The Happiness of Pursuit: Chris Guillebeau on Finding the Quest That Will Bring Purpose to Your Life

Hearing the words “once upon a time” brings a tingle to my spine: memories of hearing Dr. Seuss folklore, tales of Odysseus fighting to find home and my first read ofThe Alchemist.

There’s an element in a quest that captivates like no other and helps one re-discover life’s purpose. To explore this premise, I recently sat down to interview Chris Guillebeau, the author of The Happiness of Pursuit: Finding The Quest That Will Bring Purpose to Your Life.


Like many others post 9/11, Chris struggled to find his place in the world. He said, “I hadn’t lost anyone personally in that (9/11), but I was depressed like a lot of other people and just thought, ‘Okay, how can I contribute to something positive and meaningful?”

Chris then started a quest that many couldn’t even fathom. After four years of volunteering on a medical ship, Chris set out to travel to every country in the world. And he succeeded, completing his quest before the age of 35.

Propped up on a plastic chair in the middle of an airport in Senegal — just two countries shy of visiting every country in the world — Chris struggled through a fitful two hours of sleep. He thought in an almost masochistic way, what is it about the human experience that craves a quest?

Take a quick look around and our history is saturated with quests. Our ears perk up when we hear stories told from Homer or Paulo Coelho. Stories of human struggle, travel, and identifying purpose.

When we break free from routine schedule and travel, it’s very disruptive. Chris said, “It takes your patterns and your routines and kind of forces you to flip them and it can be uncomfortable.” In that land of discomfort, we’re forced to re-prioritize and set straight what really matters.

Not all of us can go on a 10-year journey to visit every country in the world (though Chris has proven it can be done affordably). Adding a sense of vagabonding once a year, even if it’s just for a few days, can prove to set straight one’s purpose in life. In his instructions for life, keep in mind that The Dalai Lama has also suggested that once a year, you go someplace you’ve never been.

The act of physically traveling can be impossible for some, so Chris suggests alternatives. He said, “Adventure is not exclusive to travel…there are many adaptations.” Robyn Devine, for instance, set the audacious goal of knitting 10,000 hats and creating the charity Hat-Along which gives hats to children who may struggle to afford one.

Physically unable to travel, The Female Yoda has also gone on the quest of creating a new hope for those struggling to stay positive in the dark side of lyme and chronic illness.

To create your own quest, Chris identifies 5 key qualities:

  1. A clear goal and a specific end point
  2. A clear challenge
  3. A sacrifice of some kind
  4. A calling or sense of mission
  5. A series of small steps and incremental progress toward the goal

Chris adds, “to sum it up, a quest is a journey toward something specific, with a number of challenges throughout.”

What’s your current quest? I’d love to hear it so please share it below. Make sure to provide a hyperlink so others can share in it too.

(Read the entire interview or listen to it here.)

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