Chris Guillebeau

have instead of what we do. We think things that hold us back and dampen our spirit. But it's not just about thinking. Our actions matter. It takes conscious, consistent, and creative effort to make a life worth living. This podcast is about how other people keep themselves moving in the right direction, how they feed their good wolf YEA, thanks for joining us. Our guest today is Chris Gilbo. Chris is an entrepreneur, author, blogger, and speaker. He's perhaps

best known for his book The Art of Nonconformity. Keep an eye out for Chris's upcoming book, The Happiness of Pursuit. Finding a quest that will bring purpose to your life. Here's the interview. Hi Chris, welcome to the show. Hey man, thanks so much for having me. It's a big honor. Yeah, we're we're really glad to have you on the show and look forward to talking about your your new book

that's coming out. But let's start with the way we always do, which is that, uh, you know, our podcast is based on the parable of two wolves, where there's a grandfather who's talking with his grandson and he says, in life, there are two wolves inside of us. What is a good wolf, which represents things like kindness and bravery and love, and the other is a bad wolf, which represents things like greed and hatred and fear. And the grandson stops and he thinks and he says, well, grandfather,

which one wins? And the grandfather says, the one you feed. So I'd like to start off by asking you what that parable means to you in your life and in the work you do. Yeah. I was looking that over today and the podcast description, and I really like that parable. I've actually been thinking about it for the past twenty minutes or so. I can definitely recognize both wolves in

my life. That's probably the first thing that I think of, is you know, there's definitely a bad wolf, like all those negative emotions that you mentioned about resentment and greed and jealousy. Like I I see those signs, you know, a lot. And then I also see like these signs of joy and gratitude, and and I say that I live, you know, by those signs. I mean, you know, I realized, like on my website, it's like I live, I try to live a life of gratitude. But it's a good

gut check because do I really write. And I guess I struggle in the same way that a lot of creative people do with maybe feeding the wrong wolf. So I don't know how it applies to me, but I think I'm going to carry it with me, you know, as I go preparing to go on this big tour and talking with readers about this new creative work, I'm going to be thinking about it more excellent. So let's let's talk about your your new book a little bit.

It is called The Happiness of Pursuit, which I you know, obviously it's clever, clever flip on its head of the normal pursuit of happiness, which is something we often talk about here, which is that you can't always maybe go directly after happiness. And I think a lot of what your book is talking about is sort of that very idea that it's finding something that you are interested in, and that that whole process. You really talk about everything around a quest being the things that tend to lead

towards happiness. So maybe we could start off by you defining what you mean by the word quest in this case. Yeah, great question. So the word quest or even the concept quest came to me through my own quest of visiting every country in the world. That's something I spent the past ten years doing. But fortunately I didn't want to

just write a book about myself. It's not a memoir, uh, And I connected with lots of other people who had also pursued their own quests in different ways, and part of that process was saying, okay, you know what is a quest? Well, a quest has a few distinguishing features. A quest has a destination or a goal, Like there's there's definitely something that you're working toward. It's not completely open ended, but there's also a long process and a journey,

and there's often twists and turns along the way. There's a lot of milestones, uh, you know, or or kind of time points along the way, there's usually challenge or sacrifice involved. At least there's some sort of some form of trade off in the sense that if you pursue a quest, you won't be able to do everything else. You you can still do some things, um, but you can't do everything um. And then often what we discovered

is that sometimes something else happens along the way. Someone's kind of pursuing something and then they are changed or transformed throughout the journey. So I was interested in studying what that what's that all about? And how how are

people's lives changed as they pursue a quest. And the book talks about um you come out with a bunch of different lessons about the idea of a quest, and I thought, maybe we could just run through what some of those main lessons are, and maybe as we do that, you could also if you wanted to tell some of the stories about the people in the book, because there's

a lot of really interesting people in there. The one thing that I wanted to start with, which is that you you start with something where you say adventure is for everyone. And one of the things that I really liked about the book is there's an idea in general now that I think gets overpopularized to some extent, which is that in order for life to have meaning, you have to quit everything you're doing and only do the

