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Would you like to travel the globe while financing those trips solely through your online efforts and income? How about attempting to visit every country that the world has to offer?

Right around the time we started to make final preparations for the launch of Train for Humanity, I came across the aptly titled website, The Art of Non-Conformity, which belongs to Chris Guillebeau.

His site’s tagline is:

“Unconventional ideas for remarkable people. Along the way, I visit every country in the world and profile other nonconformists.”

Certainly after starting a business in the Caribbean, all of my travels,  and a pre-mature escape from the corporate world I thought that I led a somewhat non-conformist life…but I don’t have anything on Chris.

After going through his archives and reading about various travels and adventures, one thing that immediately struck was the fact that Chris had lived and worked on the ground in Africa as an aid worker.

Before the launch of Train for Humanity I decided to email Chris to see if he would provide some feedback on TFH. Almost instantly I received a reply with some solid input and I have been following his adventure ever since.

I think most readers of MyTropicalEscape are living, or are working towards living, a life that is outside of the traditional norm and to that end, Chris has recently published an ebook, The Unconventional Guide to Working for Yourself, which is intended to help people create personal freedom via a very small business.

Below, Chris answers five questions that I had for him regarding the direction he has chosen for his life and how he funds his travels.

1. Does nonconformity run in your family? If no, what started you on your path…?

I wouldn’t say it runs in the family, but my dad was really good at encouraging me to do whatever I wanted. He encouraged me to try new things and not be afraid of failure. I think those are essential prerequisites for any unconventional lifestyle.

2. Wouldn’t life be easier if you just got a 9-5 desk job, earned a steady paycheck, and lived like a lot of other people?

No. At least not for me — some people are happy to embrace the 9-5 life, but I would be miserable doing that. Most self-employed people I know would gladly trade money for freedom. Obviously you have to make a living to some degree, but once you’ve had the freedom to make your own choices, it’s hard to go back to the cubicle lifestyle.

3. How do you fund your travels?

I support myself entirely through my own work. I create information products and occasionally consult for other small businesses.

4. What has been your favorite country to visit so far and why? What place will you never return to and why?

I don’t have a single favorite. I especially liked South Africa, the Netherlands, Ghana, Macedonia, and Hong Kong — but there’s usually something to appreciate (as well as something not to like) about anywhere you go. As to where I will never return, well, that’s a long list. It can be unpopular to say so, but there are a lot of countries that are deeply impoverished in large part because they lack good governance or because the foreign aid system has let them down. When I go to Africa, for example, I’m usually reminded that there are some things I really love about being there and other things that are a lot easier in North America.

5. What inspired you to write your latest ebook, “The Unconventional Guide to Working for Yourself?”

All of the emails! People ask every day about how I got started and what they can do to create a lifestyle that allows them to pursue their own goals and dreams. I don’t claim to have all of the answers — one of the things I try to be clear about is that there is no quick-fix system to any of this — but I hope the product will help get some people going in the right direction.

MyTropicalEscape readers might also be interested to know that Chris released the very popular (and free) “Brief Guide to World Domination” and if you are looking to save money when purchasing airline tickets, you might be interested in the other ebook in his unconventional series, The Unconventional Guide to Discount Airfare.

(Full disclosure - I have not read or purchased The Unconventional Guide to Working for Yourself or The Unconventional Guide to Discount Airfare but Chris seems like a stand-up kind of global citizen and I have no reason to believe that he is putting out an inferior product. Also those are NOT affiliate links above.)