Episode #25： The Art of Non-Conformity with Chris Guillebeau
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Summary
Chris Guillebeau is the owner of the blog The Art of Nonconformity, where he writes about challenging the status quo and living a non-conventional life. In addition to writing, Chris spends his time traveling the world and he has a goal of visiting every country in the world.
Transcript
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Brett McKay here and welcome to another episode of the Art of Manliness podcast.
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Well, as boys, we probably all had dreams of living extraordinary lives.
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Perhaps you dreamed of owning a cabin in the mountains and taking tourists on guided fly-fishing excursions.
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Or maybe your dream was to travel the world with your steamer trunk and haggling with merchants at a bazaar in Istanbul.
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But if you're like most men, you probably gave up on those dreams thinking they were just childish fantasies
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and then you had to join the real world by getting a job, settling down, and paying bills.
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Sure, you might have a decent life, but it feels so ordinary, so conventional.
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And there's still a part of you that yearns to fulfill the boyhood dream and you would give anything to make it a reality.
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Well, our guest today is a man who decided not to live a conventional life and he helps others live the life they always wanted.
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His name is Chris Guillebeau and is the owner of the blog The Art of Nonconformity,
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where he writes about challenging the status quo and living a non-conventional life.
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In addition to writing, Chris spends his time traveling the world and he has a goal of visiting every country in the world
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Chris's work has been featured in the New York Times, Washington Post, MSNBC, and Anderson Cooper 360,
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and Chris will be publishing a book based on his blog this fall called The Art of Nonconformity.
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Thanks for having me. That was a great introduction.
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Well, I wanted to introduce you well and do it well.
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So, Chris, what inspired you to ditch the typical life plan for men that's usually, you know, college, job, marriage, mortgage,
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Well, I think there were a number of turning points.
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I actually had the fairly typical plan of college and marriage, and I got married pretty young.
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But I think probably one of the big turning points was 9-11, which really affected me just like it affected many men and women all over the world.
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So I think when that happened, I was about 21, 22, and that experience just, you know, it depressed me for several months like it did for a lot of people
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and kind of helped me to ask, you know, questions about my own life of, like, what am I really doing?
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Like, I used to have these dreams of traveling and always thought that I would do something, you know, overseas to help people or, you know,
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to kind of connect my life with others or whatever, and I wasn't really doing that.
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Like, I had been working for myself, and I started a business, and that was fun, but I still thought it was kind of, you know,
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small compared to, like, the needs of the world and everything.
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So I was just really tripped out by that and ended up going with my wife and moving to West Africa.
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And that was in 2002, and we heard about a volunteer opportunity to go and be a part of this medical mission
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And so we made a two-year commitment to that, and then it turned into kind of a four-year commitment,
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just living in the region and, you know, facilitating the process of helping these nations kind of recover from a civil war.
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So that was, like, a very, very intense emotional experience, you know, over four years, the four-year volunteer commitment.
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So that was probably one of the biggest things, like, you know, actually, like, being depressed after 9-11
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and then finding a way to kind of respond and reach out and go and be a part of something that was bigger than me.
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And then, you know, 2002 to 2006, we were overseas and then came back to the States, relocated to Seattle,
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and I did grad school at the University of Washington.
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And while I was at grad school, I started another business and was doing some business consulting and different stuff,
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and I felt like I wanted to kind of transition to where I had done a lot of stuff.
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I had helped people on an individual basis with my business consulting and my volunteer work and stuff,
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but I wanted to kind of, like, move to a broader basis and, like, do something bigger.
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And so that's when, just a couple of years ago, I kind of started the writing career and started the blog
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So those are a few things that kind of led up to where I am now.
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And so I guess after the trip to Ethiopia, you were kind of in this mode where you're like,
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this is what I want to do for the rest of my life, not have the conventional life
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and live my life according to how I want to do it.
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And then also just the experience of being self-employed for a while
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and then just the broader worldview that came about through travel.
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Definitely the broader worldview of living in Africa,
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but then I'd also traveled throughout a lot of countries in Europe
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and then southern Africa as well and a bit in Asia.
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So I guess, like, the more I did, the more I wanted to do more.
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I guess, like, once you have a taste of something, then you kind of see,
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oh, there's a bigger world out there and, you know,
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I don't have to do things the same way that other generations have done
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So it's definitely been more of a process than, like, a single thing.
