Challenging authority since 1978, Chris Guillebeau has made it his goal to travel to every single country on the planet by 2013. In addition to that, he’s been helping others to create online businesses, follow their passions, and achieve the unconventional.

Chris’s blog, called The Art of Non-Conformity, also has a boatload of quality content containing priceless strategies on life, work, and travel.

With a résumé like that, it comes as no surprise that Chris’s efforts to help change the world have influenced countless other bloggers to follow in his footsteps.

I am one of those individuals.

For being such a great source of inspiration, I’ve invited him to share some of his unconventional wisdom here on HiLife2B during his travels:

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John: What inspired you to start this journey? What was the big epiphany moment that drove you to create the Art of Non-Conformity?

Chris: I began thinking about non-conformity and unconventional living during the four years I spent in West Africa (2002-2006). But the epiphany moment was after that, around 2007, when I had returned to the U.S. and was thinking about the next step. I realized I had been fortunate to have done a lot of different things, from living overseas to being self-employed for ten years, but I lacked a convergence point to all of it. I started AONC to chronicle the adventure and hopefully help other people in their own unconventional quests.

John: You’ve definitely inspired mine. I’m on my own quest to create a sustainable passive income so I can live anywhere, and do anything. It seems everyone wants to attain this goal, but how would someone go about getting started, assuming they already have a job, a home, a computer, and a family to take care of?

Chris: There are two approaches to this:

1) I always ask people to think big-picture about what they care about that other people also care about. This is important because despite what you may hear, you can’t build a business strictly around yourself. It has to be an intersection or convergence between yourself and a big enough group of prospects/customers/supporters/clients to support you. Ultimately, that is the best path to starting a business oriented about someone’s passion.

2) That said, you can also just get out there and start doing things. The “throw stuff against the wall and see what sticks” strategy can work very well, especially in the beginning when you’re not sure what you want to do. Can you list something for sale on eBay or etsy today? Create a website in a day? Offer some kind of service on a blog and see who’s interested? There are all kinds of interesting business models out there just waiting to be discovered. Look at this guy who wears company t-shirts every day for a living. Look at the infamous million dollar home page. Those ideas are taken already, so what’s yours?

John: I think I’ve got a few tricks up my sleeve (laugh).What do you think it takes to live the life you want? Is it really as easy as it seems?

Chris: I don’t know if it’s easy — it may be easier to go with the flow and do what other people expect you to — but I also don’t like it’s prohibitively difficult. We all make time for what’s important to us, one way or another. I think it’s better to do that intentionally, which requires tradeoffs and sacrifices, but is also very rewarding.

John: What do you think is the biggest challenge for people when traveling to new countries, or anywhere new for that matter?

Chris: The biggest challenge is fear of the unknown. When you enter a new environment, things work differently than in a familiar environment. One tip: to overcome this, it’s usually best to figure out how the new environment works than to insist on doing things the way you are used to.

John: What do you plan to do after you’ve visited all of the countries in the entire world?

Chris: As Jacques Cousteau said, “Jet lag is my favorite drug.” I travel for travel’s sake — I like the process, the planning, and just being on the road. I probably won’t go to places like Equatorial Guinea, where I’m writing these notes, but I’ll still keep going.

John: If you could give one last piece of advice to all of the individuals striving to achieve better lives and reach their dreams, what would it be?

Chris: Most people don’t begin to think about leaving a legacy until they’re close to the end of their lives, or maybe even on that deathbed. I think it’s much better to think carefully about legacy as early as possible.

I’d also encourage everyone to live with as few regrets as possible. This isn’t as difficult as it may sound. Start by thinking: if I had only one year left to live, how would I spend it? Then find a way to incorporate those ideas, dreams, and goals into your daily life.

John: Thanks for the interview, Chris! It was a pleasure to have you.

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I only promote what I whole-heartedly support, so I highly recommend checking out Chris Guillebeau’s website, The Art of Non-Conformity.

If you want a chance at reading some of his premium content and learning more about what Chris teaches, look into the Unconventional Guides (some of them are in my “Read These Books” section on the sidebar) and follow him on Twitter.

photo credit: gwen bell

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