I have followed Chris Guillebeau’s writing and books since 2009. His essays on travel and unconventional living have intrigued me for years. In his 2010 book The Art of Non-Conformity Chris shared views on setting your own rules.
In 2012, he published The $100 Startup, a work that shares stories and advice on how to start a successful business with $100 or less.
Based in Portland, Oregon, USA, Chris travels the world, writes books and offers digital courses for sale.
An Interview with Chris Guillebeau
Once in a while it really hits people that they don’t have to experience the world in the way they have been told to. – Alan Keightley
As leaders, it is important to develop the skill of setting ambitious goals for ourselves and those we lead.
Read on to learn about using quests in your leadership.
1. Your book suggests that happiness lies in the pursuit. What happens when you finish a given quest like visiting every country in the world?
Coming to the end of a lifelong pursuit is often a little complicated. It’s thrilling and exciting, no doubt, but it can also feel a little unsettling. In my case, the quest was a huge part of my identity for a long period of time. For ten years I knew exactly what to do, but after it was over I wasn’t sure what was going to happen next.
However, I think this is a good problem to have. The quest gave me that identity — without it, I wouldn’t have had the fantastic experience of traveling for ten years and meeting thousands of remarkable people. So I think it’s important to process the experience and use it as a springboard for something different.
2. From my reading of the book so far, it looks like most of the quests are individual. Do you see a way to applying the quest concepts to those who lead groups of people? Can you provide an example?
I talked with individuals, couples, families, and groups. My favourite group quest came from Brisbane, Australia where a classical music DJ led a team on a 28-year quest to produce the world’s largest symphony. It was his pursuit, at least initially, but succeeding required more than 800 performers, including lots of specialised talent and multiple choirs. He had to achieve buy-in and support from a lot of people, which wasn’t easy.
Another good story was the family (two parents and 10-year-old twin boys) who cycled from Alaska to Argentina. In their case, it was often the parents who needed encouragement to keep going — the boys were fully on board throughout the journey.
3. Your first two books — The Art of Non-Conformity and The $100 Startup — were largely focused on entrepreneurship. When I looked for The Pursuit of Happiness in my local bookstore, it was filed under the Self Help category. How do these books fit together?
Book categorisation is always an imprecise task. My first book was actually categorised in “Deviant Behaviour” in some US stores — which is a pretty small category!
I don’t think of them according to such labels, which are essentially designed for retailers to know which shelf to store them. I think they work together: first you think for yourself, then you establish personal freedom through entrepreneurship or other creative work, and then you pursue a quest or grand adventure.
4. You started travelling the world years ago. How and why did you start to look at that effort as a quest rather than an activity? Was there a turning point?
Going to “a bunch of countries” is a hobby or perhaps a passion. I enjoyed travelling and was excited about seeing the world. But once I created the goal of going everywhere, it took on a missional element. It was a crazy idea I couldn’t get out of my head: visit all 193 countries. Once I had it, I knew I couldn’t ignore it.
5. What is your favourite book on leadership?
[Editor’s Note: Sir Ernest Shackleton (1874-1922) was a British explorer who led expeditions to Antarctica in the early 20th century.]
6. Leadership Thoughts has a worldwide readership including many in the UK. Are you planning any UK trips or events to promote your book?
Yes, I hope so! I’m starting with a 40-city U.S. and Canada tour, but we’ve already added on India plus Australia, so I’m hoping to head across the Atlantic as well soon.
7. What is your leadership thought and why?
The quote I use in my email signature is: “Once in a while it really hits people that they don’t have to experience the world in the way they have been told to.”
This is by Alan Keightley and it represents what I hope to achieve in my work: an awakening that helps people embrace unconventional and intentional living of all kinds.
Thank you Chris!
What pursuit brings happiness to your life?