Taking Over the World, One Country at a Time: Chris Guillebeau Chats about Marathons, Cuba, and Business

It’s difficult to describe exactly who Chris Guillebeau is. That’s because he does a little bit of everything, all around the world.

Chris Guillebeau

He’s the bestselling author of The Art of Non-Comformity and the recently released The $100 Startup.

He runs his blog ChrisGuillebeau.com and his business UnconventionalGuides.com from anywhere. He has to – he’s traveling to every country in the world by the age of 35. A prolific “travel hacker,” he has about a million frequent flyer miles that he uses to fly first class around the world.

Chris is also a marathoner and has run in more exotic locations than I can even fathom (we’ll talk about his half-marathon in Cuba later).

Recently I had the opportunity to ask Chris some questions about running, motivation, business, and how to achieve what’s important to you. I think his unique experiences can help us all make time for what’s crucial in life and ignite the spark of motivation to run around the world.

To the interview!

Jason: You’re coming close to reaching your goal of visiting every country in the world. With a blistering travel schedule like that, what are your favorite strategies to stay motivated to run or workout when you’re on the road? Personally, I get incredibly lazy when it comes to running while I’m traveling.

Chris: Well, it’s tough. I don’t wish to exaggerate, because I also get lazy, and sometimes I fall behind.

But I guess at a certain point I believe that we all make time for what’s important to us. I try to remember why I run — because it’s good for me, because I’ll usually feel better after I do, because it helps my productivity, and so on.

One practical thing that helps is putting my shoes by the hotel room door when I check in and get settled. I often live out of a carry-on suitcase, so if I take the running shoes out and move them in front of the door, I’m more motivated to actually put them on and hit the road or the gym. And then, most of the time I’m glad that I did.

Jason: I’ve used that strategy before – it’s so simple but it really works. I’d love your thoughts on work-life balance since you also own your own business at UnconventionalGuides.com. There are those who think that to be successful in life – however you define that – means you have to focus 100% of your energy on your career or business.

I disagree and think valuable energy also needs to be devoted to staying in good shape. In fact, even Richard Branson said to be more productive, you should work out. What are your thoughts on this? How can busy people find the time to fit in their running?

Chris: I’m not sure who would think you have to put 100% of your focus on career or business, but you do I think you have to give 100% overall— and fitness is certainly part of that. It’s not so much about “finding the time.” Time exists independently and we all have the same amount of it.

I don’t mean to be insensitive, and as mentioned I often fall behind and don’t keep up my workouts as I should. But I also suspect that your readers will understand that running requires a certain amount of ongoing commitment, just like anything else important in our lives.

Jason: Right: if something is important enough, you’ll get it done. Okay – a quick business question. Even though I haven’t read your new book The $100 Startup, I feel like I could have been a case study. Strength Running takes my passion (running, in case you haven’t guessed by now) and what I’m good at (writing good training) and combines them into a successful business. I simply love what I do here.

$100 Startup

Based on your research from the book, what is the first 1-2 steps that people can take to make a living from doing something that they love?

Chris: That’s great! And indeed, it sounds like you could be a case study. The book is all about connecting your skill or passion with something that is desired and valued in the marketplace.

The key there is that there are all kinds of things that we’re skillful in or passionate about, but not all of them are useful to others. So above all, focus on how your idea will improve people’s lives. Next, think specifically about how you can create an offer — not just a general business idea, but a specific offer that people can respond to. In the book we have a 1-Page Business Plan and other resources that help people get to market quickly.  [note from Jason: many of these resources are available on the book’s website: The $100 Startup]

Jason: You ran a half-marathon in Cuba – not something your average runner has done! With so much travel under your belt, where are your top three favorite places in the world to run? Why?

Chris: Indeed, I’d pick Cuba as one of the top—though it’s not necessarily runner-friendly; it was just a great overall experience. I ran with my friend Stephanie, who originally inspired me to run marathons years ago.

I’d also pick Ghana, and again it’s not because it’s a great running place but because I have good memories. I lived in the port city of Tema for several months in 2006, and spent a lot of time running along the beach and mentally preparing for my return to the U.S. after four years in West Africa.

Lastly, I’d pick Seattle. I lived there from 2006-2008, and trained for my first marathon by running around Green Lake and the trail that goes out past the University of Washington. I still don’t think of myself as a serious runner, but Seattle is where I made long-distance running more of a regular habit.


Big thanks to Chris for his time and thoughtful answers! I’ve been following his journey for years and it was great to chat about running and what he’s been up to these days.

His latest book The $100 Startup recently became an instant New York Times, Wall Street Journal, and USA Today best-seller. Congratulations Chris!

QUESTION FOR YOU: Has running taken you on adventures around the world? Conversely, have you included running in your world adventures? How do you make time for running in your busy life?

Photo Credit to chrisguillebeau.com.

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