As for the word vagabonding, I used to think it was my own invention. This was back in 1998, when I was first pitching an adventure travel column to At the time, I wanted a succinct word to describe what I was doing: leaving the ordered world to travel on the cheap for an extended period of time. Backpacking seemed too vague a description, globe-trotting sounded too pretentious, and touring rang a bit lame. Consequently, I put a playful spin on the word vagabond—the old, Latin-derived term that refers to a wanderer with no fixed home—and came up with vagabonding. (Location 225)

The more we associate experience with cash value, the more we think that money is what we need to live. And the more we associate money with life, the more we convince ourselves that we’re too poor to buy our freedom. With this kind of mind-set, it’s no wonder so many Americans think extended overseas travel is the exclusive realm of students, counterculture dropouts, and the idle rich. (Location 277)

Tags: travel, money

Vagabonding is an attitude—a friendly interest in people, places, and things that makes a person an explorer in the truest, most vivid sense of the word. (Location 289)

Tags: travel

From here, the reality of vagabonding comes into sharper focus as you adjust your worldview and begin to embrace the exhilarating uncertainty that true travel promises. In this way, vagabonding is not merely a ritual of getting immunizations and packing suitcases. Rather, it’s the ongoing practice of looking and learning, of facing fears and altering habits, of cultivating a new fascination with people and places. (Location 329)

Tags: mindset, travel

At a certain level, the idea that freedom is tied to labor might seem a bit depressing. It shouldn’t be. For all the amazing experiences that await you in distant lands, the “meaningful” part of travel always starts at home, with a personal investment in the wonders to come. (Location 367)

A vacation, after all, merely rewards work. Vagabonding justifies it. (Location 413)

Rather, you should enthusiastically and unapologetically include your vagabonding experience on your résumé when you return. List the job skills travel has taught you: independence, flexibility, negotiation, planning, boldness, self-sufficiency, improvisation. (Location 433)

Tags: character, career, cv

Escape 101: The Four Secrets to Taking a Sabbatical or Career Break, by Dan Clements (Brain Ranch, 2007, ebook and print) Presents a step-by-step system to take as much time as you need from your job, career, or business, without losing ground. (Location 455) Website that includes information on sabbaticals, information for employers and employees, and tool kits. (Location 471)

LOCATION-INDEPENDENT JOB RESOURCES Freelance Folder (freelancefolder.​com) Resources for freelancers including a blog, forums, books, and job board. Upwork (www.​Upwork.​com) A website where companies find, hire, manage, and pay location-independent contractors online. Guru (www.​guru.​com) Freelancer job board. (Location 501)

Tags: outsourcing

Indeed, the freedom to go vagabonding has never been determined by income level; it’s found through simplicity—the conscious decision of how to use what income you have. (Location 659)

Tags: simplification

And, contrary to popular stereotypes, seeking simplicity doesn’t require that you become a monk, a subsistence forager, or a wild-eyed revolutionary. Nor does it mean that you must unconditionally avoid the role of consumer. Rather, simplicity merely requires a bit of personal sacrifice: an adjustment of your habits and routines within consumer society itself. (Location 661)

Tags: societal norms, consumerism, simplification

he wrote about the joy of living with people who blissfully ignore “the general demand that they consume production and therefore have to work for the privilege of consuming, all that crap they didn’t really want…general junk you always see a week later in the garbage anyway, all of [it] impersonal in a system of work, produce, consume.” (Location 673)

Tags: consumerism

What made travel possible was that he knew how neither self nor wealth can be measured in terms of what you consume or own. Even the downtrodden souls on the fringes of society, he observed, had something the rich didn’t: time. (Location 683)

Tags: money, time management

“whoever loves money never has money enough.” (Location 687)

Tags: money

Buddha whimsically pointed out that seeking happiness in one’s material desires is as absurd as “suffering because a banana tree will not bear mangoes.” (Location 688)

Tags: metaphor, desires

Despite several millennia of such warnings, however, there is still an overwhelming social compulsion—an insanity of consensus, if you will—to get rich from life rather than live richly, to “do well” in the world instead of living well. (Location 690)

