Chris Guillebeau is a New York Times bestselling author and the host of Side Hustle School, a daily podcast with more than 2 million downloads per month. During a lifetime of self-employment and side hustling, he visited all 193 countries of the world before his 35th birthday. He recently sat down with Srinivas Rao on the Unmistakable Creative podcast to discuss what we should all be looking for in a fulfilling, meaningful line of work.
Srini: I don’t imagine that everybody wakes up one day and says, “You know, [my] goal is to visit every country in the world.” What led you down that trajectory?
Chris: People always think that there are these big, strategic visions. Like, when I was 10 years old, I wanted to grow up and be an explorer, and then I prepared for the next 15 years. None of that was the case. I knew I had a love for travel. I had a mom who was married to a military guy, my stepdad, and he took us to a bunch of different places because of his assignments. I lived in the Philippines for a while, and I got comfortable with some cross-cultural stuff.
Looking back, I see a bunch of random stuff, which eventually worked together to create this focus that I have now. It’s a series of stages and interlinked pieces, along with many dead ends, but eventually it builds to something.
Srini: Let’s talk about the dead ends, and moments that didn’t really work out. What have you learned from those?
Chris: I had lots of little businesses that never worked—I had this idea for a golf membership site that costs one dollar. I was thinking it was the greatest idea, because there are so many golfers out there, and I just needed 1% of them to pay one dollar. Somebody said to me, “It’s going to be hard to have a business model where your most expensive product is one dollar.” And I was like “No, it’s going to be great!” And of course, it wasn’t. It was a total flop.
I did a lot of things like that that were super random. I would spend a little bit of time on these things, a little bit of money. Then if it didn’t work out, I’d just move on to something else.
Srini: Why do you think so many people hit a dead end, and then don’t do anything else?
Chris: Maybe they’re afraid to quit. Maybe they’re like, “I’ve already invested in this, I’ve got sunk costs, I’ve spent some time doing this.” I think people fail to back out of those dead ends and pursue something different not when they’re terrible at it, but when they’re just okay at it. It’s hard to back away from the dead ends [when] it’s working out okay, but not amazing. But I think there’s a real skill in being able to say, “It’s not amazing, therefore I’m going to try something else.”
“It’s a series of stages and interlinked pieces, along with many dead ends, but eventually it builds to something.”
Srini: How do you balance the ability to do that with the longevity that’s required to achieve mastery at a particular craft?
Chris: I don’t think everybody has to worry about mastery so much, at least for a while. The mastery comes when you find something that you truly do love, and you’re actually pretty good at it, whether it’s a natural gift or something that’s developed. [But] a lot of people don’t know that yet. A lot of people are trying to figure it out. Don’t beat yourself up over failing to pursue mastery if you’re not sure what you’re supposed to master.
Srini: I think part of it is letting go of attachments that we have to these things. It’s like you said, sunk costs can be really insidious if we’re not careful.
Chris: Of course. It’s like you’re in the grocery store and you picked the wrong line to be in with your cart of groceries, and this new line opens up. It’s going to be so much faster, but you’re afraid to leave, because you’ve already waited 10 minutes, and if you just wait a few more minutes, you might be at the front of the line. It’s very hard to give up and go do something else. I feel like that affects lots of people’s decisions in life. Sunk costs are sunk costs — they’re gone. You can’t recoup them. You have to always think about the present moment and think about what you’re working toward in the future.
Srini: [When it comes to] a ten-year quest around the world, do you think everyone has the mindset for something that significant? What can they do to learn it?
Chris: Experiment, try different things, learn broadly, take on different skills, do things that you’re a little bit uncomfortable with. Be clear about your motivations, check in on your feelings: “How does this make me feel? What do I want?” It doesn’t necessarily mean you’re always going to respond [according] to [how] you feel, because if you’re running a marathon, you might not feel that great at mile 23, but if it’s something you believe in, you’re going to keep going.
It’s helpful to do those gut checks, and to always be working towards something, to always be challenging yourself. I think it’s a dangerous place to be in, especially as a creative, when you ask yourself, “How am I being challenged?” and you don’t have a good answer for that. That’s a warning sign that maybe you need something different.
Srini: For sure. You’ve said you were a juvenile delinquent for a while. I’d love to hear about that in more detail.
Chris: Well, I thought I would be a good criminal at the age of 13. I had a small shoplifting ring for a while, and when I say shoplifting ring, it was me, my friend, and my friend’s sister. We would steal things, and I thought I was really good at it, but the thing with long-term crime is that you can get away with it 20 times in a row, but if you get caught the 21st time … It only takes once, you know?
That didn’t work out super great, and then I learned to drive by stealing a car. That was at age 14, and it also didn’t work out. My friend and I successfully stole the car and drove it around all night, so we thought we were awesome, but then as the sun rose, we were like, “What do we do with this car?” We decided to park it somewhere, but ran into a brick mailbox. Somebody called the police, the police showed up, and I was arrested. There was a series of bad choices that happened over three to four years. Finally, I came to my senses and realized that’s probably not the best life path for me.
