Interview with New York Times Bestselling Writer, Traveler, and Entrepreneur Chris Guillebeau

 This week I have another interview to share, this time with writer and entrepreneur Chris Guillebeau. 

Chris began making a name for himself when he launched a project called the Art of Non-Conformity (, which involves helping people discover how to achieve personal goals while doing their part to improve the world. This blog led to the publication of a book of the same name, which has since been translated into more than 20 languages. He followed this by releasing The $100 Startupwhich quickly became a New York Times Bestseller.

Today (September 9, 2014) Chris released his third book, the Happiness of Pursuit, which delves into the experiences he encountered as he spent the past ten years visiting every country in the world. (Yes, EVERY country.)

And now that we’re all acquainted…


Can you tell us a little bit about The Happiness of Pursuit?

In some ways, my new book The Happiness of Pursuit is about the journey to every country. I wanted to share lessons from the adventure and a few travel stories. But fortunately, that’s just a small part of the text—I didn’t want to only write a memoir, which can often come across as self-indulgent and tends to attract a limited audience. This book is much more about the quests and adventures of other people. I wanted to understand why people pursue quests, how they’re changed along the way, and what we can learn from them.

Lastly, it’s not meant to be a dry academic study. The book has a clear message: a quest can bring purpose and meaning to your life, too—and here’s how you can develop your own.

Many people find it difficult to achieve a lasting sense of life satisfaction. Why do you think this is?

Because they don’t live in the present while building for the future.

Do you think that it is presumptuous for writers such as you, me, and many others to undertake writing prescriptively? The vast majority of us don’t have degrees in anything relating to self-improvement or anything like that. I guess what I’m asking is, what gives a writer (or anybody for that matter) the authority to disseminate their views on what it means to live a better, healthier, and happier life?

If anyone has a degree in self-improvement, you should run far away from them. 🙂

I think it’s presumptuous for people to go around saying “Here’s what you should do with your life.” For the most part, I don’t do that, and presumably you don’t either. Instead, what we can do is talk about common challenges and specific solutions that we’ve found to be true.

In my case, I share from my own perspective as well as those I talk to. Some people will relate to it and others won’t. For those who don’t, I always say, “Great—please share your perspective with the world. We probably need it!”

You’ve visited every country in the world. Which countries offered the most challenges?

In my case, the greatest challenges were geopolitical and logistical. I had to get to far-off island nations with limited flights, such as Kiribati and Tuvalu. I also had to get to countries that have little in the way of formal governance, such as Somalia or South Sudan. And I had to get to the few countries that are outright hostile to (some) western visitors, such as Iran and Pakistan.

There were also lots of things that went wrong along the way, from car accidents (Italy) to deportation (Eritrea). I tried to keep focused on long-term outcomes, and I knew it would be worth it if I didn’t give up.

What’s up next for you?

I hope to continue writing and traveling for as long as I can. Now that I’m not as focused on visiting new countries, I hope to be able to better serve people and make a small difference in the world.

If you had to boil down your view on how to live well into a one or two sentence prescription, what would it be?


What’s the #1 thing that someone seeking a happier life can do today to get that ball rolling?

I used to have a screensaver that read, “Why do you do this every single day?” Every time I opened my laptop, I was forced to look at it. Maybe you don’t need the screensaver, but I think you should ask yourself why every chance you get. The better an answer for the why question, whatever it is, the happier you’ll be.

Finally, it’s time to get prophetic. What do you think our chances are as humans? Where are we headed from here?

Hmmm… that’s a tough one. There are certainly real challenges ahead, especially regarding climate change and the implicit conflicts between superpowers like China and the U.S. But I’m mostly an optimist, and I do believe in the ability of the human spirit to create positive change. So I suppose it’s a toss-up. 🙂

One thought on “Interview with New York Times Bestselling Writer, Traveler, and Entrepreneur Chris Guillebeau

  • September 16, 2014 at 12:40 pm

    Awesome interview, short and sweet. I particularly like your question (and Chris’ answer) about prescriptive writing. It’s ubiquitous these days, and it ties in with self-doubt.

    I often hear advice given to bloggers to “become an authority” to their audience. That can be a pretty daunting proposal if you don’t have any credentials to back you. But I’ve always felt that first-hand experience is just as valuable, if not more valuable than formal education. Especially in the area of personal growth as you touched on.

    Great post!


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