Tags: societal norms

On a basic level, there are three general methods to simplifying your life: stopping expansion, reining in your routine, and reducing clutter. (Location 721)

Tags: simplification

The easiest part of this process is stopping expansion. This means that in anticipation of vagabonding, you don’t add any new possessions to your life, regardless of how tempting they might seem. (Location 722)

Tags: simplification

My greatest skill has been to want little. (Location 948)

Tags: desires

Although Henry David Thoreau never traveled very far outside of New England, he promoted an uncommon view of wealth that is essential to vagabonding. Considering all material possessions beyond basic necessities to be an obstacle to true living, he espoused the idea that wealth is found not in what you own but in how you spend your time. “A man is rich,” he wrote in Walden, “in proportion to the number of things which he can afford to let alone.” (Location 950)

Tags: desires, simplification, consumerism

Note: A man is rich in proportion to the number of things which he can afford to let alone

The example of Columbus can teach us a couple of vital lessons about vagabonding. First, it shows how doing your pretrip homework—that is, harnessing the knowledge of those who examined the world before you—can lead you to fabulous new horizons. By that same token, however, you will never be able to truly appreciate the unexpected marvels of travel if you rely too heavily on your homework and ignore what is right before your eyes. (Location 979)

Tags: travel

“The world is a book,” goes a saying attributed to Saint Augustine, “and those who do not travel read only one page.” (Location 995)

Tags: travel, quotes

The goal of preparation, then, is not knowing exactly where you’ll go but being confident nonetheless that you’ll get there. This means that your attitude will be more important than your itinerary, and that the simple willingness to improvise is more vital, in the long run, than research. (Location 1019)

Tags: travel

Note: Your attitude is more important than your itinerary

The first place many people turn when planning a trip is traditional media, since it represents such a broad variety of resources. However, a lot of media information—especially day-to-day news—should be approached with a healthy amount of skepticism. This is because so many media outlets (especially television, magazines, and the Internet) are more in the business of competing for your attention than giving you a balanced picture of the world. Real people and places become objectified—made unreal—as the news media dotes on wars, disasters, elections, celebrities, and sporting events. (Location 1029)

Tags: news

“There is no need to treat a Lonely Planet book like a bible,” travel publisher Tony Wheeler once told me in an interview. “Just because we don’t list certain restaurants and hotels doesn’t mean they aren’t any good. Sometimes people even write to say they use our books only to see where not to go. They don’t want to stay with everybody else, so they go to the hotels that aren’t listed in the Lonely Planet. I think that’s great because we encourage travelers to be different.” (Location 1069)

As a general rule, good guidebooks contain useful, condensed travel information relating to a specific region: historical and cultural background; pointers regarding local languages and customs; data on the climate and environment; advice on getting visas and changing money; tips for staying healthy and out of harm’s way; instructions for using local transportation; and recommendations for lodging, food, and entertainment. Since owners change and prices are in constant flux, hotel and restaurant recommendations will be the least dependable information in any guidebook you buy. (Location 1073)

Tags: travel

The value of your travels does not hinge on how many stamps you have in your passport when you get home—and the slow, nuanced experience of a single country is always better than the hurried, superficial experience of forty countries. (Location 1199)

Tags: slow down, travel

This in mind, pack a dozen or so extra visa-sized photos of yourself, just to avoid the hassle of getting mug shots overseas. (Location 1209)

This small pack, of course, will allow you only the minimum: a guidebook, a pair of sandals, standard hygiene items, a few relevant medicines (including sunscreen), disposable earplugs (for those inevitable noisy environments), and some small gift items for your future hosts and friends. Add a few changes of simple, functional clothes and one somewhat nice outfit for customs checks and social occasions. Toss in a small flashlight, a decent pair of sunglasses, a day pack (for carrying smaller items when you leave your hotel or guesthouse), and an inexpensive camera. And then—looking down to make sure you have a sturdy pair of boots or walking shoes on your feet—close the bag and affix a small, strong padlock. (Location 1240)

