Get my FREE insider newsletter that is helping 400,000+ people MAKE MORE MONEY!

How to travel the world, create a life that doesn’t suck, and explore the happiness of pursuit — with Chris Guillebeau

I was travelling in Asia and had time to kill at the Hong Kong airport. I knew exactly who to text: Chris Guillebeau.

Ramit Sethi

Last month, I was travelling in Asia and had some time to kill at the Hong Kong airport. I knew exactly who to text.

chrisg_text1 chrisg_text2

From one picture, this dude knew exactly where I was sitting, and then recommended other lounges for me to visit based on my gate number. It takes a real weirdo to know that level of detail about anything, which is why we’re friends. In 2002, Chris Guillebeau created a quest for himself: to travel to every country in the world. As of 2013, he had traveled to 193 countries — that’s every country in the world.


Last year, I brought him on as a guest interview for my Brain Trust program.

I was inspired by his idea of “quests,” since in the last two years, I’ve decided to say YES to more things. Instead of instantly finding reasons NOT to do something — Oh, I don’t have time, I don’t know anyone there, what if I don’t end up liking that sport — I just say yes. At least once, I say yes, then I decide if I like it. Today, I wanted to talk to Chris about “quests,” the topic of his new book The Happiness of Pursuit.

Most of us are so caught up in the day to day that it’s tough to make time for long-term thinking, much less a “quest.” But what if, years from now, we could look back on our lives and know that we didn’t just answer emails and file reports…but tackled big, meaty goals in our lives? Let’s hear from Chris.

What is a quest? I hear that word and I think of Odysseus or “The Oregon Trail.”

A quest is a journey with a clear goal or destination and a lot of milestones along the way. There’s always an element of challenge—it shouldn’t be too easy. Finally, there’s also usually an element of change or transformation that occurs along the way.

The journey of Odysseus and other mythological stories are quests, yes. But they are essentially just stories. They exist to entertain or inspire us, which is great, but they aren’t true.

About ten years ago I became interested in real-life quests. I set out to visit every country in the world, and finally completed the journey last year when I visited country 193 of 193. Along the way I met a ton of interesting people and began to study their adventures. That’s what led to the new book.

Why, with everything else going on, should someone want to go on a quest?

It’s precisely that busyness that a quest can provide grounding for. I found a lot of purpose in happiness in going to country after country, year after year. As I worked through the list of countries, getting closer and closer to the goal, I felt a sense of pride and accomplishment. I think that’s what people are looking for in this age of possibility—the sense that what they are doing fundamentally matters somehow.


When I first heard you were writing a book about going on quests, I got nervous you had crossed over to the dark side. I thought you’d been sucked into the “just follow your passion and everything will work out” trap.

Yeah, that’s exactly right. Spend your time in front of the couch playing Xbox and everything will be awesome.

Actually, probably not. I do think it’s good for people to think about what they like to do and what they’re passionate about. I mean, if you’re not doing something you love at least a good portion of the time, then your life sucks. Right? But let’s go a bit deeper: how do you create a life that doesn’t suck? You do that by working toward things that matter to you. (tweet this)

I do actually encourage people to think about what they enjoy (I hope that’s not IWT heretical), but I also encourage them to think about what bothers them, what irritates them, what problems they want to find solutions for, and so on. In answering those kinds of questions, I think they’ll be more successful in their aspirations of freedom and independence.

A “quest” sounds intimidating — like something only a certain type of person could take on. Could I go on a quest? What about a 35-year-old mother of 3 from Kansas with a full time job? What if I don’t want to quit my job and travel around the world? What are some other examples of quests that real people took on?

One of the key principles of the new book is that adventure is for everyone. I heard a ton of crazy stories as I traveled the world and met questers. Here are a few examples:

  • The dude who ran 250 marathons in a single year
  • The young woman (a teenager, actually) who circumnavigated the globe in a small sailboat
  • The man who took a 17-year vow of silence (WTF)
  • The team that produced the world’s largest symphony, with more than 800 performers and multiple choirs
  • The activist who climbed to the top of a eucalyptus tree in Tasmania, then lived there for more than a year as an environmental protest

But I also heard from a lot of folks who weren’t ready for the 17-year vow of silence but had found a way to embrace adventure. There was actually a mother from the midwest who cooked a meal from every country in the world. She couldn’t travel to every country, but she found a way to bring every country to her home.

