A blog about travel, good books, and living life as an experiment.

“The Art of Non-Conformity: Set Your Own Rules, Live the Life You Want, and Change the World” by Chris Guillebeau

Chris Guillebeau's the Art of Non-Conformity

I first came across this book while listening to the Maverick Show podcast with Matt Bowles, and as soon as his guest, Sergio Sala, mentioned the book, I knew I had to buy it.

While the title, itself, is incredibly captivating, Chris Guillebeau does a masterful job at engaging readers, inviting them into his mindset, and motivating them to pursue the life they truly want instead of the conventional one that’s laid out for them.

Don’t be a Monkey

In one of the clearest examples of how most of us go through life sleepwalking like Zombies, Guillebeau shares the experiment of the 5 monkeys.

In short, there are 5 monkeys in a cage with a banana on top that’s slightly out of reach. Every time one of the monkeys tries to climb up to grab the banana, it is doused with water from a fire hose and the other monkeys below also get soaked.

After a few attempts, the monkeys learn that they can’t grab the banana. The behavior becomes so engrained that when new monkeys are placed in the cage, the other monkeys prevent it from going up the ladder because they, too, will be doused with water.

After a while, none of the original monkeys are in the cage, yet they all choose not to pursue the banana. They don’t make this decision for fear of getting doused with water—they don’t even know this will happen.

The monkeys choose not to climb up the ladder because they simply have learned, through other monkeys previously in the cage, that they can’t. 


“If you’re stuck in a cage, it’s time to smash the glass around you and crawl your way out. You don’t need anyone’s permission to climb the ladder, and you don’t need to apologize for escaping”

The Art of Non-Conformity (Gillebeau, 2010, p. 18)

Guillebeau compares this to the way many of us go through life sleepwalking, settling for what’s “good enough” without questioning what else there is to offer.

This was such a simple story that told so much. 

Of course, you go to college and get a full-time job with health insurance and maybe some time off here and there.

That’s what we do in the cage!

Guillebeau is saying, “Woah! Hold on a minute. Not so fast…”


“The purpose of this book is to transform your thinking about life and work.”

The Art of Non-Conformity (Guillebeau, 2010, p. 3)

How could you not be encouraged (and challenged)?

Page after page, Guillebeau pushes us to get out of this self-constructed bubble of conventionality and live life on our terms. 

This isn’t a popular opinion, especially among many in my parents and grandparents’ age range, nor is it an easy thing to do, but reading this book makes you want to run toward non-conformity as if your life depended on it. 

For many of us, it does.


“When faced with uncertainty about taking a leap of faith, take the leap. You’ll regret the things you didn’t do much more than anything you did, so you might as well try new things.”

The Art of Non-Conformity (Guillebeau, 2010, p. 40)

Conventional life is simply not an option for those of us who want more than what has traditionally been within reach.

For those of you who don’t already fall into this camp, I promise you this book will turn you into a believer. 

What’s the worst that could happen?

One of the simplest questions one could ask themselves, yet one of the most impactful: What’s the worst that could happen?

Guillebeau encourages us to do exactly this, and it is so empowering!

I’ve posed this question to myself time and again, particularly throughout the last few months.

Yes, this endeavor I’m about to embark on is scary—no “secure” job, living out of a suitcase, and all alone in a different country. But asking myself what’s the worst that could happen has made me realize that, in reality, the worst outcome really isn’t that bad.

I appreciate Guillebeau for reminding me of this.

Graduate School

Though there are some key differences between my situation and Guillebeau’s time in graduate school, his chapter on graduate school made me question a lot.

He writes about his experience paying $32,000 for a master’s degree that wasn’t all that valuable. He even compares what he gained from completing the degree versus what he gained writing his blog and learning outside of the classroom—by far, the latter was much more valuable. 

This was not the easiest chapter to read, given that I’m currently pursuing a Doctoral degree, and writing a blog. 

He writes how his thesis was read by 3 people who essentially said, “good job”. Further, he states how he spent so many hours doing work that was not in an anyway meaningful, whether that was completing administrative tasks or fixing stuff in his thesis that his advisors did not agree with.


“My experience in academia was that I had to focus on pleasing people far more than doing good work”

The Art of Non-Conformity (Guillebeau, 2010, p. 115)

I feel your pain, Chris!

There were some points where I thought: “should I leave school?”

All in all, I know the answer to this question, which is no

For me, personally, most of the degree has been paid for by my job. I enjoy what I’m studying very much. And lastly, it’s a great backup plan if I ever decide to jump back into the world of work.

Still, his words made me wonder…

Guillebeau’s Perspective on Work

Guillebeau’s perspective on work was indeed refreshing. 

I’ve been reading a lot lately about work: from The Pathless Path to Do Nothing, the opinions have been insightful and thought-provoking.


“I’m also skeptical of the idea of eliminating work or reducing it to its most limited elements. It’s not that I think there’s anything wrong with making more time for family or activities you enjoy. I just think that if someone is unhappy with how they are spending their workday, the answer is to find better work.”

The Art of Non-Conformity (Guillebeau, 2010, p. 102)

Yet, Guillebeau’s message is slightly different.

In contrast to those who posit we need more of “nothing” time, he’s instead saying we need to make work better for ourselves. In other words, the goal isn’t to fill our days with blank schedules, but rather to fill them with meaningful work that gives us energy.


“Dont just escape from something. Escape to something”

The Art of Non-Conformity (Guillebeau, 2010, p. 103)

His concept of “eliminating the unnecessary” is particularly important here. 

He states that if you want to live a life of non-conformity, you have to make active decisions to get to that place, one of which is eliminating unnecessary tasks as well as those you don’t value but ultimately do just for the sake of doing. 

Even before reading the book, I was actively working on eliminating the unnecessary and filling my days with more of what I want to do: in Chris’ words, this is convergence

Guillebeau’s message is so compelling  

A big reason for this is due to his writing. 


“I’d like to keep the bullshit and the mediocrity to a minimum. It’s a short book and there’s a lot to cover”

The Art of Non-Conformity (Guillebeau, 2010, p. 6)

He’s so honest, direct, and not concerned with winning you over that he does exactly that. He tells it like it is in a way that’s quite reminiscent of Tim Ferris’ Four Hour Work Week.

Moreover, unlike a lot of other books, in The Art of Non-Conformity, Guillebeau shares his perspective and the journey he’s been on—not to prove to the reader why you should be listening to him. Rather, it’s to describe how he doesn’t have it all figured out, but he has learned some things along the way that might be of value.


“I adhere to a guru-free philosophy, and I don’t claim to have all the answers. What I have done, for better or worse, is chosen freedom as my highest personal value and learned to construct a life around that choice.”

The Art of Non-Conformity (Guillebeau, 2010, p. 12)

For all of these reasons, Guillebeau’s message is that much more compelling.

If you believe in living a different life, one not dictated by the norms and conventions of everyday life, this book is for you.

If not, I guarantee this book will change your mind.

Thank you, Chris. This was an amazing read and had quite an impact on me.

‘Till Next Time Travel Friends 


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Meet Jovan

Sintra Castle

Hi, my name is Jovan. I’m a Doctoral student who’s pursuing a PhD in Higher Education. I’m also an avid traveler and striving to do it full-time! Some of the things I’m most passionate about are immersing myself in different cultures, reading, and helping others lead the lives they want to live. Thanks for visiting!