By Chris Guillebeau
My Personal Takeaways →The Happiness of Pursuit argues that having a quest — a big, meaningful, long-term challenge — is one of the deepest sources of human satisfaction. Guillebeau draws on hundreds of stories of people who undertook quests: visiting every country, completing a pilgrimage, building something no one thought possible. The pattern is consistent: the pursuit itself, not the completion, provides the meaning.
The practical takeaway is that you do not need to visit 193 countries — you need one worthy goal that stretches you over years, demands sacrifice, and produces a story worth telling. Read this if life feels comfortable but purposeless. Implement it by identifying what challenge has been quietly calling you, designing a measurable project around it, and starting this week. The quest will change you in ways the destination never could.
By Chris Guillebeau
People have always been captivated by quests. History’s earliest stories tell of epic journeys and grand adventures. Whether the history is African, Asian, or European, the plotline is the same: A hero sets off in search of something elusive that has the power to change both their life and the world.
The world’s best-known literature reflects our desire to hear about struggle and sacrifice in pursuit of a goal.
In modern times, Hollywood knows that quests are an easy sell. Consider the blockbuster franchises Star Wars, Star Trek, Indiana Jones, and countless others. The tougher the odds and the higher the stakes, the better—as long as the audience has something to believe in. We have to believe in a hero’s mission, and once we do, we’ll gladly stick around to see how the hero can overcome.
Most of these quest stories are told over and over in different ways, often with a fair amount of exaggeration. They can be engaging stories, but for the most part they aren’t real. We enjoy them because, for a brief time, they have the power to alter our belief in what’s possible. Maybe there really is an alien invasion! Maybe there really is a holy grail somewhere out there, just waiting to be discovered.
As I wandered the planet, spending years journeying to nearly two hundred countries, I discovered something important. I loved the travel, and everywhere I went had something interesting on offer. My worldview was broadened as I encountered different ways of life and learned from people in other cultures. But equally fascinating was that I wasn’t the only one on a quest. All over the world, people had discovered the same way of bringing greater purpose to their life. Some had been toiling away at a goal for years without any recognition. Going for it, whatever “it” was, was simply something they found meaningful and loved to do. “I want to make my life worthwhile,” one woman said. “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.”
Out there on his own, walking mile after mile along the dusty village roads, meeting strangers who became friends, he felt a heightened sense of being alive. Something about these people I met stood out. They spoke with intensity. They were focused on their goals, even if they didn’t immediately make sense to others. I wanted to understand why they’d chosen to pursue big goals with such determination—were they driven by the same urges as I was or ones that were entirely different?—and I wanted to learn what kept them going when others would have stopped. I had the strong sense that these people could teach critical lessons.
If you want to achieve the unimaginable, you start by imagining it. Before beginning, take the time to count the cost. Understanding exactly what you need to do, and then finding a way to do it, makes a quest much more feasible.
Yet misadventures (and sometimes even disasters) produce confidence. When I found myself spending all night in a deserted airline terminal, waiting on another canceled flight, or completely out of money in a remote part of the world, I learned that things would usually be OK. I learned to laugh at my own misfortune, or at least to not panic when something bad happened.
Coming to the end of a quest brings lessons too. The story doesn’t always tie up well. When something has been a major part of your life for years and then is gone, a sense of alienation can set in. You have to think about what’s next, and whether you can re-create the intense feelings you had during the time you were chasing down your goal.
LESSON: ADVENTURE IS FOR EVERYONE.
For the price of a plane ticket, we can jet off to foreign lands. Whatever we could possibly want to learn is readily available to us.
A quest, we decided, is something bigger. It takes more time and requires more commitment than general life improvement. Still, though, what exactly is a quest? How to define it?
After much consideration, here are the criteria we settled on. A quest has a clear goal and a specific end point. You can clearly explain a quest in a sentence or two. Every quest has a beginning, and sooner or later, every quest will come to an end. (Not everyone will understand why you undertook the quest, but that’s another matter.) A quest presents a clear challenge. By design, a quest requires that something be overcome. Not every quest needs to be dangerous or next to impossible to achieve, but it shouldn’t be easy, either. A quest requires sacrifice of some kind. There is no “having it all” when it comes to a quest—to pursue a big dream, you must give something up along the way. Sometimes the sacrifice is apparent in the beginning; other times it becomes apparent only later on. A quest is often driven by a calling or sense of mission. A calling need not be some form of divine inspiration. It is often expressed simply as a deep sense of internal purpose. Whatever form it takes, people who pursue quests feel driven, pushed, or otherwise highly motivated to keep going. A quest requires a series of small steps and incremental progress toward the goal. As we’ll see, many quests are composed of a long, slow-and-steady march toward something, with moments of glory and elation few and far between. You don’t simply arrive at the holy grail the day after you set out to find it. (If you do, it’s probably not the holy grail, and it’s definitely not a quest.)
