How to Travel Full-Time
FOREWORD TO THE 2ND EDITION
I published the original edition of How to Travel Full-Time in November of 2011. Getting it out the door was revelatory for me because it was the first book I’d written about my lifestyle and travel. Up until that point, I’d stuck to talking business and armchair philosophy, ruminating only in passing about my adventures on the road, and the strategies and tricks I’d learned along the way: the approaches to travel that made my whole lifestyle not just palatable, but an incredible growth opportunity.
Fast-forward three years, and a lot has changed. I’ve shifted my focus from branding to publishing, and my traveling lifestyle, once a novelty even to me, is so ingrained that it’s become my ‘normal.’ I’ve been on the road over four years now, and have written myriad books and missives detailing the stories I’ve lived, the lessons I’ve taken away from them, and the particulars of how such a lifestyle is possible.
Despite all the words I’ve written on the subject, this original book continues to be one of my top sellers. It’s embarrassing, in a way, when your older work is one of the first things people see — you want your first impression to be representative of who you are now, not who you were years ago. But it’s also quite flattering: Just as I’ve written hundreds of thousands of words about travel, hundreds of thousands of readers have read this book. This is data that’s humbling, amazing, and it makes me smile just thinking about it.
As the book has aged, though, I’ve been plotting and planning to give it a refurbishment; to rewrite sections and update resources and add things I’ve learned since 2011, when I was better traveled than many, but not nearly as well-traveled as I am now.
I hope the book brings you some value, and spurs your imagination about the possibilities inherent in living today: A time in which technology and social standards have evolved so that long-term and full-time travels are not only possible, but immensely practical, so long as you approach them with the right attitude and motivation.
In April of 2009, I was living the American Dream.
Some version of it, anyway. A version I had often dreamed about, which included financial and professional success, an enviable social life, and a relationship with someone who had similar motivations. After less than two years in Los Angeles, I had a big-and-growing client list, my hourly wage was sky-high, and I had opportunities on the table that would allow me to reach my long-time goal of making my first million dollars by the time I was 25 years old. Things were good.
My bank account was filling up, but my passport remained empty. I’d long aspired to travel, to see the world and become a more knowledgable person, but there was always something more important I had to do first. At age 19, I started a culture magazine while in college. A flurry of other small businesses followed, then the move to LA. After a year of working for a local studio to see what I could glean about the industry, I started up my own design and branding practice.
Things took off pretty quickly, and within a few months I was making the same money I’d made working for someone else. A few months after that, I was making double. A year later, I was pulling in more money than I ever expected to see, much less possess. I aspired to travel the world, but I was busy fulfilling another dream, one that included financial success, and all other priorities took a back seat.
They did for a while, at least. My girlfriend and I had moved in together, living in a townhouse near the beach, hosting wine and cheese parties, and doing all the other things young, cultured people are supposed to do, whether they can afford to or not. Being able to afford such things was an added bonus, and was just one of many ways I found to spend the increasing sums of money I earned each month.
It wasn’t the only way, though. In my home-office, I had eight computers. Why eight? I think the question I asked myself at the time was, why not? It’s a sad cliché, I know, but give a young person a bunch of cash when they’ve never had more than subsistence-grade funds available, and you end up with a lot of reckless spending on things that make sense in the moment, but seldom bring any happiness or fulfillment after the purchase is made.
Nearly a year after we moved in together, my girlfriend and I decided to take a trip to the exotic (to me, having never left the country) land of Canada. We set aside work for a week and drove up the coast. On the way back down, we stopped in Seattle, sat down for a drink in an underground bar, and listened to some live music. We intended to fully enjoy the remainder of our time off, which would end when we returned to LA.
Instead, we had one of the most important conversations of our lives. After sipping our drinks for a few minutes and listening to the band tune their instruments across the room, my girlfriend leaned over to me and said, “I think I want to move to Seattle.”
I was flabbergasted, as we’d never really spoken about our intentions or the future beyond our professional and social goals. I leaned toward her and said the first thing that came to mind: “I think I want to leave the country.”
This accidental exchange of long-concealed but heartfelt goals was pivotal, because it gave us the excuse we needed to stray from the paths we were following. The simple act of acknowledging desires other than the ones we were pursuing meant we would need to address them, and addressing them forced us to reassess everything. Everything we were doing, everything we were working toward, and the basis of the decisions we were making. How we spent our time. What success looked like.
