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The Art of Non-Conformity: Chris Guillebeau on Living An Unconventional Life & The Power of Divine Moments

By September 18, 2016January 26th, 2024No Comments

“We often feel paralyzed by choice and make no choice. But the thing is, no choice is a choice.”

Chris Guillebeau

In the mid-1800’s, this radical dude living alone in the woods famously wrote, the mass of men lead lives of quite desperation. What is called resignation is confirmed desperation.

As set forth in the enduring Walden, the words of Henry David Thoreau were revelatory for the time. But it’s an idea that more than holds up. Not only do I consider it daily, I would contend it perfectly encapsulates what has become the unfortunate, yet defining affliction of modern man.

This week’s guest has devoted his life to helping others avoid Thoreau’s foreboding lament – a self-experiment in purposeful living he calls The Art of Non-Conformity.

Ripe with wanderlust after a 4-year stint as a NGO volunteer executive in West Africa, Chris Guillebeau embarked on a multi-year quest to travel to every country in the world, all 193, before his 35th birthday. Along the way, he decided to share his adventures on a newly hatched blog. But what began as a rather ignored and somewhat turgid travelogue soon morphed into a globally revered portal chronicling the personal experience, lessons and wisdom earned and learned not just by Chris, but by a dynamic multitude of unconventional people overcoming conventional social mores around work, life and travel to achieve personal goals and greater life satisfaction.

The blog exploded, capturing the intrigue, trust and fascination of people all across the world thirsty for the brass tacks steps and inspiration required to pursue more adventurous and personally fulfilling means of working and living outside traditional paradigms.


With the success of the blog, it’s not surprising that books soon followed. The Art of Non-Conformity* was translated into more than twenty languages. His second book, The $100 Startup*, was a New York Times and Wall Street Journal bestseller, selling more than 500,000 copies worldwide. His third book, The Happiness of Pursuit*, was also a New York Times bestseller. His most recent book, Born for This*, will help you find the work you were meant to do.

When he’s not writing bestselling books or traveling to parts unknown, you’re likely to find Chris diligently working on his World Domination Summit —  an annual gathering he founded six years ago that brings thousands of creative, remarkable people together.

Everybody loves a good travel hack. The basic steps to launch a new business. Or the path to overnight success. If you’re looking for Chris’ answers to those questions, you’re in the wrong place.

I’m more interested in the man behind the work. What makes Chris tick. How he sees himself in the world. And how that perspective infuses his life with purpose, community, service and the strength required to continually grow and evolve.

Specific topics explored include:

  • inspiring people to live unconventional lives
  • aspiration vs. inspiration
  • following through with the journey
  • the blogosphere, ideas, and community
  • geocentricism
  • Chris’ unconventional quest
  • selfish generosity
  • what is your guiding principle?
  • following your passion through exploration
  • coping with grief & loss
  • self-help, authenticity, and transparency
  • perceiving alignment/balance
  • passion vs. obsession
  • serving, strengthening, and cultivating community

Beyond the bullet points, this one’s special — honest, raw and real. My favorite kind of exchange. When the dust settled, I felt like I found a new friend.

I sincerely hope you enjoy the conversation.

Peace + Plants,


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Background, Context & Reference

Notable Works/Books Discussed in today’s podcast

Notable People Discussed In Today’s Podcast

Related Podcasts You Might Enjoy

Thanks to Jason Camiolo for production, interstitial music and audio engineering; Chris Swan for production assistance & show notes; Shawn Patterson for graphics.

*Disclosure:Books and products denoted with an asterisk are hyperlinked to an affiliate program. We are a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for us to earn fees by linking to and affiliated sites.

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