Why Do We Dedicate Ourselves To Ridiculous Quests? And How Do You Pick Yours? (Book Giveaway)

Ever thought of something crazy and wondered, “What if I just went for it?”

Of course you have. We all have. But, for one reason or another, few of us go beyond that stage of wonder. Why? You might feel stuck in your routine—like it would take an act of God to make a change. Maybe you surround yourself with the wrong people who don’t support your adventurous nature. Or, you just fail to think about how much you’ll regret not taking chances in the future.

So, instead of taking action, you continue to dream.

But it’s funny, isn’t it? Funny how you’ll hear a story about someone—somebody just like you—who dedicated themselves to a big challenge and, when you hear them tell their story, you think to yourself, “Wow, that’s amazing, but I could totally do that, too.”

That’s how I felt when, years ago, I read about a guy who ran a marathon on every continent. The story was awe-inspiring to me, a novice runner, but I also thought, “That can’t be that hard.” So, I decided to do it myself. It took four years (I’m kind of slow) and a lot of planning, training, and sacrifices, too. But when I got to the end, I couldn’t help but think, “Hey, anyone can do this. I’m not that special.”

We all need something to strive for, and that’s why I was excited when The Happiness of Pursuit, Chris Guillebeau’s (pronounced, jill – eb – ooo… just kidding) new book, showed up on my doorstep the other day. It’s equal parts inspirational story and how-to manual for taking on a big challenge in your life.

The book chronicles Chris’ own quest to visit every country in the world along with dozens of stories and advice from everyday Joes like you and me who’ve taken an idea they had to the extreme and dedicated their lives to it achieving it.

I know you’re a motivated, adventurous person who might find a book like this not just inspiring but instructional, so I sat down with Chris to talk adventure and, well, the happiness that comes with pursuit.

But don’t worry. Just because Chris is a friend doesn’t mean I lobbed him softballs. He got the same hard-ass grilling I give to every author I feature. The book’s debut at #3 on the New York Time’s Bestseller list doesn’t sway me one bit!

Is The Happiness of Pursuit a book for you? Read our verbal kung fu match below to decide for yourself, and enter the giveaway to win a free copy, which you can use to change your life or burn in a trash can, depending on how the interview goes. (Update: Giveaway is now over; congrats to our winner, Jen!)

Verbal Kung Fu With Chris Guillebeau, Author of The Happiness of Pursuit

We’ll start this interview the same way I start every one: Have you ever had a mustache? If not, how are we supposed to trust you?

I’ve had a goatee and a beard. Does that count? A mustache was part of it.

I’ll award partial credit, but this isn’t starting well.

Where did this book come from? Tell us about your quest. How does it feel to be the youngest person to visit more than 300 countries (this is an inside joke)?

Well, I started by spending ten-and-a-half years visiting every country in the world. There are actually 193 countries, at least according to the U.N., so that was the goal: to go to all of them. Pay no attention to the people who say there are more than 193 countries.

Every good quest involves change or transformation that happens throughout the journey. In my case, along the way I met a lot of other people who also pursued quests or otherwise found a way to cultivate the value of adventure in their lives. In addition to writing about my quest, I wrote about dozens of other people:

The man who ran 250 marathons in a single year (Tyler’s note: I now feel very unaccomplished.)
The teenager who sailed around the world by herself
The woman who climbed a tree in Tasmania as protest of illegal logging… and stayed there for an entire year
The group that spent 28 years producing the world’s largest symphony
The co-workers who snuck into Apple after they were laid off and continued to work for free, eventually launching a new piece of software on every Mac computer

And, as they say, many more. However, I should be clear about something: the book isn’t a memoir or collection of stories. I think it’s important for writers to put forward a clear agenda. My agenda is: dear reader, a quest can improve your life, not just the lives of other people you’re reading about, and here’s how you do it.