We spoke at length that night, and decided that if we were going to take these intentions seriously, we’d need to get out of each other’s way. She joked that we should have a breakup party, just to wig out our friends, and we decided to actually go through with the idea. It seemed like a fitting way to end a wonderful relationship that had lived past its prime.
The party date was set for four months in the future, and in the meantime we both honed in on what we actually wanted; what life would look like if we could choose an ideal situation.
For me, travel was a key focus. It’s something I’d always dreamed of doing, as it aligned so well with my desire to know as much as possible about as many things as possible, and to learn from the best possible sources of information. Up until that point, I derived my knowledge from books, the internet, and people who had traveled. I knew everything I was hearing came burdened with inherent bias, however, and that I couldn’t be sure what was fact and what was interpretation.
I didn’t want to be the American stereotype of the guy who wants to know everything, but gets all his information from partisan sources. I didn’t want to be the guy who fakes worldliness, but has no stamps in his passport.
I started a blog, partially because I wanted a sounding board for what I was planning, and somewhat because I thought it would be an excellent platform from which to operate moving forward. I was also hoping to make connections with people who knew more about travel, and the world, than I did.
The breakup party was a success, in that it gave my now-ex and I a proper sendoff toward our new lives, and showed our friends that they needn’t choose sides; we still cared about each other very much. In the four months between deciding to have the party and it actually happening, I blogged nearly every day, figuring out the online social landscape, making incredibly valuable (and lifelong) connections, garnering a fair-sized readership, and sharing what I could with strangers who were being so generous with their own knowledge. I eventually asked my new online friends to vote on where I should go, and they were happy to help me with that, too.
We stopped through Seattle in April, I started my blog a few days after arriving back in LA, and by September, I was in Argentina; the country where my readers voted for me to live.
This book is a collection of essays and resources for people looking to make travel an integral part of their lives. For me, this means moving to a new country every four months, taking breaks for other adventures in between, and running small businesses and writing books along the way. For others, travel might be something undertaken for a few months out of every year, or could involve spending time between two homes. It could be seeing the world, weekend-by-weekend, or it could mean becoming a citizen of the world, completely without anchors.
Whatever the case may be, I hope you find the information and stories in the following pages valuable. Travel has been the most character-building, life-changing, perspective-expanding activity I have ever encountered. Making it a key part of my lifestyle is one of the best decisions I’ve made.
THE IDEA OF TRAVEL
Grand hotels bedecked with the finest linens and antique wallpaper. Luxury yachts thronging with athletic, tan poolside loungers, martinis and glasses of wine in hand. Waves lapping at your feet as you relax on the beach. A hammock. Drinking from a coconut. Driving an expensive rental car past walls of snow-frosted pines toward a multi-level cabin, the fire always roaring, the coffee always steaming, the landscape perfect like a greeting card.
The idea of travel is something we all have tucked away in our minds, expectations calibrated by Hollywood films, TV, and the slide-projector tales told by friends who have just returned from their honeymoons.
The reality of travel is something altogether different. The reality of travel is your hotel being overbooked, or not as advertised, or expensive enough that you can’t afford to eat anything other than the mints on your pillow. It’s a pool lined with pale, average-looking people doing their best to catch some sun before heading back to work a few days later, drinking sometimes with desperation, sometimes with sorrow in their eyes, and hopping into the water only when they’re too drunk to care how they look. It’s a beach covered with seaweed or garbage or aggressive seagulls. The reality is a hammock that’s relaxing for all of ten minutes, before the attention of hungry mosquitoes becomes too annoying for you to stand it any longer. It’s drinking the same beer you have back home at twice the price, or worse beer than you have back home for half the price. It’s snow that’s too slushy for snowballs, soggy boots, a fireplace that won’t stay lit, and raccoons rooting through your trashcans all night long.
Travel can be the worst thing in the entire world. It can be tragically bad, and anyone seeking to travel long-term because they think it is incredibly romantic, ideal, or otherwise perfect in whatever way should extricate themselves of that assumption before moving any further. Travel is unexpected and uncomfortable and often the opposite of what you were expecting. On every level it’s imperfect. And that’s the point. If you want ‘perfect,’ as in a situation that gives you what you’re expecting to get, stay at home. There’s nothing wrong with the known world, and if you’re wanting an upgraded version of what you have now, I recommend you make more money, get a better job, do something to change your relationship status, and move forward. Enjoy yourself. Enjoy the benefits of not having to deal with the crap that travel will throw your way.
