Living Life by Your own Rules – Interview with Chris Guillebeau


Have you ever thought about dominating the world?
What would it be like to live life according to your own rules, following your own path, forging your own way?

Chris Guillebeau has done this his entire life! The author of the book and website titled The Art of Non-Conformity, Chris radiates non-conformity and it looks like success!

According to Chris, you don’t have to live life according to someone else’s definition of success. You don’t have to follow the status quo or play by rules created by someone outside of yourself. What you can do if you want to live an extraordinary life of happiness and purpose is look within yourself for what motivates you, what brings you pleasure, what you can do, and what has meaning for you. Then make active decisions to create that reality in your life.

I use the metaphor of world domination (ruling and changing the world at the same time) to highlight all the things we can achieve when we choose to live with gratitude and purpose.” Chris Guillebeau

Chris likes to spread his enthusiasm for living life unconventionally through his writing on his website, in his books The Art of Non-Conformity and The $100 Startup, in his Unconventional Guides (created to help others looking for advice and encouragement); through his lifestyle of travel, a passion he enjoys; through a limited number of speaking engagements; and on a grand scale through his World Domination Summit, a yearly convention where thousands of like-minded individuals gather to hear speakers, take breakout sessions, watch film screenings, and participate in activities and independent meetings.

Chris spent some of his early adult years as a volunteer executive for a medical charity in West Africa, pursuing a graduate degree in International Studies at the University of Washington, importing coffee from Jamaica as an entrepreneur, working on search engine optimization, and building a small publishing company while volunteering in Africa.

Recently having completed his ten year long travel quest to visit every country in the world, Chris is currently planning on writing a book about his travels and what he has learned from them and experienced along the way.
Reaching out to his worldwide readers, Chris arranges to meet people where and when he can on his $100 Start Up world tour.

A truly inspiring individual himself, Chris Guillebeau doesn’t just advocate for making your own life happy, but for actually influencing the world you live in to make it better for everyone really. He hopes his writing can help show “how to change the world by achieving significant, personal goals while helping others at the same time.”


1. Chris, you are a successful writer, world traveler, entrepreneur, and you are also a source of inspiration for others. To what do you attribute your success? How do you measure your success?

That’s kind of you to say. I’m pretty sure whatever external success I’ve had thus far is due largely to my readers. Of course, I realize I have to be responsible for producing and creating—I have to write books, blog posts, host events, and so on—but for that I think the greatest attribution is sheer persistence. I have a lot of flaws and weaknesses, but I don’t give up. I measure success by influence and relationships.

2. In your early adult years you spent some time as a volunteer executive for a medical charity in West Africa. What prompted you to do this instead of taking a more traditional job here in the United States?

I was depressed and trying to figure out my place in the world. Being overseas, especially in Sierra Leone and Liberia, was a great way to spend a few formative years. I’d certainly recommend volunteering and traveling to anyone looking for their next step.

3. What made you decide to visit every country in the world? How old were you when you realized you had a passion for travelling?

The passion for travel largely began during that time in West Africa. As I traveled, I gained confidence, along with the desire to see more of the world. After I returned to the U.S. (in 2006) I took on the idea of a quest to go “everywhere.” I’ve been working on it ever since.

4. Now that you have travelled to every country, where will you travel? Do you plan to revisit some favorite places? In a recent blog post you mentioned that running out of countries to visit has created a sort of identity crisis for you 🙂

Good question! Indeed, it does feel like an identity crisis of sorts. I definitely plan to keep writing and traveling. I like the idea of revisiting favorite places, and I’m also doing a lot more global meetups wherever I go. But there’s no doubt that the model will change, since I no longer need to fly to places like Tuvalu (last week) or Guinea Bissau (last month).

5. Can you tell us a little more about your book, The $100 Startup: Reinvent the Way You Make a Living, Do What You Love, and Create a New Future? This book has been touted as a true guide to starting your own entrepreneurial business with only a small financial investment. What does it have to offer that they aren’t finding elsewhere?

Most business resources are vague and unspecific, and most of them deal with managing employees or trying to gain funding for a bigger startup. The $100 Startup is not a business book—it’s a manual for everyone seeking more freedom in their lives. We undertook a three-year study to understand how 1,500 ordinary people had created freedom for themselves by making something of value and sharing it with the world. Then we created a blueprint that readers can follow in their own journeys.

6. You also publish Unconventional Guides, which are available via your website and blog. These guides have helpful advice in different areas such as selling your art, using frequent flyer miles, and building a business. Do you write all of these yourself or do you also publish other writers guides that fit with your philosophy? What inspired you to offer guides to people?

I wrote most of the first ones myself. We now work carefully with a few other writers who can cover specific topics better than me. I began the project because I kept hearing the same questions from readers over and over: “How do you fly so affordably? How can I create my first microbusiness project?” and so on.

7. The World Domination Summit is a large convention in Portland, Oregon that hosts thousands of people and provides speakers, films, breakout session, activities, and more. How did that get started? What prompted you to start a convention and how did it grow to be what it is today? Also, Who would you say is the average person who attends the World Domination Summit?

WDS is a global gathering of creative, unconventional people from many different backgrounds. It came to be after my first book tour, where I visited every U.S. state and Canadian province. I wanted to do something to bring like-minded people together, not just from one location but from many. We have no average people at WDS. 🙂

8. These days you write a book about your ten year experience travelling the globe. Can you give us a sneak peak of what readers can look forward to in this future book?

Yes, I’m very excited to begin work on this project. It’s not only about my journey; it’s about the nature of a quest and the study of many other people who have undertaken them. I’ve been meeting a lot of fascinating people who have chosen to pursue quests, and I’m just now starting to outline the lessons and narrative.

9. If you could give just one piece of advice to other people who are struggling to find their happiness, what would that advice be?

My one piece of advice would be the same as the mission statement for AONC: You don’t have to live your life the way other people expect. You can do good things for yourself and for others at the same time.

Also: you are not alone.

Thank You Chris


A short video from 2012 World Domination Summit , which I was privileged to attend:


Chris Guillebeau is a successful writer, world traveler, and an entrepreneur. Visit his inspiring website at or find him to twitter @chrisguillebeau


Tal Gur is a world traveler and personal development enthusiast. An adventurer at heart, after trading his daily grind for a life of his own daring design, Tal spent a decade pursuing 100 major life goals around the globe. His journey continues as a location-independent blogger, lifestyle entrepreneur, and coach. Tal’s published two books: One Year to Freedom, a 1-Year Roadmap to Living Life on Your Own Terms; and, his most recent book and bestseller, The Art of Fully Living – 1 Man, 10 Years, 100 Life Goals Around the World.

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