thing that you love all the time. And for a lot of people that that doesn't seem to be a practical scenario in certain cases. But what I liked about the book is you had examples of people who found a way to give their life a lot of meaning through a quest while not having to sort of drop everything else in their life. They were able to continue their life, whether that be a family or a job or a combination of those things and find something important

and meaningful. And that that was one of the things that I liked the most. So maybe you could talk a little bit about that. Yeah, absolutely, And I would say that that scenario you described of, you know, not everyone can just abandon everything and go full force into the jungle or whatever. It's not only that it's not practical, it's also not desirable for a lot of people. A lot of people, you know, want to have other things

in their life. They do want to have balance, and I think that's fine, But I guess for me, the goal of adventure is all encompassing and it's not just about it. Like there were a lot of incredible stories of like this dude who ran two hifty marathons in a single year, right, So I think that's a pretty incredible story. But it's also one of those things that people are like, Wow, that's great for him, but you know,

I could certainly never do that. Or there's a guy who walked across America, you know, seven and a half month journey of just leaving his home in Maine, you know, going to the San Francisco Bay area. So I have my own biases, and I'm initially kind of gravitated toward those stories. I think it's cool, but then, um, you

know the value of adventure for everyone. Um. I talked with a woman uh in Omaha who knits hats and she had a quest or she still has a questions in the middle of it of knitting ten thousand hats and she has a family, Um, and she's always just been a crafter and she's made things. But then she came up with this idea of turning it into a

quest and making it something really challenging. It's something that's going to take her a number of years to complete UM, but the structure to it kind of gave her life greater and meeting UM. There's one more story that I like. Another woman in Oklahoma City, Sasha Martin, grew up overseas um but wasn't able to travel a lot. Now she married this guy, has a kid, and she wanted to raise her kid with an international perspective, and so she

wasn't able to visit every country in the world. But she had a culinary arts degree and she decided to cook a meal from every country in the world. And this came her project, her quest, three and a half year journey, and she began it, you know, just as her daughter was about six months old. So you know, her daughter's entire early childhood has you know, consisted of

learning about the world basically. And so I love these stories almost in more In some ways, I love the stories of ordinary people doing interesting things even more than the stories of like the guy who runs the two or fift marathons in a year. I mean, they're both interesting in different ways, but I feel that some are more relatable. Yeah, I really liked the story. I think you just said her name with Sasha in Oklahoma City,

because that was. You know, one of my favorite quotes of all time is I think it's by Arthur Ashe and it's it's you know, start where you are, use what you have, do what you can, and and I think there's a for a lot of people, it's sort of an all or nothing. If I can't live this extraordinary dream life where I do all these things, that I'm just going to live a perfectly plain and boring life.

And there's a whole world in between those two. And that's what I liked about the story of the woman in Oklahoma is she said, all right, here's where I'm at, here's what my you know, my constraints are, so to speak, and yet I'm still going to find a way to do something really interesting and extraordinary, all right, to live

a meaningful life. Exactly. That's the goal, right, The goal is to live a meaningful life, to bring greater purpose to our lives, regardless of our background, regardless of these constraints. As you mentioned, I do believe that's something that is accessible at least to everyone who's able to listen to this podcast. Ye. So one of the other themes that came up in the book, I always sort of tie things back to two themes that come up on the show a lot here, but one of them was effort

is the reward? And you know we talked sometimes on the show. Um. You know, Lewis House was the one who who introduced us, and when we had Lewis on the show, he talked a little bit about some athletic achievements where you know, when he finally achieved and me sort of sat there and felt empty at the at the ceremony. Or we talked about how often we get the thing we want and it doesn't turn out to really be the moment we expected. So talk to us

about the effort being the reward. Yeah, I think, Um, I think the way I phrase it was, effort can be its own reward, you know, if we let it. But I don't necessarily think it always is, because as you said, there's there's lots of stories of people who are very much focused on that goal or destination and then they kind of experienced this moment of alienation or disappointment or loneliness. Uh, you know, when they come to the end and maybe they realized they missed you know,

