The Art of Non-Conformity: an Interview with Chris Guillebeau

Chris Guillebeau

Photo courtesy Chris Guillebeau

Today sees the publication of a book that is essential reading for anyone who wants to create a lifestyle and business around their own passions and interests: The Art of Nonconformity by Chris Guillebeau.

I know it’s essential reading, because Chris was kind enough to send me an advance copy and to answer some questions for Lateral Action readers. The book was so good I read until 2am for the first time since my children were born last year. (The parents among you will know how precious sleep is when you’re caring for babies, and therefore what a high compliment that is.)

Many of you will be familiar with Chris’s work and adventures, but by way of introduction for the rest of you, I’d say it’s hard to think of anyone who embodies the principles of lateral action more than Chris. Read his book and you’ll discover how he managed to:

  • graduate from college 2 years early due to an original approach to curriculum scheduling
  • kick off his lifestyle business in 1999 by selling the furniture from his flat on eBay
  • build an eclectic portfolio business, combining coffee distribution, web design and jazz
  • spend four years as a medical volunteer in African war zones
  • create a wildly popular blog, The Art of Nonconformity, and a Very Small Business selling Unconventional Guides to life, work and travel

And that’s without mentioning his current quest to visit every country in the world before his 35th birthday. As if that weren’t difficult enough, he’s taking a break from worldwide travel for the rest of this year, as he sets out on an Unconventional Book Tour to promote the book – visiting every single State in the U.S. (I’m trying to persuade him London should be the next stop on the tour after that…)

So without further ado, here are Chris’s answers to the questions I asked him on your behalf.

1. Your writing and videos plus the word-of-mouth all suggest that you are a very nice guy. Yet you use a lot of military metaphors for your business campaigns – ‘world domination’, ‘Empire Building’, ‘small army’ and so on. Is this just playful fun, or is there an iron fist in that velvet glove?

Good question. I do use military metaphors, yes, but I try to keep them playful. I think in this case they are best viewed in context with the images we use on AONC, which are fun and non-violent.

As for iron fist, I’d say that I’m pretty determined, but I’m also not really opposed to anyone. I was saying to someone else recently that people who live so-called conventional lives are in two camps: those who are genuinely happy where they are at, and those who are dissatisfied but don’t know how to fix the problem. So as far as I’m concerned, I’m focusing on the second group. If someone is living the dream in their cubicle or other traditional life, good for them and I wish them well. Plenty of other people aren’t, and those are the ones who are looking for an alternative.

2. We probably don’t need to spend a lot of time persuading Lateral Action readers that it’s a good idea to challenge convention and take an original approach to life and work. But what can you tell us about how to stick to your guns and follow through on an unconventional lifeplan, in the face of resistance or criticism from others?

You’ve hit on the primary question: how to live a remarkable life in a conventional world. I think it starts by clearing understanding our own motivations and desires. In much of the western world, I don’t think this is common because we’re often gently (or not-so-gently) encouraged to stop dreaming and stop using our imaginations after childhood ends. If we can figure out what we actually want out of life, we’re already ahead of the curve.

Next, we have to begin taking action to align our beliefs with our behaviour… or as you put it, “Creative thinking is not enough.” This is when we often encounter the resistance you mention. Some people may be envious or just uncomfortable when we decide to start “backing away from the bridge” as I describe it in the new book. Over time, many of them get used to it and some may even be inspired to take steps of their own. As for the others, well, I think it was the comedian Bill Cosby who said, “I don’t know the recipe for success, but the recipe for failure is trying to please everyone.”

3. It strikes me that your career is a series of adventures or quests: you previously spent four years as a medical volunteer in African war zones, and now you’re on a mission to visit every country in the world. What difference does it make to you personally to have that sense of mission or purpose, over and above the need to earn a crust and the desire to have a good time?

It makes all the difference in the world. I can still earn a crust and have fun, but ultimately that isn’t enough for me — and probably for most of your readers as well, since you’re concerned with taking action to create change. We want to be challenged more than we want to take it easy. We want that sense of adventure more than we want to be set for life and free to lie on the beach all day. This doesn’t mean we can’t have fun, nor does it mean that we can completely ignore our responsibilities, but I think for the most part, those of us who are change-oriented enjoy life a lot more when we’re pursuing something we judge to be meaningful.

4. Clearly you’re not pursuing these missions as a cynical business strategy. And yet they doubtless have a positive effect on your business. For example, you first caught my attention when I heard about the quest to visit every country on earth, which led to me checking out your store out of curiosity. What can you say about the relationship between inspired purpose and hard business realities?

It is indeed an interesting relationship. Once in a while someone will say that my roaming the world is a business strategy, and I think “If they only knew what it’s like!” I could earn a lot more money by staying home and putting more time in the business instead of taking red-eye flights out of Africa and hunting down a good WiFi connection in Laos.

But as you point out, it’s also true that the nature of the quest can have a positive effect on business. Overall, my goal is to increase influence. I don’t mind that only 5% of my readers buy something from my shop, and the rest of them read for free. I’m not trying to convert them to customers, because if they appreciate my work, they can probably help even more by telling people about the project.