If you’re looking for novelty, however, or to grow in some way, or to discover who you really are, how the world works, what you’re capable of, what you don’t know, and what you don’t know you don’t know, then travel is the right path. Sometimes it’s glorious and beautiful and everything tastes great, but most of the time you’re rolling with the punches and making new plans on the fly. You’re expanding your horizons while adjusting your expectations. Travel can be even better than what you see on TV, but that sense of awe doesn’t stem from being on the biggest yacht or staying in the nicest hotel or finding the perfect, most picturesque cabin. It comes from discovering a part of yourself you didn’t know was there. It comes from seeing the world from a new angle. It comes from meeting new people, experiencing new things, and gasping at the knowledge that you could have gone your whole life never having seen or tried or done any of it.
The idea most people have about travel is wrong. It’s not going to solve your problems. You aren’t going to go on vacation and become a person reborn.
Travel is an adventure — a journey — and should be treated as such. If you make it a part of your lifestyle, the photos you take home with you will start to mean both less and more: Less because you won’t be taking them to show off to friends, and more because you’ll be taking photos that remind you of what you were doing, who you were with, and the meaning you found there.
Rather than brag-worthy trinkets, the things you take with you when leaving a place become bookmarks in time. Markers that allow you to page back through the epic book of your life to stories you’ve lived. Chapters that help you write the rest of your tale.
TYPES OF TRAVEL
There are as many flavors of travel as there are people. Travel can be a quick jaunt to the next town over from yours, it can involve airplanes or boats or camels or skateboards, and it can be cheap or expensive, time-consuming or relatively snappy.
My focus is on long-term and full-time travel, because moving around, seeing and trying out new things, and meeting new people is key to my happiness and growth. This isn’t the case for everyone, and there’s no right or wrong way to go about exploring the world. I know plenty of people for whom the unknown is exhausting, so they would much rather parcel out their adventures into smaller, bite-sized portions; maybe a week or weekend overseas once or twice a year. That’s legit; it’s not for me, but neither are my travel preferences right for everyone.
This is something I want to get on the table early on in the book, because there’s a perception, I think, that travel must be something specific. It must be romantic or dramatic or adventurous or memorable. In reality, though, it needn’t be any of these things. Maybe you travel to relax and get away from the stress of your normal life.
Maybe it’s just an extension of your normal life, as is the case with how I travel. Not every day can be an adventure, even if your lifestyle revolves around travel. Some days, I’m just going to the grocery store, paying my taxes, and getting a cup of coffee at the same place I always get my coffee. This all takes place in a foreign country, but it’s my home nonetheless. I’d probably die young if I didn’t have these calm, restful habits.
So if there’s no right or wrong way to do it, how do you establish what role travel fills in your life?
A big part of the equation requires that you figure out why you want to travel in the first place. Do you crave novelty? Want to flesh out your perception of the world? Are you hoping to learn about a particular culture, a particular trade, or a particular economic/political/culinary situation?
Since there’s no right or wrong way to integrate travel into your life, there is no right or wrong reason to travel; though be warned that if you’re running from something — you want to travel because you think the road will provide a solution to your troubles — you might want to reconsider. There’s plenty of wisdom and freedom to be found in the world, but travel also amplifies all the existing problems you already have. If you’re broke at home, you’ll be more broke after paying for plane tickets and hostel beds. If you lack confidence, traveling will put your shortcomings front and center, forcing you to acknowledge them in an unforgiving environment.
Some people start with troubles and end up with solutions, but in most cases it’s a good idea to establish a firm foundation before you bring the stresses of travel into your life. Save a little money to serve as a ‘just in case’ buffer. Get your relationships to a healthy place. Know a little bit about who you are so that what you learn while traveling will add to your sense of self, rather than replacing it.
The experiences you have on the road can be the most impactful that you’ll ever encounter, and getting yourself to a good spot before leaving makes it far more likely that those experiences will be impactful in a good way, rather than being horrible or bland.
Once you’re certain you’re in a good place, and you’ve established why you want to travel to begin with, it comes down to choosing the best possible option, based on your needs.
What I mean by that is you may want to travel full-time, to hit the road and never come back, but your work, which you also love, requires you to be in a given city for half the year. It could be that you’ll be able to find work you enjoy just as much, which also allows you to travel full-time, but to start, it’s best to figure out a solution that will give you the chance to dip your toes into internationalism while also allowing you to pull in a paycheck and do work you enjoy. I’m a big proponent of taking big leaps out into the world, but I also encourage you to seek stability where you can, which allows you to make better choices and take less of a risk when it comes to traveling.