To sum it up, a quest is a journey toward something specific, with a number of challenges throughout. Most quests also require a series of logistical steps and some kind of personal growth.
You also must become a better person than you were before you started. You must improve throughout the journey.
As I traveled the world and traversed my inbox, a few themes kept coming up:
Real-life adventure isn’t only about traveling the world (although many of this book’s stories do involve travel) nor is a quest always about leaving home (although it often involves breaking out of a comfort zone).
For the most part these individuals were successful not because of innate talent, but because of their choices and dedication. Much of the time, the goals grew in proportion with time and experience. Those I interviewed often spoke of their perceived feebleness, or of their belief that “anyone” could do what they did—but as you’ll see, few would have the resolve to persist as they did.
Everyone who pursues a quest learns many lessons along the way. Some relate to accomplishment, disillusionment, joy, and sacrifice—others to the specific project at hand. But what if you could learn these lessons earlier? What if you could study with others who’ve invested years—sometimes decades—in the relentless pursuit of their dreams? That learning opportunity is what this book is about. You’ll sit with people who have pursued big adventures and crafted lives of purpose around something they found deeply meaningful. You’ll hear their stories and lessons. You’ll learn what happened along the way, but more important, you’ll learn why it happened and why it matters. It’s my job as the author to provide a framework and issue a challenge. It’s yours to decide the next steps.
What excites you? What bothers you? If you could do anything at all without regard to time or money, what would it be?
Remember: A quest has a few key features, including a clear goal, a real challenge, and a set of milestones along the way. Pay attention to the ideas that draw your interest, especially the ones you can’t stop thinking about. This book isn’t just a study of what other people have done. You, too, can identify and pursue a quest.
Research shows that we enjoy planning a vacation as much as taking the vacation. Anticipation is a powerful force.
Discontent is the first necessity of progress. —THOMAS A. EDISON
LESSON: UNHAPPINESS CAN LEAD TO NEW BEGINNINGS.
“The sense of being at the reins of my life.” She was taking control as part of a broader life mission to reinvent herself.
Start with ‘why’
What causes someone to undertake a big adventure for little reward—in many cases with a real chance of failure or at least major sacrifice?
I found the real answer as I dug deeper into the mix of frustration and inspiration that drives action. Most of the people I talked to, in one way or another, had been dissatisfied with their normal lives. They wanted something deeper than they had known or experienced, and they either found it or created it.
“Something had to give,” she said. “I was settling into the comfortable rut of wife and mother, but losing my sense of adventure.” Losing something—in this case, the sense of adventure—and going back in an effort to reclaim it is a common characteristic of beginning a quest. In quests of old, the hero had to travel across distant lands in search of reclaiming a grail or key. These days, we often have to recover something more intangible but no less important. Many of us undertake an adventure to rediscover our sense of self.
“A crazy idea that wouldn’t leave me alone.”
“I just couldn’t live that way anymore.”
“I didn’t want to make a small adjustment; I had to completely shift directions to find a new way of life.” LESSON: When you sense discontent, pay attention. The answer isn’t always “go for it” (though often it is), but you shouldn’t neglect the stirring. Properly examined, feelings of unease can lead to a new life of purpose.
Discontent is a powerful spark. When you’re filled with a sense of dissatisfaction that isn’t easily resolved, you may start wondering about making some changes. On its own, however, discontent is not sufficient to start a fire—or inspire a quest. Lots of people are walking around unhappy, but most don’t make radical changes in their lives, especially to the point of pursuing a quest. Discontent may be the instigator, but what is the motivator? What causes someone to take action? If you want to get the embers burning, you have to blend dissatisfaction with inspiration, and then you have to connect the dissatisfaction to a greater purpose. Mash-up: Dissatisfaction + Big Idea + Willingness to Take Action = New Adventure
She tells them that happiness is a choice, and that no one has be special to pursue a dream.
It’s not all about happiness, although happiness often results from doing something you love. Instead, it’s about challenge and fulfillment, finding the perfect combination of striving and achievement that comes from reaching a big goal. Metaphorically, discontent is the match and inspiration is the kindling. When discontent leads to excitement, that’s when you know you’ve found your pursuit.
Remember: Many quests begin from a sense of discontent or alienation. If you find yourself feeling discontented, pay attention to the reasons why. Add action to discontent: Find a way to do something about the uncertainty you feel. Asking yourself a series of questions (“What do I want?” “How am I feeling?” and so forth) can help you find your next steps.
LESSON: EVERYONE HAS A CALLING. FOLLOW YOUR PASSION.
High level of risk tolerance.
“It is no wonder that people challenge me. I am challenging myself.”
“When a person is really happy they don’t have to tell people about it. It just shows.”
The journey will produce its own rewards.
