The Passion of the Non-Conformist
Wisdom on Living Fully with Chris Guillebeau
“The way I’ve always been wired is a little bit different. I have this principle of non-conformity… you don't have to live your life the way others expect.” — Chris Guillebeau
Chris Guillebeau walks to the pile of boxes stacked high against the wall, grabs one from the top, hoists it over his shoulder, and adds it to the stack in the FedEx truck.
And another. And another.
He glances at his watch. It’s just after 12 a.m. and, yet again, he’s sacrificing sleep and daylight to just follow more instructions. It will be this way for another few hours.
But at least he has something preoccupying him to pass the time — his new digital eBay store. He can’t wait to get home to put the final touches on the latest auctions, including old cameras, Lego toy sets, phone cards, and other items he found scattered around his apartment.
“This is way better,” he says to himself as he finally sits down at his computer around 3 a.m. No one is telling him what to do. He can set his own schedule. He can use his creativity. He can make more than minimum wage. “There are problems to solve as opposed to boxes to load.”
Guillebeau quits his job the next day. But he doesn’t just quit FedEx. He quits a life of conformity — and decades later, he hasn’t looked back once.
Even more than that, though, he’s brought others along with him.
Guillebeau’s collection of published book titles says it all: The $100 Startup, The Happiness of Pursuit, Born for This, Side Hustle, 100 Side Hustles, The Money Tree, Gonzo Capitalism, and, of course, The Art of Non-Conformity. He publishes the wildly successful blog by the same name and has a daily podcast, Side Hustle School, which he’s put out every day since 2017.
Somehow, that’s not all. He was also the founder of the World Domination Summit, a cultural gathering I attended year after year that helped ignite my desire to be an entrepreneur, let alone introduced me to some of the coolest people on the planet. The central theme of the summit? How to live a remarkable life in a conventional world.
Above all, Guillebeau walks the talk. He is one of only a handful of people to ever visit every country in the world. He figured out how to carve a career out of blogging before it was a thing. He has even led four world record attempts, including holding the world's largest breakfast-in-bed party and gathering the most people in dinosaur costumes. He’s always been drawn to figuring out how to live life on his own terms.
Guillebeau has been a personal inspiration ever since his book, The $100 Startup, helped to inspire my first major pursuit, my global fitness and lifestyle project 12 Minute Athlete, and since I met him at his summit.
So that’s why I was so excited Guillebeau agreed to my request to be the first On Fire wisdom profile, where instead of telling the story of a passionate person, I interview an expert on the art of living fully. To mix things up and zoom out, I’ll aim to try this about once every ten profiles.
Guillebeau is full of advice on how to live a life that makes us feel on fire. Here are three of the tips that stood out the most to me.
Lesson #1: Be Weird, Together
Travel has been a constant theme in Guillebeau's life. Since he was a kid, he moved around a lot, first with his mom and stepdad with the Air Force, then after getting a graduating with a master’s degree in international studies and deciding to spend a few years volunteering in West Africa as an aid worker. There, he caught the travel bug even more, realizing at one point that he’d already visited over 50 countries — and he was only in his early twenties.
“Why not get to 100 countries?” he thought to himself. As he got closer to that goal, he realized that number would never feel like enough.
“100 is approximately half the countries in the world,” he realized. “The real challenge is to go to all of them.” He officially made it his quest to visit every country in the world — all 193 of them — before he turned 35.
But he didn’t want to do it alone. Guillebeau knew that if he was interested in living a life outside of the typical 9-to-5 approach, others must be, too. That’s when he decided to start his blog, The Art of Non-Conformity, to share his journey with others.
“I thought I was just starting a little travel blog,” he tells me in our interview. “I don’t think I truly understood the power of it until maybe six months into the blog where I started having meetups in different places and the people who came to the meetups had really interesting stories,” he says.
