Part One — Beginnings
Prologue — On the Road
People have always loved quest stories. Whether the story comes from Africa, Asia, or Europe, the plot is the same. A hero sets off in search of something hard to find, something with the power to change both their life and the world. Think of Star Wars or Indiana Jones. Most of these stories aren’t real, but you enjoy them because, for a little while, they change what you think is possible.
Chris Guillebeau found out that real quests are everywhere. He spent about ten years traveling to every country in the world, 193 in all. The bigger surprise was that he wasn’t the only one on a quest. All over the world, people had found the same way of bringing more purpose to their lives. Some had worked toward a goal for years without anyone noticing. “I want to make my life worthwhile,” one woman told him. “I consider myself an instrument, and if I don’t put myself to work for the greatest possible good, I’ll feel like I wasted a chance that will never return.”
These people spoke with intensity. They were focused on their goals, even when those goals didn’t make sense to anyone else. He wanted to know why they’d chosen such big goals, and what kept them going when others would have quit.
A few lessons show up right away. If you want to achieve the unimaginable, you start by imagining it. Then you count the cost. Knowing exactly what you need to do, and finding a way to do it, makes a quest much more doable. Things will go wrong, but misadventures build confidence. On his own quest, he spent whole nights in empty airports and ran out of money in remote places, and each time he learned that things would usually be OK. The end of a quest teaches something too. When something has been a big part of your life for years and then it’s gone, you can feel lost. But before any of that comes a simpler question: what is a quest, exactly?
Chapter 1 — Awakening
The first lesson is that adventure is for everyone. But a quest is bigger than self-improvement. It takes more time and more commitment. A few marks set it apart. A quest has a clear goal and a specific end point, and you can explain it in a sentence or two. It presents a real challenge. It doesn’t have to be dangerous, but it shouldn’t be easy. It requires sacrifice. There’s no “having it all,” and to chase a big dream you have to give something up. It’s often driven by a calling, which is usually just a deep inner sense of purpose. And it moves forward through small steps. Most quests are a long, slow march, with moments of glory few and far between. You don’t find the holy grail the day after you set out. If you do, it probably isn’t the holy grail, and it definitely isn’t a quest.
Put simply, a quest is a journey toward something specific, with challenges along the way. You have to become a better person than you were when you started.
The people in these stories were after different things. Some wanted self-discovery. Some wanted to let a little risk into their lives or take a stand. Not all of them traveled, but almost all of them left their comfort zones. Most succeeded not because of talent but because of their choices and dedication. Many said “anyone” could do what they did. Maybe so. But few would have kept going the way they did.
This book is a chance to learn their lessons earlier, from people who’ve spent years chasing their dreams. So start with a few questions. What excites you? What bothers you? If you could do anything at all, without worrying about time or money, what would it be? Pay attention to the ideas you can’t stop thinking about. Even dreaming counts for something. Research shows people enjoy planning a vacation as much as taking it. For a lot of people, though, the first stirring of a quest isn’t excitement at all. It’s unhappiness.
Chapter 2 — The Great Discontent
Thomas Edison once said, “Discontent is the first necessity of progress.” Why would anyone take on a big adventure for little reward, often with a real chance of failure? Most of the people in these stories had been unhappy with their normal lives in one way or another. They wanted something deeper, and they either found it or made it.
Often the unhappiness comes from losing something. “Something had to give,” one woman said. “I was settling into the comfortable rut of wife and mother, but losing my sense of adventure.” In the old stories, the hero crossed distant lands to recover a grail or a key. Today what you’re trying to recover is usually harder to see, but just as important. Many people set out on an adventure to find themselves again.
Others described it differently. It was “a crazy idea that wouldn’t leave me alone.” Or, “I just couldn’t live that way anymore.” So when you feel discontent, pay attention. The answer isn’t always “go for it,” though often it is. But don’t ignore the stirring.
Still, discontent by itself isn’t enough. Lots of people are unhappy, and most never make big changes. You have to mix your dissatisfaction with inspiration and connect it to a bigger purpose. It works like a simple formula: dissatisfaction plus a big idea plus a willingness to act equals a new adventure. Discontent is the match. Inspiration is the kindling. When your unhappiness turns into excitement, you know you’ve found your pursuit. If you feel stuck, ask yourself simple questions, like “What do I want?” The answers can point to your next step. Sometimes they point to a calling.