Intelligent Travel (intelligenttravel.​nationalgeographic.​com) Travel news and links from National Geographic Traveler. Nomadic Matt (www.​nomadicmatt.​com) Tips, photos, videos, commentary, and links related to travel. Alltop Travel (travel.​alltop.​com) A no-nonsense aggregator of travel blogs. Vagabond Journey (www.​vagabondjourney.​com) Blog about long-term travel that includes tips and resources. Go Backpacking (gobackpacking.​com) This blog is dedicated to inspiring and motivating others to make their travel dreams come true, whether it be a one-week vacation or a five-year vagabonding odyssey. Road Junky (www.​roadjunky.​com) This guide includes information on working, health, budget, ideas, and culture on the road. The Art of Non-Conformity (chrisguillebeau.​com) Chris Guillebeau’s unconventional strategies for life, work, and travel. Worldette (www.​worldette.​com) Inspirational travel-related content. (Location 1427)

The subtle buzz of the unknown, initially a bit of a fright, will soon prove addictive: Simple trips to the market or the toilet can turn into adventures; simple conversations can lead to charming friendships. Life on the road, you’ll soon discover, is far less complicated than what you knew back home—yet intriguingly more complex. (Location 1571)

If there’s one key concept to remember amid the excitement of your first days on the road, it’s this: Slow down. Just to underscore the importance of this concept, I’ll state it again: SLOW…DOWN. (Location 1577)

Tags: slow down

For first-time vagabonders, this can be one of the hardest travel lessons to grasp, since it will seem that there are so many amazing sights and experiences to squeeze in. You must keep in mind, however, that the whole point of long-term travel is having the time to move deliberately through the world. Vagabonding is about not merely reallotting a portion of your life for travel but rediscovering the entire concept of time. At home, you’re conditioned to get to the point and get things done, to favor goals and efficiency over moment-by-moment distinction. On the road, you learn to improvise your days, take a second look at everything you see, and not obsess over your schedule. (Location 1579)

Tags: slow down

Make a point, then, of easing your way into your travels. Shortly after arriving at your initial destination, find a “beachhead” (be it an actual beach, an urban travelers’ ghetto, or an out-of-the-way town) and spend a few days relaxing and acclimating yourself. Don’t strike off to “hit all the sights” or actualize all your travel fantasies from the get-go. Stay organized and interested, but don’t keep a “things to do” list. Watch and listen to your environment. Take pleasure in small details and differences. Look more and analyze less; take things as they come. Practice your flexibility and patience—and don’t decide in advance how long you’ll stay in one place or another. (Location 1589)

Tags: travel, slow down

As the Koran says, “Did you think you should enter the Garden of Bliss without such trials as came to those who passed before you?” Indeed, everyone starts out as a vagabonding greenhorn, and there’s no reason to presume you’ll be any different. (Location 1613)

Tags: challenges

“One of the essential skills for a traveler,” noted journalist John Flinn, “is the ability to make a rather extravagant fool of oneself.” Thus, allow yourself to laugh and grow through your mishaps. Not only will you learn new things about yourself and your surroundings in the process, but you’ll also get a crash course in the traveler’s life (Location 1624)

Tags: people dont care, laughter

Don’t set limits. Don’t set limits on what you can or can’t do. Don’t set limits on what is or isn’t worthy of your time. Dare yourself to “play games” with your day: watch, wait, listen; allow things to happen. (Location 1699)

Tags: travel, push limits

In this way, vagabonding is like a pilgrimage without a specific destination or goal—not a quest for answers so much as a celebration of the questions, an embrace of the ambiguous, and an openness to anything that comes your way. (Location 1710)

Tags: favorite

But if you wander with open eyes and simple curiosity, you’ll discover a much richer pleasure—the simple feeling of possibility that hums from every direction as you move from place to place. (Location 1713)

Tags: curiosity

If in doubt about what to do in a place, just start walking through your new environment. Walk until your day becomes interesting—even if this means wandering out of town and strolling the countryside. Eventually you’ll see a scene or meet a person that makes your walk worthwhile. If you get “lost” in the process, just take a bus or taxi to a local landmark and find your way back to your hotel from there. (Location 1720)