Let’s talk a little about the types of travel you might consider.
I’ve already mentioned the light integration of travel, which can include vacations to other cities or towns, frequent or infrequent jaunts overseas, and even the occasional cruise. If this does it for you, fantastic. Figure out a way to do it regularly enough that it becomes part of who you are. Enjoy it.
Expats are folks who live full-time in a country other than their own. Though expats tend to be exploratory and adventurous people by nature, for the purposes of most of my explanations about full-time travel, expats live a different sort of lifestyle. They’ve set up new homes in a different country, certainly, but some of the issues I’ll be discussing throughout this book apply less to them, because they’ve moved but aren’t in transit constantly.
Long-term travel is far more difficult to manage. There aren’t many work situations that allow you to leave your home regularly, and even fewer that pay well or give the sense of professional fulfillment most of us want in our work. Some people who opt for this route upend their professional life in the tradeoff, go freelance, start their own location independent business, or negotiate for a change in their work situation so that they might work from anywhere. These are all possibilities and equally valid, and all come with their own risks and rewards. Consider them carefully before you jump.
Some examples of long-term travel are people who spend part of their year in another city, people who go on extended camping trips, or folks who take time off to do around-the-world-style adventures.
The next step up is full-time travel. This is even more difficult to accomplish, because there’s no way you can be hired for geographically tied work, and whatever you do to make a living must be mobile enough that you can do it from anywhere (well, anywhere you’d want to go). This is my preference, and I can tell you from personal experience that it dramatically impacts every aspect of your life. I’ll be explaining some of these repercussions in depth in the next chapter.
Some examples of full-time travel are people who live in motor homes and travel the great open road, people who work with clients around the world and move with each new project, and folks like me who travel at regular intervals in order to see as much as possible.
Make no mistake; the long-term and full-time travel lifestyle has a massive impact on everything you do. It influences your relationships, your work, your health, and the way you see the world.
For many, these influences are positive ones, and I hope that if you’ve pulled the trigger on changing up your day-to-day in this way, you have thought through the consequences first. In this chapter I’m going to cover some of the specifics of what changes you can expect and the ramifications of those changes.
Traveling full-time has changed absolutely everything about how I operate. My daily routines, my short- and long-term plans. How I make money. How I date.
When you stay in one place for long periods you tend to nest. You look for a nice place to live, you fill that place with the trappings of success (whatever that happens to mean for you), you make friends in the community, and you establish routines based on all these things.
When you travel full-time, you can’t really do that. You have a bag or two and the clothes on your back, and anything beyond that is excess. Anything you can’t easily carry becomes a liability, not an asset, so nesting is kept to a minimum.
Before I started traveling, I loved to always have the newest gadgets and a closet full of clothing options. These days, my focus is on clothing that is practical and portable, electronics that travel well and help me work from the road. A bag that will carry these things safely. My trappings of success no longer involve a big TV or artwork on the walls. I measure my possession-success on whether or not I can easily carry what I own. on whether what I own allows me to do what I love and enjoy the experiences I crave.
Similarly, friendships work very differently when you’re in transit full-time. I often tell people that it’s a wonderful time to travel, because there are no more ‘goodbyes,’ just ‘see you laters.’ As soon as you hop on a flight, leaving behind an array of wonderful people, you can log into the onboard WiFi and start emailing/Facebooking/Twittering with them. You can Skype with them when you touch down. You can Snapchat with them a week later, and forevermore.
So long as you’re willing to accept that relationships can remain strong and get stronger, even at a distance, geography ceases to be an issue in bonding with incredible people around the world. This means you can develop friendships with people you’ve never met — using the technologies available to connect over topics of shared interest — and it means you can stay in touch with folks you know in real life and want to keep up with.
Some of my best friends are people I met years ago in a country I haven’t been back to since. Some of my best friends are people living down the street in the country I’m living in now. Some of my best friends are people I’ve never seen in person.
In addition to friendships and other somewhat casual relationships, romantic relationships are very possible from the road, you just have to adjust your expectations. I’d always dated in the traditional sense before I hit the road, and I still enjoy elements of that approach. I like meeting new people, seeing if there’s chemistry, and if there is, seeing where things go. At the same time, I know that long-distance exclusive relationships don’t work for me and what I want from dating, so open relationships tend to work better.