Chapter 3 — The Calling
Everyone has a calling, and the advice is simple: follow your passion. A calling doesn’t have to impress anyone else. Jiro Ono, the famous sushi chef in Tokyo, talked about feeling victorious over a particularly nice tuna. Miranda Gibson lived in the treetops of Tasmania for more than a year to protest illegal logging. One found a calling in something to love, and the other in something to fight. Your passion may not matter to anyone else, but if it matters to you, don’t ignore it.
People who follow a calling tend to have a high tolerance for risk, and they get pushback for it. “It is no wonder that people challenge me,” one of them said. “I am challenging myself.” But they also carry a quiet joy. “When a person is really happy they don’t have to tell people about it,” another said. “It just shows.” For some people, though, the call only gets loud when life reminds them how short it is.
Chapter 4 — Defining Moments
In Catch-22, Joseph Heller wrote about a man who “had decided to live forever, or die in the attempt.” The lesson here is that every day matters. “Live like you’re dying” sounds like a cliché, but it’s exactly what many people on a quest do. What changes is how deeply they know it. Knowing it in your head sounds like “No one lives forever.” Knowing it in your gut sounds like “I will someday die.”
Once you really feel your own mortality, the small things stop mattering. Sometimes that feeling comes from a friend’s death or your own health scare. Other times it’s a stirring in your soul that grows louder until you can’t ignore it. Either way, the more you feel that your time is limited, the more you want to live with purpose.
That awareness also shows the difference between a hobby and a quest. You can stop thinking about a hobby. A quest takes over your attention. Playing golf on weekends is a hobby. Setting out to lower your score is a goal. Setting out to play every course in Scotland within a set amount of time is a quest. Once you’ve found something like that, the next step is to set out.
Part Two — Journey
Chapter 5 — Self-Reliance
Not everyone needs to believe in your dream. But you do. One way to get past the fear of failing is to get used to it. Jason Comely made up a real-life game called Rejection Therapy. The goal is to ask for something and be told no, on purpose. If you get a yes, that’s a bonus, but you’re not done for the day until someone turns you down. Jia Jiang played the game and learned that rejection, like experience, builds confidence. Just continuing to ask, after failure after failure, was empowering. As Comely puts it, “Your comfort zone may be more like a cage you can’t escape from than a safe place you can retreat to.”
Over and over, people told Guillebeau some version of the same thing: “If I didn’t do it, I would always wonder about what could have been.” That’s exactly how he felt about visiting every country. You have to believe your quest can succeed, even if no one else does. Other people’s opinions usually depend on how things turn out anyway. If a risky adventure works, people call you brave. If it fails, they call you naive and arrogant.
Before he died in the Alaskan wilderness, Chris McCandless, whose story Jon Krakauer told in Into the Wild, wrote a letter to a friend that has led many people to rethink their lives. “So many people live within unhappy circumstances,” he wrote, “and yet will not take the initiative to change their situation because they are conditioned to a life of security, conformity, and conservatism.” In reality, he said, “nothing is more damaging to the adventurous spirit within a man than a secure future.” Life itself is risky. You get to choose your own level of risk. And that choice doesn’t have to mean leaving everything behind.
Chapter 6 — Everyday Adventure
Eleanor Roosevelt said, “Do one thing every day that scares you.” You can have the life you want no matter who you are, where you live, or how old you are. But you have to make adventure a priority. It has to matter more than routine.
Sasha Martin did that from her own kitchen. Her big idea was to explore the world’s cultures through their food. She called it “Stovetop Travel,” and she cooked meals from countries around the world, one country at a time. She played music from each country and invited friends to dinner. She also gave herself a deadline, and deadlines keep showing up in these stories. Every good goal has one. What made Sasha’s project a quest was that she picked something specific to work on over time, something fun, challenging, and meaningful.
Others found their own versions. One person, who goes by “Glacial Explorer,” spent nearly ten years jumping into every lake in Glacier and Waterton Lakes National Parks. There are 168 of them, many reachable only by hiking off-trail. A couple named Allie and Jason set out to visit every basilica in the United States.
Not every change needs to be big. One man started by visiting the art museum on his lunch break and taking a photography class. Since then, he’s been much happier. Breaking out of old habits takes just one moment of strength. Start a conversation with a stranger. Stop carrying an umbrella when it rains. You might get wet, but you probably won’t melt.
