“You don’t have to live your life the way other people expect,” is point number one in Chris Guillebeau’s philosophy. The bestselling author of motivation-packed books The Art of Non-Conformity, The $100 Startup, and Side Hustle, Chris has forged his own path in life, balancing his interests – such as a passion for travel – with humanitarian work in West Africa, and more recently, with his ambitions as a writer and public speaker.
You have taken an unconventional career path. Was this something you knew you wanted to do from a young age?
I didn’t think much about career paths when I was young. I mostly thought about how to make money without getting a job. Once I figured that out, I discovered music, travel and humanitarian work. Those things kept me busy for a decade.
After returning to the US from West Africa, where I volunteered on a hospital ship and moonlighted to support myself, I began a quest to visit every country in the world before my 35th birthday.
The first half of the quest wasn’t public at all, it was just something I did for myself because I enjoyed the challenge. Then I started writing about it, and my whole life changed. It’s only since I’ve been an author that I’ve had any sort of career path at all.
Who do you admire most in business or in life? Did you have any mentors?
The people I admire the most aren’t necessarily “known” people. They are humanitarians who toil away without recognition, or anyone devoted to a cause even if it brings them no glory.
As for mentorships, that’s also a bit tricky. I’ve learned from a lot of people. Long ago I was a musician and made the mistake of saying I was self-taught. An older musician corrected me, saying: “No one ever showed you any chords? You don’t copy phrases or rhythms from the masters like we all do?” I understood his point: we’re all influenced by those we encounter or look up to.
Still, I think formal mentorship is overrated. A lot of people who say they’re looking for a mentor are just procrastinating or seeking approval. If you have a dream, you don’t need anyone to justify it. It’s your dream, right? You can choose to follow it or let it die; those are the only two options.
If a definition of an entrepreneur is “someone who will work 24 hours a day for themselves to avoid working one hour a day for someone else”, how do you avoid burning out?
Well, there is probably some hyperbole in that quote. I do try to take a holiday of some kind at least once a year.
I honestly feel very fortunate. I love what I do. I have an amazing community of people all over the world. I’m able to write and to travel, two activities that I greatly enjoy.
People often ask me about productivity tips. I’ve found that the best hack is to find work you enjoy that also helps people in some way. Then, when you find it, do everything you can to protect and improve it. There’s no burnout in that.
Do you think self-employment and entrepreneurship is the future of work for most people? What will the workplace look like in 20 years from now?
I’m not really a futurist. If you’d asked me three years ago what I think about podcasts, I’d have said they’re on the way out. Obviously that was completely wrong, and now I host my own podcast, Side Hustle School, every single day.
It’s clear that the workplace, at least in the western world, is in the process of being reconstructed. I don’t necessarily believe everyone should become an entrepreneur, but I do think everyone should learn to think entrepreneurially. And we all need more than one source of income.
That’s what’s great about a side hustle. You don’t have to take a huge risk, you can start where you are, using the skills you already have, and create an asset for yourself – all without leaving your job.
You have visited every country in the world. What have been the most memorable places?
I love travel for the sake of travel. I’m that person who looks forward to spending hours in the terminal – I realise that some people just want to get to their destination as quickly as possible, but I savour the journey.
That said, a few particularly memorable places include: Liberia, where I lived for nearly a year while working as an aid worker after that country’s decade-long civil war; Macedonia, which I found to be an especially tranquil place after a long overland journey; Laos, where I’ve never returned but it’s always on my list when revisiting south-east Asia, and Australia, which I understand is hardly unconventional but is nevertheless a place where I feel right at home.