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So part of your kind of lifestyle you've chosen to live is to travel a lot.
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And, you know, you have the goal of reaching every,
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Yeah, this kind of started, like, right around the time
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when I came back from Africa and went to Seattle.
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I had a lot of school breaks just with the cycle of grad school.
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And so I started doing, like, these two-week trips just by myself going off.
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And by that point, I had traveled a lot in West Africa,
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so I was pretty comfortable, you know, in difficult countries or poorer countries.
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Just kind of crazy little out-of-the-way places like that.
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And I guess after I had done this a little while,
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I started counting up the number of places I had been to just non-strategically.
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And so I realized I'd been to, like, maybe between 50 and 100 countries.
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And I thought, well, let's set a goal of visiting 100 countries.
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And so I kind of, like, worked out how much that would cost.
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My first thing is, like, oh, how can I do that?
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And how, you know, how much money is that going to cost?
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And I realized, like, having been to about 50 countries,
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it would cost me about $30,000 or so to go to the next 50.
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And my first thought was, like, wow, that's $30,000.
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You know, of course, on the one hand, it's a lot of money.
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But on the other hand, it's actually not as much as I would expect to do that
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over a number of years and to really set this as a personal goal
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and to make sacrifices in other areas, you know, so that I can focus on that.
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And then as I got closer to 100, then I started thinking, like, oh, what's next?
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You know, like, I was turning 30 years old, and I was like, okay,
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But, you know, why not go to every country in the world?
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So that's how that came about, which is a little bit more difficult
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because with just 100, you can kind of pick and choose, you know,
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and you can go to some of the easier countries or whatever.
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But, you know, to go to every country, you can't just, you know,
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put something off the list because you don't want to go there or whatever.
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My goal is to do it before my 35th birthday, which is coming up in about three years.
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So I'm down to about two and a half years left to get to the final 50.
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And so when you go, when you travel, what exactly do you do?
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Are you just seeing the sites or do you do volunteer work when you're there?
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I mean, how do you fill the time when you're visiting these countries?
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Yeah, I'm not doing a whole lot of volunteer work, at least not overseas right now.
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That's difficult to do when you're just going somewhere for a briefer period of time.
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Like now that I work as a writer, that continues, you know, wherever I am in the world
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And I have a small business that kind of works with the blog where I sell information products.
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So everywhere I am, you know, I'm always working.
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I usually work a few hours a day and then I go out.
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Like if I'm somewhere for a few days, I might work in the morning and then go out in the afternoon.
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And one thing that's really interesting that's kind of changed a bit over the past couple of years
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is I'm naturally a pretty shy, introverted person.
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But now that I have this blog, like I've got readers all over the world.
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And so I've learned that I actually don't have to prepare very much at all.
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If I'm going somewhere, like I'm probably going to know at least somebody, usually, you know,
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And so I've been doing meetups in the different countries I'm going to.
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And like some local people will come and meet me and then take me around and show me,
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you know, whatever they want me to see or whatever, which is really quite fun
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because I can see stuff that I wouldn't ordinarily, you know, be able to see
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But now I don't even need a guidebook, you know, I just show up and there are people there to take me around.
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So you mentioned a little bit about the price of traveling the world.
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You know, I know there's a lot of men who would love to travel more,
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but they don't because they just don't think they have the money.
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I mean, is it pretty affordable to travel like you do?
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I think there's a few things we could say about this.
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And we could talk about this probably for an entire podcast.
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But I'll try to be concise and say a couple of things.
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The first thing is, like, whenever I think about spending money, whether it's for travel or for anything else,
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like, I always try to think about priorities and values.
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Like, my priorities and values won't be the same as anyone else's.
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But I always try to, you know, be very conscious about, you know, what I'm choosing to spend my money on.
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In some ways, I'm very frugal, perhaps even to a fault in some ways.
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Like, we've been living back in the States for three years, and we don't own a car.
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We've chosen to rent a home rather than own a home, which I know is not the right thing for everybody.
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So I guess the first thing is, like, I've just kind of chosen to really identify this goal as something that's important to me,
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and that's what I'm willing to invest in, and that's what I put a lot of disposable income into.
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But then secondly, because I've been doing this for a while, like, I've learned quite a bit, usually through trial and error, a lot of error.
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But now I do this thing that I call travel hacking, which is kind of like life hacking or, you know, hacking different things on your MacBook or Gmail or whatever.
