How to Create Your Own Freedom, Live an Adventure, & Do Work That Matters: A Chat with Chris Guillebeau
Wherever you look, there are voices telling you to “live a better story” or do something “epic.” They make it sound easy. But it’s not so simple, is it? The truth is the epic life requires more than just blind courage. Few people understand this better than Chris Guillebeau.
Chris is a friend, mentor, and patron to the work I do (he graciously endorsed my book, Wrecked). What impresses me most about Chris is his ability to stay true to his values of generosity and adventurous living while wisely providing for himself so that he can sustain those passions.
So when I had a chance to sit down with Chris and chat about these ideas, I really wanted to know one thing: How do you live a life full of adventurous experiences and creative endeavors without going broke? That’s what we discuss in this interview.
Below you can listen to the audio version of the interview, read the abridged text version, or download the 7000-word transcript. Your choice. Enjoy!
Listen to the interview
Reader’s Digest version
Jeff: So, Chris, you just finished visiting your last country in your trek to visit every country in the world. How does it feel?
Chris: It feels pretty good. I was actually kind of worried about it. This has been an 11-year process. Eleven years unofficially and, then, about five or six years since I’ve had this stated goal I’ve been writing about it. So, it depends on how you count it. But it’s been a long journey.
So, maybe a year or two ago I started just kind of started feeling worried about the end. Like, what am I going to do? This has been my identity and my focus for a long time.
But it was actually really good. I enjoyed it. And I’m glad to have done it. I’m going to keep traveling and going different places, but I’m also glad to move on to something different.
J: What’s interesting about you, Chris, and it’s obvious now that you’ve just talked about visiting every country in the world, is that you have this unique perspective on life — it doesn’t need to be boring. You don’t have to wait until you retire to live the life you want to live. Can you talk a little bit more about that?
C: There are so many more people who are doing interesting, remarkable things now. People are beginning to become aware that there are more possibilities, and more opportunities than perhaps there were before.
We’re able to ask a lot higher-level questions than many of us were previously, like, “What kind of work would we like to do?” “How would we like to spend our free time?”
I don’t feel like I’ve started anything in that regard. If anything, I have this community of people that are doing amazing things.
For me, I just wasn’t good at doing things the normal way. I wasn’t a good employee. When I tried to work for people I just did a terrible job. And I was a juvenile delinquent. I stole cars, which probably isn’t the best career path forward. But that’s how I was when I was 15. Then when I went overseas, and I learned a whole new way of life.
Once you experience things like that, once you begin to travel or you’ve started working for yourself, it’s very hard to go back. Once you have an initial amount of success or something that’s new or different, you just want to explore it more. You just want to see where it can go.
So I always encourage people to just do whatever you can to have that moment of inspiration or discovery. And I think that will lead to more opportunities later.
J: If we want to live a more interesting life, do we have to do scary things like travel the world?
C: Do we have to do scary things? Well, I don’t know. I don’t think anyone has to travel the world, of course not. Not everyone wants to travel the world, and that’s fine.
But I do think we should do things that stretch us and challenge us. For a long time I wanted to be a writer instead of actually being a writer and just sitting down and doing it. I had to overcome that.
It’s important for all of us to think about, “OK, what do we really want for ourselves?” What do we want for ourselves? What do we really want to do, or become, or achieve? And how can we structure our life in a way that allows us to get closer to that?
And, then, what I always encourage people to think about is, “OK, so you’ve got this amazing life, or at least you’ve got a pathway to an amazing life, what’s next? What are you contributing? What are you doing for others?”
Because that’s the other missing link. And everyone should think about that.
J: I see you living a creative life. What motivates some of the decisions that don’t make sense? For example, having an event and then giving away $100,000 to the attendees. That doesn’t make sense. You’re doing some things in your life that get people talking and get people thinking differently. Why?
C: Because it’s exciting. Because it’s fun. And I think all of us have to pay attention to what makes us excited, right?
You mentioned the thing that we did last year at the conference where we invested $100,000 directly back into the lives of all the attendees. When I first thought about that, I thought, “This is a crazy, ridiculous idea.” And it sound so exciting. It will be so fun. It would be so fun and so meaningful.
If you give 1,000 people $100 each, probably not all of them are going to go and do something great with it. Some of them will just go out to dinner, and that’s fine. But probably some of them will do something interesting. They probably will do things that we haven’t thought of.