He had decided to live forever, or die in the attempt. —JOSEPH HELLER
LESSON: EVERY DAY MATTERS. THE EMOTIONAL AWARENESS OF MORTALITY CAN HELP US PURSUE A GOAL.
“At the end of their lives, people are incapable of bullshit.
As much as it sounds trite to “live like you’re dying” or “live every day as if it were your last,” that’s exactly what many people obsessed with a quest do. This shift from an intellectual awareness that we will someday die to an emotional awareness can be a guiding light to discovering what really matters.
Intellectual Awareness of Mortality: “I know that no one lives forever.” Emotional Awareness of Mortality: “I know that I will someday die.” Once you start thinking about your own mortality, the small things just don’t matter anymore. This new awareness may come in response to an external event, such as the death or sudden illness of a friend, or from confronting a serious health problem. Other times, there’s a stirring of the soul that increases in tempo until it’s impossible to ignore. Whatever it is, the more we are emotionally aware of our own mortality, the more we feel compelled to live with a sense of purpose.
“How interesting it is that men seldom find the true value of life until they are faced with death.”
What’s the difference between a hobby and a quest? You can stop thinking about a hobby, but a quest becomes a total fascination. Playing golf on the weekends is a hobby. Setting out to play St. Andrews or lower your score is a goal. Setting out to play every course in Scotland, in a set period of time, is a quest.
LESSON: NOT EVERYONE NEEDS TO BELIEVE IN YOUR DREAM. BUT YOU DO.
One way to “get over it” is to learn to become comfortable with failure. Jason Comely created a real-life game called Rejection Therapy that encourages players to engage in social experiments. The goal of the game is to ask for something and have the request denied, stretching your comfort zone. If you ask for something and get it, that’s a bonus—but the day’s round of Rejection Therapy isn’t over, because you ultimately have to be rejected before moving on.
Jia learned that rejection, like experience, produces confidence. The act of moving forward, continuing to make requests despite a number of failures, was empowering.
“If I didn’t do it, I would always wonder about what could have been,” was repeated over and over and in many different ways by the people I talked with. I understood it well, because it’s exactly how I felt when I first began to ponder the goal of traveling to every country. I had to do it! It was such a ridiculous idea that I knew I’d always wonder about it if I didn’t try.
You must believe that your quest can be successful, even if no one else does. You can deal with setbacks, misadventures, and even disasters as long as you still believe you can overcome the hardships and see your way to the end.
WHAT PEOPLE SAY ABOUT AN ADVENTURE OR QUEST THAT INVOLVES PERCEIVED RISK:
Ultimately, assessments of a quest’s worthiness depend on the result.
Before his death, he wrote a letter that was later quoted by Jon Krakauer in the book Into the Wild. The excerpt below has inspired many people to rethink their lives and routines. I’d like to repeat the advice that I gave you before, in that I think you really should make a radical change in your lifestyle and begin to boldly do things which you may previously never have thought of doing, or been too hesitant to attempt. So many people live within unhappy circumstances and yet will not take the initiative to change their situation because they are conditioned to a life of security, conformity, and conservatism, all of which may appear to give one peace of mind, but in reality nothing is more damaging to the adventurous spirit within a man than a secure future. The very basic core of a man’s living spirit is his passion for adventure. The joy of life comes from our encounters with new experiences, and hence there is no greater joy than to have an endlessly changing horizon, for each day to have a new and different sun.
Life itself is risky. Choose your own risk level.
Jason: “Your comfort zone may be more like a cage you can’t escape from than a safe place you can retreat to.”
Do one thing every day that scares you. —ELEANOR ROOSEVELT
LESSON: YOU CAN HAVE THE LIFE YOU WANT NO MATTER WHO YOU ARE.
You can do this no matter where you live and no matter how old you are. If you want to make every day an adventure, all you have to do is prioritize adventure. It has to become more important than routine.
The Big Idea she settled on was to embrace culture through cuisine. “Stovetop Travel” was Sasha’s project to introduce meals from around the world into her home kitchen.
Every good goal has a deadline (Pay attention: This is a recurring theme of many stories),
Whenever possible, Sasha would play music from the country she was featuring, and invite friends to join the dinner.
Sasha’s project was bigger because it was a quest. She chose something specific to work on over time—an endeavor that was fun, challenging, and meaningful.
“Glacial Explorer,” devoted nearly ten years to jumping into every lake in the Glacier and Waterton Lakes National Parks. These parks contain 168 lakes in total, many requiring off-trail hiking through dense vegetation and rough mountainous terrain to reach, and including land on both sides of the U.S. and Canada border.
Allie and Jason decided to turn it into a project: They’d visit every basilica in the United States, telling the story along the way.
As Josh grew up, he planned to see a game in every Major League Baseball stadium.
But he began changing his routine however he could, on the theory that even a small degree of change would be beneficial. Since he began his initial life experiments, which were as simple as visiting the art museum on his lunch break or taking a photography class, he’s been much happier.
breaking your programming requires a single moment of strength.
