Chris Guillebeau is a writer, traveler, and world dominator. His main site - Art of Non-Conformity – is a blog and a diary of his travel adventures in 100 countries and counting.
I was lucky to meet up with Chris at SXSW 2010, and had a great time talking and learning from him. Definitely check out his blog to learn more about how you can dominate the world if your own way.
As Chris travels extensively, what follows is our email interview.
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Q. Your site – The Art of Non-Conformity (AONC) – is an awesome resource for people that also want to stay away from the “real job” problem. How did you come to the realization that you didn’t want to have a “real job”?
I just wasn’t good at real jobs. My last one was at age 20, when I realized I could make more money wholesaling coffee on eBay than I could slinging boxes on the third shift at FedEX. Then over the next few years, I learned about running a business that would allow me to work from anywhere and do what I want. Ten years and counting — I’ve never gone back.
Q. How did you arrive at the name?
Non-conformity is all about questioning assumptions and conventional wisdom. That’s what I try to do in most of my work, so thus the title AONC.
Q. You’ve turned your experience of traveling, speaking, and writing into a series of Unconventional Guides. Is that your primary money maker, or do you pay your bill some other way(s)?
I’m a full-time writer and entrepreneur. I do freelance work and write books (here’s my first one.) I also do some limited speaking and startup consulting. But in terms of money, yes, UnconventionalGuides.com now provides the bulk of my income.
Q. When did you start turning your experience into a product?
It was quite unintentional in the beginning. People just started asking questions — the same ones — over and over. “How can I fly from city x to city y? How can I run a web-based business?” And so on. I started creating guides on the site that ended up being quite popular. Then I realized, hey, this could be a real business.
Q. What advice do you give to those thinking of doing the same?
Make sure you have a demand for what you offer in advance. It’s hard to create demand, but it’s much easier to respond to a demand. (Better to have an audience without a product, than a product without an audience, in other words.)
Q. Apart from your site and your computer, what other tools do you use to operate your business?
That’s about it. I do a lot of outlining and brainstorming in a paper notebook, but the MacBook I’m writing you from now contains the entire business. Thankfully, a lot of things are web-based these days, which makes life easier when working from 20+ countries a year as I do.
Q. And are you the sole operator of your business, or do you have some behind-the-scenes help?
Good question. I am the primary operator of the business, meaning that I do almost everything, including customer communication. But now that we’re growing a bit, I have some help from time to time. And from the beginning, superstar designer Reese Spykerman has helped me craft the branding to be consistent for the whole network. I can’t recommend her highly enough.
Q. You stopped consulting in order to write the AONC book. What can we expect to learn from the book that we cannot find on your site or in your current guides?
The book is more personal than my other work, and presents a complete story as opposed to a single subject or narrow topic. It’s also a good souvenir of AONC for everyone who enjoys the message of the site.
Q. What’s the plan after the book is published? World tour?
Exactly. I’ll be visiting 63 cities in North America (every state, every province) to meet readers. Sign up to come out on UnconventionalBookTour.com.
Q. What advice can you give to people that are considering becoming freelancers? What nuggets of wisdom do you have now that you wish you had when you started out?
In terms of freelancing, the more specific the service, the better. A lot of people want to be “life coaches” or other things that aren’t clearly defined. I’m sure there’s a lot of benefit to working with the right life coach, but most people don’t want to hire life coaches. So think about the problem you can solve and offer a clear solution.
That’s for freelancing, but I’m not a freelancer by design. I’m kind of a one-man show, for better or for worse. And I learned that for one-man or one-woman shows, as long as you have a compelling message that benefits readers or fans, you actually don’t need to be that targeted at all.
So I guess the lesson is, choose which side you’re on and don’t look back. 