Those early meetups helped Guillebeau realize that he wasn’t alone. He had found his tribe. What had started as a personal travel blog had become so much more — it was a place he could connect with others who had similar passions. He continued building his tribe through his blog, books, podcast, and his summit. To this day, he is one of the best community builders I’ve ever met. But it all started with a realization that one of the best parts of having a passion is sharing it with others, especially when your pursuit is lonely.
Lesson #2: Befriend Naivety
In Guillebeau's story, we find not only belonging, but also beginning — over and over again.
When he first decided he wanted to put on the World Domination Summit, which ended up running for ten years and attracted over 10,000 people from all over the world, he had no previous event planning experience and no idea where to start.
That’s how he likes it.
“There’s a lot of benefit in attempting something you’ve never done before because you don’t know how hard it is, right?” Guillebeau observes. “And maybe if you knew, you’d feel intimidated.”
This initial stage of any project or pursuit, often characterized in psychology as unconscious incompetence, is marked by an obliviousness to the challenges ahead. We don’t yet know what we don’t know.
As a result, we can let our imagination and creativity run free without being bogged down by the knowledge of all the hard work ahead. This is in contrast to stage two, conscious incompetence, where the realization of our knowledge gap hits. We start to realize just how much we don’t know.
“Stage one is way better,” he responds with a chuckle as I summarize the theory to him. “I like stage one.”
Of course, it’s clear that Guillebeau also thrives on the more demanding parts of the learning process. He’s one of the most prolific people I’ve ever met. He consistently sees each challenge through to its resolution.
How does he manage this? By breaking down everything into checklists. He believes everything is doable when we break it down enough (this approach reminds me of B. Earl’s micro-actions suggestion — there are so many passion patterns if we learn to look for them!). This is how he built the World Domination Summit, one checklist item at a time.
But it all started by permitting himself to be naïve enough to go for it — and assume he ultimately would find a way to realize the dream.
Lesson #3: Look for the Layers of Love
But even those with many passions have to choose among all the options. How does he decide where to put his heart?
Usually, he says, his passionate pursuits come to him in layers. He starts with a spark of an idea, takes notes, makes outlines, and continues to build on it until the idea crystalizes in his mind.
This is what happened with his latest project, A Year of Mental Health, where he writes about purposeful productivity and his own experiences with ADHD, anxiety, and depression.
“There was a series of confirmation messages,” he says when I ask him how he came up with the idea. First, somebody reached out to him from Substack. Then he noticed the positive reception he was getting from sharing more about neurodiversity on social media. "At some point, I decided I want to go into this and go deeper with it.”
And since he likes having a clear package and format for sharing his ideas, he reached out to his contact at Substack and his newsletter was born.
His advice for others trying to figure out which passion to pursue? Let yourself be drawn into your passions. At first, it can feel daunting.
“It can feel discomforting at times because you're like, ‘I feel like there's a gap between where I am now and where I want to be — and I can't get over that gap. And until I get over that gap, I'm not going to be able to start the thing or make progress.”
Having taken those steps himself again and again, he says, he wants people to know that the rewards on the other side far outweigh the initial fears and doubts.
“For me,” he says, “sometimes it’s helpful to ask, ‘Okay, if I have this idea, and I'm drawn towards something, but I don't do anything about it, how am I going to feel?’”
Whenever he’s gripped by an idea he can’t shake, he knows he must chase it, despite any initial doubts or fears. The alternative — living with regret and self-resentment — is not an option for him.
“Whereas if I take that step,” he says, “I know I'm going to actually feel proud that I did it. I don't know what's going to happen with it. I don't know what the outcome will be. But that's not the important point.”
“The important point,” he adds, “is to believe in yourself and worry less about the perfection of it and more about the initiative of it.”
Love this one!!! Living a life of non-conformity is both challenging and invigorating...as well as being just a tad bit scary 😉
Such and important article! Especially for those young adults who are feeling so utterly dissatisfied with life and dive to the black hole of depression, self-loathing and hopelessness. Would love to know if Chris has any insights to coaching models accessible for those in the black hole. Another superbly written article, Krista!