Here’s a quick list of possibilities.
Should You Document Your Quest? Yes, probably, in some fashion. But how? Some people I talked with said that they wished they’d been more attentive to documenting their journey, others happily chronicled everything, and a third group was happy to pursue their project without keeping track of all the details.
Options for documentation include:
Are you busy? Join the club. Everyone is busy, yet we all have access to the same amount of time. If you want to prioritize adventure but can’t find the time, something’s got to give.
There are two popular theories of change making: 1. Make small and incremental (but regular) changes. Mix it up. 2. Do it all at once. Quit smoking immediately. Take cold showers. Enter boot camp for the soul—whatever you need to do, don’t wait. Either of these options can work, but there’s no third theory of waiting for change to knock on your door and announce its arrival. You must do something. The sooner, the better.
I loved travel, even aimless travel with no set goal, but attaching it to something of greater significance gave it more weight.
Even though it was ultimately more about the journey than the eventual destination, having a destination in mind provided an anchor.
LESSON: BEFORE BEGINNING A QUEST, COUNT THE COST.
Since it would be a ten-year journey, I couldn’t stay excited on a daily basis by thinking about the finish line. That’s when subgoals proved helpful.
The more specific you can be in your planning, even if you’re making rough estimates, the easier it will be to get your head around the goal. What is the goal, really? What does success look like? At the beginning of a quest, you should estimate the toll it will take.
Matt Krause had a dream like Nate’s: to walk across Turkey. Matt 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 planning spreadsheet. The spreadsheet included data on the elevation of each day’s proposed walk, as well as the climate and average temperature for all the different areas he passed through. Hard-core? Maybe. But Matt says that the granularity of the information helped him to understand what he was getting into. It also helped him demonstrate to curious people that he knew what he was doing. It wasn’t just a passing thought; it was a plan.
He considered the rest of the curriculum and visualized which parts would be more challenging.
Quest: To walk the Camino de Santiago
Quest: To learn a new language in a short period of time.
The thirty-six-line poem is full of lessons on choosing a purpose, proceeding with abandon, and ignoring critics. One of my favorite parts illuminates how to value both journey and destination: Always keep Ithaca on your mind. To arrive there is your ultimate goal. But do not hurry the voyage at all. It is better to let it last for many years; and to anchor at the island when you are old, rich with all you have gained on the way, not expecting that Ithaca will offer you riches.
Yes, it’s all about the journey and voyage, but having a destination in mind will help. Thinking logically about your goals and breaking down the obstacles is good for you. If you’re going to run a race, you should plan. The more prepared you are, the more spontaneous you can be.
Annual Review: Every year since 2006, I’ve set aside an entire week in December to review the year that has almost ended and prepare for the next. More than anything else I do, this exercise helped to keep me on track with the round-the-world quest, as well as many other projects. The review begins with a set of journaling exercises, focused on two questions: What went well this year? What did not go well this year? A core principle of the review is that we tend to overestimate what we can accomplish in a single day, but underestimate what can happen in a year.
I jot down at least ten to twelve answers for each of the two questions, focusing on successes, struggles, and projects—whether completed, in progress, or stalled. This leads to the next, longer stage of the planning process where I look ahead to the forthcoming year, thinking about which projects I’d like to pursue and which actions I need to take to ensure their success. I then set a number of goals based on specific categories. Your own categories may vary, but some of mine include: Writing Business Friends and Family Service Travel Spiritual Health Learning Financial (Earning) Financial (Giving) Financial (Saving) The review takes place over a week, while I’m not doing as much other work. Thinking through the categories one by one, I set an average of three to five measurable goals for each.
Toward the end of the week, after I’ve set thirty to fifty goals across my various categories, I define the overall outcomes for the year ahead. One year from now, what do I want to have accomplished? I usually write this statement as a short paragraph. Here’s an example from a few years ago: Outcomes: At the end of 2009 I will have finished the manuscript for my first book and published 100 essays on the AONC [Art of Non-Conformity] blog. I will have visited 20 new countries, recovered from my running injury to complete a fourth marathon (or two half marathons), and built a new small business that supports my primary writing goals. I also choose a word or overall theme for the year. Past years have been dubbed “The Year of Learning” (when I finished a graduate degree), “The Year of Convergence” (as I sought to tie together a number of unrelated projects), and “The Year of Scale and Reach” (where I began touring more extensively, hosting or speaking at seventy events with readers around the world).
A good plan allows for plenty of spontaneity and room for change—but without a plan at all, it’s difficult to work toward something significant over time. As several people in this book have argued, planning well and being specific with your intentions is a great help as you progress through your journey.
