Chris Guillebeau on the Art of Nonconformity

by Susan Johnston

3 min read

Chris Guillebeau (@chrisguillebeau to his 60,000-plus Twitter followers) has the kind of lifestyle that many people only dream of. This globe-trotting entrepreneur is on a five-year personal quest to visit every country in the world and has been self-employed his entire adult life. He also penned the bestselling book, The Art of Nonconformity, and sells a variety of informational products through his website.

The Intuit Small Business Blog asked Guillebeau how he balances business with pleasure and what tech tools he uses on the road.

ISBB: What do you think is the biggest hurdle to successful self-employment?

Guillebeau: Lack of knowledge is probably number two. Some people don’t know how to start or what to do. That’s easy to help with, because people who want to learn are easy to teach. But I think the greater issue is a perceived lack of security in working for yourself. I use the word perceived because I believe that’s all it is — many of us find that self-employment creates far more security and independence than “working for the man” ever would.

Is it possible for people whose businesses involve more than just a computer to become location independent? If so, what strategies would you suggest?

Two points here: One, yes, not everyone wants to be a blogger or creative freelancer, and I’m not in the business of persuasion. However, I do think it’s important to think about the whole “knowledge economy.” Isn’t this what the world is shifting to? And it’s not for everyone, but if you want to be location independent, why not choose to develop your skills in a manner that supports that goal?

Secondly, for those whose businesses involve equipment, I do still think it’s possible to see the world and have a life. My friends at the Tom Binh company in Seattle do that — they work half the time in the factory, and live the rest of the time out on an island. The strategy for doing both involves setting up a deliberate structure that allows for that freedom, entrusting others with responsibility, and so on.

Myself, I’m better at keeping the operation very light (I have no employees) and building things that don’t require constant attention. I love entrepreneurship, but I also love writing and traveling.

What are your must-have apps or tech toys for when you’re traveling?

I’m pretty basic. My whole operation, whether home or abroad, is run on an entry-level MacBook Pro. I don’t even have a world phone. As long as I have Wi-Fi, which I relentlessly search for wherever I am, I’m good. As for apps and software, I use Dropbox, Things (a Mac task-management program), Evernote, and OmniOutliner. I write mostly in OpenOffice and spend a ton of time with Gmail and Twitter.

Nowadays there are tons of informational products on the market, and yours seem to be doing pretty well. How did you break through all the internet noise and build trust with prospective customers?

Well, I think it has to do with cultivating relationships and developing a reputation over time. Producing consistent work that helps people is what I think about every day. If you do that for years, outside noise isn’t really a problem. Marketing-wise, I also try to tell good stories and always answer the “reason why” — why is this project needed now? I also work with a great designer who is very brand-conscious. She and I both try to ensure that everything we build is in alignment with the core mission.

How do you balance spending time exploring a new place with time working on your business?

Good question. I guess balance is the key word there — I make sure I take time to do both. In my case, I often split up the morning and afternoon — working in the mornings, then exploring in the afternoon. But the key point is that my work allows me to travel, so I don’t begrudge the work. I also enjoy my work, so it’s not like I’m simply completing tasks to get to the “real” fun.

Of the places you’ve visited thus far, which one has been your favorite?

Out of 150+ countries so far, I don’t really have a single favorite. But I especially like South Africa, Macedonia, and Hong Kong.

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