BOOK REVIEW: “Side Hustle: from idea to income in 27 days”

In Book Review, Consumer, Travel Deals, Trip Report by scott

That’s me with Chris (center) and Stephanie Zito (right) on the set filming a “Creative Live” course for frequent flyers in Seattle.

Side Hustle is Chris Guillebeau’s newest book, a step-by-step guide to develop some additional income.

As the title suggests, the idea is not to give up your day job with its security, insurance and other benefits. Rather, the quest is to identify something you love to do and develop it as a hedge against economic uncertainty. 

I’ve always had a side hustle. It started with part time jobs in grade school. But Chris’s advice isn’t necessarily to get an additional part time job, although many of us have done that. Rather, he shares how a system and technology can help you establish a business of your own. You can be your own boss, on your own terms. In the book, these ideas usually start out small. But then they grow–often to the surprise of the founder!

Using a combination of real life stories and step-by-step guides, Chris lays out a strategy to identify which of your ideas is the best prospect for a side hustle. Then, he sketches out some metrics to determine the most profitable idea. There are even some drill-down analytics of offering a product versus a service.

The real life examples provide glimpses into why people start side hustles. Sometimes its to fund a specific project or to pay off some credit cards. Other times its a tool to give a person a little more financial security.

Since I first met Chris a few years ago, it has been his own side hustles that have been an inspiration. He had some specific goals, like visiting every country in the world before his 35th birthday. Along the way he set up income producing projects like the “Travel Hacking Cartel” to help frequent flyers get more rewards. I also like a stand-alone website “” which offers recommendations on the best rewards-earning credit cards. These are just a couple of examples, but they are consistent with Chris’s advice to readers. “Anyone can build a fast track to freedom by increasing their income—using the skills they already have,” he writes.

Based on his own experience and on interviews with people from around the world, Chris dispels some oft-told business myths:

You don’t need a lot of money, an MBA or business degree or an inordinate amount of time. You do need to be willing to act, though.

Chris’s system is broken into 27 days and he’s clear about specifics: how to price your offer, how to identify your ideal customer and how to test the results. Just because the system is simple doesn’t mean it’s easy, though. You have to have a willingness to learn and experiment. Just for clarity, Chris spells out the steps at least three times in the book, with detailed guidelines in between. Further, the book is part workbook, where you fill in the blanks to get your mind humming on the best ideas.

One of the best qualities of the book is the chance to make it your own. It’s not just a passive manifesto on how things get done. Rather, the fill-in-the-blank parts give you a chance to carve your own path on your side hustle. Chris’s suggestions on websites, technology aids and workflow suggestions are great, as long as you have the key ingredients: a good idea and a willingness to act!

In addition to the book, Chris has a “Side Hustle School Podcast” which features interviews and tips. Chris’s evangelization of the side hustle continues after the book with free resources and a network of fellow hustlers.

At the end of the day, I’m a bit jaded. I love the side hustle. I’ve had one or two at all times, in part because I’ve had trouble with “regular jobs.” In fact, that’s why Chris and I get along—he’s the same way. So for those of you who can hold down a steady job, my hat is off to you. I encourage you to explore the side hustle—and enjoy the freedom and confidence it brings. Chris’s book offers a detailed road map to turn your best ideas into money making enterprises.

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