Earnings And Yearnings: Life Uncharted

Chris Guillebeau is an independent spirit who lives by thoughtful design. He's currently on a mission to visit every country in the world by his 35th birthday. (At 31 he's covered 100.) His Web site, The Art of Non-Conformity: Unconventional Strategies for Life, Work, and Travel (chrisguillebeau.com), is full of advice for making money in nontraditional ways, adventuring abroad, and doing good work. It's based on his own experiences as an erstwhile volunteer for a medical charity in West Africa and as someone who has never worked for anyone but himself (he's been a coffee importer and search engine optimizer, among other pursuits). Guillebeau lives with his wife in Portland, Oregon.

What aspects of your life are unconventional?

I think hard about my motivations for doing what I do. I like travel and I like big challenges, so I put the two together. Also, I enjoy going places like Pakistan that have a mysterious, often negative perception in the U.S. I find that more often than not, the "real story" about Pakistan or wherever is much different than what we hear from a distance.

Do you have a negative stance toward the corporate world?

Not at all. The only "against" comes in when dealing with people who try to prevent others from making their own choices.

Was it your conscious choice to never work for someone else?

Since I was 19 or 20, I really couldn't imagine going to an office. I'm not opposed to work—I'm not trying to go on vacation for life. I wouldn't want to sit on the beach forever. That wouldn't make me happy.

Do you plan to start a family? It seems much harder to be unconventional when you are responsible for children.

We don't have a plan right now. I can't say for sure what our experience will be if we do. A lot of people warned me: "Things will change once you're married." But they didn't change, so I'm inclined to think they won't if we have kids, either.

What have you sacrificed in order to live the way you do?

I honestly don't feel that I've sacrificed anything. I haven't had a car for three years, but I'm very good at getting around Portland via public transportation.

I've had a wide range of income as an entrepreneur. One year I made $15,000 and another I made $150,000. My happiness level wasn't different during those two years. I learned that it's more important to focus on what I need the money for and not worry about the rest.

I earn all of my income from my site and my book contract, and should end 2009 with more than the per-capita income here in Portland but less than six-figures. I spend about 20 percent of my income on international travel.

What sort of family did you grow up in?

My parents divorced when I was young. My mother married a guy in the Air Force, which enabled me to live in the Philippines as a teenager. My father was a traditional man, an engineer, but he fed my imagination by buying me a lot of books.

What do you hope to learn or feel by seeing the whole world?

Once I started working out the logistics and mapping out the possibility of seeing every country, I thought if I didn't do it, I would regret it. But as for the reason to do it, I'm still working that out.

My worldview has been affected by all of my travels. I tend to view things as much more nuanced than I used to, whether it has to do with politics, religion, or culture. For example, I have been a Christian for most of my adult life, and still am, but when I went to Jordan and Syria I realized for the first time that if I had been born in that part of the world I would be Muslim. That realization brought about more respect for Islam and Judaism than I had before.

I'd also say travel has helped me change from being a pessimist to being an optimist. Hope is a better message than fear or scarcity, and besides, which side would you rather be on?

What are your favorite countries?

South Africa and Syria.

Can you share your most trying moments in travel?

I double booked myself on two nonrefundable tickets to Japan. I also got kicked out of a guesthouse in Mongolia in the middle of the night. I was miserable, but I also knew it would eventually make a great anecdote.

Doing it Our Way

Tales, trials, and advice from people who have carved out their own paths.

Matthew Cook

I lived in rural Pakistan for four years, I trekked on horseback through the Karakoram with my 6-month-old, and we all lived in a tiny apartment on the edge of the desert without hot water and (half the time) electricity. We loved every minute of it.

We are told to sweat and sacrifice in school to get a good job. And then, in turn, to sweat and sacrifice to get a good promotion. This seems like a dangerous convention to me.

Brooke Thomas

I'm a single mom to a 2-year-old boy and I support the two of us working for myself as a Rolfing practitioner and via my Web site, The Well Practice. I've never worked in the corporate world or a cubicle of any kind.

My biggest hurdle was feeling like I was head-butting a curb for a long time. I even spent three years working four extra jobs. But all the skills I gained as I pushed through those hard times are what make it a pretty smooth and joyful process now.

Nathan Hangen

I built a blogging and consulting business while I was deployed to Afghanistan. Rather than use my free time to play video games, I learned the ins and outs of building an online business. And this year I finally achieved my dream of becoming a triathlete.

The biggest hurdle was learning how to keep working once the initial buzz and excitement wore off. Quit living in fear. Ignore critics and spend time with those who inspire you.

Crystal Williams

I prefer reading a book to watching TV, I'm happily married and contentedly childless, I travel alone, and I stay up into the wee hours planning to liberate everyone from jobs they hate.

I tried for decades to fit in with what my parents and friends wanted me to be.

After I didn't feel obligated to eat, wear, watch, read, and do like everyone else, I found there was all this off-the-beaten-path stuff to discover!

Adam Baker

Our quest to live a 100 percent debt-free life is unconventional by today's standards. And we recently sold all of our belongings to backpack through Australia and New Zealand with our 1-year-old daughter.

My wife and I have control over the direction of our lives.