Chris Guillebeau’s Secrets to the Happiness of Pursuit

Want to conquer the world, or at least your very own tiny piece of it? Then get to know Chris Guillebeau, the easy-on-the-eyes, hard-to-put-down-books-writing self-help helper extraordinaire. His very popular blog, The Art of Non-Conformity, explores entrepreneurship, travel, and personal development topics. At his site you can also download his Brief Guide to World Domination and learn more about the World Domination Summit he organizes each year.  As the author of The $100 Startup: Reinvent the Way You Make a Living, Do What You Love, and Create a New Future, Chris is the go-to guru for fledgling entrepreneurs. I was lucky enough to get an advance copy of Chris’s brand-new book, The Happiness of Pursuit: Finding the Quest That Will Bring Purpose to Your Life. It’s a great read full of inspirational stories of people who find purpose in their lives pursuing their own unique “quests.”  A “playbook for making your life count”, it encourages readers to make their lives about something — and follow-up with the focus and commitment needed to make their quests a reality. (Chris knows from where he speaks, literally. He recently completed his quest to visit every country in the world before turning 35!)

I was extra lucky to get a chance to catch up with the very busy Mr. Guillebeau to find out about the book’s backstory and get his insights on how we can find happiness and success pursuing our own “quests”:

DIXIE: WHAT MOTIVATED YOU TO WRITE THIS BOOK? WHO NEEDS THIS MESSAGE MOST?

CHRIS: I wrote the book partly as a way to reflect on my journey to every country in the world—but fortunately I didn’t stop with that. Along the way, I also met a lot of people who were also undertaking quests. Many of these quests were travel-oriented, like mine. I met a young woman who sailed around the world in a small sailboat, and I met a young guy who walked across America. But many of the people undertaking quests had very different projects: to knit 10,000 hats, for example, or to produce the world’s largest symphony, or to train an untrainable horse.   I wanted to take all these stories and combine them into a single message: the story of living for adventure. The book is for everyone who wants more out of life, everyone who enjoys a challenge and wants to craft a truly remarkable life as they make plans for the future.

DIXIE: HOW DOES ONE FIGURE OUT JUST WHAT ONE’S LIFE PURPOSE IS? HOW DO WE IDENTIFY OUR “QUESTS”?

CHRIS: Well, “life purpose” can be a tough one—but I think you start by figuring out what you’re excited about and what you’re bothered by. In the book we used a checklist to ask people if they might be especially well-suited to a quest. It looks something like this:

  • Do you like making lists and checking things off?
  • Have you always enjoyed setting goals?
  • Do you feel motivated by making progress toward a goal?
  • Do you enjoy planning?
  • Do you have a hobby or passion that not everyone understands?
  • Do you ever find yourself day-dreaming or imagining a different kind of life?
  • Do you spend a lot of time thinking about your hobby or passion?

The more answers you say “yes” to, the more likely you are to enjoy pursuing a quest.

DIXIE: HOW DO YOU DEFINE THE “QUEST”? WHAT ELEMENTS SHOULD EVERY QUEST HAVE?

CHRIS: Every quest has a few things in common. First, there’s always an end or final destination. Ultimately the process is more about the journey, but you also need something to strive for. It helps to have something specific: in my case, I went to every country in the world, not just “a bunch of countries.” The woman who’s knitting 10,000 knits isn’t just “knitting every day.” Having a clear goal or outcome makes a big difference. Every quest should also have a real element of challenge to it. If your quest is to take a long walk in search of a Frappuccino, that’s not a quest. This doesn’t mean that it needs to be impossible—but somehow it should involve challenge, sacrifice, or at least a real tradeoff as you have to say no to some things in order to say yes to the quest. Finally, we learned something else: most of the time, something else happens along the way. Almost everyone who undertakes a true quest is changed along the way.

DIXIE: IN THEIR QUEST TO BE HAPPY AND/OR SUCCESSFUL, WHAT DO PEOPLE GET WRONG?

CHRIS: They think that happiness is dependent on external circumstances of some kind. Don’t get me wrong: circumstances matter. It’s a lot better to be rich than poor. But you can also be happy in challenging circumstances, and you can be miserable in comfortable circumstances. In the end, happiness is a decision you make more than a temperature you check. You have to understand what you find meaningful, and you have to take the time to do those things.

DIXIE: WHAT ABOUT PEOPLE IN MID-LIFE WITH RESPONSIBILITIES, FAMILIES AND OTHER PERCEIVED OBSTACLES OR ROADBLOCKS TO FULLY PURSUING THEIR QUESTS — WHAT ADVICE (OR ADMONISHMENTS) DO YOU HAVE FOR THEM?

CHRIS: I certainly don’t have any admonishments. In some ways I think it’s easier when you have those responsibilities and roadblocks, because you have more limited time and thus you need make that time truly count. One thing I learned from the book was that a lot of creative people are always talking about how we should “think out of the box”—but that’s not always helpful advice. Many times, to get what we really want, or to pursue a big dream, we need to limit ourselves and focus on what matters. Essentially, we need to “get in the box”! I also think the theme of reinvention, which is a big part of my overall work, is very applicable to people in mid-life. After you’ve had a number of career and life experiences, you may be better suited to knowing what you like and dislike. You have the benefit of many successes and probably at least a  few failures. Perhaps you’re also more conscious of the matter of urgency—the fact that life is short and the imperative to make our lives count. Lastly, there’s a reason why most people don’t start running marathons until well past young adulthood: the long game becomes more attractive as time goes by. In mid-life, you have emotional and intellectual stamina that perhaps wasn’t as strong as your early days. If you want to focus, if you want to truly invest in something, you know you can give it your all. So I think you’re in a good place, in other words.

DIXIE: WHAT DO YOU WISH YOU’D KNOWN AT 20?  

CHRIS: When I was 20 I was busy learning a variety of skills, some of which ended up being helpful while others ended up being useless. This is fairly normal, I think. But in addition to learning skills, I also felt pretty unconfident and insecure about a lot of things. So if I could have go back and teach myself something, I don’t think it would be a specific skill; it would be more of a pep talk. I’d say, “Hey, 20-year-old self, keep working on stuff. Someday you’ll make something that matters to people. It’s okay if you get frustrated, but don’t hate yourself and don’t be unkind to others just because you don’t always see the path that lies ahead.” –

Calling all my Dames: What’s YOUR quest?  We’re dying to know! Meanwhile, check out Chris’s blogs or books to get the inspiration you need to get goin’!

A version of this interview also appears on LikeaBossGirls.com

Dixie Laite - Dame Town Writer

Author: Dixie Laite

I'm a bullshit-slaying, life-figure-out-ing, pop culture-enjoying, DAME. A woman long obsessed with figuring out how to be...a woman. Through my own crazy life, pop culture, and the old movies I grew up on, I've learned a lot. Much of which I'd love to share. Much of which I need, desperately, to UNlearn. I'm straightforward, unfiltered, sassy, heartfelt, vulnerable and bold. Yep, all that. I'm into kindness, animals, books, the new Coach collection, and the perfect pair of black moto boots.

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