What this means in practice is that dating stays flexible to ensure everyone gets what they want from it. When I’m in Iceland, for example, there’s a wonderful girl I play house with; we live together, date each other exclusively, and enjoy the benefits of a boyfriend/girlfriend situation. When I’m not there (and she’s not visiting me), we date other people. We stay in touch, and we’re fantastic friends regardless of who’s seeing whom, but this is a practical flexibility we’ve found in the system. Neither one of us is into the ‘just dating around’ thing full-time, but neither one of us wants to give up the freedom of seeing who we want, either. So we talked and figured out a way of doing things that worked well for both of us.
If you intend to travel long-term or full-time, I encourage you to think hard about what you want in a partner (if you want a partner; it’s totally legit to focus completely on yourself, too), and to consider what that might look like in real life. Maybe you want someone who travels with you; a partner in crime. Maybe you want someone who’s back home, waiting for you to return, but absorbed in their own world when you’re gone. Maybe there’s someone out there who is also traveling, but along a different course than you. I know a few people who do things this way: they meet up from time-to-time along the way, and then head off in different directions after a few weeks together.
Like anything else, there’s no right or wrong way to approach relationships if you’re living a non-standard lifestyle, but you’ll be much better off if you leave yourself open to trying new things, and figure out what you want at the most basic level so that you can shape the most ideal relationships possible. Anything goes, so long as everyone is informed about what’s going on, no one is getting hurt or used, and all parties’ needs are taken into consideration. Beyond that, be creative and have fun.
Routines, like relationships, are best left malleable if you’re going to live a life in transit.
Before I left LA and started traveling full-time, I had habits galore. I had established myriad good habits to help me stay productive, get more done in a day, stay healthy, and everything else I thought was important in a well-rounded individual.
There’s nothing wrong with these types of habits, but it’s best to know ahead of time that many of them are wildly impractical on the road. There are some routines you can be reasonably confident in being able to maintain (morning yoga, for example), while others will only lead to disappointment (morning coffee at a nearby café).
I want to really emphasize this point, because it’s one most people (including myself) don’t consider before they leave. Most of us know the world outside our comfort zones are very different places, but it doesn’t seem to hit home that this implies differences on every level. Yes, some other cities will have coffee shops like the one you depend on for your morning ritual, but many cities don’t. Many cities are too poor to sustain such a thing, or don’t have the coffee culture you may be accustomed to.
I thought I was so clever, adjusting my workout routine to include more running and less gym-related exercises, carrying with me barefoot running shoes (which pack easily) and the will to explore all my new neighborhoods on foot, while getting my exercise. Time and time again I was flummoxed to find that I lived in neighborhoods without sidewalks. Or with rampant street violence. Or with roads and paths covered in cow dung. Or filled with people for whom running outside is borderline offensive. It took me over a year to recognize that something I thought I could reasonably expect everywhere — sidewalks suitable for running — were not, in fact, reasonable things to expect. I eventually changed my workout routine to be more self-contained, integrating body-weight resistance, stretches, and yoga, instead; all things I could do next to my bed, which is something I usually have.
Speaking of working out, many people who start a new lifestyle focused on travel are surprised to find their formerly bulletproof immune system torn to shreds. I once took pride in never getting sick. I would proudly work 100+ hours each week, and still somehow dodged whatever flu was going around. Today, I get sick a few times a year, and really sick (dengue fever, throat infections, etc) once every few years.
The reason for this is that when traveling, you’re essentially exposing yourself to a whole new swath of germs, bugs, bacteria, and other microorganisms. Your body may have become ironclad in dealing with your regional micro-flora, but the rest of the world has different species of the little beasts, and as such, your system will take some time getting used to them. You’ll also find that airports, trains, buses, and other public places where you’ll be spending a lot of time are hot-spots for disease transmission. Though you may know what not to touch and where not to go in your hometown, in other cities you’re always accidentally touching the wrong handrails, sitting in the wrong parts of the boat, and generally putting yourself in even worse positions than you might have, had you more knowledge about local customs and habits.
I get eye infections about once a year, now, and I never had one before I started traveling full-time. Why? Because I wear contact lenses, and I often find myself taking them out for a late-night bus ride through the middle of nowhere, or putting them in on a plane full of maybe-sick people. I get food poisoning sometimes. Why? Because I had first world dietary habits in the urban, coastal US, but they don’t have Trader Joe’s in Bangkok. They don’t have Safeway in Kolkata. They don’t have Walmart in Buenos Aires. Thanks to globalization, there are plenty of food options most places you’ll go, but thanks to local customs, cultures, backgrounds, and food handlers, the specifics of the food you get will vary.