Too busy? Everyone has the same amount of time. If you want adventure, something has to give. You can make small, regular changes, or you can change everything at once. Either can work. But there’s no third option where you wait for change to knock on your door. You have to do something, and the sooner the better.
It also helps to have somewhere to aim. The author loved travel, even aimless travel, but tying it to something bigger gave it more weight. Having a destination in mind gave him an anchor. And once you have a destination, the next question is what it’ll take to get there.
Chapter 7 — Time and Money
Before you begin a quest, count the cost. Guillebeau’s own quest took ten years, and he couldn’t stay excited every day by thinking only about the finish line. Smaller goals along the way helped. The more specific your plan, even with rough estimates, the easier it is to get your head around the goal. What does success look like? What will it cost you?
Matt Krause dreamed of walking across Turkey, and he planned his route far in advance. “I’ll be walking 60 miles a week, for a total of 22 weeks,” he wrote in a detailed spreadsheet. It even listed the elevation and average temperature for each day’s walk. Hard-core? Maybe. But the detail helped him understand what he was getting into. It wasn’t just a passing thought. It was a plan. You can break almost any quest down the same way. List what might stop you, and then a way around each thing.
The Greek poet C. P. Cavafy wrote a poem called “Ithaca” that shows how to value both the journey and the destination: “Always keep Ithaca on your mind. To arrive there is your ultimate goal. But do not hurry the voyage at all.” Yes, it’s about the journey. But a destination helps. The more prepared you are, the more spontaneous you can be.
His favorite planning tool is an annual review. Every December since 2006, he has set aside a whole week to look back on the year and plan the next one. He starts with two questions: What went well this year? What didn’t? Then he sets three to five measurable goals in each area of his life, like writing, friends and family, travel, health, and money. He even gives the year a theme, like “The Year of Learning.” The idea behind it is that you tend to overestimate what you can do in a day, but underestimate what can happen in a year.
But you can also get stuck planning forever. If you tend to overthink, just start. Tom Allen, an Englishman who left home on a bicycle to see the world, hears almost every day from people who want to do the same. Most ask about gear. “What gear do you use?” is the wrong question, he says. The better question is “What am I waiting for?” His advice is now simple: “Pick a departure date. Start saving. Get a bike, tent, and sleeping bag. And go.” Sometimes the first step is just writing down everything you want to do.
Chapter 8 — Life Listing
People are motivated by progress. It feels good to check things off. That’s why so many people keep a bucket list, or a life list. It’s a good start. But what if you went further and built your life around one main aim? When people ask, “What do you do?” you can name your job. But once you have a quest, you have another answer. Your identity isn’t tied to a job. It’s who you really are.
Some people turn a single year into a quest. A. J. Jacobs read the whole Encyclopedia Britannica and wrote a bestseller about it, and a whole genre of books followed. Julie Powell cooked all 524 recipes in Julia Child’s French cookbook in one year. John Kralik, a lawyer struggling with a divorce and a failing career, wrote 365 thank-you notes in a year, and it changed his life.
Steve Kamb went bigger. He turned his life list into an “Epic Quest of Awesome,” set up like a video game. He earns experience points every time he crosses something off, and every five items he levels up. The first items were easy, like getting off the couch. Later came the fun ones, like “Complete a James Bond weekend.” He checked into a casino resort in Monte Carlo on hotel points, put on a rented tuxedo, walked up to the blackjack table, put down $200, and said, “Deal me in.” Making it a game, he says, “tapped into that part of my brain that loved to level up in video games.”
To make your own list, follow a few rules. First, avoid fuzzy goals. Losing weight and saving money are good, but they’re vague. “See the northern lights” is better, because you’ll know exactly when you’ve done it. Second, mix it up. Don’t write down climbing Everest just because other people have. Ask what you really want to be, do, and achieve, and include more than travel. Third, think big, and ignore fear as much as you can. If something feels scary, tell yourself, “It’s only a list.” People’s lists ranged from getting out of debt to hugging a panda. Once you have yours, put a deadline on a few items and write one next step for each. That’s all you need. Then the real work begins, and most of it isn’t glamorous.
Chapter 9 — Forward Motion
One of the book’s lessons sounds almost like a joke: quests are boring, and all you have to do is put one foot in front of the other. Ultrarunners talk about slipping into a trancelike state, high on endorphins, running mile after mile. But when they look back on all those long training runs, many also talk about how monotonous they were. The path to the summit is made of repetitive steps. But it’s exactly the hard, repetitive work that makes the accomplishment epic. And every step adds up. Experience produces confidence, and confidence produces success.
