Finding the Quest That Will Bring Purpose to Your Life
Chris Guillebeau
The pursuit itself — not the destination — is where meaning lives. Find your quest.
Guillebeau spent years interviewing people engaged in audacious personal quests and found a consistent pattern: the pursuit itself generated more meaning and joy than the finish line. Humans are wired for progress, not arrival.
Everything Guillebeau wants you to walk away with
Research shows we enjoy planning a vacation as much as taking it. Anticipation is a powerful force. Humans are wired for progress, not arrival. The tougher the odds, the better — as long as there's something to believe in.
You don't arrive at the holy grail the day after you set out. If you do, it's not the holy grail and it's not a quest. You must become a better person than you were before you started. You must improve throughout the journey.
Most people who undertook quests had been dissatisfied with their normal lives. They wanted something deeper. Dissatisfaction plus big idea plus willingness to take action equals new adventure. Pay attention when you sense discontent.
The quest will reveal what it requires as you go. You don't need full clarity before taking the first step. Misadventures and even disasters produce confidence. Things usually turn out OK — and you learn to laugh at your own misfortune.
Those interviewed often spoke of their perceived feebleness, believing 'anyone' could do what they did. But few would have the resolve to persist. The goals grew in proportion with time and experience.
This book is that opportunity. Sit with people who invested years in relentless pursuit. Learn not just what happened but why it happened and why it matters. Then decide your own next steps.
Understanding exactly what you need to do, and then finding a way to do it, makes a quest much more feasible. What excites you? What bothers you? If you could do anything without regard to time or money, what would it be?
Coming to the end of a quest brings its own lessons. The story doesn't always tie up well. You have to think about what's next, and whether you can re-create the intense feelings from the time you were chasing your goal.
Many quests begin from losing something — a sense of adventure, a sense of self — and going back to reclaim it. 'Something had to give. I was settling into a comfortable rut but losing my sense of adventure.' The stirring shouldn't be ignored.
Happiness often results from doing something you love, but the deeper reward is finding the intersection of risk, purpose, and progress. The hero sets off in search of something elusive that has the power to change both their life and the world.
These notes are inspired by direct excerpts and woven together into a readable guide you can follow from start to finish.
By Chris Guillebeau
People have always been captivated by quests. History’s earliest stories—African, Asian, European—follow the same arc: 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. Hollywood knows quests are an easy sell: Star Wars, Star Trek, Indiana Jones, and countless others succeed because the audience has something to believe in. The tougher the odds and the higher the stakes, the better—as long as we believe in the hero’s mission.
Most of these quest stories are told and retold with a fair amount of exaggeration. They can be engaging, but for the most part they aren’t real. We enjoy them because, for a brief time, they alter our belief in what’s possible.
While journeying to nearly two hundred countries, Guillebeau discovered something important: he wasn’t the only one on a quest. All over the world, people had found the same way of bringing greater purpose to their lives. Some had been toiling away at a goal for years without recognition. Going for it—whatever “it” was—was simply something they found meaningful and loved to do. As one woman put it, she considered herself an instrument, and if she didn’t put herself to work for the greatest possible good, she’d feel like she wasted a chance that would never return.
These people stood out. They spoke with intensity. They were focused on their goals, even when those goals didn’t immediately make sense to others. Walking mile after mile along dusty village roads, meeting strangers who became friends, they felt a heightened sense of being alive. Understanding why they’d chosen to pursue big goals with such determination—and what kept them going when others would have stopped—became the driving question.
⟡ Principle
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. Spending all night in a deserted airline terminal or being completely out of money in a remote part of the world teaches you that things will usually be OK. You learn to laugh at your own misfortune, or at least to not panic when something bad happens.
Coming to the end of a quest brings its own 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 while chasing down your goal.
Lesson: Adventure is for everyone.
For the price of a plane ticket, you can jet off to foreign lands. Whatever you could possibly want to learn is readily available. But a quest is something bigger than general life improvement. It takes more time and requires more commitment.
◆ Definition: What Is a Quest?
A quest has a clear goal and a specific end point. You can explain it in a sentence or two. Every quest has a beginning and an end. Not everyone will understand why you undertook it, but that’s another matter.
A quest presents a clear challenge. By design, it requires that something be overcome. It doesn’t need to be dangerous or impossible, but it shouldn’t be easy either.
A quest requires sacrifice of some kind. There is no “having it all.” To pursue a big dream, you must give something up along the way. Sometimes the sacrifice is apparent at the beginning; other times it becomes apparent only later.
