If you are interested in joining the ranks of first-time business owners, turning a passion into an income-creating side venture, or pursuing a path that better aligns with your goals, you are not alone. According to a study conducted by the US Small Business Administration, there are 31.7 million small businesses in the US, and 81% of small businesses are solopreneurs. That’s over 25 million people operating businesses on their own. In addition, nearly 5.4 million applications were filed to form new businesses in 2021 (Census Bureau Business Formation Statistics), beating the 2020 number of 4.3 million.

New York Times best-selling author and Side Hustle School podcast host, Chris Guillebeau has made a career of creating and sharing inspiring entrepreneurial stories, starting with his own. Over 25 twenty years ago, at the age of 19, Chris traded in his job (working the night shift packing shipping boxes) for the new frontier of online auctions. The control he gained over his time, activities, and income potential ($12-$15 an hour at the time), was enough to sell Chris on a life of entrepreneurship. He had no idea that act of non-conformity would one day lead him to inspiring people all over the world into entrepreneurial action through his “the art of non-conformity” blog, best-selling books, and the Side Hustle School podcast that is downloaded millions of time a month. 

Q&A with Chris Guillebeau

Now, let’s get to our interview with Chris.

Why did you pursue entrepreneurship? 

“I didn’t want to work for anyone else. I was very drawn to the creative freedom of working for myself. I liked the idea of being able to have some control over my schedule, and not just the schedule, but over what I actually did. So, in the beginning it wasn’t a high-level thing. It wasn’t like, ‘Oh, I want to change the world, here’s the 20-year roadmap.’ It was more just, like, this is pretty cool that I can do this now, and I can do whatever else I want too.”

When did you know you weren’t meant to work for someone else?

“I think I kind of always knew that. Well, I always knew that I was somewhat rebellious. I was diagnosed with Attention Deficit Disorder (ADD) at a young age, and I just had a hard time with formal learning and the structure of school. Although, I really liked learning. If I was excited about something, I would dive into it and just spend hours and hours obsessed with it. But, when it was like, “here’s what you need to learn” or “here’s what you need to do for the job,” if I wasn’t passionate about it, it was very difficult for me. That’s a very common ADD characteristic.”

The gateway to entrepreneurship

“Obviously, there were entrepreneurs that were also selling things online or doing other things then, but it was much less common, and so I didn’t know that there was another way [entrepreneurship]. And so, when I discovered that there was another way, there was no going back. Why would I want to possibly go back to anything where I don’t have control over my destiny, or at least my schedule? It’s very difficult to retreat from freedom.”

(In case you missed the introduction of this post, at the age of 19, Chris went from working the night shift packing shipping boxes to selling household item on online auction sites. The control he gained over his time, activities, and income potential, sold Chris on entrepreneurship.)

The next eight years

“There was an eight-year journey from after I left my job packing boxes before starting the blog. I moved to West Africa and was an aid worker there for much of that time. That was just a fantastic experience. I never would have been able to do that if I hadn’t been working for myself.

I started traveling to other parts of the world, eventually ended up with this goal of going to every country in the world. I officially started that in 2008. I’d been going to a bunch of places before then, but started that goal, and then I started a blog called the art of non-conformity where I told the story. I shared how I was going to every country in the world and why I was doing it. Naturally people had questions like, ‘how do you pay for it? I’m like, ’oh, well, I’ve always worked for myself.’ ‘Well, what have you done?’ ’Well, I did a few different things. I did online auctions, Google ads, internet marketing, just various different things.’

So, people were like, ‘well, tell me more.’ And so that’s when I thought, okay, well, there is interest in the blog, and people are interested in the project. Maybe there’s a way to create resources for sale, for those who would want them.’

Want to hear more from Chris? 

Watch Five Ways to Increase Income in a Small Business , the keynote from the Amazon Business Small Business Summit. Also, stay tuned for the second installment in this series with Chris to learn about the first time he got paid for a piece of content he produced or

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