Nonconformity, Self-Reliance, And Starting Over: An Interview With Bestselling Author Chris Guillebeau

Epictetus tells us about how the Stoic Agrippinus was like a red thread, the piece of fabric that stands out. People often asked Agrippinus why he couldn’t just be “normal,” why he couldn’t just be like everyone else. “And if I do that,” Agrippinus liked to answer, “How shall I any longer be the red?” One biographer tells us about how Marcus never stopped reading, studying, or attending lectures even though “others continued to sneer at him for his commitment to philosophy.” In short: the Stoics were different. They had the courage to be their true, authentic, selves. Cassius Dio points out that Marcus had no interest in doing anything for the sake of posturing, “Nothing could force him to do anything alien to his own character.” 

Chris Guillebeau—the New York Times bestselling author of The $100 Startup, Side Hustle, and The Art of Nonconformity—has helped millions of people live authentic, self-reliant, meaningful lives. His new book The Money Treehis first work of fiction—is the story of overcoming significant struggle and uncertainty and emerging stronger. After our recent podcast interview with Chris, we were eager to learn more from Chris during these uncertain times. Below, Chris tells us more about how he’s handled launching his new book during a pandemic, what it means to live meaningfully and why spreading that message is so important to him, what advice he has for those facing the challenge of starting over, and more. Please enjoy this interview with Chris Guillebeau!

You were about a month out from the launch of your new book The Money Tree and a 40-city international tour when the pandemic brought the globe more or less to a halt. It’s the core Stoic teaching: we don’t control the world around us, we only control how we respond. Talk to us about how you’ve handled all this.

Well, first, I’ve thought a fair amount about that core teaching. It aligns well with some of the other things I’ve been learning or working through recently, apart from my vocation as an author.

But second, there’s a logical extension to it: sure, we don’t control the world, but we do have some autonomy over our daily decisions.

Practically speaking, I decided to take on a new challenge: instead of visiting 40 cities, which obviously requires a lot of time spent on transit, back-and-forth, setup and take-down at the events, etc. —I’ll spend the same amount of time speaking to people from afar, wherever they are and in whatever mediums I can use.

It’s been an interesting reframing for me, because I’ve become somewhat used to the process involved with going everywhere, city by city, person by person. For a long time, I identified with that model, but maybe I was also getting too comfortable with it.

So I’m learning new skills and stretching myself a bit through all of this along with everyone else, which of course is ultimately good for me.

Can you tell us more about The Money Tree? It’s a genre you’ve never written in before. What were some of your goals with this project?

In terms of the big picture, The Money Tree is the story of becoming self-reliant through financial independence. Practically speaking, it’s about using creative thinking and application to get out of debt and reduce the impact that external factors (your boss, the economy, etc.) can have on you.

One of my goals is to reach people who wouldn’t read Side Hustle or one of my other how-to books. I wrote the book in a way that’s easily readable and (hopefully) entertaining, so that a reader can experience it without necessarily wanting to learn about starting a business. It’s not meant to be a Trojan horse, per se, but I did try to create some layers to where different readers will take away different lessons.

Ultimately, I hope that people will read it and feel inspired to advance their own story by overcoming a significant struggle, particularly debt and the sense of desperation that can accompany it.

At the core of everything you do—your blog, your books, your podcast, your talks, your summit—is inspiring others to live authentic, self-reliant, meaningful lives. Can you talk about what it means to live meaningfully and why spreading that message is so important to you? How did you get into this focus area?

Thank you for noticing that.

One of the things I believe is that if you don’t make choices for yourself, someone else will come along and make choices for you. So for me, at some point long ago I identified nonconformity as a value I wanted to live by. I’m not entirely sure of the genesis of this; I think it was a combination of formative moments and experience.

Simply noticing things as you go along and being willing to ask “Why?” can produce a lot of insight, both into human behavior as well as opportunities for entrepreneurial ventures, side hustles, etc.

One of my favorite quotes is from Martin Luther King, Jr.: “Nothing pains some people so much as having to think.” If you embrace thinking and questioning—as I’m sure most Daily Stoic readers do—you are well positioned to thrive in a time of chaos and disorder.

You’ve helped millions of people who want to reinvent themselves and their careers. There are now millions of people who are going to need to do that. What advice can you share with readers who are facing the challenge of starting over?

Millions of people may have read my books—or at least purchased them—but for whatever they’ve done to reinvent themselves, the credit goes to them. I hope to provide tools, examples, stories, and resources … but again, the act of doing the work is far more important.

So let’s focus on the other part of the question. For everyone facing the challenge of starting over—well, first of all, congratulations on reaching such a remarkable opportunity. We live in interesting times!

Starting over means you have the chance to build what you really want. Imagine building a sand castle, and then seeing it destroyed by a freak tidal wave. You’re disappointed, right? But then you start over, and maybe the new one is better. It doesn’t take as long to build, and you make improvements as you go based on the sand castle-building skills you’ve acquired.

Or maybe you just realize that you’re tired of building sand castles, so you leave to do something else. If the tidal wave hadn’t shown up, you’d still be stuck doing something you no longer enjoyed. On the other side of this disordered state we’re all in now, I think we’ll see a number of tremendous shifts and positive changes from so many people.

Something we’ve been talking about here is how we always have a choice between alive time and dead time, whether what we face is an obstacle or an opportunity. Your message has been similar. Can you talk about that and how you’ve been trying to make the most out of these uncertain times?

Yes, that’s a wonderful way to put it (alive time and dead time).

Whenever there is progress, some people and industries are harmed. So the same must be true for disorder: even though we tend to focus on the negative effects (which, to be clear, are not small in the case of the pandemic we’re experiencing), when some groups are harmed, others advance.

This is good to think about in terms of building economic security for yourself. Who are the “winners” during this time? It’s not just companies like Zoom and Purell. People all over the world are desperately seeking connection and community. What can you do to solve one small part of the problem?

For me I’m using some of the time to reflect on the timeless wisdom of “everything is temporary.” In many ways, we won’t go back to “the way things were” even when this is over—so what kind of world do we want to build? How will I be part of that—and how will you?

Could you leave the Daily Stoic community with a final piece of advice? It could be a question to journal on, a philosophical practice to try, or just something to think about as they go about their day.

For as long as I can remember, my core belief and life philosophy has been: You don’t have to live your life the way others expect.

I probably don’t have to explain this to Daily Stoic readers because they are smart, but just to cover the bases, I should note that this doesn’t mean you go around acting like an asshole and being selfish all the time. The point is that you can do good things for yourself and for others at the same time. It’s not a dichotomy; in fact they are connected.

My quest to go to every country in the world might be a good example. Taken by itself, it was primarily an individual goal. I wasn’t raising money for charity. I wasn’t trying to be the first, the fastest, the youngest, or whatever. I just wanted to prove to myself that I could do it.

In other words, no one really benefitted from that except me—which is fine! But when I started writing about it, somewhere around halfway through the journey, I discovered that a lot of other people ended up connecting with the story and starting their own quests and projects, sometimes leading to incredible and unpredictable results.

So back to the Daily Stoic readers: readers, you don’t have to live your life the way others expect. There is another way!