Best-Selling Author Chris Guillebeau Talks Side Gigs and Financial Freedom

Chris Guillebeau remembers clearly the sense of freedom he felt the first time he earned money on his own terms, not his employer’s.

It was circa 1998, Guillebeau was in college and was working the graveyard shift at FedEx. He didn’t know what he was doing with his life. But he knew he was fed up.

Then, by chance, he stumbled onto eBay, joined the gig economy and everything changed. That was 21 years ago.

Since then, Guillebeau has traveled all over the world, keeping himself afloat through side gigs while he studied the side gigs of other cultures. Then he authored several best-sellers and started the successful podcast “Side Hustle School.”

He sat down with us to chat about the gig economy, things to consider before taking on a side gig and his latest book, “100 Side Hustles: Unexpected Ideas for Making Extra Money Without Quitting Your Day Job.”

A Q&A Interview With Chris Guillebeau

This interview has been edited for length and clarity.

Adam Hardy: The terms “side gig” or “side hustle” mean different things to different people. Before we jump in, can you first explain how you define these terms?

Chris Guillebeau: I define it as an income-generating project that you start aside from your day job. Ideally, it’s not a part-time job. It’s something that has the potential to be an asset for you.

That’s why just about every story in “100 Side Hustles” portrays a gig that generates money for that person in a way that’s not dependent on some other platform, like freelance websites or some other structure.

AH: “Follow your passion” is common career advice. What are your thoughts about this phrase? How does it relate to your definition of a side hustle?

CG: The problem with that phrase is that there are all kinds of things you can be passionate about that aren’t going to make you money. And there are a lot of things you should be passionate about that shouldn’t make you money.

When it comes to having a money-making project, it’s more important to follow your skills. Ask yourself: What am I good at? What skills do I have that could be applied in a different way than my day job? When you follow your skills, it can also lead you to things that you are passionate about because we tend to get excited about the things we’re good at.

So it’s not like you’re pursuing the most dispassionate thing, but it’s more about asking yourself what are you good at that other people value, and that can set you up for financial success.

AH: A lot of people may think that they don’t have a marketable skill to start a side hustle. What’s your advice to them?

CG: This comes up a lot when I meet with my readers at book events. I’ve never, after about a 10 minute conversation, come across a person that doesn’t have a marketable skill.

So I think it’s a perception issue. Usually people who ask that are thinking, “Well, I don’t have a marketable skill because I didn’t get a degree in X field, therefore I’m not qualified.”

A big part of what I do with my podcast is show a different story every day ― 850 days and counting — of different ways people are making money. Most of those people probably said at one point. “I don’t have a marketable skill.”

But they found a way: They bred rabbits to pay for their college, or they designed literature books and started a Kickstarter campaign that raised $50,000.

I really, really do believe that everyone has a marketable skill. Now I’m not a get-rich-quick person — I know that not everyone out there is going to have a huge business. But I do think it’s about uncovering that skill, adapting it and applying it to this new economy.

AH: You traveled to every country on earth. What are some of the most interesting side hustles you came across in your travels?

CG: Through traveling and being an aide worker in Western Africa, that kind of started everything for me. The greatest realization is that we have such a Western perspective on what a side hustle is and what entrepreneurship is. This kind of thing really isn’t new. Some of the technology is new, but the concept isn’t.

All over the world, and in parts of the world that don’t have a more formal economy, this is how everyone has been making a living for generations and centuries. All those people are entrepreneurs, whether they call themselves that or not.

While I was traveling in India, I knew I had made it as an author when I came across a merchant who was selling a pirated copy of my book. My team was like “Whoa, we gotta shut this down,” but I was really excited about it. I was like “No, I want pictures of this!” The book was actually photo-copied. Like how long did that take, first of all?

AH: Wow, that’s some dedication right there. In terms of our economy, though, do you view side hustles as a necessary evil because there aren’t enough fulfilling and high-paying jobs, or do you see side hustles as a way for people to escape the current restraints of the economy?

CG: Yes and yes, and a little more on top of that. I don’t think side gigs are evil, but a lot of people are gravitating toward them for two reasons.

One, there’s a realization that we can’t depend on corporations, organizations or government for our well-being. That doesn’t mean they are all inherently bad. It’s just that we are starting to understand that no one is going to better look out for our well-being than we are.

The other thing is that I hear over and over again is about the confidence people gain and the self-worth people feel when they are able to make income on their own.

I do think people are recognizing the necessity of this, but it can be something that brings you joy not something you dread or have to check off a list.

Side hustles should be sustainable, not just another job you go to after an eight- or 10-hour day. They should help you have more options in the future.

AH: Before your books and podcast ― when you were living off side hustles — what was the highest amount of gigs you held at once?

CG: I guess I’ve never really counted them up, but I’ve always had more than one side gig at a time. I’ve never been the kind of person to do just one thing.

But I would guess somewhere around five to eight projects at once. I try to focus on maybe three main things and the rest are either passive things I have set up, or they come up in the process.

Some people thrive on that, and other people get really overwhelmed. It depends on your goals. It can be really empowering to make your first $100. If you’ve never made money outside of a paycheck from your employer, it can feel really good. But I wouldn’t recommend doing 10 things at once. To start, pick one thing and see what you can do with it.

If it doesn’t work, stop after 30 days and do something different.

AH: What was your first $100 working for yourself?

CG: I can tell you exactly what that was. This goes back 21 years. I was going to school and I worked the night shift at FedEx, like 10 p.m. to 2 a.m., loading boxes on a truck.

Then I learned about online auctions for the first time, and I looked up how to do it. I knew nothing about copywriting or taking photos, but I sold some random stuff from my apartment (on eBay and other sites) and made a couple hundred dollars from it.

I looked at the hourly rate and thought, wow, this is more than twice what I’m making at FedEx, breaking my back during a night shift. It wasn’t just the financial aspect, it was the freedom.

Everything I do stems from that.

AH: How important is creating a game plan or some kind of larger goal when starting a side hustle?

CG: I think people tend to get hung up on this and think they have to have a life plan. Goals are good, of course. Are you trying to pay off debt? Do you need extra money? Are you trying to replace the income from your day job? All good things to think about.

But I also see and hear from a lot of people that get hung up on this. They get kind of stuck in analysis paralysis. So if you’re not sure what you want to do, just do something. And if you don’t like it after about 30 days, do something else.

Not everything has to connect to your larger life purpose. If you’re 20 years old, you don’t first have to figure out what your life purpose is to start a side gig.

AH: You’ve mentioned that number a couple times: 30 days. Is this a good amount of time to give yourself to try out a new gig? Is that the best way?

CG: I would say after 30 days, cut your losses and start over. Don’t be afraid to say “I thought this was a good idea but it wasn’t.” Maybe you can learn something from that process that motivates you to try something different.

I feel that most successful people in this world have false starts, and that’s normal. Whereas those who struggle, they might think they have to persist because they hear, “persistence is the key.” Well, not necessarily. I think adaptation is the key.

Take the experience of your failure and ask: With what I’ve learned here, what’s a better way of going about this?

That’s when you’re going to be more successful. Don’t be afraid of letting go of something.

AH: To wrap up, I want to ask a question about something you’ve hinted at in a couple of your answers: Are side hustles for everyone?

CG: The simple answer is yes. I don’t see any downsides to it when we’re talking about starting something that doesn’t require a lot of risk and you’re not investing a lot of money.

You know, what could go wrong?

Adam Hardy is a staff writer at The Penny Hoarder. He specializes in ways to make money that don’t involve stuffy corporate offices. Read his ​latest articles here, or say hi on Twitter @hardyjournalism.