The Art of Non-conformity: Q&A with Chris Guillebeau

On March 11th, 2016

Visit his website or subscribe to his semiweekly newsletters and you quickly get a feel that Chris Guillebeau is happy, inspired, and living life to the fullest. The thing is, he genuinely seems to want the same for you and me.

His website, The Art of Non-conformity, promotes unconventional ways of living, working, and traveling—with the idea that you don’t have to live your life the way that people expect you to. Refreshing, huh? I think Chris eloquently expresses an ideal that many Vagabonders aspire to.

In his travels, Chris has the running goal of visiting every country in the world (he’s well on his way already, having been to 111 of 197 countries). Many of his newsletters find him reporting from far-off countries—most recently the Cook Islands and Suriname.

I caught him by email recently at his home in Oregon, where he very kindly answered a few questions for me:

What compelled you to change things up, and follow/promote an alternative lifestyle?
It started in two places. The beginning of AONC started when I turned 30, returned from Africa after four years abroad, finished grad school, and began thinking more seriously about what I really wanted to do with my life.

But before that, the foundation for everything else definitely began with the decision I made with my wife to go to West Africa in 2002. We ended up staying until 2006, volunteering for a medical charity, and those experiences helped me define how I see the world.

What has surprised you the most about living a life of non-conformity?
I’ve been mostly surprised by how easy it is. Some people assume that the unconventional life is more difficult, but really the opposite is true. For me, travel without a backpack or checked luggage is actually easier than lugging a bag around. The same is true with my work. Once I cut out meetings and obligations that had no clear value, I found I had a lot more time to do real work that had a lasting impact.

Do you have any favorite budget travel tips?
I use round-the-world tickets to facilitate a lot of my travel, and once I arrive in hub cities I tend to head off on buses or other overland transport. I’m also very active in the pursuit of frequent flyer miles—I think I have about 600,000 right now, but that’s not really a huge amount compared with all of the travel I do. I’ve started writing more about the cost of my trips on the site, and some people seem to enjoy that. They are usually surprised by how relatively little it costs.

What advice would you give to someone just starting to think about an around-the-world trip or other unconventional way of living?
I’d like to say, “Don’t be afraid to take the leap,” but that’s a bit simplistic. Most of us are afraid of any life choice that departs from convention. The trick is to acknowledge the fear while finding a way to overcome it. Asking yourself if you’d regret NOT making the choice 20 years from now is often helpful. So is asking, “What’s the worst thing that could happen if something went wrong?” I’ve found that the world doesn’t usually end even when things go wrong. Most of the time, everything works out just fine.

You inspire me! Who are your own role models?
Thank you. I am continually inspired by all of the people who read AONC and share their thoughts with me through comments, emails, Twitter, and around the world when I travel. They are a primary motivation for why I’m enjoying this so much.

Otherwise, I’m interested in people who have overcome significant challenges in pursuit of a worthy cause or independent thinking. A few of them that come to mind immediately are Malcolm X, Ayn Rand, and Ralph Nader. My favorite novelist is Haruki Murakami.

What’s next in your travels and projects?
I’m currently gearing up for a big trip to four continents that begins at the end of June. I’ll start off in Bolivia, finish up the rest of the South American countries I haven’t been to yet, head over to the Middle East (Jordan) and Persian Gulf (Kuwait and Saudi Arabia), then come home via Hong Kong and Malaysia. I haven’t had a monster trip like this in several months, so I’m looking forward to it.

Otherwise, my biggest project is writing the book that will expand the ideas of unconventional living I write about on AONC.

Ready plan a Round The World adventure?

Image: Tim Gouw (