THE HAPPINESS OF PURSUIT by Chris Guillebeau

• People have always been captivated by quests. History’s earliest stories tell of epic journeys and grand adventures.
• The world’s best-known literature reflects our desire to hear about struggle and sacrifice in pursuit of a goal.
• If you want to achieve the unimaginable, you start by imagining it.
• Courage comes through achievement but also through the attempt.
• As Don Quixote learned many years ago, quests do not always develop as planned. Travelers are often waylaid or misdirected, and some challenges prove especially difficult. Yet misadventures (and sometimes even disasters) produce confidence.
• Lesson: ADVENTURE IS FOR EVERYONE.
• A quest has a clear goal and a specific end point. You can clearly explain a quest in a sentence or two.
• A quest presents a clear challenge. By design, a quest requires that something be overcome.
• 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.
• 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.
• A quest requires a series of small steps and incremental progress toward the goal.
• 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.
• 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).
• Quests bring meaning and fulfillment to our lives.
• Why should you consider a quest? Because your life is good, but you don’t feel completely fulfilled.
• 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.
• Lesson: UNHAPPINESS CAN LEAD TO NEW BEGINNINGS.
• When discontent sets in, it’s time to make some changes.
• Your identity shapes everything about you—how you spend your time, your work, your priorities, and everything else.
• There are two kinds of challenges: those where you can take action to remedy the situation, and those where you’re relatively powerless. It’s always good to know which kind of challenge you’re facing. If you can influence the situation for the better, you can then make a plan for change. If you can’t, then you can move to a plan for acceptance of the bad news.
• You won’t always have the answers to everything.
• 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.
• Dissatisfaction + Big Idea + Willingness to Take Action = New Adventure
• If you’ve ever felt a strange sense of sadness or alienation, there’s a potential way out of the confusion—just shift this feeling to a sense 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.
• When discontent leads to excitement, that’s when you know you’ve found your pursuit.
• 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.
• You have to be the best at whatever you are called at. Whatever you do. You ought to be the best at it—highly skilled. It’s about confidence, not arrogance.
• Be attentive to what happens when you lose yourself in the moment.
• Embracing new things often requires us to embrace our fears, however trivial they may seem. You deal with fear not by pretending it doesn’t exist, but by refusing to give it decision-making authority.
• Lesson: EVERY DAY MATTERS. THE EMOTIONAL AWARENESS OF MORTALITY CAN HELP US PURSUE A GOAL.
• Any given moment can change your life.
• This is a fact: All of us will someday die. Yet not all of us live in a state of active awareness of this reality.
• Once you start thinking about your own mortality, the small things just don’t matter anymore.
• As I discovered in visiting every country in the world, once you set a big goal it is often easier to work toward it than you first expect.
• To truly live without regrets, pay attention. Ask yourself hard questions and see where they lead.
• People who live their lives in pursuit of quests or adventures understand that they have to be deliberate about doing things that matter.
• The awareness of our own mortality can keep us focused. Eyes on the prize!
• Lesson: NOT EVERYONE NEEDS TO BELIEVE IN YOUR DREAM, BUT YOU DO.
• If you’re trying to do something new, you may feel uncomfortable with the idea of starting, or you may worry that your idea won’t be accepted by everyone. One way to “get over it” is to learn to become comfortable with failure.
• Being told you can’t do something is supremely motivating.
• Judgments about whether a quest is brave or stupid tend to be relative.
• Sometimes life itself is risky. There are few goals worth pursuing that are totally risk free.
• You have to believe in your quest even if others don’t.
• We tend to judge risk based on outcome—but the outcome isn’t always up to us.
• Life itself is risky. Choose your own risk level.
• Lesson: YOU CAN HAVE THE LIFE YOU WANT NO MATTER WHO 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.
• Every good goal has a deadline
• Lesson: Complete the kind of recording that makes sense to you, not what you feel you should do.
• 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.
• Don’t just do something “fun.” Find a way to create structure around a project and build in a timeline.
• Connect your skills and interests with an extended challenge—
• Lesson: BEFORE BEGINNING A QUEST, COUNT THE COST.
• Another way to consider a big goal is to start from the end point and plan backward.
• we tend to overestimate what we can accomplish in a single day, but underestimate what can happen in a year.
• A measurable goal is a good companion, and the numbers are your friends.
• Jump in with both feet. Stop making excuses.
• 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.
• Lesson: WE’RE MOTIVATED BY PROGRESS AND ACHIEVEMENT. IT FEELS GOOD TO CHECK THINGS OFF.
• Your identity isn’t tied to a job; your identity is who you really are.
• Regardless of how it begins, a quest provides a focal point. Once you have a task to pursue, you have a new way of looking at the world, a new point of identity.
• If you pursue the project primarily for your personal development or curiosity, it’s a quest.
• Avoid fuzzy goals. Make your list specific! Many goals are basic and unmeasurable:
• The fewer limits you place on your list, the better it will be.
• As you compose your list, remember that the basic rule of brainstorming is “Don’t limit yourself.”