If you’re planning to travel long-term, it’s best to have as few dietary restrictions as possible; they’ll laugh you out of the restaurant if you ask for ‘gluten-free’ anything in South America. If you’re going to find something healthy-ish and edible anywhere in the world, that means eating what you must in order to get sufficient calories and vitamins.
My personal life isn’t the only thing that’s changed as a result of my lifestyle-shift. My work has changed dramatically, and I didn’t have a conventional job to begin with.
In LA, I was working with clients, building their brands and doing consultations; everything I did could theoretically be done from anywhere in the world. I did a trial run at one point and took some client calls from the Grand Canyon in Arizona. It worked pretty well. I was confident when I packed up shop and headed out.
Man, was I wrong. The complexities of working from the road vary depending on where you go and what you do while traveling, but there are some constants.
One of the things I was wrong about was assuming that internet-access is a god-given right everywhere I might traverse. Some places, I assumed, would have slower speeds, but they all plug into the same network, right? I’d be fine, even if the speed at which I worked might suffer in some cases.
The problem with this assumption was that my work required high-speed connections. Some of the work I did (writing copy, answering emails) didn’t require that much bandwidth, but a lot of the other work (building websites, sending large graphic files, Skyping) required a lot more than I would have thought.
When I first arrived in New Zealand, I saw no reason why I wouldn’t be able to function, despite their tragically slow internet speeds, and the incredibly high prices attached to even the slowest, dial-up access point. It wasn’t until a few weeks in that I realized how bad my position was. Yes, I could sometimes send an image to a client, but usually my connection would fail before the whole file was delivered, and I’d have to start over. I’d try to have a Skype call to explain the situation, and not even voice-only mode would work across the abysmally slow network. By the time I invoiced the client, I’d end up spending most of my profits paying for the terrible internet service that caused me so many headaches along the way.
Sometimes electricity is the problem; not that it isn’t available, but that the outlets are different from the adapters you brought with you. This is very common in older buildings, as they may not have shifted to the new standards used by the rest of the country.
Sometimes the location itself is the issue. I can’t tell you how many people I’ve met who have hit the road with their backpack and a job that would pay them enough to survive — a job they could do from anywhere in the world, no less — only to find the job was keeping them from living, or life was keeping them from the job. Most of them end up looking for alternatives or heading home to save up some cash so they can go back out into the world, responsibility-free.
It’s both pro and con, living in a place that keeps you so incredibly distracted, but it’s something you’ll have to work into the algebra of your new lifestyle. I’ve figured out a reasonable balance between the work I do and the life I live, but that’s partially because I’m doing work that I can do from anywhere, and that is informed by my lifestyle. My work and life blend, so neither one conflicts or distracts from the other, but this is not always possible or desirable. In such cases, you may have to figure out how many hours a day you’ll allow yourself to play, and how many hours a day you’ll dedicate to work that pays for your fun. It’s not always an easy choice, but it’s the type of necessary adjustment you’ll have to make if you want to keep traveling.
Finally, there are some inherent difficulties and risks worth mentioning that come with traveling long-term or full-time.
The threat of violence or theft, for example, is something inherent in everything you do. It’s strange that in many cases these threats are actually more likely back home, where we came from, but they seem more possible on the road. There was a much better chance of my home being burglarized in LA than in Reykjavik, for example, but I still find myself more cautious and mindful of such things when I’m overseas because the environment is so unfamiliar.
There’s also the threat of nationalism, regionalism, religious intolerance, and the like. Gender-discrimination is something women have to be mindful of in many places. It’s a good idea, in general, to avoid protests because you never know when a peaceful act could spiral out of control, even if you wouldn’t have the same concerns at home. There are enough unknowns in such instances, and enough chances that you’ll be taken as an unfriendly ‘other’ by those nearby, to warrant caution.
Dangerous animals, diseases, drugs, and scams are issues you will likely worry about at some point while traveling. Being mugged, burgled, pick-pocketed, or ripped-off are also valid concerns.
You may find yourself in the middle of nowhere after hopping on the wrong bus, alone on the docks, in freezing weather, without mobile phone reception. This happened to me, once.