Alternative: Forget Planning, Just Start While it’s probably best to count the cost before undertaking a lifelong commitment, you can also end up mired in planning paralysis. If you’re predisposed to overthink, the answer is simple: Just do it. Tom Allen, the bike guy who left England for foreign lands, says that almost every day he hears from people who write in to ask how they can follow a similar passion. For a long time he dutifully answered their questions, which were often about gear and packing. After a while, though, he realized that this wasn’t the real problem. Asking “What gear do you use?” is the wrong question, he says. The better question is “What am I waiting for?”
But he’s also quick to say that the technical problems can be solved along the way. His best advice has now been simplified: “Pick a departure date. Start saving. Get a bike, tent, and sleeping bag. And go.”
Jump in with both feet. Stop making excuses.
Remember: Ask yourself what it will cost to follow your dream. Get specific. Be sure to clearly understand the time, money, and other costs before you begin. Generate confidence by listing the questions that your project provokes, and also the objections that you’ll want to deal with in advance. Planning is good … but if you spend all your time planning without making progress, try doing something instead.
For an expanded version of this exercise with a free template for your own annual review, visit https://chrisguillebeau.com/how-to-conduct-your-own-annual-review.
LESSON: WE’RE MOTIVATED BY PROGRESS AND ACHIEVEMENT. IT FEELS GOOD TO CHECK THINGS OFF.
A number of websites cropped up, providing users with an opportunity to create their own list of “Things to Do Before You Die.” A few years later, the “quantified self” movement attracted followers interested in documenting their lives to an extreme degree. I’m not very sophisticated in the life tracking or quantified self movements, but I’ve noticed that even the occasional use of it can be helpful.
Your basic life list—a term we’ll use as a synonym for bucket list—isn’t a bad start. But what if you could go further? What if you organized your life around a single, principal focus or aim? You know how you meet people and they ask, “What do you do?” You can always say that you’re a teacher or a student, an accountant or an artist, or whatever your vocation. But once you have a quest, you have another answer, too. Your identity isn’t tied to a job; your identity is who you really are.
The Twenty-Year Life List
A. J. Jacobs popularized an entire genre of modern-day short-term-quest literature. After his book on reading the Encyclopedia Britannica, The Know-It-All, became a bestseller, he found a pattern he could replicate for other projects.
Julie and Julia: My Year of Cooking Dangerously. Julie Powell sets out to make 524 recipes in a year—every recipe from Julia Child’s classic French cookbook. • A Simple Act of Gratitude: How Learning to Say Thank You Changed My Life. Lawyer John Kralik is on the down-and-out, struggling with divorce and a failing career. Over the next year he practices gratitude by writing 365 detailed thank-you notes to people he encounters. • Dream On: One Hack Golfer’s Challenge to Break Par in a Year. John Richardson has a full-time job and a family, but does everything he can to improve his golf game over the course of a year. Will he make it? Spoiler: He does. But as with any good memoir, the joy is in the struggle and the lessons. • Not Buying It: My Year Without Shopping. Judith Levine and her partner, Paul, spend a year without purchasing anything except that which is completely necessary for living. Along the way they learn various lessons and question society. • Living Oprah: My One-Year Experiment to Walk the Walk of the Queen of Talk. Robyn Okrant, a “thirty-five-year-old average American woman,” devotes a year to following all of Oprah Winfrey’s advice. What happens when the advice conflicts? You’ll just have to read the book.
Fifty Dates in Fifty States
I’m on an Epic Quest of Awesome to level up my life in all aspects: travel, personal health, wealth, language learning, and more. The entire quest is structured like a giant video game in which I’m the character. I earn “experience points” every time I cross an item off my list, whenever I complete five items I “level up” (I’m currently up to Level 10!), each continent is a different “level,” and there are “master quests” that are more difficult than the others. The first items on Steve’s list were easy. He had to get off the couch and get in shape, beginning a new lifestyle of living actively and looking past the potato chips at the grocery store.
One of the tasks was “Complete a James Bond weekend.” To accomplish it, Steve used hotel points to check into a luxury casino resort in Monte Carlo. He changed out of his usual outfit of T-shirt and flip-flops, rented a tuxedo that required the purchase of fancy dress shoes, and strolled into the casino. Not used to the life of the ultrarich in the French Riviera, he wasn’t sure what to do next—but he knew that projecting confidence was an important part of being James Bond. He walked over to the blackjack table, slapped down $200, and said “Deal me in.”
“By assigning point values and structuring the whole list like a game,” he told me, “it tapped into that part of my brain that loved to level up in video games.
Your First (or Tenth) Life List: What if we could come to the end of our lives and, looking back on our rich history of experiences, relationships, and accomplishments, feel truly fulfilled? Either metaphorically or literally, what if we could point to a list of steadily pursued dreams that had turned into accomplished goals?