Srini: What are the lessons in human behavior and personal relationships from that time that later played a role in the way you’ve run your business and your life?
Chris: I guess there was an element of creativity to it, a desire to say, “Is there more than one way to do this?” At the time, it was like, “Oh, I want the new Metallica cassette. I don’t want to pay for it. Therefore, I’m going to steal it.” That thinking evolved and I stopped stealing things, but throughout college, entrepreneurship, travel, blogging, et cetera, I was always asking, “Is there another way to do this?” For sure, that was part of it.
Srini: The theme that I keep hearing is one of resourcefulness.
Chris: I guess I always wanted to try something new. If something failed, I wouldn’t necessarily try the same thing again, just like I stopped stealing cars after the bad experience at age 14. But yeah, I guess I would always try to find another approach or do something different. I’m focused on the goal, even if I [have] to change the strategy, which I think is a wonderful thing that entrepreneurs, or artists, or anybody else can do.
Srini: Fair enough. Let’s shift gears, and get into the framework of the book, and this whole idea that we’re born to do certain things, and we can find what those things are.
Chris: I run into a lot of people who say things like, “Oh, I love what I do. It’s the best job in the world — I would do it for free! I feel like I’ve won the career lottery.” What do these people have in common? Did they always know what they wanted to do, or was it more of a non-linear journey? Did they do a lot of different stuff like I did?
One thing I learned is that there’s a lot of people working entrepreneurially within a larger company or organization, because that’s the kind of work they want to do, or because they’re a better fit in that kind of environment. I tried to unpack the lessons and the experiences of those people, then present them in a way that’s not just anecdotal, but actually prescriptive for everybody out there who is trying to find the work they’re meant to do, whether it’s just [one] ultimate path or more than one path.
Srini: One of the things it said on the back of the book was finding this intersection of joy, money, and flow. Let’s talk about those three things in more detail.
Chris: What I found through my research is that people are different—we all want different kinds of work. [But] joy, money, and flow are essentially things that I think everybody wants. Everyone wants to do something that they love, or at least that they enjoy. That’s where joy comes in. Money is that sustainable piece. I’m writing about careers, not hobbies, so if there’s something you love to do that doesn’t make money, that’s fine, but that’s not your income-producing work. Then flow is developed skill, or that point at which we lose ourselves in our work. Hours go by because we’re [so] good at it.
So the intersection of those three things, that convergence point of joy, money, and flow, is essentially the goal. Whenever you come across a career decision, whether big or small, ask yourself about these points. Does it meet all three of these things? If I’m deciding between two things, which is the closer fit?
At different times in our life, we may have to make compromises, and that’s fine. For a while you might work a job that you don’t necessarily love because it pays well, and it provides for something else. That’s totally fine. [But] I think winning that career lottery is something that has all three of those things.
Srini: Why do we often miss or overlook those points of intersection when they happen?
“That convergence point of joy, money, and flow is essentially the goal.”
Chris: I don’t think anyone teaches us to be aware of them. [So] check in with your feelings, and then combining the feelings check with a more objective, research-based check where we’re like “Okay, am I really good at this thing? Does it produce the kind of income that I would like?” Putting those things together is really important.
Srini: You [said] that nobody teaches us these things. Given that you have a master’s degree, what is your perspective on education?
Chris: Fortunately, I think education is changing, at least in terms of recognizing that there is more than one path—like working for yourself. I’ve worked for myself my entire adult life — I’m 37 now. When I was in my early 20s, it was kind of a weird thing. There were plenty of other people doing business online even then, but I didn’t really know any of them. They were scattered everywhere, and my parents didn’t really understand what I did for a living. But now it’s much more common to work for yourself. With education, it’s now much more common to pursue a different path, and have that be totally okay.
I don’t regret any of the education I had. I think it was very helpful, teaching me to write well, to formulate arguments, maybe teaching me some social skills that I didn’t get during my juvenile delinquent years. [But] it clearly didn’t really prepare me for a specific career track—at least not in line with the investment that I made in it.
Srini: I have one last question: What do you think it is that makes somebody or something unmistakable?
Chris: The willingness to find the thing that they were born to do. There’s this thing out there that you have to find, and maybe it’s a calling, maybe it’s a life quest, maybe it’s a business, maybe it’s an artistic expression, maybe it’s something that I haven’t mentioned at all. But there is this thing out there, and to be unmistakable, you keep forging your way toward it. And you don’t necessarily even know what it is in the beginning, just like I certainly didn’t know where I was going with my life back when I stealing cars — or even as an adult.
But you keep working toward it, and you back out of those dead ends that we talked about. You find another way forward. You try, try again, but you don’t try the same thing necessarily. You’re unmistakable because you keep working toward that, and you do everything you can to find it.