These are all things you will worry about, but so long as you’re worrying, that means you’re aware, and very likely nothing will happen to you. Stay alert; ask around (and online) about local customs, scams, and other dangers. Don’t be afraid to ask for help, or for clarification. Don’t be afraid to brazenly make friends and build relationships. There’s some seriously bad stuff that can happen to a traveler, but the point of all these warnings is to make clear that the experience is worth it, despite the possible negatives, and maybe partially because of them.
You never know what you’re made of until you’ve experienced hardship, and you never know how good small-but-significant victories can feel until you’ve worked your way back home from the docks, out of the freezing cold, despite lacking a phone signal or any idea of where you might be.
A travel-focused lifestyle forces you to change, and that’s part of why many people love it so much. I, for one, am a way better version of myself for having undergone so many trials.
Because there are so many considerations to worry over when figuring out how to make travel a more integral part of your life, I often tell people to turn it into a project; to view it the same way you would an experiment.
Doing so gives you the leeway to establish boundaries, variables, timelines and time limits. It allows you to step back from the situation — which is very personal and important — and view things from an outside, practical standpoint. It allows you to say, ‘this makes sense,’ and ‘this doesn’t make sense,’ and even more importantly, allows you to say, ‘how will I make this work?’ even when you want to say ‘it’ll work, don’t worry about it.’
I tend to view my lifestyle as a project because when I started out, I only knew one thing: I wanted to travel. I felt like I was making up for lost time, too, since I had never left the US before, so I wanted to travel a lot. I wanted to see all I could, and do all I could, and really push my own limits. I found that it was difficult to figure out a starting point for such a lifestyle, though; where do you go when you want it all? Where do you kick off from when everything so is soft and nebulous?
I needed to establish something concrete. Something I could use as a launch pad, adjusting course after I’d set out on the road and had more data to work with. That meant establishing some guidelines; some ground rules. I decided that I’d spend four months in each country, and that my blog readers would vote on where I moved. I’d do no research ahead of time (other than reading the Wikipedia article for the country where I’d be living), and that I’d choose a city after the country had been decided for me. Everything else would be up in the air, and I’d be free to change how it all worked later if I wanted to. Changeable or not, that framework gave me something to work toward. I suddenly had goals to reach before I even got started. I had solid ground from which to launch.
I encourage others who are intending to make travel a part of their life to start by making some rules for yourself to follow, though you’ll likely use very different ones than I did for my project. I wanted some very specific things from my travels, and the protocols I put into place were ones I thought would help me reach them. You’ll have different rules to adhere to based on what you want to achieve, and staying within them (at least at first) will help you find your footing in a world that otherwise might seem too big and aimless to get your bearings.
One of the most overlooked benefits of travel is an increase to the traveler’s cultural relativism.
Cultural relativism, in short, is being able to put yourself in someone else’s shoes. Beyond trying to understand where someone is coming from, it also means that you understand that we’re all just people, the exact same species, and the only differences between us stem from our environments, experiences, and upbringing.
An example of this would be the treatment of women in some parts of the world. Growing up in the United States to a middle class, educated family, I believe that women are equal to men and should be treated as such, both socially and under the law. There any many countries in which this isn’t the case, however, due to religious mandates, cultural history, or even simple legal writ. As a result, when I travel to these countries, I sometimes encounter a large number of people who believe something fundamentally different than I believe. People whose worldviews are fundamentally different from my own.
How does one deal with such a situation? I may think the way they treat women is barbaric, but I’m in their country, and as such must abide by their rules (or face potentially serious consequences). What’s a traveler to do?
Such situations are where cultural relativism is very practical. The thing to do is to recognize that the people you’re meeting in this foreign place are not inherently bad for believing differently from you; they’ve just been brought up under very different circumstances from the ones in which you were raised. Step back and you’ll realize that had you been born in the same country at the same time to the same parents, you would feel the same way they do. You would feel that way because they aren’t born putting women on a lower tier, they’re born the same as you: a blank canvas for whatever markings society sees fit to add.
This response allows you to view people who believe differently from you as people, too: they were simply brought up to believe different things. They are no worse and no better than you are, just as you are no better or worse than they are. By your standards, you have the superior morality, but by their standards, you carry the weight of inferior teachings. If you can both set these judgements aside, however, and treat each other as humans first, then you have a bridge; a place to start understanding each other.
Maybe you can teach them something by making your views available should they want them (better not to preach, though, because that only puts the other person on the defensive). Maybe they can teach you something in the same way.