something along the way. Um, and I felt that in different ways, you know, to at different points along the quest. So I think that the idea is, you know, to value the effort, to value the process, you know, in my quest to go to every country in the world. You know, I was sometimes criticized for not being a great travel writer because I'm not a great travel writer. It's completely fair criticism. I'm not really good about, you know, writing these detailed, like long essays about you know, places

and people. I read when other people do and I'm like, that's great, that's fantastic. It's not me. But I actually enjoy the process of travel. I actually like, you know, being disrupted from a routine at home and going from place to place and being on the road. And I think we're actually recording this while you're on the road. So I don't know what your thoughts are on that, but um, I guess embracing the process and seeing that that there's actual value in the process process of doing it,

regardless of what happens, you know at the end. Yeah, I like the I like the balance of you've got a quest, which is to to accomplish something, but along the way is being able to appreciate those things as they come. And I'm a frequent offender of having my eye on something that's out in the future, and you know, days and weeks slide by where I'm not even present at all to what's going on in my own life. And uh, and I do like being on the road also.

I like traveling. I like the disruption of it to some degree, everyday matters. That was That was another one that you had, and you talked about being conscious of our own mortality. I discovered that as I talked to all these different people, you know, many of whom came from various backgrounds, men and women, young, old, different countries, pursuing different quests, they did have a few things in common. And one of those things was I noticed, surprisingly, so

this wasn't something I expected or even ask about. A lot of them, you know, spoke about this concept of urgency, and a lot of them spoke, you know, using the same kind of language about how, you know, I just want to make my life count. And I realized that, you know, life is short, and so I started asking about it more, and I noticed that there was sometimes a distinction between, you know, people who pursue these kinds

of really big projects and those who don't. And it's not a percent, but just you know, generally speaking, I feel like a lot of people who are pursuing these quests or adventures, they have what I called an emotional awareness of mortality. And the distinction there is that everyone has an intellectual awareness of mortality in the sense that we know that everyone dies, but an emotional awareness to mortality is just more a conscious awareness of the fact

that someday I will die. And I heard that express to a lot not in a super negative or depressing way, but almost as a as a motivator for a lot of these people, you know, as a motivator of like, I'm just aware that you know, today is almost over, you know tomorrow's a new day. I'll never get back you know, today again. So what am I gonna do tomorrow that's gonna help me build for the future, while also, hopefully, as you alluded to, still living in the present and

enjoying the moment. So I felt that a lot of people are very conscious of this. Do you have any thoughts on how people become more conscious of that, because you're right, it's pretty easy to say, yes, I know I'm going to die. Getting that awareness in a more tangible way, in an emotional way, like you say, is

is harder to do. Uh. The certain Buddhist traditions have people meditate in the graveyard, which might be taking it a little bit far, But I'm wondering if you've got any ideas between between meditating in the graveyard and and not thinking about it. Yeah, that's funny. It was actually a cemetery in my my home home neighborhood of Portland, Oregon that actually enjoy walking in and running and I don't actually find it depressing. So maybe it's uh, maybe

it's kind of like that, I think. Uh, you know a lot of people I talked to you have first mentioned it. There often was some kind of defining moment that led to that. Maybe it was the passing of a of a close friend or a family member, especially an unexpected passing, like someone who died in an accident. Um. There were a couple of stories of people who had received like their own terminal diagnosis for some kind of illness.

In one case, there was a woman who was was was really into word watching, and she just discovered this hobby or this passion, you know, a bit later in life. I think she was in her mid thirties, early forties and she just kind of started pursuing it and then you know, she received what was initially a terminal diagnosis, and her very first thought was, oh, no, there's so many things left that I still want to do. You know, I feel like I haven't used my time well or something. Unfortunately,

in her case, um, the diagnosis was premature. She went on to live almost three decades longer after that, and she devoted the rest of her life, you know, to pursuing this quest of seeing more birds than anyone else. But you know, I don't think that we have to receive that terminal diagnosis, right, you know, to to somehow adopt that model of urgency. And that's kind that's the word that I think of more than mortality, so much is is urgency is you know, urgency and opportunity. You know.