• Fear of failure, and even the fear of success, holds us back from attempting many of the things we secretly wish for.
• Every good goal has a deadline, so let’s put a deadline on some of these ideas.
• A quest can provide a focal point or purpose.
• We feel motivated by making lists and checking things off.
• 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.”
• Experience produces confidence, and confidence produces success.
• Having a way to measure your goal is critical.
• Better to be in control of your circumstances, I thought. Better to make the active choice.
• The mantra of the traveler is to make peace with waiting. The mantra of the quester is to keep moving forward. Whatever it takes, whether facing an immense challenge or spirit-sapping tedium, just keep making progress.
• The long, hard slog is a key part of most quests.
• We can’t opt out of monotony, but we can choose which form it takes.
• When you have the option between backtracking and making progress, choose progress.
• Lesson: EFFORT CAN BE ITS OWN REWARD.
• Smart companies understand that financial compensation isn’t the only reason people come to work.
• 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. If you get to keep playing, sooner or later you’re gonna make it succeed. 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!3
• As soon as you stop practicing, the pathway begins shrinking back down.
• Both Seinfeld and Leno believe that continually getting onstage without a safety net is key to their ability to thrive.
• The obsession with continuously refining a small thing can be a quest of its own.
• If you’re doing something you love, it doesn’t matter that it’s challenging. You can keep going for a long time as long as you’re motivated—just make sure you choose the right starting point.
• Effort can be its own reward if you let it.
• To be creative, “get in the box”—create structure and routine that allows you to keep working.
• Lesson: SOME ADVENTURES SHOULD BE SHARED.
• If your family or close friends don’t understand your dream, you need to find people who do.
• Must a dream have only one owner? Not if two or more minds see the world from the same perspective.
• Even with the support of others, it’s hard to struggle through hardship without sufficient motivation of your own.
• Lesson: FIND WHAT TROUBLES YOU ABOUT THE WORLD, THEN FIX IT FOR THE REST OF US.
• If you’re trying to find your own quest, you may find it helpful to ask yourself a few questions.
• Having an enemy or opponent (even an imaginary one) can keep you focused.
• What’s worth living for? matters more than What’s worth dying for?
• Understanding what bothers you is just as important as understanding what excites you.
• Lesson: THE MIDDLE OF A QUEST CAN BE THE HARDEST PART. DON’T GIVE UP TOO SOON!
• The long, slow grind of working toward something is all about loving the process. If you don’t love the process, the grind is tough.
• The grind is also a dangerous time. It’s when you’re tempted to give up, call it a day, or at least cut corners.
• Nothing else matters except sitting down every day and trying.”
• Most quests are about taking action rather than acquiring “stuff”—and most actions can be quantified into a time-and-money model where you figure out exactly what it costs, then you calculate how to pay for it.
• When it comes to travel, I’ve learned that there are very few places on the planet that require breaking the bank to get to for a few days.
• The concept is that there is nowhere in the world you can’t visit if you save even a small amount of money over time.
• If you can save even more than $2 a day, you can probably get wherever you need to go sooner.
• The lesson is to know your own motivations. That way, you’ll keep going even if no one else cares.
• 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.
• Lesson: CHOOSE YOUR FAILURES, AND HAVE THE RIGHT KIND OF DISASTERS.
• The best stories come from near-disasters, but that doesn’t mean they’re much fun at the time.
• If you’ve always felt like you don’t fit in, one of the happiest experiences of your life will be discovering that there are others like you.
• Loneliness is part of many quests, but that doesn’t mean you should always be lonely.
• 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.
• Sometimes stopping is the right decision. When considering a shift, ask: Is my heart still in this?
• Lesson: AS YOU MAKE PROGRESS TOWARD A SMALL GOAL, THE BIGGER VISION EXPANDS.
• In the end, all the clichés hold true: If you can’t change the world, at least you can change yourself.
• When it comes to travel, you should create your own itinerary and not have it be dictated by others.
• People who pursue quests are often motivated by achievement, process, or simply a belief in daily adventure.
• You can’t achieve anything deeply satisfying without a drawn-out process leading up to it—and yet process demands a goal.
• It’s inevitable: Undertake a quest or any long, challenging project, and you won’t come out of it the same.
• Everything has a season.
• As you gain confidence, “I can do this!” becomes “What else can I do?”
• 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.
• Conquering planet Earth as a modern explorer is amazing. But coming to the end of such a quest is also complicated.
• 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.
• The more you experience something outside of what you’ve known, the more open-minded you become … but this worldview can also be somewhat alienating, especially to people at home.
• The Real World Is What You Make It
• In the same way that the first level of a game can become boring and repetitive, once you’ve leveled up, you may not be able to go back to the same habits and routine.
• How do you go back? In many ways, you don’t. You can’t.
• To climb out of a post-quest funk, you start by realizing that the real world is what you make of it. You’ve grown, you’ve changed, and you can’t go back. You’re not the same, so don’t expect everyone else to be the same either. Next, you start again. You need a new quest and a new mission.
• 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.
• Every quest has an end.
• 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.
• 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.
• 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 it 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.