Talking to Chris Guillebeau About His New Book, ‘The Happiness of Pursuit’


I have been a fan of Chris Guillebeau’s work for years. I took his Empire Building Kit course when I was starting my first ventures into entrepreneurship, and continued my education with his book The $100 Startup.

Chris’s newest book, The Happiness of Pursuit: Finding the Quest That Will Bring Purpose To Your Life, released last week. I was lucky enough to receive an advance copy, and as soon as I finished reading the book I asked Chris if he’d be willing to answer two questions about his book for Billfold readers.

Nicole: I really liked that you were realistic about how much the various quests you profiled cost to complete, and that you offered low-cost or free alternative suggestions to readers who might want to do something like “walk across the United States” but not want to quit their jobs or not have the available funds. If people are worried about the monetary cost—or opportunity cost—of going on a quest, what advice do you have to help them in their decision-making?

Chris: Make no mistake: a quest should involve some kind of cost. If you believe in something and want to pursue it, it will inevitably involve some degree of tradeoff with something else. And that’s okay! It’s not a quest without cost, and it shouldn’t necessarily be easy.

That said, one of the things that was extremely helpful in the beginning of my quest was when I began clearly delineating and preparing for the expected “time and money” costs. I was able to visit my first 100 countries for just $30,000. I don’t mean to suggest this is a small amount of money, but compared to the wealth of experiences I had, it was completely worth it. So in other words, it’s also helpful to think about value, not just cost.

Nicole: In June 2013, I completed a three-year-long quest: first I put music on YouTube for 100 consecutive weeks, then I toured the country playing geek music at conventions, then I recorded an album in a professional studio with a Los Angeles band. When I read your book, I thought “I’ve sold my stuff, uprooted my life, and quested, but now I want to stay where I am and build.” Do you think that the urge to quest goes in cycles? Does it alternate with the urge to find home again and build a life? Are these two desires exclusive, or can they co-exist?

Chris: What an awesome project! I remember following some of it through your blog.

I’m not sure about the urge to quest but I think the urge to strive is somewhat constant. There are different seasons to questing. It completely makes sense that you’d want to do something different after completely such a big adventure. I don’t think you should write off questing forever, though. It’s a hard habit to quit.

So now I’m curious: what are your thoughts on the idea of questing, striving, uprooting, building? Do you feel like monetary costs and opportunity costs get in the way? Are there quests you want to take but you don’t know yet how to take them? Have you ever regretted going on a quest, or regretted not going on a quest? Chris’s book has a lot to share about the idea of questing, but let’s start the discussion here.

Photo: Jeff P



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