To bring it back to the wolf that we talked about in the beginning, you know, I guess the way that I try to feed the good wolf is you know, by recognizing and acknowledging in my life with gratitude all the different opportunities that I have and all the privilege that I have, and with that comes responsibility. With that comes okay, great what am I gonna do with this? You know, it's amazing that I was able to travel to all these places, like you know, very few people

could do that, So what's next. I feel that that helps me a little bit. One of the other lessons that you came up with was that smaller goals can expand you talked about how people often start with I think you described yourself. You didn't intentionally start out to travel every country in the world. You start out traveling because you found it enjoyable, and you you build on that.

And I thought that was really interesting, a in the way that that quests work and be in the way that really building anything works, you know, is that idea of on the show, we often talk about sort of starting small and connecting the dots, you know, over time, So maybe you could elaborate more. I like, I like starting small, connecting the dots. That's that's a good analogy. In my case. I don't think I ever would have had the vision to visit all a hundred ninety three countries.

You know, if after I took my first overseas trip, you know, and I went to my second or third country, someone said, hey, Chris, wouldn't it be great for you to do this. You know, I spent the next ten years of your life. I don't think I ever would have had that that vision or been able to take that on. And so it was. It was a thing of as I traveled. I lived in West Africa for a few years, was traveling in some regions that are a little bit difficult, and I became comfortable with that.

I just thought that was normal. It's how that's how it works, you know. Um. Then I might set the first goal of going to a hundred countries, and at the time that was like this huge audations goal for me. And then I realized like, well, that's only half the countries, and the real challenge, of course, would be to take on you know, all of them, and but I don't. Again, the confidence came through, like the more I did, the more I work towards something, the greater confidence that that

I had as I went along. And the other thing I felt that produced confidence, I don't know how you feel, um, was that misadventures as I call them, or mistakes or even so called failures, all of these things actually kind of worked for my benefits as I went along, Because you know, at first, if I would travel to a new place or something. I was super careful and I was even like nervous and just checking things all the time. And then things started to go wrong because they always do,

you know, when you travel. And at first, you know, I'd be in some situation where I was really worried and how am I gonna get out of it? And that you just go, you go through those things and it's usually okay, and the worst case scenario usually doesn't happen. And I guess by the end, I was actually making more mistakes because I was I was careless, you know, because I gained confidence, you know, through all the things going wrong, through the fact that I was you know,

two thirds of the way through or whatever. So I'm a big believer in like, just identify the goal that you can accomplish, you know, I mean, stretch yourself a little bit. Obviously you should challenge yourself, um, but take on whatever is is challenging and meaningful for you. You're the person in your own life who determines what that

is not someone else. That was another one of the ones from your lessons that I had highlighted that I wanted to talk talk about was the misadventures produce confidence because I'm I'm interested in that overall theme of you know, misadventures producing confidence is one way to put it. The other is that we interviewed Krista Tippett from the show on Being and and we talked about the idea she's got in one of her books where she she talks

about people who are great. You know, pick your Gandhi or your Martin Luther King or your and they didn't become great in spite of their disadvantages and challenges. They became great because of them because I think we all try so hard to avoid the things that are hard and um it's I think there's an old there's an old quote that's coming to mind now that I can't quite get, but it's basically about, you know, good weather, it doesn't make good sailors. Something to that that extent.

What is something that people can do if they want to? Obviously they can read your book, Um, but what are some ways that they can start to think if they think that a quest might be something for them, where some places they can go to start learning more about that or to think more about it. Yeah, I think they can go within themselves and they can go and say, okay, what are some things I'm interested in? You know what, what are some things that I'm excited about? What am

