Chris Guillebeau | Side Hustle (Episode 663)

Chris Guillebeau (@chrisguillebeau) rejoins us to explain what a side hustle is and what a side hustle isn’t as outlined in his new book Side Hustle: From Idea to Income in 27 Days.

The Cheat Sheet:

  • Understand why you don’t need to be an “all-in” entrepreneur to have a side hustle.
  • Learn how to take inventory of your existing skills and how they can be applied to your first side hustle.
  • Wrap your head around what a side hustle is and what a side hustle isn’t.
  • Aside from generating a little (or a lot of) extra spending money, discover the other benefits of a side hustle.
  • Figure out how to pick your best side hustle idea to pursue based on certain criteria.
  • And so much more…


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These days, everyone’s talking about the importance of having a side hustle. But there are many misconceptions about the process, a lot of people have tried before and failed (so they feel like there’s something wrong with them), and most resources in this field focus on telling people to be entrepreneurs — and that’s a totally different thing.

Chris Guillebeau rejoins us (check out his last appearance on the show here) to talk about his new book Side Hustle: From Idea to Income in 27 Days. It provides us with a plan to start our own side hustle using skills we already have — and without spending much money to make it happen. Listen, learn, and enjoy!

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More About This Show

These days, everybody’s got (or is thinking about getting) a side hustle — a little side business that generates money beyond what a dedicated day job affords. But even if you think a side hustle’s not really your style for any number of excuses, Chris Guillebeau — author of Side Hustle: From Idea to Income in 27 Days — is here to tell you otherwise.

“This book is not for entrepreneurs,” says Chris. “I’m deliberately trying to write for regular people who have jobs and just want to create more security for themselves. They don’t necessarily want to have a startup or be an entrepreneur or quit their job tomorrow or anything like that.”

So what’s the difference between a side hustle and a part-time job? Chris believes a side hustle should help an individual develop their own assets under their own control. Contrast this with increasingly common participation in today’s so-called gig economy — driving for a ridesharing service or delivering sundries on behalf of a larger entity — which Chris says is more akin to a glorified part-time job than a true side hustle.

“I’m trying to make this for busy people who don’t want to work forty hours for their job and then go and work twenty hours for somebody else,” Chris says. “What I’m trying to help people do essentially is to create an asset for themselves and to be able to create something that they look at and say, ‘I made that thing. I have control over it; nobody can take it away.'”

One of the biggest misconceptions about side hustles is that they originate from a place of contempt. Many in the entrepreneurial crowd would have you believe you’re sucker if you actually like your day job. If you’re not working for yourself these days, and if you’re not willing to risk all worldly possessions for a chance at the high-risk, high-reward lifestyle, there must be something wrong with you.

“You can do this with the skills you already have without spending a lot of money in a short period of time,” says Chris. “Look at the amount of time you’re spending and the small amount of money you’re investing. If it doesn’t work, then you’re going to have a learning experience; you can go on to do something else. But what if it does work? What if it does actually have the potential to change your life and do something amazing for you?”

Listen to this episode of The Art of Charm to learn more about what you can gain by not going “all in” the first time you come up with what seems like a feasible side hustle, how to know when it is time to go all in, how to know when it’s time to give up on a side hustle, bad advice given often by entrepreneurial “experts” that you should ignore for the sake of your own health and sanity, how limited time and resources can be a boon rather than a burden when experimenting with a side hustle, and lots more.


If you enjoyed this session with Chris Guillebeau, let him know by clicking on the link below and sending him a quick shout out at Twitter:

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Jordan Harbinger - author of 952 posts on The Art of Charm

Jordan Harbinger has spent several years abroad in Europe and the developing world, including South America, Eastern Europe, and the Middle East, and speaks several languages. He has also worked for various governments and NGOs overseas, traveled through war zones, and been kidnapped -- twice. He’ll tell you the only reason he’s still alive and kicking is because of his ability to talk his way into (and out of) just about any type of situation. Here at The Art of Charm, Jordan shares that experience, and the system borne as a result, with students and clients.


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