Avoid fuzzy goals. Make your list specific! Many goals are basic and unmeasurable: to lose weight, save money, or have better posture are all good things, but they’re also somewhat fuzzy and vague. Far better are goals like “Meet the Dalai Lama” or “See the northern lights.” If you set specific goals, you’ll know exactly when you’ve accomplished them.
Mix it up. Don’t just make a note about climbing Everest because other people have done it—think about what you really want to do. Some adventure goals are good, but be sure you have other goals as well. In trying to figure out what to put on your life list, think, “What do I really want to be, do, and achieve?” Remember, the idea is to dream big and avoid limitations.
Be realistic. Think big. The life list is for your whole life! As you compose your list, remember that the basic rule of brainstorming is “Don’t limit yourself.” You should also avoid thinking about your present situation. This is your whole life list; it’s meant to be something you work on and refer to for a long time. In other words, discard reality … or more precisely, what you think of as reality. As your journey progresses, you may very well find that what you thought was reality was actually quite limiting. As much as possible, you should also ignore fear when you write your life list. Fear of failure, and even the fear of success, holds us back from attempting many of the things we secretly wish for. If what you have in mind seems daunting, just tell yourself “It’s only a list.”
Travel or Adventure
Personal Development
Finally, a few unexpected responses seem worth noting:
Every good goal has a deadline, so let’s put a deadline on some of these ideas. Goal: Deadline: Next Step: All you need is one next step. Don’t worry about thinking the whole thing through yet.
A good life list should include goals in multiple categories, not just travel or adventure.
LESSON: “QUESTS ARE BORING. ALL YOU HAVE TO DO IS PUT ONE FOOT IN FRONT OF THE OTHER”
Ultrarunners speak of the transformation that takes hold of their bodies after completing even longer distances. If they’re lucky, at a certain point they enter a trancelike state, jacked up on the natural high of endorphins as they run mile after mile. But as they look back at all those long training runs, ranging farther and farther from home weekend after weekend, many also talk of the monotony that comes with the task.
The path to the summit consists of repetitive movements, but it is precisely the arduousness of the task that makes the accomplishment an epic one.
Experience produces confidence, and confidence produces success.
Shoes by the Door = Instant Accountability. On the road, I’m frequently tired from long flights, time zone changes, and the occasional tequila drink. Upon entering my hotel or guesthouse room, the first thing I do is unpack—no relaxing or checking email just yet! Whatever I expect to need for the rest of my stay gets placed in one or two areas, usually a workstation at the desk and one side of the closet for clothes. Then, if I know I should exercise, I remove my running shoes and place them by the door. This accomplishes two goals at once: First, it’s one less thing I have to worry about when waking up tired to hit the gym or nearby sand dunes. Second, it creates instant accountability. I could skip the exercise, but I’ll have to look at my shoes every time I head out the door, and I’ll have to repack them later. Putting the shoes by the door is a good way to make sure you don’t take the easy way out. Maddog Wallace chose an even more effective way to make himself accountable: He told everyone what he was doing, and they watched. Even better—or worse, on the hard days—they counted on him to finish the task.
Whatever it takes, whether facing an immense challenge or spirit-sapping tedium, just keep making progress.
LESSON: EFFORT CAN BE ITS OWN REWARD. Some people are motivated by achievement, others by process—but still others are motivated by a specific blend of both. These people are all about making things and sharing them with the world, over and over. Why create? Because you can.
The lesson, as he explains it: “If I fail more than you do, I win. Built into this notion is the ability 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.”
LESSON: To be creative, don’t think outside the box. Make yourself a box and get into it!
“I read an article a few years ago that said when you practice a sport a lot, you literally become a broadband: the nerve pathway in your brain contains a lot more information. As soon as you stop practicing, the pathway begins shrinking back down. Reading that changed my life.
“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.
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. —HARUKI MURAKAMI
LESSON: SOME ADVENTURES SHOULD BE SHARED.
“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.”
Must a dream have only one owner? Not if two or more minds see the world from the same perspective.
The most subversive people are those who ask questions. —JOSTEIN GAARDER
LESSON: FIND WHAT TROUBLES YOU ABOUT THE WORLD, THEN FIX IT FOR THE REST OF US.
And yet, every single day, each of us gets to answer a far more interesting question: What’s worth living for? If you could only pursue one thing, what would you craft a life around and do every day? And what if real sacrifice was involved … would you stick with it?
Some people find their quests by focusing on passions and interests—something they love to do or parts of the world they want to explore. If that doesn’t work, though, try a different approach. Instead of asking what excites you, ask what bothers you. There is no shortage of problems in the world, but which one are you most troubled by? What problem are you able to do something about?
LESSON: THE MIDDLE OF A QUEST CAN BE THE HARDEST PART. DON’T GIVE UP TOO SOON!
Steven Pressfield, author of a dozen books, says, “The most important thing about art is to work. Nothing else matters except sitting down every day and trying.” So, too, for a quest. The most important thing is continuing to make progress.