A quest is often driven by a calling or sense of mission. A calling need not be divine inspiration—it is often simply a deep sense of internal purpose. 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. Many quests consist of a long, slow-and-steady march, 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.
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 must become a better person than you were before you started. You must improve throughout the journey.
As Guillebeau traveled the world and traversed his inbox, a few themes kept coming up among people who had embarked on quests: self-discovery, letting a little risk into your life, reclaiming something lost, responding to external events, a desire for ownership and empowerment, and taking a stand for something.
Real-life adventure isn’t only about traveling the world, nor is a quest always about leaving home—although it often involves breaking out of a comfort zone. For the most part, the individuals he met were successful not because of innate talent, but because of their choices and dedication. Much of the time, goals grew in proportion with time and experience. Those interviewed often spoke of their perceived feebleness, or their belief that “anyone” could do what they did—yet few would have the resolve to persist as they did.
✦ Key Insight
Everyone who pursues a quest learns many lessons along the way—about accomplishment, disillusionment, joy, and sacrifice. 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 provides: a framework and a challenge. Your job is 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? Pay attention to the ideas that draw your interest, especially the ones you can’t stop thinking about. Research shows that we enjoy planning a vacation as much as taking it. Anticipation is a powerful force.
☐ Remember
A quest has a few key features: a clear goal, a real challenge, and a set of milestones along the way. This book isn’t just a study of what other people have done. You, too, can identify and pursue a quest.
“Discontent is the first necessity of progress.” — Thomas A. Edison
Lesson: Unhappiness can lead to new beginnings.
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? The answer starts with “why.” Many people who embark on quests 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. Taking control—being at the reins of your own life—was part of a broader mission to reinvent themselves.
Losing something—a sense of adventure, a sense of self—and going back in an effort to reclaim it is a common characteristic of beginning a quest. In quests of old, the hero traveled across distant lands to reclaim 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. Common catalysts include “a crazy idea that wouldn’t leave me alone,” feeling that “I just couldn’t live that way anymore,” or a conviction that a small adjustment wouldn’t be enough—only a complete shift in direction toward a new way of life.
✦ Key Insight: The Adventure Formula
Discontent is a powerful spark, but on its own it is not sufficient to inspire a quest. Lots of people are walking around unhappy, but most don’t make radical changes. If you want to get the embers burning, you have to blend dissatisfaction with inspiration and connect it to a greater purpose.
Dissatisfaction + Big Idea + Willingness to Take Action = New Adventure
Metaphorically, discontent is the match and inspiration is the kindling. When discontent leads to excitement, that’s when you’ve found your pursuit.
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.
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. Happiness is a choice, and no one has to be special to pursue a dream.
☐ 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?”—can help you find your next steps.
Lesson: Everyone has a calling. Follow your passion.
Those who pursue quests tend to share a high level of risk tolerance. They face challenge willingly—“it is no wonder that people challenge me; I am challenging myself.” The journey itself will produce its own rewards.
⟡ Principle
When a person is really happy, they don’t have to tell people about it. It just shows.
“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 pretense. As trite as it sounds to “live like you’re dying,” that’s exactly what many people obsessed with a quest do. The shift that matters is from an intellectual awareness that we will someday die to an emotional awareness—and that shift can be a guiding light to discovering what really matters.
| Awareness Type | What It Sounds Like |
|---|---|
| Intellectual awareness | ”I know that no one lives forever.” |
| Emotional awareness | ”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 confronting a serious health problem. Other times, there’s a stirring of the soul that increases in tempo until it’s impossible to ignore. The more you are emotionally aware of your own mortality, the more you feel compelled to live with a sense of purpose.
◆ Definition: Hobby vs. 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 comfortable with failure is deliberate practice. Rejection Therapy is a real-life game created by Jason Comely that encourages players to engage in social experiments. The goal 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 isn’t over until you’ve been rejected. The lesson: rejection, like experience, produces confidence. The act of moving forward, continuing to make requests despite a number of failures, is empowering.
“If I didn’t do it, I would always wonder about what could have been”—this sentiment was repeated over and over by the people Guillebeau talked with. 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.
✦ Key Insight: Perception Depends on Outcome
Ultimately, assessments of a quest’s worthiness depend on the result.
Life itself is risky. Choose your own risk level. Your comfort zone may be more like a cage you can’t escape from than a safe place you can retreat to.
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.