I motivated to do? And then how can I you know, create some kind of packaging or rapper for that. That's what a quest is all about. That's the distinction between you know, a hobby and a passion or a quest. I think I use this, uh you know analogy of golf in the book just kind of funny because I don't really play golf. I don't know anything about it, but I said, you know, if if you like golf, like if you go out to play golf once in

a while, great, it's a hobby. Um, if you go out, you know, if you if you really start focusing on your game and playing more frequently, maybe getting some coaching

or something, maybe it's turning into a passion. If you decide to go and play like every golf course in Scotland, which I'm understanding that there's quite a few of them there, and you have a specific deadline, I'm gonna do this within two years or something, That's that's when it becomes a quest, right, And so I feel like, what what helps with the quest is to have that rapper, to have that packaging, because until I had that, I was just traveling. And that's fine, But I was really motivated

by goal setting. I was really motivated by making lists. That's another thing a lot of people had in common in the book. They all like to make lists and you know, write things down and check them off. Not

all of them, but a lot of them. And I guess for me, like once I found the parameters or the constraints to use that word again, Um, just the logic of saying, Okay, I'm traveling, but according to this specific goal, and here are the number of countries, and here's the deadline that I set for myself, you know, eight years into the future of my thirty fifth birthday. Um, that's when it became much more real to me. So I guess I would encourage them. Um, let's think about

all the things that you're interested in. How can we take them to the next level? You know, that's what a quest or or a big adventure as if I was kind of like leveling up. Yeah, I like that.

And I and I was working on writing an article today and I came across a study that just made me think of this and it basically said that depressed people tend to have very general goals and so kind of to the point of what you're talking about, a generalized goal would be something like I like to travel, I want to travel more, right, Whereas when you when you start to get really you put a package around it, to use your words, you it gives you direction and drive.

And I think that's one of the things that I think depression can cause. Is very difficult to make choices. It's very difficult. I'm I'm not sure, maybe I'll do this, maybe I'll do that. Whereas if you're getting more specific and a quest could be a way to do that, it sort of keeps you moving in the right direction. Yeah, well that's what that's what the whole point of, you know, using a quest or an adventure or whatever term you'd like to use, you know, to bring purpose and meaning

to your life. You know, I've also struggled with depression in my life. I'm doing general care right now, you know, but from the top time to time, like I experience anxiety or whatever, and it was it was really helpful over that ten year process. Like I was doing lots of other stuff, it wasn't my only thing. But over ten years, like I kind of knew more or less what to do next, you know, I kind of knew like, OK, you know, well I've got this. You know, next year,

I gotta do fifteen countries. You know, here are the fifteen I think I to do. Here's more or less, you know, I'm going to plan my life around. I kind of like that. You know, it wasn't I don't

mean to say it was a diversion. I don't mean to say it was something like to you know, keep my mind occupied when I should have been thinking about something else, Like, it was actually really helpful and actually, and throughout the process that I'm gaining that confidence that we spoke about, it's it's helping me in other ways and I'm really just experiencing my own little personal change and transformation. So that's that's kind of what I mean by just you have this thing, and you know, here's

what I'm working towards, and you're building. You're building something that you believe in, your building something that matters to you. So that was great, greatly helpful for me. You wrapped the book up by saying that you know, quests don't always tie up in a clean way, maybe share a little bit about a couple of the stories there and then also maybe for you when you hit the last country. So if you study you know, quests historically, Um, most of the narrative is all about the process. Most of

the narrative is all about the journey. And sometimes, uh, the beginning is you know, super short. It's just like all of a sudden things were disrupted. Why were they disrupted? Why did the aliens you know, invade the earth? We don't, we don't know, but there they are. We gotta do something about it, right, Um. Why you know, why did this person have to to go and save his village

or reclaim the magic item or whatever. Um. And the ending is also you know often kind of like and that was it, you know, we say the village things were good, right, So it's all about that middle portion. Um. They don't always tie up so well in real life.

And you know, often, as you alluded to with with Lewis and his story, like you come to the end and you're kind of like huh, okay, or you go home and people don't relate to it, your friends or family or somebody who wasn't a part of that direct experience, UM kind of ask you to be like, what's it like? And the way that they're they're asking you is kind of like just asking you to describe, like, you know, last night's TV episode or something like what was it like?