I wanted to tell the stories as context for the prescriptive aspect. How do you begin a quest? How do you choose what to do? How do you keep going when times are hard? That’s the goal.

Why do I need a quest in my life? I generally distrust words that start with Q. I don’t like to quit. Quilts are just weird blankets, and I don’t even know what quaff means. Q is like the bandit of the alphabet. What makes a quest something worthy of pursuit?

Sometimes it’s good to quit. If you’re working at a job that sucks, should “never give up” be your mantra? Let’s hope not, because that’s depressing. Life is short, so you should quit. And if you were freezing, you’d probably accept a quilt even if it was just a weird blanket.

I will freeze to death before I accept a quilt. But, please, continue…

So let’s look at quests in particular. Quests involve challenge, which is the essence of adventure. Without the challenge, there isn’t much of a journey or much of a sense of accomplishment when you reach the end.

Also, the structure matters. For me, the quest wasn’t just “to travel to a bunch of places.” That’s not a goal! There’s a woman in Oklahoma, Sasha Martin, who wanted to adopt the principle of visiting every country in the world, but wasn’t able to travel much with a young family. So she decided to make a meal from every country in the world. What a great project! Again, it wasn’t just “make a bunch of foreign foods” — it was specific and measurable and required incremental progress.

The parameters will help you. That’s when it becomes a quest. And, as I learned through the journey and show throughout the book, a quest can bring purpose and meaning to everything you do.

That was a great answer. Are you sure you’ve never had a mustache?

So, you’re doing a bunch of research for this book and asking everyone you know, “What quest are you on? I want to tell your story.” What was the weirdest one where you were like, “There is absolutely no way I’m putting that in my book and, actually, I wish you hadn’t told me that?”

Hmmm. Good question. One of the lessons I learned was that you must believe in your dream even if no one else does. I met people who were fascinated by trains, sushi, birds, alarm clocks … and really all kinds of things that I don’t wake up feeling excited about. (Well, sometimes I wake up thinking about alarm clocks, but that’s putting function before form.)

I’m not sure if there was a weirdest or strangest story. I wasn’t really looking at hobbies, which is where more of those labels would apply. I was looking at lifelong, missional events—sometimes people described them as a calling or something they simply had to pursue. Even when they were a little off-the-wall, it was still interesting to see why people chose to focus on them to the exclusion of a lot of other things.

I was really hoping for something like, “This one guy told me he ate snails for breakfast every day for 40 years,” or something. But that’s fine. Sushi is cool, too.

Is a quest for everyone? I mean, some people are just big ol’ sissies and not very skilled. Take me for example. I have very few useful skills and I’m afraid of heights. Can I still find a pursuit-for-beginners that’s going to make me happy?

Is a quest for everyone—well, what I’m trying to push forward is the ideal of adventure. Remember Sasha’s story, who made a meal from every country in the world. There’s another woman, Robyn Devine in Omaha, who’s knitting 10,000 hats. At my tour stop in Atlanta a few days ago, I met someone who followed a similar approach and is drawing 10,000 flowers. All of these people say that the practice and the parameters help them to develop this value of adventure despite not being ready to parachute from outer space or something.

10,000 knitted hats!? That totally could have gone in the “weirdest quest” question! (Much love for Robyn!)

Is there a set of guidelines that make a personal quest worthwhile? Any rules or limits?

There must be a destination or goal. (It may ultimately be more about the process or journey, but there must be an end point.)

There’s usually a set of milestones or markers of incremental progress along the way. (You can’t achieve your goal right away.)

Once again, challenge is the essence of adventure and a key feature of quests. There’s always something you must overcome, trade off, or sacrifice along the way.

You gain confidence through the quest (I believe that you, Tyler, explained this concept well in your TEDx talk.)

Most of the time, something else happens along the way. Once you go down the road of adventure, you don’t always know where you’re going to end up.

Flattery will get you everywhere!

Why does toiling away at something meaningless to everyone but ourselves make us so damn happy? Why are we such masochists? What is wrong with us!?

