Hoi An, Vietnam.

I made friends with Hoai Linh, who owned the restaurant around the corner from my house. For the five weeks I was there, I would have lunch at his restaurant, and then he would spend a few hours teaching me Chinese chess, explaining business in Vietnam, and introducing me to his friends.

I felt like I was hanging out with one of the cool kids. What luck to meet a man who wanted to open up and share three of my favorite subjects (games, business, and connecting people) with me!


What have you learned through traveling?

Travel seems to break down the us/them dichotomy. While back in tribal days, it probably made sense to fear the “other,” these days I think that fear is one of the main causes of global conflict.

For example, while traveling through the Laos countryside, the people I encountered were stone-faced, which I interpreted as anger. But when I smiled at them, they’d smile right back and were generally quite friendly. Quite the opposite of Laos’ next-door neighbors in Vietnam, where people of all ages when out of their way to smile and shout hello to you, even as you zoom by on a motorbike.

I wondered how entire countries of people learned to carry themselves in a different ways. Regardless, so long as we don’t make snap judgments about one another and are open to understanding different cultural norms, we stop seeing an “us/them” world. Travel creates empathy for global citizens.


The great debate: aisle or window?

Aisle, because I have long legs and can stretch them out in coach.

Best travel tips…go! 

Buy clothes on arrival (rather than packing them).

Purchasing local clothes helps you fit in, and double as souvenirs.

Throw a party to make fast friends.

Be “that guy” – the one who invites people you just met to dinner or an event. It makes you the hub of the network, and creates quick friendships by including others right away.

Read up.

I love to read a brief cultural history of each place (even from the back of a guidebook). It gives a lot of context for how people behave in day to day interactions.


Whereto next?

My goal is to get at least 5 new countries each year. This year I want to focus on exploring the Andes and Eastern Europe.

Stay up to date with Derek at The Art of Adventure or via Twitter @derekloudermilk.


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