The “Lucky” Ones – An interview with world-traveling New York Times Bestselling author Chris Guillebeau

How do I write an introduction for my next interviewee that expresses my unabashed excitement while maintaining a sense of dignified professionalism? No really, I’m asking. Because Chris Guillebeau is kind of a big deal in the world of blogging and publishing, and I’m beyond psyched that he agreed to answer a few questions for me. Read on to learn more about the non-conformist with the fully stamped passport.

Chris Guillebeau

Anguilla. Angola. Djibouti and Nauru. Recognize these names? They’re just a few of the countries The Art of Non-Conformity blogger Chris Guillebeau has checked off his list. In fact, Chris has visited every country—all 193 United Nations member states—in the world. He recently reached the end of the world (Norway, in his case) just in time to celebrate his 35th birthday. You could say he’s well traveled.

Chris is also well accomplished, but he got off to a rocky start. A high school dropout, he learned how to drive by stealing cars and spent his first job as a dishwasher throwing away the pots that were too difficult to clean. His rebellion would eventually be used for good, however. Now, Chris is a New York Times Bestselling author of The $100 Startup, a book on entrepreneurship that shows how you can make a living doing what you love for a small investment (and it profiles 1,500 people who did exactly that with success). Chris is also the author of the book based on his blog as well as multiple manifestos, and his writing has appeared in Huffington PostBusinessWeek, and USA Today. Despite all the success and reaching his goal of visiting every country in the world, one gets the impression that Chris is just getting started.

And on that exciting note—welcome, Chris!

You’ve inspired and influenced a lot of people with your unconventional lifestyle. Who are some of the people that inspired and influenced you?

I was originally inspired by a surgeon in California who left home to volunteer his services in West Africa for more than twenty years. These days, I’m inspired by many of the people in the AONC community who are all pursuing big dreams and crazy projects of their own. I host a lot of meetups and events around the world, and always go away feeling motivated to improve my work in response to what other people are doing.

The concept behind The $100 Startup is that anyone with the desire, skills, and $100 can create freedom through entrepreneurship. But, if it’s that simple, why aren’t more people out there chasing their fantasies?

There are actually a lot of people out there doing it. Working on one’s own used to be very unusual, but now it’s slowly becoming mainstream—or if not totally mainstream, at least not that abnormal.

Chris Guillebeau

Visiting numerous countries, did you always manage to immerse yourself into the local culture, or were there times when you felt like a perpetual tourist?

It’s more of a third-culture thing. I couldn’t say with integrity that I “immerse myself into the local culture” wherever I go, but I’m also not a tourist. Instead it’s more of its own sense of identity, perhaps that of a modern nomad or wanderer.

Is your idea of home, then, different from others’? Is it difficult to establish roots, or is home wherever you are?

I have a home in Portland, Oregon, and I travel the world about half of the time. I feel at home in Portland and in any number of other cities. Whenever I’m home for a while without traveling, I miss the road. After I’ve been on the road for a while, I miss life in Portland. It’s not one or the other.

Which has played a bigger role in your success—luck or persistence? And what’s your response to people who tell you how “lucky” you are to travel the world?

Both. Perhaps you could say that luck favors the persistent.

As for being “lucky” to travel, that’s another story. There are plenty of people in the world who aren’t able to travel, but most of the people who would say something like that aren’t among them. I’m able to travel because I’ve made choices that support that lifestyle.

The $100 Startup

When you’re your own boss, downtime can be hard to come by. How can entrepreneurs and self-starters avoid burnout?

You don’t burn out by working too much, you burn out by doing things you don’t want to do. I always think it’s dangerous in the long-term to continue to push yourself when you’re unmotivated. But when you’re eager and excited to do something, why would you burn out?

You stress the importance of helping others. Why is that so essential to personal growth? Is it all about karma, or something more?

It’s generally a good idea to be a nice person, but it’s not just about karma. I like the concept of “selfish generosity,” where we ourselves benefit as we seek to engage and contribute. Most of us want to be part of something bigger than ourselves. We can find that fulfilment through helping others.

Chris Guillebeau

Now that you’ve accomplished your goal of visiting every country in the world, do you have other big goals or plans in the works you can hint at?

Yep! First, just because I’m done visiting every country doesn’t mean I’m finished with travel. I love being on the road and have no plans of stopping—I hope to continue writing and traveling for many years to come. Right now I’m working on a new book about the nature of quests, not only my own but those of other people who have chosen to orient their lives around a big journey or lifelong pursuit.

Besides your own, what are some of your favorite books?

I mostly read fiction. Murakami is my favorite author, so I’ll pick A Wild Sheep Chase by him, A Prayer for Owen Meany by John Irving, and Girlfriend in a Coma by Douglas Coupland.


Chris, thank you so, so much for taking the time out of your schedule (which is packed, no doubt) to chat with me. It was a pleasure getting to know more about you, and I can’t wait to see what you do next. Have questions, comments, or general exclamations of giddiness (I know I do!) for Chris? Leave them in the comments!