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And so now I've kind of learned to travel quite affordably.
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And my average plane ticket cost now is about $300 to $400, and that includes, like, lots of long-haul flights to Hong Kong or to Johannesburg or wherever.
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I think right now I have about 800,000 frequent flyer miles that I'm, like, constantly cycling,
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and I'm, like, every year I'm getting a few hundred thousand more from different promotions and things,
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and I'm using a few hundred thousand, you know, to go on all these trips.
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And for someone who's not trying to do what I'm doing, which I assume is almost everyone,
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if someone just wants to travel a little bit, they're not trying to go to Iraq or, you know, wherever,
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Because now, actually, it's getting a little bit more expensive for me because I'm getting down to these final countries that I have to get to.
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But if I just wanted to go to Thailand or Australia or, you know, somewhere,
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then I don't think that's too difficult at all.
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So, again, first of all, with the mindset of priorities and, like, we're going to save up for this because it's important to us.
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But then secondly, with, like, thinking about the creative approach of different ways to do it with miles,
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with award tickets, around-the-world tickets, you know, or whatever.
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So instead of buying the new excursion, you put the money into an account to go traveling, is what?
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I have a separate savings account that I use just for my travel stuff.
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And that's really made my life a lot easier just to kind of have it there and not think too much about it.
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And you share some of these kind of travel things you've learned in the information products you sell on your site.
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I mean, I also share some of it just on the blog.
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If someone has a specific question, I'm more than happy to help with that.
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But then, yes, I do have, like, a Frequent Firemaster product that kind of goes into it in much more detail
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and talks about, you know, how all the different promotions work and how the airline alliances work
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and how you can kind of get some of these deals.
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So, Chris, your blog and the different products you sell are all geared towards helping people live unconventional lives.
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What do you think is the number one thing that holds men back from living the life they want?
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So I would say for myself, I would say that the number one thing that held me back for a long time was my own fear and my own insecurity.
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I guess, you know, I think, let's see how to put this.
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A lot of us live our lives kind of out of the desire for approval or out of, like, the fear of what other people think of us.
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And I know that's certainly true in my life for a long time.
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But I think I just kind of learned, you know, over time to overcome that, not really to get past the fear,
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but just to find a way, like, to work with it or whatever.
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I mean, I wish, you know, the experiences that I'm having now with the site and the travel and stuff,
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Like, I had been thinking for five years about starting a blog.
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But I think for a couple of years, you know, the main reason why I didn't,
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didn't have anything to do with anything practical or with money or with anything else in my life,
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but just kind of with fear and, you know, insecurity and, oh, what are people going to think about me and that kind of thing.
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And going on that, talking about kind of the fear of what other people think,
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I think a lot of men do things because, and a lot of people,
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but I think particularly men do things because it's expected of them.
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I think with men, they often, like, tie it up with kind of their masculinities.
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I mean, what do you think, what should a man do?
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How do you deal with that pressure of dealing with kind of those social expectations
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and explaining to mom and dad or your mentor that, you know,
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I'm not, sorry, I'm not going to be an attorney at a high-powered firm.
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I actually want to teach kids how to sculpt with clay.
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what advice would you give to a man to kind of deal with that pressure?
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We're going to take a quick break for your words from our sponsors.
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I think that a lot of us probably, specifically men, do feel that pressure.
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I guess, let's see, I'd say a couple of things.
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The first thing is, you know, we really do need to, if we're going to, like, you know,
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come into our own identity as men, I think we have to figure out, first of all, like,
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You know, answering all those personal questions, which I do think,
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even though they're kind of like introspective, I think are quite important.
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And then secondly, trying to find the link or the bridge between, you know,
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those personal things and, you know, how our lives are connected with other people.
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So, in other words, what's it really all about and how are we going to change the world
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and, you know, how are we going to combine our own dreams and stuff with something that's
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And I think, you know, I think once we begin striving towards those things, I think obviously
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we're going to come up against, you know, different expectations or assumptions or pressure.
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I guess I would say, for my case, it's gotten easier.
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The more that I've been, like, the more small, like, I started taking small steps and then,
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I remember when I first started traveling, you know, like, my parents were freaked out
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and they would call and they would hear that I'm in Hong Kong or something and they would,
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And now it's like they don't even know what continent I'm on.
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They're like, we don't know where you are, Chris, but, you know, let us know if anything.