You know, how do you how are you supposed to distill this? And so um, you know, there is kind of a season, I think, not just a moment, a season of figuring out, Okay, you know, how what am I doing now? Um? And I experienced that. I think almost almost everybody I talked to in the book one way or another did my My season for that came a bit before the Quest came to an end. It was kind of the last year essentially that it just kind of hit me. It was like, this has been

my identity for a long period of time. You know. If I meet somebody or somebody hears about me, there's like, here's this guy. His name is Chris. We can't pronounce his last name, but he's the guy who's going to every country in the world. Right It's been like my little one letter that's whatever, you know. So I don't want to live in that forever, you know, I don't want to and like, for a few months maybe afterwards, or a little maybe now with the book or something,

it's like, oh, that's Chris. You know, he's the guy who went to every country in the world. But I guess long term, um, I don't want to live. I want to have something, you know, I always want to be working on something new. I wanted to continually be forging a new identity. So a little bit of struggle

with that. But then again, like what's the alternative. You know, the alternative would be to not undertake the question in the first place, to not have these incredible experiences all over the world, you know, to not meet all these other people pursuing quests. I think we always have to continue to try and find meaning in life, and it's not always while you have the quest going. That's a good way to give give life meaning, but there's always

a period where we have to continue to search. And that was one of the things I liked about the concept of the Quest was, Um, I think it's easy to get hung up on what's the meaning of life? And and I'm a fan of Victor Frankel. I don't know if you call a guy who went through a holocaust, if you're a fan of his But but but you like, like I got his posters up in my my bedroom. Um, but he talks about how there isn't a meaning to life.

We all have to create our own meaning. And that's what I thought was really this quest was a way to create that meaning and put some structure around it. What's the other quote by Joseph Campbell? You said, Um, you know, I don't think people are looking for the meaning of life. I think they want the sense of being alive. Yeah, that's another one of my favorite ones. So what is uh next for you? Obviously you've got this book to our coming up. You're promoting the book,

but I'm sure you've got got something else brewing. So the book tour is not really just a book tour, you know, it's it's a it's a series of community events. And my whole, my whole project, you know, began from community.

And I started writing about the journey to every country a few years ago and started doing meetups with my readers all over the world, and I really realized they were the greatest part of the quest essentially, you know, because I was just an independent traveler doing my own thing, and and then I started connecting with all these great people. So it's not so much about promoting the book, you know,

and the tour. It's it's more about hearing their stories and maybe sharing this message hopefully kind of nudging people towards pursuing their own adventure and help and nudging them towards embracing the value adventure in their lives. And I see that as as kind of a mini quest of its own. You know, I'm doing forty cities to start out with, but then I hope to add another thirty cities later. I hope to do this for a while.

It's something I really enjoy doing. And you know, we also have an annual event that we put together in Portland, Oregon, and be great to have you guys out sometime. Um that's like a weeklong event with thousands of people. Again, it's it's very much focused on community. So I guess whatever it is that I'm doing next, you know, various business projects and books and things like, I'm hoping that's that's kind of the value that that shines through all

of it is is it's not just about Chris. He's trying to do something that, you know, to bring like minded people together or to encourage people along the way. Is it true that anybody that interviews you for a podcast gets free tickets to the World Domination somewhe or is that just something I dreamed up in my head? You must have you must have seen that on Twitter or something somewhere. But that's great. I would love to have you guys. We'll figure it out. I would love

to get out there. I hear wonderful, wonderful things about that event. Well, I think that takes us near the end of our time. Is there anything you want to talk about and related to quests that you don't think we covered, or any other thoughts on the theme? This is great. This is really a thoughtful questions you know, it's so much better than going on the radio for like a two minute segments when like Chris tell us everything like right now, I'm like, God, I don't know

what to do. No, I'm really honored to be on this, you know, great thought podcast. If I can never help you or any of the listeners with anything, please fread to contact all right, Chris, Well, thanks so much for your time and hopefully we will get to see you while you're out on the road. Awesome sounds great. Thank you all right, take care, okay, take care of a good night. You can learn more about Chris Gilbo and this podcast at one you Feed dot net slash Chris, that's c h r I s