Author-entrepreneur Chris Guillebeau says you can side-hustle your way to financial freedom

Chris Guillebeau is a writer, entrepreneur, and traveler who built a passionate following from his blog The Art of Non-Conformity, where he chronicled traveling to 193 countries before his 35th birthday. His first book, named after the blog (here's a great review), became the first of many bestsellers, including The $100 Startup and The Happiness of Pursuit.

In 2017, Guillebeau ("Gil-a-bo") launched a podcast called Side Hustle School (here is the first episode) and committed to releasing one episode a day for one year, and then reevaluate.

"I've been doing this for [more than] 20 years, my own side hustles—my whole life is a collection of side hustles," Guillebeau told me. "Every day, I'm going to tell a different story, a true story of an employee who starts a side hustle, income-generating project without quitting their job. And I'm going to do it in less than 10 minutes a day because I'm making it for busy people."

Well, after one year of releasing an episode a day, as promised, Guillebeau kept going. And going. Now in its third year, Side Hustle School, which has more than 880 shows and counting, garners millions of downloads every month.

The podcast and his companion books—Side Hustle: From Idea to Income In 27 Days (Currency/Crown Business, 2017) and the just-released 100 Side Hustles: Unexpected Ideas for Making Extra Money Without Quitting Your Day Job (Ten Speed Press)—promote the idea that anyone can and should start a side hustle, a.k.a. a scalable service or other small business, in order to thrive both financially and creatively.

"It's also fun. Starting a side hustle is like 'playing entrepreneurially' without making a huge commitment," Guillebeau writes on his website. "The stakes are low and the potential is high."

For years, I've been a voracious consumer of books, blogs, and podcasts related to entrepreneurship, personal finance, and investing. So I knew I needed to talk to Guillebeau, 41, about the podcast and his books. I interviewed him a while ago but for reasons not worth going into, the story didn't see the light of day—until now.

Here is our Q&A, edited for clarity and length.

I noticed that some of your podcast episodes you found people to talk about that had found you through the podcast. So it's really become this full-circle interactive thing. Is that exciting to you to see that?

GUILLEBEAU: Very, very much. First of all, in committing to do it every day for a year, I didn't know what the show was going to look like as it went along. It's not like I had 300-plus episodes identified. I had like 30 identified. Hopefully, I'm going to find the rest of the people. So it was a bit of a risk there but it was really good because as you said, people listening to the show began referring other folks. So I feel like it's a self-reinforcing thing, which is great, so I actually really love to hear stories like that of somebody who is like, 'God, I just stumbled on this podcast and now I have this project that's making money." I think that's great.

The notion of having a side hustle or a side job or a side gig or a second job is certainly nothing new. But the term "side hustle" seems to be really hot. It's a buzzword right now. Is it something to do with the modern economy? Something to do with the job market as it is in the U.S. and the world right now? Is it about just being enthusiastic about starting a business?

GUILLEBEAU: I think you've actually hit on the twin reasons for why there's such a convergence of it. The first one is this is a time of uncertainty and anxiety even though certain economic numbers are good. People still feel worried and just understand "I can't trust my well-being to a corporation even if I love my job." Maybe, "I love my job, I have a good company I work for, but nobody's going to care about my well-being as much as me." And combining that with just the fact that this is much more mainstream than it ever used to be.

When I started doing this stuff 20 years ago, I didn't know a lot of other people who were doing it. Whereas now you can go into Starbucks or any coffee shop on the corner, and there's seven people in there doing their little hustle. And they're setting up a coaching call or they're taking PayPal payments or whatever. And so I think it's become much more accessible. E-commerce adoption has grown so much that my grandma has a PayPal account.

Is [this] a danger as someone who wants to start a side hustle: They have to ask themselves, "Am I really bringing someone value or am I just making it up as I go along?"

GUILLEBEAU: Well, "value" is the keyword. Value essentially means helping people. Value is one of these like another buzz word that is dropped all the time in business-speak and like what does value mean? It essentially means helpfulness, usefulness, improving someone's life. I see the problem being much more the other way—people just not feeling confident and people feeling like, "Am I good enough to do this?" So I think it's much better to help people look at the skills that they have and [ask] "What is your life experience? What are you good at? What are people asking you about all the time?" Because that very often can be where your side hustle can come from.