“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. One approach is to embrace culture through cuisine: “Stovetop Travel” was one person’s project to introduce meals from around the world into a home kitchen, playing music from the featured country and inviting friends to join. Every good goal has a deadline—this is a recurring theme. The project worked because it was specific, fun, challenging, and meaningful.
The same principle scales in every direction. One person devoted nearly ten years to jumping into every lake in the Glacier and Waterton Lakes National Parks—168 lakes in total, many requiring off-trail hiking through dense vegetation and rough mountainous terrain across both sides of the U.S.–Canada border. Others turned visiting every basilica in the United States into a project, or planned to see a game in every Major League Baseball stadium.
Even small changes matter. Visiting the art museum on a lunch break or taking a photography class can shift your entire outlook. Breaking your programming requires a single moment of strength.
☐ Action List: Quick Ways to Break Your Routine
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.
⟡ Principle: Two Theories of Change
Make small and incremental (but regular) changes. Mix it up.
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 option 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.
Travel—even aimless travel with no set goal—gains more weight when attached to something of greater significance. Even though it was ultimately more about the journey than the eventual destination, having a destination in mind provided an anchor.
☐ Should You Document Your Quest?
Yes, probably, in some fashion. Some people wish 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. Options include: photography or videography, writing or blogging, collecting souvenirs or mementos, keeping a scrapbook (traditional or digital), or something else entirely.
Lesson: Before beginning a quest, count the cost.
Since a quest might be a ten-year journey, you can’t stay excited on a daily basis by thinking about the finish line. That’s when subgoals prove 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. At the beginning of a quest, ask: What is the goal, really? What does success look like? Estimate the toll it will take.
Detailed planning pays off. One person planning to walk across Turkey mapped his entire route in advance: 60 miles a week, for a total of 22 weeks, with data on elevation, climate, and average temperature for every area. Hard-core? Maybe. But the granularity helped him understand what he was getting into and demonstrate to curious people that he knew what he was doing. It wasn’t just a passing thought; it was a plan.
◆ Example Framework: Learning a New Language
Time: Six months (or whatever you decide). Cost: Variable, but can be done affordably or even free.
Obstacle 1 — Lack of confidence. (“I’m not good at speaking other languages.”) Way Around It: Begin slowly. Ask for help. Accept that everyone starts as a beginner.
Obstacle 2 — Uncertain how to proceed. (“Do I take a course? Get a tutor? Download podcasts?”) Way Around It: Attempt all of those things and see what works best. Just start!
Obstacle 3 — Perception of not enough time. (“I’m too busy.”) Way Around It: Incorporate it into your regular routine. Carry index cards with new vocabulary. Listen to music in the language. Study in ten-minute breaks.
Yes, it’s all about the journey, but having a destination in mind will help. Thinking logically about your goals and breaking down the obstacles is good for you. The more prepared you are, the more spontaneous you can be.
✦ Key Insight: The Annual Review
Every year, set aside an entire week in December to review the year that has almost ended and prepare for the next. Begin with two journaling questions: What went well this year? What did not go well this year?
A core principle: we tend to overestimate what we can accomplish in a single day, but underestimate what can happen in a year.
Jot down at least ten to twelve answers for each question, focusing on successes, struggles, and projects—whether completed, in progress, or stalled. Then look ahead to the forthcoming year. Set three to five measurable goals for each of your life categories. Categories might include: Writing, Business, Friends & Family, Service, Travel, Spiritual, Health, Learning, Financial (Earning), Financial (Giving), Financial (Saving).
Toward the end of the week, after you’ve set thirty to fifty goals across your categories, define the overall outcomes for the year ahead as a short paragraph. Also choose a word or overall theme for the year (e.g., “The Year of Learning,” “The Year of Convergence,” “The Year of Scale and Reach”).
For a free template, visit: chrisguillebeau.com/how-to-conduct-your-own-annual-review
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.
⟡ Principle: Planning vs. Just Starting
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. Asking “What gear do you use?” is the wrong question. The better question is “What am I waiting for?”
The technical problems can be solved along the way. Pick a departure date. Start saving. Get what you need. And go.
☐ Remember
Lesson: We’re motivated by progress and achievement. It feels good to check things off.
Websites offering “Things to Do Before You Die” lists and the “quantified self” movement both tapped into the same impulse. Even the occasional use of life tracking can be helpful. But a basic bucket list isn’t quite enough. What if you organized your life around a single, principal focus or aim? Once you have a quest, you have a new answer to “What do you do?” Your identity isn’t tied to a job; your identity is who you really are.