Tags: walk

Keep a journal from the outset of your travels, and discipline yourself to make a new entry every day. Feel free to be as brief or as rambling as you want. Keep track of stories, events, feelings, differences, and impressions. The result will be a remarkable record of your experiences and growth. (Location 1724)

Tags: journal

Never check into a room without asking to see it first. Check to see that the electricity and water work properly, and make sure the door locks are functional. (Location 1751)

Note the location of your room in relation to discos, mosques, factories, major streets, or other surroundings that might prove noisy at certain times of the day or night. (Location 1752)

It’s so easy to set out with a backpack full of enthusiasm and travel hard and fast, like an experience-junkie, getting your next fix from the new, the novel, or the iconic. Most people do. If you keep going long enough, the hard burn wears off, and you begin to slow down, to go your own way. And you realize that the greater value is not in what you’ve seen and checked off the list, but in what you’ve learned deeply, the hard way. Have the guts to step off the backpacker highway sooner rather than later. Lay down the guidebook, and just open your eyes. (Location 1804)

Tags: travel, slow down

Focus on the quality of your experiences instead of the quantity. Get to know a few places really well, and try to avoid racing around the world on some over-ambitious itinerary, doing everything through your iPhone. In other words, try to live it and experience it, not just gather stories for later. (Location 1811)

Tags: experiences

“We see as we are,” said the Buddha, and rarely is this quite so evident as when we travel. Unlike a simple vacation (where you rarely have time to interact with your environment), vagabonding revolves around the people you meet on the road—and the attitude you take into these encounters can make or break your entire travel experience. “If you view the world as a predominately hostile place, it will be,” wrote Ed Buryn. By this same logic, of course, a positive worldview can lead to inspiring, human-centered road experiences. (Location 1844)

Tags: outlook

Those who visit foreign nations, but associate only with their own countrymen, change their climate, but not their customs. They see new meridians, but the same men; and with heads as empty as their pockets, return home with traveled bodies, but untraveled minds. (Location 1864)

The point of travel, then, is not to evaluate the rightness or wrongness of other cultures (after all, you could stay at home to do that) but to better understand them. (Location 1893)

Tags: travel, culture

if you can find joy in insults—if you can learn to laugh at what would otherwise have made you angry—the world is indeed “all yours” as a cross-cultural traveler. (Location 1936)

Tags: insults, laughter

Conversely, be sure to carry photos of yourself, your hometown, and your family to show to people on the road. (Location 2076)

Tags: photos

Note: carry photos of your family and hometown

As a vagabonder and a cultural guest, learn to pay back what you’ve received by spotting need and practicing generosity elsewhere (even with other travelers) as you travel from place to place. (Location 2117)

Thus, even in an indirect way, try to give as much as you take when you travel—even if this means taking an attitude of generosity home with you. (Location 2121)

It’s always the people who make the journey—fellow travelers, couchsurfing hosts, random hook-ups. Say “yes” as much as possible, leave your shy side at home, and let loose. (Location 2240)

Tags: say yes

The secret of adventure, then, is not to carefully seek it out but to travel in such a way that it finds you. To do this, you first need to overcome the protective habits of home and open yourself up to unpredictability. As you begin to practice this openness, you’ll quickly discover adventure in the simple reality of a world that defies your expectations. More often than not, you’ll discover that “adventure” is a decision after the fact—a way of deciphering an event or an experience that you can’t quite explain. (Location 2317)

By definition, divining chance means leaving yourself open to both good and bad experiences. Good judgment can come from bad experiences; good experiences can come from bad judgment. The key in all of this is to trust chance, and to steer it in such a way that you’re always learning from it. (Location 2336)

“Good people keep walking whatever happens,” taught the Buddha. “They do not speak vain words and are the same in good fortune and bad.” (Location 2361)

Tags: buddhism, good life, walk

The man who is truly good and wise will bear with dignity whatever fortune sends, and will always make the best of his circumstances. (Location 2363)

Tags: good life

Learn to treasure your worst experiences as gripping (if traumatic) new chapters in the epic novel that is your life. (Location 2368)