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And I think at some point you just have to take the leap.
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And I know it's not easy, but nothing worth doing is never really easy, you know?
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You write and you do these things to kind of fund your flexible lifestyle that you have.
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What advice would you give, kind of just basic advice, would you give to a man, you know,
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if he's working the nine-to-five job but would eventually like to do what you're doing,
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kind of have the flexibility to travel or do whatever?
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Does it have to be done through a blog or can you create a small business doing something else that he's passionate about?
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I think it's actually a lot easier to create a small business doing something else without a blog
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or maybe by, you know, using the blog to support something else as opposed to, you know,
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starting a blog with a primary goal of creating a new career.
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I think actually, like, it's much easier to look at something that you're passionate about,
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but not only that you're passionate about, but other people are also passionate about and willing to spend money on.
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I think that's the key point that I try to address in a lot of the small business stuff that I do
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is to really, like, look for the convergence between what you're really excited about, your passion,
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and what other people are also excited about and interested in,
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which I think is something that the Art of Manliness community has done really well, right,
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because it's something that you have this interest in, and then, you know,
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there's a whole community of people also interested in the same thing.
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So that's kind of a common mistake people make when they talk about, like, following your passion,
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and you have to – it has to be your passion, but it has to be somebody else's passion as well.
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So I always encourage people, like, to look for that convergence.
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And if you're working 9 to 5, in some ways that's easier than if you're not,
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because then you, like, you can't mess around, basically, if you don't have unlimited time,
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And, you know, you can totally start anything on the side.
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Most businesses are not started, like, with venture capital, with, you know,
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a team of 10 people who are going to work full-time.
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You know, most businesses are started just, you know, the way you started out of manliness
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or how I started unconventionalguides.com or whatever.
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You know, you can start small and then see how people respond and, you know, go from there.
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So, yeah, so it's don't – I guess, moonlight first and then kind of test the waters out
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Yeah, well, I think everyone's situation is different.
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And I don't have to counsel people, like, you know, to quit their job without anything there or whatever.
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I mean, I think we all have a desire for security, and I think that's totally fine.
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I mean, I just like to kind of redefine security and look at what security really is.
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You know, is security a 9-to-5 job or is security your own competence?
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You know, security – you know, if your own competence is a security, then you can do that in a job
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It may be a different fit at different times in your life, and, you know, there may be some times you go back and forth,
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and all of that's totally fine, but I just think it's good to kind of – let's look at what we're, you know,
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what we're really all about and what we're doing.
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So what about men who are, you know, who actually enjoy working the traditional 9-to-5 job?
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You know, they like to clock in at 8 o'clock and then leave at 5.30 or whatever.
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Can they still live an unconventional life or an art of nonconformity lifestyle?
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Well, sure, because the main thing about an unconventional lifestyle, at least, you know,
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in the kind of writing that I do, is firstly thinking about motivations and thinking about, like,
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And so I have, like, my desktop screensaver is this image that comes up and it actually says,
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So it's really good because, like, I log into my computer and I'm like, oh, why am I doing this?
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It's a good thing, you know, good thing to think about this because it's so easy.
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Whether you're self-employed or work for somebody else, it really doesn't matter.
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I mean, it's so easy to just fall into habit that we're doing stuff because that's what we did yesterday
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So I think in some ways it's almost irrelevant whether, you know, whether it's the day job
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or something else or the art of nonconformity lifestyle or whatever.
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I mean, the most important thing is figuring out why we do what we do.
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And if someone's motivated, you know, to punch the clock, if they're doing really good work, you know,
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if they're part of a good company or organization, if they feel like they're making a difference, then that's great, you know.
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So maybe there's a way they can introduce some other elements, you know, to their life.
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If they're interested in travel, maybe they can take a one, you know, one to two-week trip every year.
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And they're also, like, reading up, you know, well in advance of the trip and maybe connecting with other people, you know,
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In some ways they're probably going to have a better experience in that country than I would because I'm going places all the time.
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So I definitely think, you know, the most important thing is figuring out, like, why we do what we do
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and then, you know, figuring out what we want and then, you know, gradually making changes to where it's a little bit closer to, you know,
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Yeah, I think that's a good point because I think you read a lot of these lifestyle design blogs out there
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and they make it sound like the only way you can be happy is if, you know, you're doing, like, working four hours a week
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and, you know, you're dancing tango, like, on the beaches of Argentina or whatever.