Travel can be disorienting and unstable. You’re out there in an unfamiliar place, doing new things and adopting different patterns.
There are so many reasons to travel: for holiday, getaway, challenge, adventure, hiding
“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.”
What is the cost of my proposed quest or project? • How long will it take me to save this amount of money? • Is there any other way to get the money (crowdfunding, selling something, extra work, robbing banks)? • Do I need to wait to start until I have all the money? • If getting the money will be difficult, is there a way to reduce the cost?
You do it for the same reason John F. Kennedy offered for visiting the moon—not because it’s easy, but because it’s hard.
Remember: The middle of the quest can be the hardest part. As long as you still believe in the goal, don’t stop! By saving as little as $2/day for just a few years, you can go anywhere in the world. If your quest relies on external recognition, be sure you have sufficient internal motivation as well.
Read more on the $2/day experiment at ChrisGuillebeau.com/3×5/your-one-place.
LESSON: CHOOSE YOUR FAILURES, AND HAVE THE RIGHT KIND OF DISASTERS.
Nevertheless, there are a few factors to keep in mind when evaluating this tough question. 1.Motivations. Why did you begin this project in the first place? What drove you to challenge yourself? Presumably, there were many different options you could have chosen for your quest or adventure, but for some reason, you settled on this one. Are you still driven by the same motivations? 2.Long-term happiness. Short-term relief and long-term happiness can be very different things.
3.Rewards. Can you create a small reward at the end of your day, or at the completion of an important task?
4.Engagement of others.
Regret is what you should fear the most. If something is going to keep you awake at night, let it be the fear of not following your dream. Be afraid of settling.
Remember: The right kind of misadventures—the ones that yield information—can produce confidence. If you’re going to worry about something, worry about the cost of not pursuing your dream.
When you have completed 95 percent of your journey, you are only halfway there. —JAPANESE PROVERB
LESSON: AS YOU MAKE PROGRESS TOWARD A SMALL GOAL, THE BIGGER VISION EXPANDS.
When I found myself getting frustrated, more often than not the problem was my own expectations.
People who pursue quests are often motivated by achievement, process, or simply a belief in daily adventure.
Every day it was all about completing a checklist, measuring progress, and making a plan for the next day.
Many other people I talked to also mentioned the importance of measurable progress. Count things down! Check them off! Be aware of your progress as you proceed down a path.
Which perspective is better? Perhaps the best way to think of it is that the two are inextricably intertwined. You can’t achieve anything deeply satisfying without a drawn-out process leading up to it—and yet process demands a goal. You can’t love one without at least appreciating the other.
It’s inevitable: Undertake a quest or any long, challenging project, and you won’t come out of it the same.
The best thing that the walk did for me was make me confident that I could handle even the toughest of tests and scenarios, 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.
We spend more time looking for adventure on the way to where we’re going, rather than waiting for adventures to come to us, or making elaborate plans to visit some of the more common cities to look for adventure.
Don’t 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.
it’s important to remember that dreams tend to grow as you pursue them.
Remember Pursuing a quest can boost your confidence and establish your independence. Those who pursue quests find themselves focusing more and expanding their vision as they go along. “I’m glad I did it” was the most common statement from people who’d completed a quest.
LESSON: MAKE A PLAN FOR THE NEXT STEP.
And then she came home. Everyone asked the big question, “What was it like?” Some really wanted to know, but others were just being polite. Here’s what Meghan had to say: They ask a complex question, but seek a one-sentence answer. It’s akin to inquiring, “In seven words or less, describe your relationship with God.” So you say, “The race was wonderful” and “I loved it” and “It’s an experience I hope I don’t forget.” 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.
When you’ve given everything you have in pursuit of something great, it’s hard to toss off a few quick sentences on “what it’s like.”
Like Meghan Hicks in her post-Sahara experience, I had to deal with two big challenges: the public aspect of it and the inner aspect. For the public aspect, I eventually stumbled on a clear answer: Don’t try to explain everything, but do tell a few good stories. For the private aspect, I learned to reflect—and also to consider the future.
Remember those sunsets … those moments of wonder … the challenge, the process, the waiting? That’s right—that’s what it was about. When in doubt, come back to the stories.
LESSON: Don’t forget to debrief. You may need another goal at some point, but be careful to process before jumping back into the grind.
“Suppose that all your objects in life were realized; that all the changes in institutions and opinions which you are looking forward to, could be completely effected at this very instant: would this be a great joy and happiness to you?” And an irrepressible self-consciousness distinctly answered, “No!” At this my heart sank within me: the whole foundation on which my life was constructed fell down. All my happiness was to have been found in the continual pursuit of this end. The end had ceased to charm, and how could there ever again be any interest in the means? I seemed to have nothing left to live for.
A large part of how I’d defined myself simply was no longer there.” This wasn’t just an existential crisis; Howard really didn’t know what to do next.