Guillebeau has a simple trick for keeping himself moving on the road. When he checks into a hotel and knows he should exercise, he puts his running shoes by the door. He could skip the run, but he’d have to look at those shoes every time he walked out. Maddog Wallace found an even stronger kind of accountability for his own long challenge. He told everyone what he was doing, and they watched. Even better, or worse on the hard days, they counted on him to finish.
Whether you’re facing a huge challenge or mind-numbing boredom, just keep making progress. For some people, that daily work stops feeling like a grind and becomes the whole point.
Chapter 10 — The Love of the Craft
Effort can be its own reward. Some people are driven by achievement, others by the process, and some by a mix of both. These people are all about making things and sharing them with the world, over and over. Why create? Because you can.
Making things means failing a lot. Seth Godin puts it this way: “If I fail more than you do, I win.” The point is that you get to keep playing. “The people who lose are the ones who don’t fail at all, or the ones who fail so big they don’t get to play again.”
Creative work also needs limits. Don’t think outside the box. Make yourself a box and get into it. And it needs steady practice. One person read that practice turns the nerve pathway in your brain into something like broadband, and that it starts shrinking when you stop. “Reading that changed my life,” they said. As another saying goes, “It’s better to be at the bottom of the ladder you want to climb than the top of one you don’t.” Effort can be its own reward, if you let it. And some ladders are better climbed with someone else.
Chapter 11 — Joining Forces
The novelist Haruki Murakami wrote, “In this world, there are things you can only do alone, and things you can only do with somebody else. It’s important to combine the two in just the right amount.” Some adventures should be shared.
Tom Allen, the cyclist from England, once said that “a dream can have only one owner.” But a dream can have more than one owner if two or more people see the world the same way. For one man, sharing a quest changed how he saw everything. “I’m no longer the most important person in my life,” he said. “Whatever the direction is going to be, it’s going to be pursued together.” Even if your quest isn’t a team effort, other people will likely take part in your dream along the way. And some people find their quest not in a dream at all, but in a problem they can’t leave alone.
Chapter 12 — Rebel for a Cause
The writer Jostein Gaarder said, “The most subversive people are those who ask questions.” The lesson here is to find what troubles you about the world, and then fix it for the rest of us.
Every day, you get to answer an interesting question: What’s worth living for? If you could pursue only one thing, what would you build your life around? And if it cost you something real, would you stick with it? Some people find their quest by following something they love. If that doesn’t work for you, try another way. Instead of asking what excites you, ask what bothers you. There’s no shortage of problems in the world. Which one troubles you most? What problem can you actually do something about? Whatever you choose, the hardest part usually isn’t the beginning or the end. It’s the long stretch in between.
Chapter 13 — The Long Road
The middle of a quest can be the hardest part, so don’t give up too soon. The writer Steven Pressfield says, “The most important thing about art is to work. Nothing else matters except sitting down every day and trying.” The same is true for a quest. What matters most is to keep making progress.
The road also costs money. One woman put it this way: “I don’t think I can put a price tag on it, but it costs what life costs. My boyfriend and I choose to live a simple, frugal life so that we can do things we are passionate about.” If money is holding you back, ask what it will really cost, whether you can lower the cost, and whether you truly have to wait until you have all of it. Saving as little as $2 a day for a few years can take you almost anywhere in the world.
Why keep going through the long middle? For the same reason John F. Kennedy gave for going to the moon: not because it’s easy, but because it’s hard. As long as you still believe in the goal, don’t stop. And if your quest depends on other people noticing, make sure you have enough motivation inside you too. Along the way, some things will go wrong.
Chapter 14 — Misadventures
The lesson here is to choose your failures, and have the right kind of disasters. Every quest has setbacks, and some will make you wonder whether to quit. There’s no easy answer, but a few things are worth weighing. First, your motivations. Why did you choose this quest, out of all the ones you could have picked? Are you still driven by the same things? Second, long-term happiness. Relief right now and happiness later can be very different things. Third, rewards. Can you give yourself something small at the end of a hard day? And fourth, other people. Get them involved.
Getting stuck, shut out, or set back is never fun, but it’s part of the journey. When something goes wrong, try to treat it as an investment in learning. The right kind of misadventures, the ones that teach you something, build confidence.