Short-term quests have become their own genre. Examples include spending a year making every recipe from a classic French cookbook, writing 365 detailed thank-you notes, doing everything possible to improve a golf game in a year, spending a year without purchasing anything except necessities, or devoting a year to following all of a talk show host’s advice. In each case, the joy is in the struggle and the lessons.
One person structured his entire life list like a giant video game in which he was the character. He earned “experience points” every time he crossed an item off, leveled up every five items, treated each continent as a different “level,” and designated harder tasks as “master quests.” By assigning point values and structuring the whole list like a game, it tapped into the part of his brain that loved to level up in video games. The first items were easy—getting off the couch, getting in shape, beginning a new lifestyle. Later tasks got wilder: one was to “Complete a James Bond weekend,” which involved checking into a luxury casino resort in Monte Carlo, renting a tuxedo, strolling into the casino, and projecting confidence at the blackjack table.
⟡ Principle: Life List Rules
Avoid fuzzy goals. “Lose weight” or “save money” are 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 list adventure goals because other people have. Think about what you really want to be, do, and achieve. Dream big and avoid limitations.
Be realistic—which means thinking big. The life list is for your whole life. Discard what you think of as reality; as your journey progresses, what you thought was reality may turn out to have been quite limiting. Ignore fear when you write your list. Fear of failure, and even fear of success, holds us back. If it seems daunting, tell yourself: “It’s only a list.”
Include multiple categories. A good life list should include goals in travel/adventure, personal development, academic/creative pursuits, and more—not just one area.
Sample categories and goals to spark ideas:
☐ Action: Put a Deadline on It
Every good goal has a deadline. For each idea on your list, write down the goal, a deadline, and a single next step. All you need is one next step—don’t worry about thinking the whole thing through yet.
What if you could come to the end of your life and, looking back on your rich history of experiences, relationships, and accomplishments, feel truly fulfilled? What if you could point to a list of steadily pursued dreams that had turned into accomplished goals?
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 after completing very long distances. If they’re lucky, they enter a trancelike state, jacked up on endorphins mile after mile. But as they look back at all those long training runs, 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.
⟡ Principle
Experience produces confidence, and confidence produces success.
✦ Key Insight: Shoes by the Door = Instant Accountability
When you arrive somewhere tired, the first thing to do is unpack—no relaxing or checking email yet. If you know you should exercise, remove your running shoes and place them by the door. This accomplishes two goals: it’s one less thing to worry about when waking up tired, and it creates instant accountability. You could skip the exercise, but you’ll have to look at your shoes every time you head out the door and repack them later. Putting the shoes by the door is a good way to make sure you don’t take the easy way out.
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.
✦ Key Insight: The Failure Advantage
“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.
To be creative, don’t think outside the box—make yourself a box and get into it. Constraints fuel creativity. And like any skill, creative work requires practice. When you practice something 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.
⟡ Principle
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.
Must a dream have only one owner? Not if two or more minds see the world from the same perspective. When you commit to a shared quest, something shifts: “I’m no longer the most important person in my life. Whatever the direction is going to be, it’s going to be pursued together.”
“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.
Every single day, each of us gets to answer a far more interesting question than how we’ll die: 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?
✦ Key Insight: Flip the Question
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, 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!
The most important thing about a quest is continuing to make progress. As Steven Pressfield, author of a dozen books, puts it: “The most important thing about art is to work. Nothing else matters except sitting down every day and trying.”
Travel can be disorienting and unstable—you’re out in an unfamiliar place, doing new things and adopting different patterns. There are so many reasons to travel: for holiday, getaway, challenge, adventure, hiding. But whatever the reason, the cost question always comes up. The key questions to ask yourself: What is the cost of my proposed quest or project? How long will it take me to save this amount? Is there any other way to get the money (crowdfunding, selling something, extra work)? 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?
⟡ Principle
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.
One person described the cost simply: “I don’t think I can put a price tag on it, but it costs what life costs. We choose to live a simple, frugal life so that we can do things we are passionate about.” If your quest relies on external recognition, be sure you have sufficient internal motivation as well.
☐ 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.
Lesson: Choose your failures, and have the right kind of disasters.
When you’re deep in a quest and things go wrong, there are a few factors to keep in mind when evaluating whether to continue:
◆ Framework: Evaluating Whether to Continue
Motivations. Why did you begin this project in the first place? What drove you to challenge yourself? Are you still driven by the same motivations?