The more you experience something outside of what you’ve known, the more open-minded you become
Several people I spoke with for this book described how, after they’d finished their quests, they’d heard a certain phrase uttered by their friends and family. The phrase was “real life” or “the real world,” and the words were sometimes delivered callously. “Guess you’ll have to get back to real life now” was one way of putting it. “That would never work in the real world” was another.
“Life on the road was the real world,” he reflected. “Back in England, it was modern society that seemed to be a place of isolation and abstractions.”
What started as an adventure in self-discovery had become a global endeavor, complete with sponsors who expected reports and media outlets that were eager to interview him. He finally had to unwind what he created and “deinstitutionalize the beast,” focusing once again on the no-strings-attached journey he’d longed for from the beginning.
To climb out of a post-quest funk, you start by realizing that the real world is what you make of it.
Next, you start again. You need a new quest and a new mission.
Remember Sometimes quests don’t tie up well. Sometimes it’s hard at the end. If it’s hard to explain the totality of a quest, focus on a few stories. The real world is what you make of it. After completing a quest, the next steps are up to you.
LESSON: THE END IS THE BEGINNING.
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. —PAULO COELHO
“To arrive there is your ultimate goal, but do not hurry.”
The core message is that a quest can bring purpose and meaning to your life, too. Why pursue a quest? Because each of us in our lives is writing our own story, and we only have one chance to get it right.
“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.”
From my own 193-country journey to the stories of many other people who were kindly willing to share, I’ve tried to extract and convey the lessons of modern-day quests. The experiences of fifty people pursuing big goals varies immensely, but a number of lessons are close to universal:
Unhappiness can lead to new beginnings. If you’re not happy with your life, or even if you feel a faint stirring to do something different, pay attention to the dissatisfaction. Ask yourself “What if” questions. What if I actually pursued that dream or idea? What if I made that big change? Discontent can be a source of growth and inspiration.
Adventure is for everyone. You can have the life you want no matter who you are. There’s a quest waiting for you to find, claim, or create.
Everyone has a calling. Follow your passion. Pay attention to the things that excite you and the things that bother you. Remember Jiro Ono, the sushi chef from Tokyo who talked about feeling victorious over a particularly nice tuna, and remember Miranda Gibson, who live in the treetops of Tasmania for more than a year in protest of illegal logging. Your passion may not matter to anyone else, but if it matters to you, don’t ignore it.
Every day matters. The awareness of our mortality can help us pursue a goal. We all have a limited amount of time on earth. Those who live in active awareness of this reality are more likely to identify goals and make progress toward them. Or to put in another way: Everyone dies, but not everyone truly lives.
Not everyone needs to believe in your dream, but you do. The support and understanding of others will vary. It doesn’t matter what anyone else thinks about your quest, but if you don’t have sufficient motivation to see it through, it will be tough going.
Before beginning a quest, count the cost. In the early days of my journey to every country, someone criticized it by saying all it required was a certain amount of time and money. I later realized that this perspective could actually be helpful. If I clearly understood exactly what was involved in “going everywhere,” and if I then began working on each part of the goal step-by-step, it no longer seemed overwhelming. Whatever you choose to do, count the cost as much as you can.
We are motivated by progress and achievement. It feels good to check things off. Lists are both fun and motivational. We enjoy breaking things down step-by-step and incrementally conquering big challenges.
We can’t always opt out of monotony, but we can choose which form it takes. Odysseus fought off sea monsters and escaped from an island prison, but he also endured a lot of boring days at sea. Most quests consist of a set of milestones that take a long time to reach. To stay on track, choose forward motion—keep making choices that bring you closer to the goal, even if it seems like reaching the end will take forever.
The effort is the reward. If you measure success by the opinions of others, you’ve effectively set yourself up for failure. But if you measure success by your own effort, focusing on what you produce and contribute, any additional praise or fame will be a bonus. The work itself can serve as its own motivation.
Some adventures should be shared. Tom Allen said that “a dream can have only one owner.” But some challenges can be conquered jointly, and even if your quest isn’t a tag team effort, chances are that a number of people will participate in your dream as you move toward completion.
Misadventures produce confidence. Getting stuck, detained, shut out, or set back is never fun, but these experiences are a necessary part of the journey. When something goes wrong, strive to accept it as an investment in learning. Hopefully, you won’t make the same mistake twice … or at least, not over and over.
As you make progress toward a small goal, the bigger vision expands. Many people featured in the book started with a small goal that grew in scope as it became more feasible. If at first you can’t picture a tremendous accomplishment, start with an achievable one. (Conversely, when you work toward a tremendous accomplishment, watch out: The next one may be even bigger.)
Quests do not always tie up well. **Sometimes the ending is glorious, and sometimes it’s bittersweet. Either way, take the time to process all you’ve been through. When you’re ready, choose a new adventure.