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Spinning Plates With Side Hustle School’s Chris Guillebeau

Side hustle advocate, Chris Guillebeau, talks about the fine art of managing life when you’re navigating several roles at once.
by Eugene Yiga | Aug 14 2020

Chris Guillebeau is a bestselling author of six books, most recently The Money Tree, and the man behind the daily podcast — yep, that’s 7 days a week — Side Hustle School. Guillebeau is an advocate of leaning into that which makes you uniquely you, and thus finding projects that can be part-time money-spinners while you get on with your day job. An entrepreneur in his own right, he considers himself fortunate to have a wonderful community of awesome people doing interesting things all over the world. Here, our writer talks to him about his work and how exactly he manages his varied life.

How would you describe what you do and what you hope to achieve through your work?

My entire focus recently shifted to helping people build their side hustle. When I say ‘side hustle’, I’m not talking about a part-time job and I’m not talking about the gig economy; I’m talking about creating an asset that works for you. It’s something that has the potential to help you earn money while you sleep. If I can achieve that in some small way, I’ll be happy.

Which aspects of your work do you love the most?

I love a lot of things I do. I love being able to travel [before COVID-19], I love being able to work for great people, and I love the creative process of thinking through how to write a book or create another kind of project.

What parts of your work are challenging?

I sometimes get overwhelmed. I’m way behind on far too many things but I don’t know how to fix that because I’m fully immersed and fully committed to this new process I’ve created that’s outlined in Side Hustle: From Idea to Income in 27 Days.

My greatest motivation is hearing stories from people that are applying the process: taking action, using the skills they already have, and starting their side hustles without quitting their jobs and without going into debt. But I often get behind in keeping up or replying, and that bothers me.

How do you spend the first hour of your day?

I’m not a believer in that whole thing about how you shouldn’t check your email before a certain time. I try not to get sucked into my email but I don’t think it’s bad to do a quick check to see what’s going on. Then I always have coffee (of course) and get to work doing my other things.

What is your typical daily routine after that?

Every day, seven days a week, I record a podcast, so that’s a big thing in terms of the preparation, the recording, the editing, and getting things organized and shipped out. After that it depends on the day, because I do a lot of different things.

What’s your number one productivity tool or app?

​The greatest productivity hack is to love what you do. Because if you love what you do, everything else gets much easier.

What’s your top app to help you get work done and achieve your goals?

Omnifocus. I’ve been using that for years to track my projects and tasks and, as a big list-maker, I love the structure of it.

What other tips or life advice you can share with our readers?

First and foremost, you don’t have to live your life the way others expect. That’s the philosophy of The Art of Non-Conformity, and what I’ve built my brand on for almost ten years. With the new book and the new focus, I would encourage them to know that no matter who they are and no matter what their experience, they’re good at something and there’s a way to make money from that.

If you’ve tried before and you’ve failed or it hasn’t worked out, it might not have been your fault; maybe you just didn’t know what to do. Side Hustle is all about helping people figure out what to do so that they can experience extra income for more security, more options, more freedom, and all kinds of other good things.

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