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I mean, I don't even know if there's beaches in Argentina, but, you know, you're whatever.
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And I think it kind of sets people up for something like they're like, man, I should be doing that, but I don't want to, you know.
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Well, the other thing is I think I'm actually pro-work, you know.
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I think if we hate our work, it's probably because we're doing the wrong kind of work, you know.
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I think most of us, I mean, speaking of men, I would say most men probably have a desire to, like, contribute to something meaningful
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and to leave some kind of impact, and, you know, that involves work.
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So, I mean, however you do it, whether you're doing it for yourself or you're doing it for something else that you believe in, you know,
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All right, so how does your wife feel about your lifestyle?
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Is she, I mean, I guess, I mean, it sounds like she's all on board because you guys did the mission trip together, right?
00:21:40.960
Yeah, yeah, we were overseas together for four years.
00:21:43.220
So, yeah, I don't want to speak for her too much, of course, because, you know, she speaks for herself.
00:21:46.600
But I would say, you know, we've been married a long time, and we did the four years in Africa together,
00:21:53.700
and now she works as an artist, so she has kind of an unconventional life of her own.
00:21:58.960
The travel is something that we definitely had to kind of work out together, because now I'm mostly traveling by myself.
00:22:03.980
She does come on some things, but most of the time when I'm going off on these, you know, two-week adventures,
00:22:10.280
So that's actually the answer to the question people sometimes ask me, which is, why do you only go for two weeks at a time?
00:22:16.180
And I say, well, because I'd like to stay married.
00:22:18.960
So I travel, and then I come back, and I'm here for two to three weeks in my home base of Portland, Oregon.
00:22:27.920
It's an ongoing conversation, and, you know, I want to make sure that I'm doing what I want to do,
00:22:35.000
but also not neglectful of my responsibilities and obligations.
00:22:39.340
Yeah, something I guess that kind of leads to my next question.
00:22:41.860
I mean, what kind of advice would you give to a man who's like, all right, Chris, I'm ready to do, like, live the dream.
00:22:49.980
I'm going to, like, quit my job and, you know, become a blacksmith or whatever.
00:22:58.000
What should I do to, like, sell her on this idea?
00:23:02.940
I guess, you know, the more that she can be a part of it, maybe the more she might be supportive of it.
00:23:09.960
Like I said, that was one thing when we first went overseas.
00:23:13.200
That was not something I considered doing on my own because that was such a long commitment that, like, talked with her.
00:23:19.100
And she was, you know, to her credit, she was really up for it from the beginning.
00:23:26.700
Maybe there's a way that, you know, maybe she has some kind of dreams in this situation that she's not pursuing.
00:23:33.020
So I might want to say, well, what, you know, is there something that you'd like to be doing that you haven't done or something that you thought about when you were a kid but you just kind of forgot about because you thought, like, it wasn't realistic or whatever?
00:23:42.800
Or, you know, how can we craft a story together?
00:23:49.260
And, you know, somewhat those are individual stories.
00:23:51.720
But, like, since we're married or we're in a partnership or whatever, like, how can we craft some kind of story together?
00:23:59.380
I do hear from a lot of people that both men and women that kind of ride in with that same question and say, oh, I want to do this, but my partner has a different idea.
00:24:09.280
But, you know, I do see a lot of examples where it ends up working out.
00:24:12.320
Yeah, it just takes a lot of communication, I guess.
00:24:16.120
All right, well, Chris, any parting advice for men who are looking to live an unconventional lifestyle?
00:24:23.840
I'm trying to think of if there's anything we haven't covered.
00:24:26.600
I've been doing this conversation, and I'm a big fan of the Heart of Men community.
00:24:31.160
So if anybody's out there and has any other questions, definitely feel free to contact me if anybody needs help with the travel stuff
00:24:37.480
or if they've got a business thing they're working on or just a question or whatever.
00:24:43.660
I can't think of any huge parting words or advice, except you guys are great, and I'm really thrilled to be a part of your community.
00:24:56.520
Chris is the author of the blog, The Art of Nonconformity, and you can find out more information about Chris's work at chrisguillebeau.com.
00:25:03.860
Well, that wraps up another edition of the Art of Manliness podcast.
00:25:13.700
For more manly tips and advice, make sure to check out the Art of Manliness website at artofmanliness.com.