The other interesting thing is that I’m not sure that a model like this could have existed a decade ago, or maybe even five years ago. We do live in interesting times, as the old Chinese proverb suggests.

5. I deal with a lot of artists and creatives who would much rather focus on their artistic work and forget all about the messy business of marketing and running a business. What’s it like for you? Do you enjoy being an entrepreneur, or would you rather have more time for writing?

I enjoy both sides. I think it would be difficult otherwise — which is not to say you have to love everything, because there are certainly tasks I don’t enjoy. But I like both the business work and the writing work. Mostly I enjoy creating, and I find the same satisfaction from creating a good business project as I do from writing something non-commercial.

6. Can you describe your daily or weekly writing routine? Any tips for getting creative work done in the midst of an activity-filled life?

Yes. I don’t have a daily routine in the sense of a managed time schedule like a lot of creatives have. I think the idea of having set times is a good one, and books like Steven Pressfield’s The War of Art have definitely had a big impact on my work habits. But since my location is so frequently in flux, what I do instead is focus on deliverables instead of time schedules.

I’m writing you now from a coffee shop in Portland, Oregon. I sat down an hour ago and have been alternating between this and one other short writing project. And because I don’t follow the rules about shutting out distractions, I sometimes stop to write emails or see what’s happening on Twitter. (I know, I know — those things you’re never supposed to do but everyone does anyway.) These two projects are coming up towards the end of the day, so when I finish them, I’ll be done until tomorrow morning. Then I get up and start thinking about more deliverables. I consider the writing practice like exercise: I can miss a day once in a while with no ill effects, but if I miss several days in a row, I start feeling bad.

7. One of the most powerful ideas in your book is ‘your legacy starts now’. Can you explain what you mean by ‘legacy work’?

The way I think of legacy itself has nothing to do with money or something you do at the end of your life; it has everything to do with relationships, influence, and how we can transfer knowledge and create opportunity for those around us. Legacy work, therefore, is something we are proud of that makes a positive impact or otherwise helps the world become a slightly better place.

I like the way that Michael Bungay Stanier in Toronto thinks about work: we all do some combination of bad work, good work, and great work. Everyone knows you aren’t supposed to shuffle your Inbox around or check Twitter while you’re on deadline — tasks that are traditionally defined as bad work. But we fail to understand that even good work can interfere with great work or legacy work. I transitioned to a writing career and started The Art of Non-Conformity in 2008 because I had done a lot of good work that had no overall convergence. I still have a long ways to go, of course, but making this choice has been incredibly rewarding.

I should also note that when we start working towards the concept of legacy, small goals have a habit of becoming much larger as we make progress. In retrospect, my project initially had a very limited vision. Then people started reading and contributing, and I realized that we needed to think bigger. I guess the lesson is: when you start thinking about legacy, be prepared to be challenged, be prepared to work hard, and be prepared to have a lot of fun.

Pick up your copy of The Art of Non-Conformity online through the usual outlets, from your local bookstore – or in person from Chris on his Unconventional Book Tour.

Chris Guillebeau travels the world and writes for a small army of remarkable people at Follow his adventures on Twitter @chrisguillebeau.

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  1. I’ve read several interviews people have done with Chris in the last few days (and am also terribly jealous that you were one of those who got a review copy!). I’ve been a fan of Chris’s for quite some time, and he was a huge part of how I began doing what I do.

    Just wanted to say that I think the questions you ask are the most insightful — and interesting — that I’ve seen. Nice job. I really like the way you tied Chris’s work in with theme of your blog (and your readers’ interests).

    Well done, you!

  2. Thanks Liz. I must admit it was hard to resist the temptation to Tweet that I had a copy of the book! 🙂

    As for the questions, it was actually pretty easy to tie them in with the theme of the blog, given that Chris is such a great example of the kind of attitude to life and work I write about.

  3. “Start working towards the concept of legacy”

    This phrase really helps to put things into perspective.

    Thank you!

  4. Wonderful interview Mark!

    Fantastic questions to ask Chris and great answers from him. The man is an inspiration. I agree with Marcy above – let’s start thinking about legacy …

    With admiration as always


  5. Great interview, Mark!

    Thank you for asking about the military language. I have wondered about that myself since Chris is such a peaceful person.

    Now I get it: he uses these terms to daunt the status quo. By using the same terms the establishment has utilized for their missions, he provides a laugh at their expense. I doubt there is anyone in the AONC tribe anticipating a hostile takeover; it seems like more of an awakening.

    “Legacy” has been popping up everywhere lately – I can’t wait to read what Chris has to add to that conversation.

    Thanks for a fine Q&A!


  6. Hi Mark

    Great interview questions indeed. I just posted up mine with Chris (aren’t we both lucky to have him in our life). It amazes me how he has time to answer all the questions from his army but then he is a truly great emperor.

    Unlike you I’m half way through the book and loving it. It will b one of those books that I’ll refer back to often, like Influence.

    I also like that you asked how he schedules his day, because like Chris I’m never in the same place for long and it makes me feel better that he has no strict regime. I find that tends to kill my creativity. And his admission to checking Twitter and email in between creative project is endearing and makes me feel better for doing the same.

    Thanks for sharing his wisdom and yours.

    Natalie @womanzworld