Interview by Jon Shadel

Chris Guillebeau, the New York Times best-selling author, talks about pursuing a passion. And why it's O.K. to not have a clue what you're doing.


In his early twenties, Chris Guillebeau set an ambitious goal for himself: visit every country in the world by the time he turned 35 years old. And as crazy as it sounds, this jetsetter accomplished just that, visiting 193 countries in total. In the meantime, he also found time to write a handful of New York Times best-selling books, including “The Art of Non-Conformity” and “The $100 Startup,” and organize the annual World Domination Summit in Portland, Oregon.

This kind of radical goal-setting defines Guillebeau’s unconventional career. He’s never had a “real job.” He’s never earned a steady paycheck. And since he was 19 years old, the Portland-based author has worked for himself, choosing instead to run circles around the world and achieve jaw-dropping success on his own terms.

And while his published work provides a pragmatic and specific roadmap for how anyone with a dream can accomplish similarly impressive things, we wanted to gain a more intimate perspective on Guillebeau’s unscripted life. We sat down with the busy author and entrepreneur to discuss everything from living a life of radical non-conformity to the rare creative clarity found in moments of in-betweenness.  

JS: In your bestseller, “The Art of Non-Conformity,” you write, “The path to world domination, or whatever it is you want to do, begins with clearly understanding what you want to get out of life.” Without reciting verbatim your entire first book, what are some key steps someone can take to really understand that?

CG: I think the first and most important step is to really start asking a lot of questions. Asking questions like, “Why do you do what you do?” The answer may be that you have to fulfill this requirement for schooling or that you have to do this thing for you work, and that’s fine.

But throughout the day, even though we’re super busy, most of us have a lot of opportunities to do a lot of different things.

I used to have this screensaver on my computer that would say, “Why do you do this every day?” And it helped to challenge myself: Here I’m sitting down at my computer, maybe ready to spend eight hours a day working online in one form or another, and I’d have to ask myself — What’s the point? What am I trying to work for?

What I’m encouraging people to do is to think for themselves, to ask, “Why?” And then start identifying what matters to them and what they hope to achieve.

I used to have this screensaver on my computer that would say: Why do you do this every day?

If you don’t know, that’s O.K. You can explore. You can experiment. A lot of people in my community are into “life experiments,” which is just about forcing a change in your routine and doing things differently — maybe going to an art museum if you never go or attending a baseball game if you’ve never gone to a baseball game. Whatever it is, it’s through exploration of different paths that we understand that there’s a lot more out there beyond our narrow perspective.

Ultimately, I am interested in helping people create more personal freedom so they can do whatever that thing is, whatever it is that they want.

And as we understand what we’re trying to do and what we want to work for, and as we have some of these initial successes and become more comfortable with risk over time, we may learn that it’s actually not that risky to do something really big — to step our on our own, to travel the world or whatever it is. Over time, your vision expands. I think this is a very positive, self-reinforcing circle. As we do different things and go through this process of self-examination, we are changed through it. And made better by it. And in the end, we have a much bigger vision than what we started with.

JS: I recently saw David Howitt, the author of “Heed Your Call,” speak at Wieden+Kennedy’s headquarters in Portland, and he essentially said that when we’re in the metaphorical pit — questioning our lives and in a state of in-betweenness — that we have the greatest creative potential to redefine who we are. What do you personally make of these moments of limbo when it comes to determining what we want to do with our lives?

CG: Moments of uncertainty are extremely powerful because if everything is settled and you’re already on-track, you know exactly what to do and things are laid out in front of you. There’s some comfort in that. Maybe the discomfort is the thought that there is something greater, and the question of how you might find it if you’re already committed to something else.

I think the greatest risk is to have everything all planned out and to wake up one day feeling like you wish you had done something else.

This moment of uncertainty and transition is extremely healthy, and it shouldn’t be rushed. It may feel unsettling when you go through it, but it has great potential to lead you to something far, far better.

I think the greatest risk is to not have those moments. I think the greatest risk is to have everything all planned out and to wake up one day feeling like you wish you had done something else, but never really had the chance to consider it.


JS: Maybe the clichéd way of describing it would be a “wakeup call?” You’re jolted out of a daily routine to a place where you can critically examine your own life and determine whether you really are satisfied waking up and doing what you do everyday.

CG: Yes, I think of this quote where people who were pushed out of a situation — laid off from a job and ended up doing something much better — said, “If I had never been pushed, I would have never taken the leap.”