Tags: experiences, challenges

Note: I’m race and cherish your worst experiences

Adventure can be whatever makes you smile—in the short or long term (you might not be smiling now, but if you survive, you will!). I don’t really look for adrenaline rushes, and my best adventures would be totally dull to someone else. It is so often circumstance that makes an adventure, not a place or an action. (Location 2467)

Tags: adventure

“The traveler sees what he sees,” wrote G. K. Chesterton in the 1920s, “the tourist sees what he has come to see.” (Location 2536)

“Travelers are those who leave their assumptions at home, and [tourists are] those who don’t,” wrote Pico Iyer in 2000. (Location 2541)

This is why vagabonding is not to be confused with a mere vacation, where the only goal is escape. With escape in mind, vacationers tend to approach their holiday with a grim resolve, determined to make their experience live up to their expectations; on the vagabonding road, you prepare for the long haul knowing that the predictable and the unpredictable, the pleasant and the unpleasant are not separate but part of the same ongoing reality. You can try to make vagabonding conform to your fantasies, of course, but this strategy has a way of making travel irrelevant. Indeed, vagabonding is—at its best—a rediscovery of reality itself. (Location 2572)

Tags: travel

In many ways, embracing reality is daunting—not because of its hazards but because of its complexities. Thus, the best way to confront reality is not with a set method of interpretation (which will allow you to recognize only patterns you already know) but with a sincere attitude of open-mindedness. (Location 2588)

Tags: outlook

open-mindedness is a process of listening and considering—of muting your compulsion to judge what is right and wrong, good and bad, proper and improper, and having the tolerance and patience to try to see things for what they are. (Location 2614)

Tags: outlook

What such reflexive pessimism overlooks, of course, is that societies have always changed, and that “tradition” is a dynamic phenomenon. “The evaluation of tourism cannot be accomplished against a static background,” wrote tourism scholar Davydd J. Greenwood. “Some of what we see as destruction is construction. Some is the result of a lack of any other viable option; and some the result of choices that could be made differently.” (Location 2629)

Tags: societal norms, culture

Often I feel I go to some distant region of the world to be reminded of who I really am….Stripped of your ordinary surroundings, your friends, your daily routines, your refrigerator full of your food, your closet full of your clothes, you are forced into direct experience. Such direct experience inevitably makes you aware of who it is that is having the experience. That’s not always comfortable, but it is always invigorating. (Location 2665)

Tags: experiences

Too often travelers pride themselves on avoiding touristy places. Remember that just about every major tourist spot is popular for a good reason. Yes tourists flock there now in droves alongside tacky souvenirs and inflated prices. But strive to be the kind of traveler who can look past that and see the draw of the location for its original appeal. You’re traveling in a time where very few places are left in this world that have yet to be discovered. Finding a perfect, isolated spot may be a challenge, but seeking a perfect experience or local connection will lead to a much richer experience. (Location 2728)

Note: Every touristy spot is popular for a reason

But on an even simpler level, heightened spiritual awareness is the natural result of your choice to put the material world in its place and hit the road for an extended time. Where your treasure is, your heart will be also—and your decision to enrich your life with time and experience (instead of more “things”) will invariably pay spiritual dividends. Travel, after all, is a form of asceticism, which (to quote Kathleen Norris) “is a way of surrendering to reduced circumstances in a manner that enhances the whole person. It is a radical way of knowing exactly who, what, and where you are, in defiance of those powerful forces in society that aim to make us forget.” (Location 3048)

In The Snow Leopard (thought by many to be the best travel book of the last century), (Location 3111)

The Essential Koran, translated by Thomas Cleary (Book Sales, 1998) (Location 3151)

Travel will challenge your well-worn assumptions and accumulated habits. It will shake up your boring old patterns, make you feel every raindrop and taste every bite of mango. It will inspire you again, kindling that lost flicker of creativity until new ideas start to boil and bubble from deep within. It will restore your sense of childlike wonder for what was already there. (Location 3167)

Tags: favorite, travel

In trying to make sense of this homecoming experience, people often quote T. S. Eliot’s “Little Gidding”: And the end of all our exploring Will be to arrive where we started And know the place for the first time. As inspiring as this sounds, however, “knowing” your home for the first time means that you’ll feel like a stranger in a place that should feel familiar. (Location 3206)