“When I Feel Anxious, I Make Lists: ‘What’s Going Well Right Now?’ & “What Bothers Me?’”

Chris Guillebeau with his book 100 Side Hustles

Chris Guillebeau and I have been friends and colleagues for a long time—so long that I don’t remember how or when we met. I’ve attended his terrific conference, World Domination Summit; we’ve done book events together; and his excellent daily podcast Side Hustle School is part of the Onward Project, the family of podcasts headed up by me, all about making your life better (along with Do the Thing with Whole30’s Melissa Hartwig Urban, Happier in Hollywood, and Happier with Gretchen Rubin).

And Chris does so much more! For one thing, he has visited every country in the world.

Plus he writes New York Times bestselling books, such as Side Hustle, The $100 Startup, Happiness of Pursuit, Born for This, and The Art of Nonconformity.

Now he has a new book that’s hitting the shelves: 100 Side Hustles: Unexpected Ideas for Making Extra Money Without Quitting Your Day Job.

This book is a little different from his other books, because it’s much more visual: it’s printed in color, on heavy paper, and is packed with photography. It gives you a rich, visual sense of these 100 side hustles and the people behind them. It’s a pleasure to look at as well as to read. It would make a great gift to someone (or yourself) who’s diving into the world of side hustles.

Chris and I often talk about happiness, work, the Four Tendencies (see below), habits, productivity, and related subjects, and I was glad to get the chance to ask him questions systematically.

Gretchen: What’s a simple activity or habit that consistently makes you happier, healthier, more productive, or more creative?
Chris: I’m a list-maker. When I feel anxious—or any other state of being that’s opposed to feeling happier, healthier, productive, or creative—I try to take a deep breath and write down a few things in response to prompts. Two of the most common I use are:

A) What’s going well right now? (Because no matter what I’m anxious about, there’s usually something that’s going well or that I can otherwise be grateful for.)

B) What bothers me? (Because identifying the root cause of distress is the first step towards remedying it.)

Writing answers to both of these lists in my notebook just takes a few minutes and usually leads me to feeling better about myself. It also leads me to do something about whatever’s bothering me, which of course contributes to more positive feelings in the end.

What’s something you know now about happiness that you didn’t know when you were 18 years old?
If you have a bad day—or even a bad season—it’s not the end of the world. Life includes hardship or pain for everyone at some point, but our happiness doesn’t depend on a single circumstance or experience.

You’ve done fascinating research. What has surprised or intrigued you—or your readers—most?
The fact that even small amounts of money can feel disproportionately satisfying when the payments are from a new project or arrive out of nowhere, like waking up to find that someone has purchased something from you while you were sleeping.

Over and over I hear stories of how overjoyed people feel when they get paid for performing a service or selling a product apart from their regular job. This is a big part of why I shifted my focus to telling more stories of people getting started, instead of full-time entrepreneurs who always knew they wanted to work for themselves.

It’s also great because earning a small amount of money is something that anyone can do. So in other words, there’s no guarantee that every side hustler will earn six-figures a year or be able to quit their job, but that’s not the point. Some of them will be able to do those things, and even the ones who don’t will still be better off.

Would you describe yourself as an Upholder, a Questioner, a Rebel, or an Obliger
I am proud to be one of your Rebel archetypes! Although as a Rebel, naturally I have some questions … I find that I’m usually fairly good at fulfilling my own expectations and doing something that I put my mind to. It’s all the other times that I end up struggling. So maybe I’m a Rebel with some Upholder tendencies? [Gretchen: You’re a Rebel who tips to Questioner!]

Does anything tend to interfere with your ability to keep your healthy habits or your happiness? (e.g. travel, parties, email)
Definitely not parties! I’m very much an introvert who goes to bed at 10 pm and sticks to a routine under normal circumstances. But I do travel a lot, so I have to find ways to maintain my exercise routine and eat as well as possible (which, sadly, is not always easy on the road).

And as for email, I’m constantly behind and still haven’t found the best answer for that. I probably need to re-read some of your books to follow your lead…

Is there a particular motto or saying that you’ve found very helpful? (e.g., I remind myself to “Be Gretchen.”)
Lately I’ve been thinking a lot about a simple phrase: “There is another way.” Those four words are essentially a life philosophy for me. Throughout much of my life and work, I’ve had the most success not when I followed what other people were doing and just tried to do it better, but rather when I found my own, entirely different approach.

I was fortunate to learn at an early age that the options most commonly presented to you in life are not the only ones available to you. You know how when someone says “Would you like A or B?” Often they’re presenting you with a false choice, and the best answer is to say “I’d like C, my own choice.”

Much of my work is about providing an alternative perspective, path, or model for those who are interested. And these days, it’s based on research and stories from my community, but in the early days I came to this viewpoint instinctively.



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