How Do You Live A Remarkable Life?

Learning From Chris Guillebeau

Ep 2. Question Everything, CITR Radio 101.9 FM, Vancouver, BC

As a New York Times Best-selling author and the first person under the age of 35 to travel to every country in the world, Chris Guillebeau is the very definition of remarkable. Chris is the author of four books including his latest book Born For This, which focuses on helping people find the work that they were meant to do. Chris also hosts an event in Portland each year called the World Domination Summit which brings people together to explore the question, “How do you life a remarkable life in a conventional world?”

In today’s episode, we learn how Chris began his eleven year quest to visit every country in the world and talk about what it takes to accomplish large goals that seem unattainable. We discuss how important it is to establish connection and community through your work, and how you can live a remarkable life by listening to the voice of fear and stepping into it.

Here are the top 10 insights that Chris shares for anyone who is struggling to find the work that they were meant to do.

Can you start by telling us what inspired you to travel to every country in the world?

It wasn’t a big strategic plan in the beginning. I just loved to travel. I loved making new discoveries and exploring. I spent about four years living in West Africa onboard a hospital ship. I was an aid worker there and because of that experience I went to lots of different countries in Africa and in Europe as well. After I had been to maybe 30 countries or so, I set the goal of going to 100, and I got closer to 100 I thought, I need a real goal because if you go to 100 that’s about half the countries so you can pick and choose and maybe just go to the easy ones. So that’s when I decided to double up and go to every country in the world. It turned into an eleven year quest that I wrote about on my blog.

When you told your family and friends about that goal, were they supportive or did they discourage the idea and think you were crazy?

I think at that point, my friends and family were used to me doing some crazy things, so it’s not like it came out of the blue. I was always an entrepreneur and wasn’t good at working for other people (in fact I was a terrible employee) so I had always worked on my own. They were used to me doing different things and at first they said “We’ll see if he actually does that,” but I followed through and over time they got used to it.

Traveling the world is something that most people dream about their whole life, but I can imagine that it would have been incredibly difficult and scary for you at times. What was the biggest challenge that you faced on that journey?

When you said it was scary, I think that the things that were scary were not physical danger for the most part. It was an eleven year quest so there certainly were some things that may have been some scary things along the way, but I think the most daunting thing was contemplating, “Do I say yes to this adventure?” You asked if my friends thought it was a crazy idea, but I actually thought it was a crazy idea. Is this really possible? Can I actually do this and see it though? So I thought about it for several months before I decided to actually go for it. But once I had that idea it just wouldn’t leave me alone. If you have a crazy idea, I think you should pay attention to it because often it’s going to lead to something that’s important for you.

How did you develop that mindset? To make that commitment can be really scary.

Well, for sure. I don’t think it’s about overcoming the fear or conquering the fear–all of these masculine verbs we use like “We’re going to kick fear in the face and pretend it doesn’t exist.” I see people using that language a lot online. I’m a person who had a lot a lot of insecurities and self doubt. I guess the way you get over that is by doing smaller things and as you do smaller things, you get a greater vision as you build confidence. For that particular project, I didn’t have the vision of going to every country in the world until I had spent time in a bunch of different places. So the more I did the more comfortable I became taking risks, but I don’t think that anyone is an innate risk-taker.

Having gone through all of that and accomplishing such an incredible goal, do you have any advice for people who have far-fetched goals that seem unattainable?

If they have goals like that then that’s wonderful! I talk to a lot of young people who don’t necessarily have this large goal but they have a longing. They want something but they don’t quite know what it is. They feel so much pressure in our North American society. They feel pressured to know “Here’s my life purpose at age 20. I’m going to follow this linear path.” So I’d say let’s do anything we can to remove that pressure and say “Ok, I may not be able to have everything figured out for a bit so I’m going to expand my horizons–I’m going to travel, I’m going to volunteer, I’m going to try to start a small business. I’m going to experiment and go down different paths and that’s how I’ll find my purpose and the work I was meant to do. And maybe that’s how I’ll find those big goals too.” Most people don’t have this big goal in mind from a young age. They only come to it as they go down different paths and learn what they like and what they don’t.

I wanted to speak about your latest book Born For This. In the book you share stories of people with really diverse backgrounds and interests who have found the work that they were meant to do. When you were first starting out your career, were there any books or people who helped you discover what you were passionate about?