I loved that story because it shows what’s possible when you think about how to embrace adventure in your own situation or context.

How do you go from “that’s something I’d like to do someday” to actually making it happen? People have so many invisible scripts about doing simple things like speaking up in meetings or asking their boss to pay them what they’re worth. How could someone drop everything or rearrange their lives to go on a quest? The initial “oh, this is cool” motivation burns out really quickly.

First up: don’t rearrange your whole life just yet. Start with smaller steps in pursuit of the goal. There’s nothing wrong with experimenting before committing to collect every piece of artwork in the world or whatever.

Oh, and if you aren’t sure what the final goal is, ask yourself some questions:

  • Ask what you liked to do when you were ten years old.
  • As mentioned earlier, ask what bothers you about the world.
  • Ask what scares you right now—sometimes the thing that scares us the most is closely related to the thing that we need to do.

Another lesson is that experience produces confidence, not the other way around. I didn’t have the full idea to visit every country until I’d been to almost 70 of them. The more I traveled, the more I realized I could create some structure around it and pursue this huge goal—but I wouldn’t have been able to come to that point had I not stepped out and started traveling in the first place.

So you don’t have to have all the answers in the beginning, but you do have to take action. Without action, your odds of success are essentially 0%.

Quest also implies an end point, a goal. What if we don’t reach it? What about you, what if something came up and you hadn’t been able to get to every country?

Here’s the thing: failure would have sucked, but not nearly as bad as failing to try. I mean this wholeheartedly.

Once I had the idea to “go everywhere,” it stuck with me and wouldn’t leave me alone. I knew if I didn’t at least attempt it, I’d always regret it. I didn’t want to say, oh, one time I thought about going to every country in the world, but then there were some really good TV shows on, so I just decided to abandon that whole idea.

The fear of regret is a very powerful motivator. You should think about what you’ll regret if you don’t make the attempt.

Your quest changed your life — you travelled to every country in the world. How do you top that? Do you want to top it?

The other night on book tour, this guy said he had a suggestion for me. His suggestion: “You should go back to every country in reverse order.” I told him that sounded like a great quest for him or anyone else. (If you’re out there and trying to figure out your own quest, feel free to jump on that one.)

As for me, I’m still traveling and writing. Last year I went to 15 countries after I’d finished going to #193 of 193. But whatever the next quest is, I think it will focus a lot more on community. Through the books and events, I’ve met thousands of people who are all living unconventional lives of their own. I want to do whatever I can to support them and help them connect with one another.


What happens when your friends and family (or others) don’t “buy in” to your quest? I’m sure people you love called you crazy? How did/do you deal with that? How can we deal with it during our quests?

One of my favorite stories was from Alicia Ostarello, who had recently had a breakup and decided to go on an extended road trip and have 50 dates in 50 states, documenting it along the way. Her family didn’t get it at all, especially at first. But they didn’t have to—it was Alicia’s quest, so she went anyway. When it’s your thing, you don’t need other people to buy in.

I do think support is important, but there’s more than one way to find support. If your friends don’t understand, you need to find some other friends.

I have to ask, what’s your favorite airport or travel hacks?

Hmmm… it’s safe to say there isn’t much I wouldn’t do for miles and points. Here are a few of the greatest hits from the blog:

  • One time I applied for 13 credit cards in one day … and it didn’t ruin my credit like everyone said it would
  • Another time I purchased $8,000 worth of stickers in exchange for miles … which I then promptly recycled
  • And still another time I borrowed a homeless man’s shopping cart to return thousands of dollar coins to the bank

(Oh, and you can currently test-drive a Cadillac in exchange for 7,500 AAdvantage miles. Obviously I’m working on this myself…)

A gift for IWT readers

To help you on start your quest, I want to give you the first chapter of The Happiness of Pursuit, downloadable here.



Do you know your earning potential?

Take my earning potential quiz and get a custom report based on your unique strengths, and discover how to start making extra money — in as little as an hour.

Start The Quiz