It’s because we like striving (and, as you discuss often, the idea of perceived risk). Again, challenge is the essence of adventure.

One story I’ve been telling on the road: Imagine you went to the old-fashioned cinema to see an epic movie like Star Wars, Indiana Jones, or Lord of the Rings. You’ve got your popcorn and you expect to be there for a good three hours (a billion dollars was spent on this movie, and it’s been talked-up for years). But then, once the journey begins and the heroes get underway, they actually find that it’s really easy. There’s a non-stop flight to the final battle. Once they get there, the dragon they were supposed to fight is asleep. They recover the holy grail or whatever they were searching for, and they head on back without the need to change clothes. “That’s a wrap!” they say as the credits roll after 15 minutes.

That movie would suck. And if your life were like that, your life would suck too.

Do quests have an escape hatch? What if I get halfway through this thing I think is going to transform me, and I’m like, “F*** this! I quit!” Am I a failure?

As I alluded to earlier, I think there are plenty of times in life when it’s okay to give up. If you’re working a miserable job in a field that you’ve learned to despise, does it matter that you spent years earning a degree in that field? If your relationship is unhealthy or abusive, is it really the best plan to stick around and hope that things will improve?

So too with quests: if you really feel like quitting, you should quit. You’re not a failure.

However, before you make that decision, you should probably think long and hard about your motivations. Are you really ready to pack it in and move on to something else? Do you no longer have the motivation to sustain a long-term effort toward the declared outcome?

Perhaps it’s also good to consider the length of time that remains until the end of your journey. If I’d wanted to quit in year 2 of the ten-year quest to visit every country, I probably should have just quit. But if I felt like quitting in year 9, I think the best advice would have been, “Suck it up and keep going. You’re almost there.”

What about when you get to the end of an epic quest—you’ve dedicated yourself for years and sacrificed so much—and you’re like, “Hmm… is that it? I thought there’d at least be fireworks.” But, instead of fireworks, your grandma is like, “Why don’t you ever call?” Is there a way to avoid this, or is that part of the package?

It’s part of the package. When something has been a huge part of your identity for a long time, it’s hard to handle the bittersweet feeling of victory—which as you noted, may not actually include fireworks. (Sometimes there are permitting issues, municipal regulations, etc. Fireworks are a hassle.)

However, one observation: I’ve been traveling North America to talk with readers about the book, and someone said an interesting thing to me the other day. When I talked about how my quest was a huge part of my identity, they said, “Well, yeah, but the quest gave you that identity.” In other words, I never would have had this whole lifestyle were it not for the fact that I said yes to the call of adventure. I thought this was a good point.

A quest gives and a quest takes away, I suppose you could say. But mostly it gives.

Okay, last question: Would you consider a trip to a real bookstore to buy The Happiness of Pursuit a meaningful quest? Do I have to do something after I buy it, or is reading it good enough?

As awesome as it will be when every Riskology reader makes the trek to a real bookstore to buy The Happiness of Pursuit (and actually, they should buy multiple copies to be safe), I don’t think that counts as a quest or even something that makes me happy on its own. I want people to take action! I want them to find their own quest!

I want them—no matter what their status or situation in life—to find a way to pursue an adventure. That’s when the book will be a success, and more importantly, that’s when their lives will be changed as well.

Now It’s Up To You (Giveaway Details)

Well, now it’s up to you. Did Chris convince you of the value of his book even though he’s never had a mustache? If so, head out to your local bookstore or your favorite online shop. This book is already a hit, so you should find The Happiness of Pursuit just about anywhere.

I’m also giving away a free copy to one lucky reader. If you want that lucky reader to be you, leave a comment below telling us about the quest you’re on now or the one you want to pursue. I’ll randomly choose the winner on Monday and ship your book anywhere in the world.

(Update: Giveaway is now over; congrats to our winner, Jen!)