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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.

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Greetings - someone recently emailed and asked if I was going to be posting anything soon. That made me feel good because I thought only my mother read this site.

It has been a VERY long but good year since we bought our business here in the Caribbean. Unbeknownst to me my drive for writing, which is minimal to begin with (remember - I am an idea person!) decided to take a holiday.

So, being that I am going on a real vacation to Nicaragua next week, I decided to declare myself on blog + not writing + vacation = blogcation

When I get back some friends of mine and I are going to launch a pretty cool humanitarian project that we have been working on putting together for the past couple of months. I think eventually we will have the ability to help some people that don’t necessarily need our pity, but they need our ACTION. Some of you already know what the premise is and for the rest I look forward to your feedback once we go live.

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Yesterday I ran part one of my interview with Cindy Price who is a freelance travel writer for the New York Times. Below is the second installment.

What has been your most dramatic travel experience? What has been your most “creative” meal while on the road?

That’s a tough call. For sheer drama, probably going to Rome for three weeks when I was 19. I grew up in a family of six in Jacksonville, Florida, so we couldn’t exactly foot six airline tickets. Most of our travel had to be by car. We took a lot of trips to Orlando, chilled on the People Mover, then beat it home.

So Rome blew my mind. I don’t know what I expected – I was a sheltered American kid. I think I thought all the women would be squat and walking around with pots on their shoulders like those old Sicilian renderings you see at Olive Garden.

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Editor’s note: This is a FANTASTIC guest post from Doug Mayle. He and his wife recently quit their jobs and relocated their lives to a sailboat so that they could pursue their dream of a global sailing adventure. Currently, they can be found in the Caribbean.

Living the dream

When I look out my window, only a few feet away, I see beautiful turquoise water glowing in the illumination of a tropical sun. I have to pinch myself to be certain that I am not dreaming. The pinch makes me realize that I am quite awake and that this dream-like existence is now my reality.

My window is actually a porthole, because we live on a sailboat in the Caribbean, present location: Culebra, Puerto Rico.

How did they do it?

Three years ago, my wife and I lived a life more typical of the norm in the United States. We were a dual income couple, no kids, with a three-bedroom house in the suburbs. Our journey from there to here is a fine example of goal setting and lifestyle re-design.

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Well, you might have heard, there is a little election tension up in the United States between Barack Obama and Hillary Clinton. For the first time in a long time in US HISTORY we have two candidates that do not fit the typical politician stereotype (i.e. white and male).

image source: son of broccoli

While I was working this morning I was wondering, there is eventually going to be a loser in this political conflict and I wonder where they will go to recover?

I know that Barack spent time in Indonesia during his childhood and that Hillary (and Bill) are fond of Martha’s Vineyard, but will they head to either of these destinations?

Maybe, the loser will decide to join the Peace Corps and really give something back, or maybe they will grab a backpack and spouse and head out on an around the world trip…? Will they retreat and recover quietly at home or a Ritz Carlton?

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(Editor’s note: This is the first [brief] post in a series of articles that I am going to be writing on how to take your first extended trip. Also, an update, out of the gates Jarkko Laine is way ahead of me in the Make Money Online Challenge but I will have a full post of my ideas before the end of the week.)

 
image source: ruvjet 

Do you long to take a trip that is longer than one or two weeks?

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