I’m writing a new book about quests right now. And I’m talking to all these people who have done crazy things. There is a guy who walked for 17 years without using a car. Other people have circumnavigated the globe. There’s all kinds of different stuff. And they all say the same kind of thing:
It was difficult. And it was challenging. It was crazy, but that’s why I did it.
I’m motivated by things that I find to be fun and enjoyable. And I hope other people enjoy them, too. But if not, at least I know that I will.
J: How do you balance risk-taking with responsibilities?
C: Experience produces confidence. The more you do these kinds of things, the more your vision expands. The more you do things, the more confidence you have.
I have a lot of business projects now. I’m not super wealthy, but my business does well. I’m a successful author. I have products that sell. I have good passive income. Since I built this over a number of years, it does allow me to take more risks.
But for anyone who doesn’t have that, you can still take risk. You can still start with what you have. And everybody has the ability to contribute to something.
J: What got you started as an entrepreneur?
C: What got me started was initially a motivation to do anything I possibly could to not work for someone else. This was age 19.
I wasn’t like trying to change the world or anything. I delivered pizzas. I had worked at FedEx in the middle of the night hauling boxes in Memphis, Tennessee. And these jobs do not offer a lot of advancement potential. They were not high-paying jobs. And, so, initially I was just like, “How can I do something?”
So that’s how I started learning about working online which is like now 13 years ago when people were just starting to do this and buying and selling different things, and learning about website design and all this different stuff.
The initial motivation was freedom and independence. I want to be on my own. I was a jazz musician and loved playing music. But music doesn’t pay that well; at least it didn’t for me at the time.
So, initially it was just, “How can I create something that can support a lifestyle that I hoped to have?”
J: In your best-selling book, The $100 Start Up, you emphasize the ease it takes to start a business. Now, there is very little risk. Obviously, it takes a lot of work, but it can be easy to start. Explain this more.
C: We did a two-year study of about 1500 people. And from all over the world, all different walks of life, men and women, different ages. That was the best part of the whole experience of writing and publishing the book.
This is a movement. People are really creating their own freedom in a very easy way. As you said, it takes a lot of work to run a business, of course. But the point is the costs have greatly lowered. Access to information is lowered.
J: So, if it’s easy to start, why don’t more people do it?
C: Well, I think a lot of people are doing it. It’s becoming much more common. I don’t think it’s mainstream yet. But I do think it’s becoming more common to meet people not just in urban centers, or cities where change happens, but all over the place that are doing it.
As to why more don’t, I really do believe that probably the biggest obstacles in anything like that are more internal than external. The biggest obstacles are we all have our own fears, and our own insecurities, our own anxieties. I think we’re just busy with other stuff. We haven’t prioritized.
So we are all at fault for wanting to do things but not creating an environment around us that allows us to do those things. One of the things I try to do is encourage people to start, and to start with where they are, with what they have. And, then, seeing where things go from there.
J: You’ve got a great course about that addresses this, aptly named “Adventure Capital.” But could you give maybe a few practical tips from it?
C: I think we like to make starting a small business very complicated. Or maybe that’s what we’ve always heard. However, a business is just three things:
- It’s a product or a service.
- It’s a group of people interested in that product or service.
- It’s a means of getting paid.
I encourage people to focus on only those three things in the beginning.
If you’re not sure what area to focus on, ask yourself what people ask you about. Then do whatever you can do to get the website up, or if it’s an offline thing, however you’re going to put that offer out to the world. I would encourage you to do that as quickly as possible.
What I hear over and over is that whenever people got their first sale, they found that very empowering. Even if they sold something for $10, they talked about how excited they felt. Because all of a sudden they’re making income from a source that’s different from their employer. And that was the beginning for a lot of people to then go on and grow their business much more.
But they didn’t wait six months. They didn’t wait a year. They didn’t write a business plan that no one else would ever read. They got started as quickly as possible.
Download the transcript
If you want the full text version of this interview, click here to download the free PDF (thanks to Eva P. Scott for her wonderful transcription wizardry!).
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To find out more about Chris and his writing, check out his excellent website.
If you want some in-depth help building or growing a business, check out Chris’s new course, Adventure Capital (affiliate link). Registration is only open for the next week, so hurry up if you’re interested. Click here to find out more about it.
Have you ever considered the kind of life you want to live? What would it take for you to live it? Share in the comments.