I was partly inspired by a lot of the people I worked with in West Africa. They’re not online celebrities, author or bloggers, but they were doing some really great humanitarian work and I found that very challenging. Some of those people have been there for 10 years or 20 years, and I thought, if they are doing all of that then surely I can do something. As for books, I really like the book WishCraft by Barbara Sher. She’s someone who was writing about this kind of field of finding multifaceted work, doing more than one thing, not necessarily following a traditional path. She was doing that a long time ago before it became a popular thing, so I think it’s always good to go back to her work.

Are there any philosophies that you live by?

I have this mantra that I built the art of non-conformity around: You don’t have to live your life the way others expect. I’ve expanded on that in different ways throughout all my work, whether it’s about entrepreneurship, travel and seeing the world, or alternative education. We live in a society where people have assumptions and expectations. They aren’t all bad, but some of them are. Some of them aren’t good or bad, they are just kind of traditional and people have gone down these paths maybe because that’s what their peers have done or what their parents have done. So my goal is to shine a spotlight on alternatives and to encourage people to choose a different path. Or, if they do want to follow a traditional path, that’s great too, but let’s ask ourselves if that is what we really want, and if not, then let’s do something different.

You first started out in university studying accounting and then switched to sociology. Was it difficult for you to say “No, this isn’t what I want to do” even though it was what you thought you wanted or thought what was expected of you.

Fortunately I was very bad at accounting, so the choice was kind of made for me. I could have persevered, but I would have been a mediocre accountant and been barely above the curve. I just realized that there was something I was much more interested in and that was sociology, studying people in groups. This brings up a good point because one of the main lessons that emerged through the book’s research is that, in our society we have this belief that is pushed on us that winners never quit, and that you should always persevere and perseverance is the predictor of success. You hear all of these inspirational stories of people who failed 10 or 20 times and then they finally succeed. But what I found through the research is that winners actually quit all the time. Winners are not afraid to give up on something and to say, “I thought this was the right path for me, but it’s not. I’m going to go back and take a different path. Or, maybe it was the right path for a season.” Maybe I was supposed to have two semesters or quarters of studying accounting and then I figured out that it’s definitely not for me. It was the path for a season but now I want something different. So I think it’s really important to be able to change your mind, to be able to say, “I’m going to go in different directions and that’s alright.”

You’ve interviewed so many different people about their experiences and shared them in your books. What is the most rewarding part of that?

For me the most rewarding part (there are lots of different pieces to the whole thing, the research, the editing, the writing, the publishing, the sharing, etc) but for me the most rewarding part is when there is some kind of connection created between me and a reader. Or even someone who is maybe listening to this show. When I say connection, my goal is to help them take action in some way. That’s what really motivates me and inspires me. I don’t necessarily want people to say, “I read this book and I liked your book, or I listened to this interview and thought it was a good interview.” What I want them to say is, “I read your book, or I heard this conversation with Carly in Vancouver and then I went and did something different. It helped me in some way. I applied this to my life. It gave me a bit of insights. It showed me how to do something.” So that is very motivating and rewarding to me.

That reminds me of something you said in one of the TEDx talks you’ve presented, in which you talk about how we make a bargain with fear, and how we ask it not to show up, as long as it lets us live our quiet little lives. How would you encourage people to overcome that fear or to step into it?

I would encourage them to pay attention the discontent that they feel. This discontent is that little voice that’s saying, “Sure, you could do things this way and that would be fine.” You aren’t a bad person and you could have a good life, but maybe there is something else underneath the surface that you really want to do. Maybe you know what it is and you’re just trying to figure out how to do it, or maybe you just have that sense, that longing. You know? I actually don’t want that quiet life. I actually want something that’s more active. I do want to challenge myself. I think you should pay attention to the discontent, because a lot of people do make these bargains with fear and discontent, as you said, but I really believe that if you let that into your life and say, “I’m going to respond to this, I’m going to engage with this, I’m going try to explore different paths, even if I have that fear or whatever the obstacle is, I’m going to live with this.” I think that’s a positive thing.

You’ve done so many different things. You’ve published four books, you’ve been to every country in the world, and you’ve created an incredible community through your work. But when you’ve achieved so many things that most people dream of for their whole life, do you ever find it difficult to figure out what to do next?

Just like I said, fortunately, I wasn’t good at accounting. Something I am good at, or at least what I’m motivated by (in addition to connecting with people) is creating things. I like to build things and make things. I actually like it just for the process of making and creating. So for me, it’s not so much about the four books or whatever. I’m thinking, what’s the next thing? What do I do? I take enjoyment in that so I am still very motivated.

To learn more about Chris Guillebeau and his work, visit chrisguillebeau.com

To stay up-to-date with the latest episodes of Question Everything, follow host Carly Sotas on Twitter + Instagram

This interview has been condensed and edited.