A lot of people go through these forced situations, but in some ways I think it is almost more admirable for someone who is not being pushed, someone who has things going O.K., to deliberately go through this self-examination process and ask how they could better define their future.

In other words, you can create uncertainty. You don’t have to wait to be forced into this moment of in-betweenness. You can create it for yourself, and that can be extremely powerful.

JS: Of anyone I could speak to, I should probably ask you about the transformative nature of travel — you’ve visited every country in the world. But instead, I’d like to ask you about the importance of everyday adventures, what you think about finding opportunity or possibility wherever we’re at. What do you make of finding the traveler’s sense of adventure in our everyday lives?

CG: Well, I think “adventure” is a very good word, and adventure can mean a lot of different things. I like the words exploration and discovery, as well. You don’t have to fly around the world to explore, make discoveries or challenge yourself.

The key is asking, “What are my growth areas? How am I going to enjoy myself?” And when I say enjoy, I don’t mean sitting on the couch and watching “Game of Thrones.” I mean asking yourself, “How am I going to pursue an active lifestyle?” And even “active lifestyle” doesn’t have to mean hiking; it can mean intellectually active.

We all have to define what these terms mean for ourselves, but the point is that world traveling, for example, doesn’t have to be the answer — not everyone is interested in visiting every country in the world, but everyone can do all kinds of amazing things wherever they’re at in life.


JS: How do you stay grounded in your vision of your true self when everything seems to be working against you? Is it all about staying focused on the small, daily steps forward?

CG: “Staying grounded?” That’s interesting. I’m not really a big fan of balance. A lot of this stuff can be really disruptive. It is disruptive when you’re doing something new and different. A lot of people around you may not understand.

One thing that’s important is finding a community that can support you. That community can be a virtual one — maybe you find a group online — or it can be a physical group — meet-ups or mentors. If you can surround yourself with people who have accomplished a dream, even if it isn’t the same dream, that can certainly help.

But when you start talking about “staying focused,” I think a lot of people may not be able to relate to that or might not be sure what to do. I like the word “intentionality.” When someone has a goal or a dream, it’s through their daily steps and the ultimate belief in an outcome that keeps them going.

But with all that said, it’s O.K. if that all of this changes along the way.  

JS: One thing I really enjoyed about your book “The $100 Startup” is what you wrote about passion, and finding where your passions intersect with a need in the marketplace. But for a lot of us who might not be entrepreneurs, that’s a different way of thinking about passion. What are some ways someone can think more strategically about their passions?

CG: We talked in the beginning about self-examination and asking questions about yourself, which is great and helpful. But when you’re talking about something like an entrepreneurial venture, a nonprofit or some sort of cause that involves other people, you really need to move away from just asking questions about yourself and start asking questions about the world.

Ask yourself questions like: What is it I can do that’s actually going to benefit other people? What’s missing? What’s the resource, the service or the product or the organization that’s going to solve this problem that a lot of people have that seems like, for some reason, no one’s ever done it, or the existing solution is subpar?

Ask yourself questions like: What is it I can do that’s actually going to benefit other people?

This is where things really get exciting. Here, we move beyond listing the top things you’re passionate about. Sure, those things are great, and you’ll find a lot of things you love to do. But many of those things are just hobbies. If you really want to delve into something, have some impact, be commercially successful or whatever the goal is, your vision has to extend far beyond yourself — it has to be this little slice of yourself that connects to something much greater, the needs and desires of others.


JS: You’re an undeniably creative and productive individual. But even when you’re doing something you’re really passionate about, it can be really easy to get stuck in a rut. What are some of the things you do every day to renew that sense of creativity and keep a fresh outlook on your routine?

CG: Well, my readers keep me honest. I get a lot of feedback of all kinds, and it really helps to know I’m actually interacting with people. And that’s hard in the beginning, because you’re building something that no one is responding to just yet. But even if you can form a small community in the beginning — it doesn’t have to be huge — their feedback can create a positive loop.

Another thing I do is that, even though I’ve got a lot of stuff going on, I try not to over schedule my actual hours. I may be working on lots of projects and deliverables, but I try to avoid having schedules where four hours a day are booked up with meetings and calls. Even if I’m working long days, I like to have the flexibility so I can work on the things I’m motivated to work on. A lot of my creative projects are stretched out over a longer period of time. For example, I’m not going to drink a lot of coffee and crank out a book over a weekend. It’s something that I’ll work on a every day for a year. And to accomplish that, I really need to guard my space.

Jon Shadel is a Portland-based writer and the editor of Limbo.