If you’re going to be afraid of something, be afraid of the right thing. Regret is what you should fear most. If something is going to keep you up at night, let it be the fear of not following your dream. Be afraid of settling. Keep going through the setbacks, and something starts to change. Not just your progress, but you.
Part Three — Destination
Chapter 15 — Transformation
A Japanese proverb says, “When you have completed 95 percent of your journey, you are only halfway there.” As you make progress toward a small goal, the bigger vision grows. If you can’t picture a huge accomplishment yet, start with one you can reach. Just know that dreams tend to grow as you pursue them.
Some people on quests are driven by achievement. They want to accomplish something, like scaling the wall. Others are driven by process. They want to do something, like build step by step or go on a long journey. Which is better? The two are tied together. You can’t reach anything deeply satisfying without a long process, and a process needs a goal.
One thing is certain. Take on a quest or any long, hard project, and you won’t come out of it the same. One long-distance walker said the walk gave them the confidence to handle almost anything, “from knocking on the door of a stranger’s house and asking if I could camp on their property to almost getting run over by big trucks.” A quest also teaches you not to settle. Don’t finish bad books. If you don’t like the menu, leave the restaurant. If you’re not on the right path, get off it. When people finished their quests, the most common thing they said was “I’m glad I did it.” But coming home brings its own challenges.
Chapter 16 — Homecomings
Meghan Hicks ran a race across the Sahara Desert. When she came home, everyone asked, “What was it like?” “They ask a complex question, but seek a one-sentence answer,” she wrote. “So you say, ‘The race was wonderful’ and ‘I loved it.’ These statements are true but they toss a fuzzy, feel-good blanket over the whole Sahara Desert. There is no short answer for that question.”
After his own quest, Guillebeau faced the same two problems, the public side and the private side. For the public side, he found a clear answer. Don’t try to explain everything, but do tell a few good stories. Remember the sunsets and the moments of wonder? That’s what it was about. For the private side, he learned to reflect, and then to think about the future. Before you jump back into the grind, take time to debrief.
The end of a quest can be surprisingly hard. Long ago, the philosopher John Stuart Mill asked himself whether he’d be happy if every goal in his life came true at once. “An irrepressible self-consciousness distinctly answered, ‘No!’” he wrote. “All my happiness was to have been found in the continual pursuit of this end.” A man named Howard felt something similar after his quest ended. “A large part of how I’d defined myself simply was no longer there,” he said. He really didn’t know what to do next.
Then there’s the phrase “real life.” Friends and family may say, “Guess you’ll have to get back to real life now.” But one traveler who came home to England saw it the other way around. “Life on the road was the real world,” he said. So how do you climb out of a post-quest funk? Start by realizing that the real world is what you make of it. Then start again with a new quest and a new mission. The next steps are up to you.
Chapter 17 — Finale
The writer Paulo Coelho put it this way: “It is always important to know when something has reached its end. Closing circles, shutting doors, finishing chapters, it doesn’t matter what we call it; what matters is to leave in the past those moments in life that are over.” The last lesson is that the end is the beginning.
Remember the line from “Ithaca”: “To arrive there is your ultimate goal, but do not hurry.” A quest can bring purpose and meaning to your life. Why pursue one? Because you’re writing your own story, and you only get one chance to get it right. As one of the people in the book said, “It has become ever more clear to me that if I had spent my life avoiding any and all potential risks, I would have missed doing most of the things that have comprised the best years of my life.”
Appendix — Lessons from the Journey
From Guillebeau’s own journey to 193 countries and the stories of about fifty others, a handful of lessons hold almost everywhere. Unhappiness can lead to new beginnings. Every day matters, because everyone dies, but not everyone truly lives. Count the cost before you start. Early on, someone criticized his quest by saying all it took was time and money. Later he saw that was actually helpful. Once he knew exactly what “going everywhere” required, it stopped feeling overwhelming.
You can’t always escape boredom, but you can choose what form it takes. Odysseus fought sea monsters, but he also sat through a lot of boring days at sea. Measure success by your own effort, not other people’s opinions. And know that quests don’t always tie up well. Sometimes the ending is glorious, and sometimes it’s bittersweet. Either way, take time to process all you’ve been through. When you’re ready, choose a new adventure.
Guillebeau made it to all 193 countries. But what stayed with him wasn’t the last stamp in his passport. It was who he became on the way. That’s the gift of a quest. You set out to reach a goal, and the goal ends up changing you. So pick something that scares you a little, count the cost, and start.