Chris Guillebeau's 'The Happiness of Pursuit'

The Happiness of Pursuit

Feeling dissatisfied with the daily grind? Craving a sense of purpose and meaning in your life? According to Chris Guillebeau, you might need to go on a quest. Natasha reviews his latest book The Happiness of Pursuit, and shares its key lessons.

I really wanted to love this book.

Chris Guillebeau is a world traveller, blogger, travel hacker, author, creator of the World Domination Summit, and an inspiration to thousands.

His first book, $100 Startup, is one of my favourite career-change go-to guides, and I was buzzing with excitement when I saw the title of his latest offering: The Happiness of Pursuit.

The book centres around the idea of a ‘quest’: "a journey toward something specific, with a number of challenges throughout. Most quests also require a series of logistical steps and some kind of personal growth."

Quests, Guillebeau explains, often arise as a reaction to a sense of discomfort or discontent with life: boredom with the status quo or, as one interviewee explained, "that horrible feeling that other people were steering my life". They are projects designed to regain a sense of control or meaning over your existence, or to imbue life with a direction and purpose that previously felt missing. A quest seeks to answer the question: What do you live for? Once your basic needs are met, why are you here?

The Happiness of Pursuit goes on to explore the common features, themes and challenges of quests – ultimately, it seems, to help show you how to create and go on a quest of your own.

Written in 17 chapters over three parts ('Beginnings', 'Journey', and 'Destination'), Guillebeau covers topics such as Self-Reliance, Time and Money, Misadventures and Homecomings. How do you decide what your quest should be? What makes your quest a quest, rather than a project? What happens when things go wrong? How do you deal with other people on your journey?

Like $100 Startup, The Happiness of Pursuit was researched through interviews. Guillebeau contacted hundreds of people who had been on quests of their own, and used their stories to inform and support the book.

We meet people like Miranda Gibson, who spent a year at the top of a eucalyptus tree in Tasmania to combat the industrial logging companies in the country. We meet John and Nancy Vogel, who took their twin boys on a three-year cycling journey from Alaska to Argentina. And we hear of people like John Francis, who decided to travel only on foot, and to take on a vow of silence to boot. 

While this was a practical and engaging approach in $100 Startup, it missed the mark this time around.

While the examples Guillebeau uses are fascinating, he leans far too heavily on the quantity of examples he has gathered, rather than teasing out their quality. Guillebeau uses as many as seven people’s stories in a single chapter, leaving the reader feeling both over-stimulated and under-satisfied. I was left feeling repeatedly cheated, full of questions, and often dizzy with the number of stories I had to keep up with in each chapter. Which one was Sandi again? Wait, I thought we’d left Tom back in Chapter Three... is this the same Tom we’re talking about or a new one?

In The Happiness of Pursuit, Guillebeau has attempted a balance between high-level theoretical exploration and practical, hands-on advice; as a result, he's slightly missed the mark on both.

As a surface-skimming introduction to the idea of a quest and a theoretical How-To guide, The Happiness of Pursuit is an interesting read. An if you enjoy tales of adventure and high-level daydreaming about what you might do if you had no mortgage / no full-time job / more guts, you’ll enjoy dipping in and out of it.

But if you actually want to take on a quest and are seeking guidance on how to go about it, don't rely on The Happiness of Pursuit to show you the way. It’s inspiring to read the stories of those who have paved the way, but, as Guillbeau says in Chapter Five ('Self-Reliance'), it’s ultimately down to you.

Top Takeaways:

  • Quests arise in the space where discontent and inspiration meet: "If you want to get the embers burning, you have to blend dissatisfaction with inspiration, and then you have to connect the dissatisfaction to a greater purpose."
  • Planning is good, but at some point you have to just do it: "Asking 'What gear should you use?' is the wrong question. The better question is 'What are you waiting for?'"
  • A quest isn’t just something you do. It becomes who you are: "You can always say that you’re a teacher or a student, an accountant or an artist, or whatever your vocation. But once you have a quest, you have another answer, too. Your identity isn’t tied to a job; your identity is who you really are. 'I’m trying to visit every country in the world. I’m going to produce the largest symphony ever performed.'"
  • The reality of a quest isn’t in its fulfilment; it’s in the hard slog in the middle: "The long, slow grind of working toward something is all about loving the process. If you don’t love the process, the grind is tough."