It's not so much going out and acquiring a bunch of new skills. Don't make an app if you don't know how to code. That's the other thing. People are like, "I want to make an app." "Are you a web developer?" "No." "Do you know how to code?" "No." "Well, maybe do something different."

What are some of the biggest roadblocks that you're seeing people encountering? You mentioned that they feel like they don't have the confidence—that seems like a roadblock. Is that one of the biggest ones?

GUILLEBEAU: That's a big one. I think also not knowing what to do. Like, "I've got an idea but what do I actually do with that idea?" Maybe also not understanding the connection between an idea and an offer, which is very much something I'm trying to take people through the 27-step process [in Side Hustle: From Idea to Income In 27 Days].

We as consumers—if you just think about it as a person—you don't buy ideas. There's no Idea Store where you go to buy ideas like you buy products, you buy services. You buy those products and services in response to an offer. Here's the product for this price, you exchange money, and you get this. So I'm trying to help people really quickly go from thinking about general, vague ideas to thinking about offers. So that's one. Well, you said the confidence, that was one.

So I would say the third one is just the perception that it takes money to do this, that it's going to take this expertise that you don't have. There's some legislation or some regulation that prevents you from starting your side hustle—just maybe a lack of understanding that you can do this with the skills that you have without spending money and it's actually a great thing.

Do you also see certain recurring mistakes that people seem to make? What would those be and hopefully they should avoid?

GUILLEBEAU: Maybe not thinking enough about the value question in the beginning? I never use the phrase "Follow your passion, follow your dream." It's important to do something that you're motivated to do. But it also has to be valuable and helpful to other people. So maybe some people are like, "What do I like to do? Oh, I like to do this, therefore that's my side hustle." Not necessarily.

So I tend to encourage people to focus a bit more on problems: What bothers you? What frustrates you? What pissed you off today? What is inefficient? What could be made better? If you start thinking about that, that tends to align a lot closer to thinking about actual business ideas, actual offers that you can make.

Then maybe the failure to actually put something forward. I'm trying to encourage people to launch before they feel ready. You're never going to feel super ready, you're never going to feel like it's perfect. Maybe that's another common misconception that comes from the startup world—that you're supposed to validate before you begin. A lot of these things you can't validate. The response from the market is the validation.

So you launch the side hustle and you're testing it essentially to see if it will work. And sometimes it doesn't, so you move on or you pivot.

GUILLEBEAU: Because your risk is low. You haven't spent a ton of money. You haven't spent a ton of time. If it really doesn't work out, you ask yourself, "What's the worst that can happen? OK, it's a learning experience. All right. I'm going to take that knowledge into my next project and, hopefully, the next one will work." Anything that we can do to remove pressure from people actually helps them to take action on that side hustle idea.

What piece of advice would you tell someone who's looking to start a hustle; what's step No. 1?

GUILLEBEAU: Step No. 1: Determine your side hustle goal. Because people are doing this thing for all kinds of different reasons and some people just want to make some extra money, which is fine and well, it's great. They want to pay off debt or whatever. Other people actually are trying to create a significant second recurring source of income. Other people are trying to replace their full-time income and eventually go into it.

The most important thing I would say to them is, "Well, you know you need this, you understand that a second income is important and good." But I would also say, "You're equipped to do that. You already have those skills that you need." And all I try to do is pull those skills out and show people how to apply them in different ways. So I'm not really giving anybody skills—I'm helping them find it themselves that they can do it.

This is important for your life. And you should try to find a way to take the next step. ###

The Side Hustle School podcast lives here. Check out a list of side hustles ideas to get you started.

100 Side Hustles: Unexpected Ideas for Making Extra Money Without Quitting Your Day Job (Ten Speed Press) is out now. Catch up with Guillebeau on his book tour.

Arun Kristian Das is a senior digital content creator for and a budding side-hustler. Follow him on Twitter @arunwithaview.