Jack Covert Selects

Jack Covert Selects - The Happiness of Pursuit

Sally Haldorson

September 12, 2014


Chris Guillebeau didn’t know he had set out on a quest to travel to every country in the world until he had traveled to the first 50.

The Happiness of Pursuit: Finding the Quest That Will Bring Purpose to Your Life by Chris Guillebeau, Harmony Books, 292 pages, $25.00, Hardcover, September 2014, ISBN 9780385348843

Chris Guillebeau didn’t know he had set out on a quest to travel to every country in the world until he had traveled to the first 50. At that point, he realized he could achieve the kind of goal that at one time might have seemed indomitable. But, Guillebeau writes:

Experience produces confidence, and confidence produces success.

To have traveled the world over, literally, brings to mind a super hero or Indiana Jones-type adventurer, but I’ve had the pleasure of meeting and talking with Chris and I don’t think he would mind me telling you that he is pretty much a regular guy. And that fact is key to the message of The Happiness of Pursuit, as well as his other books, The Art of Non-Conformity and The $100 Startup. Anyone, Guillebeau tells us, can set out on a quest and pursue adventure. And everyone, he assures us, has a calling (in any form, big or small) and the capability to answer that call.

The Happiness of Pursuit drops us directly into Chris Guillebeau’s quest. He has arrived in Dakar, on his way to Guinea-Bissau, the only country in Africa he has yet to visit. But this book is less a memoir of Guillebeau’s travels, and much more a celebration and recitation of the quests that other “regular” people undertake in an effort to bring meaning into their lives.

Why are we recommending this book to a business audience? Because Guillebeau has long since encouraged people in business to work differently, to push the boundaries of what is comfortable, in order to scratch whatever itch they become obsessed with in the name of innovation, creativity, or self-fulfilment. Now Guillebeau extends his encouragement beyond the workplace and, in his humorous and accessible style, argues again that the solution to discontent isn’t passivity or fatalism.

Metaphorically, discontent is the match and inspiration is the kindling. When discontent leads to excitement, that’s when you know you’ve found your pursuit.


Intimidated? You needn’t be, because the stories told within The Happiness of Pursuit range between the everyday quest (Sasha Martin, in a rut in Tulsa, decides to make and serve a full meal from every country in the world for 195 weeks, and Alicia Ostarello, single and frustrated in San Francisco, CA, visits all fifty states and goes on a date in each) to the mind-boggling (John “Maddog” Wallace has run over 300 marathons, and Tom Allen took a cycling trip around the world despite little experience biking) to the famous (Chris McCandless’s fatal adventure in Alaska) to the manageable (making a “bucket” list and checking off each small change one by one, or setting out to acquire enough rejections—manuscript submissions or just asking for a discount—so that rejection itself doesn’t hurt so much.)

Quests can also be inspired by a desire to improve the world. Consider Scott Harrison who started the nonprofit Charity: Water, or Miranda Gibson who took up residence in a eucalyptus tree on Tasmania to protest industrial logging. Guillebeau isn’t requiring us to lay down our lives; he is simply encouraging us to seek meaning, however that is defined for us as individuals.

Not every calling is religious or explicitly moral. People who are nonreligious, or whose religious practice is more personal, also speak of embracing a calling when they inch closer towards the goals they set. Whether it’s writing, crafting, or saving the world, submitting to a purpose greater than yourself can prove fulfilling.


Guillebeau organizes his book in three sections: Beginnings, Journey, and Transformation, following the classic narrative arc of adventure stories. Within each section are thoughtful and entertaining chapters, most notably, “Defining Moments,” which tackles the sobering topic of mortality as a prime motivator. Guillebeau believes that “the more we’re emotionally aware of our own mortality, the more we feel compelled to live with a sense of purpose.” And the included stories make clear that we should not wait until the end of our lives to live them.

Many of us feel overwhelmed by the idea of setting forth on a lifelong, or even a year long, quest. Guillebeau offers methods to reduce the stress, finance the journey, and manage the details, as well as a handy chart to inspire your own choice of adventures. After all, he has traveled to nearly 200 countries: he knows something about packing light while gaining a world's worth of self-reliance, perspective, and satisfaction, all of which he wishes for you, as well.

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