Long-term happiness. Short-term relief and long-term happiness can be very different things.
Rewards. Can you create a small reward at the end of your day, or at the completion of an important task?
Engagement of others. Can you draw others into the effort to sustain momentum?
⟡ Principle
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.
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 you find yourself getting frustrated, more often than not the problem is your own expectations. People who pursue quests are often motivated by achievement, process, or simply a belief in daily adventure.
| Motivation Type | What It Looks Like |
|---|---|
| Achievement-motivated | Wants to accomplish something — scale the wall, rid the empire of invaders, reach the summit. |
| Process-motivated | Wants to do something — collect or build step-by-step, go on a long journey, follow a daily practice. |
For the process-motivated person, every day is about completing a checklist, measuring progress, and making a plan for the next day. Many people emphasized 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.
✦ Key Insight
It’s inevitable: undertake a quest or any long, challenging project, and you won’t come out of it the same. The walk—or whatever form the quest takes—builds confidence that you can handle even the toughest of tests and scenarios. You spend more time looking for adventure on the way to where you’re going, rather than waiting for adventures to come to you.
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. And 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.
When you come home from a quest, everyone asks the big question: “What was it like?” Some really want to know, but others are just being polite. They ask a complex question but seek a one-sentence answer—akin to inquiring, “In seven words or less, describe your relationship with God.” So you say “It was wonderful” and “I loved it,” statements that are true but toss a fuzzy, feel-good blanket over the whole experience. 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.”
✦ Key Insight: Handling the Two Challenges of Coming Home
The public aspect: Don’t try to explain everything, but do tell a few good stories.
The private aspect: Learn to reflect—and also to consider the future. Remember those sunsets, those moments of wonder, the challenge, the process, the waiting. When in doubt, come back to the stories.
| Dimension | Practical Response |
|---|---|
| Public challenge | Share a few vivid stories instead of trying to summarize everything. |
| Private challenge | Debrief, reflect, and design a meaningful next mission. |
Several people described how, after finishing their quests, friends and family uttered the phrase “real life” or “the real world,” sometimes callously: “Guess you’ll have to get back to real life now” or “That would never work in the real world.” One person reflected the opposite: “Life on the road was the real world. Back in England, it was modern society that seemed to be a place of isolation and abstractions.”
The post-quest identity crisis is real. When a large part of how you’ve defined yourself simply is no longer there, you may not know what to do next. What started as an adventure in self-discovery can become something institutionalized—complete with sponsors expecting reports and media outlets eager to interview you. Sometimes you have to “deinstitutionalize the beast” and refocus on the no-strings-attached journey you’d longed for from the beginning.
⟡ Principle: The Post-Quest Paradox
John Stuart Mill once asked himself: suppose all your objects in life were realized at this very instant—would this be a great joy and happiness to you? His answer was “No.” All his happiness had been found in the continual pursuit of the end. The end had ceased to charm, and how could there ever again be any interest in the means?
The lesson: to climb out of a post-quest funk, start by realizing that the real world is what you make of it. Then 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. Don’t forget to debrief—you may need another goal at some point, but be careful to process before jumping back into the grind. 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. 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.
⟡ Principle
“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 Guillebeau’s own 193-country journey to the stories of many other people who were willing to share, the lessons of modern-day quests vary immensely—but a number are close to universal:
✦ The Universal Lessons
Unhappiness can lead to new beginnings. If you’re not happy, or even if you feel a faint stirring to do something different, pay attention. Ask “What if” questions. 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. Your passion may not matter to anyone else, but if it matters to you, don’t ignore it.
Every day matters. 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. Everyone dies, but not everyone truly lives.
Not everyone needs to believe in your dream, but you do. The support 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. If you clearly understand exactly what’s involved and begin working step-by-step, it no longer seems overwhelming.
We are motivated by progress and achievement. 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. Most quests consist of milestones that take a long time to reach. Choose forward motion—keep making choices that bring you closer to the goal, even if reaching the end seems like it will take forever.
The effort is the reward. If you measure success by the opinions of others, you’ve set yourself up for failure. If you measure success by your own effort—focusing on what you produce and contribute—any additional praise or fame will be a bonus.
Some adventures should be shared. Some challenges can be conquered jointly, and even if your quest isn’t a tag team effort, 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. Strive to accept them as an investment in learning.
As you make progress toward a small goal, the bigger vision expands. Many people started with a small goal that grew in scope as it became more feasible. If you can’t picture a tremendous accomplishment, start with an achievable one. And 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.