Does this mean you should drop your morals when going to another country? That when I visit a place where women are second-class citizens, that I should treat them as such, and change my views while there? No way! But it does mean I check my assumptions at the door and settle into my new home, happy to explain my own views if asked, but otherwise adhering to the local customs as much as possible, much the same as I would entering someone else’s home.
What would I gain by being a missionary for my views in a place where they have no reason to believe the same as I do? What would I gain by trying to convince them without being able to provide that context? Other than a cold shoulder, that is.
If friends ask me to remove my shoes before entering their home, I’m not going to stick out my tongue at them and stomp around their hardwood floors to show them I think their rules are stupid. If I can stand to take off my shoes, even if I wouldn’t prefer it, I will. If some rule is brought up that I truly can’t abide, then I’ll leave. The same applies to visiting other countries.
Beyond the practical nature of this idea, cultural relativism also helps a traveler gain new perspective. If you can step back and wonder what it must be like to grow up under different conditions from the ones in which you grew up. Imagine what it’s like to believe in gods or spirits or historical interpretations or traditions that are very different from the ones you hold dear. Conceive of looking up to different heroes, reading different texts. If you can understand from where a person’s beliefs are derived, you can better understand the person.
This is something I do every time I move, and many times within a country, since there are so many opposing viewpoints found within every culture. When I encounter an idea I can’t quite wrap my head around — I wonder how they could possibly believe such a thing — I drift into this thought exercise. “Well,” I think to myself, “they grew up here, in this type of house, with this religion, with those parents, with this recent history, with this longer-term history, with these politicians, with this food, with these priorities, with those dangers and restrictions, with this kind of mass-transit,” and on and on and on.
I’m not going to say that I truly understand the views of everyone I meet, and I’m not going to say those views are justified, even after I put myself in their shoes, to the best of my ability. I will say that even without fully grokking a person and how they see the world, it does help immensely to step away from my default point of view sometimes to see the world from a different angle.
Although it doesn’t necessarily change my mind about anything, achieving new perspective helps me understand how things I see so clearly, or think I do, can look so fuzzy, indistinct, or completely warped from just a few inches to one side. Likewise, when others step in to see the world from where I usually stand, I like to think they get where I’m coming from a little bit better; even if they don’t end up agreeing with me as a result of their new understanding.
The topic of travel-related ethics is expansive enough to warrant an entire book, but I want to touch on the subject so that, if nothing else, you can keep the broad scope in mind while on the road.
Consider this: tourism changes a culture. It changes the landscape, the regional economic infrastructure, and the way locals see the world. The impact is massive, and as a traveler — someone who dips in and out of other peoples’ lives and homes — it’s important to be aware of that impact.
Consider that your currency might have astronomically greater or lesser value than the local currency. Consider how this influences your purchases, and how those purchases change the economy. What kind of local entrepreneurs and small business owners do you want to support? What kind of country do you want to leave behind?
Voluntourism. Good for locals? Or good for a small pocket who host such adventures, and detrimental to everyone else? Could it be good for our own sense of accomplishment and morality at the expense of others? Are there other ways to accomplish more, but with less posturing?
Is the trip you’re taking worth the economic and ecological impact of your luggage, flight, taxi rides, and everything else we consume while on the road, but seldom consume otherwise?
The point here is not to make you feel guilty about exploring the world, but to be aware of the many realities of travel. Consider your trip and your actions from the perspective of those living — actually living, not vacationing — where you’ll be visiting. How can you enjoy yourself while reducing the amount of negative impact (or increasing the amount of positive impact) you have on them?
I don’t have any answers for you on this topic, because despite their being plenty of data, each person’s interpretation of that data (and what’s good and bad within that context) will be unique. What’s important is that you’re aware of this perspective and thinking hard about it as a result.
Beyond that, all you can do is act morally, whatever that might mean for you.
A good jumping-off point for information related to the topic of ethics and travel.
PUNCHES AND ROLLING
I’m frequently asked what kind of person you have to be to travel full-time. To dare to live such an extreme lifestyle, and not just tolerate the downsides, but embrace them; enjoy them.
My answer is that the type of person who enjoys this lifestyle is one who can roll with the punches; that is, they can be malleable enough at all times to follow life wherever it takes them.
That’s not to say that planning isn’t welcome, and that even someone who enjoys this type of lifestyle never has ideas of where they’ll go next. It does mean that folks who live this way tend to have more of a framework than a brick-and-mortar monument to planning. Everything is bendable and re-shapeable, and plans change in a snap. This is a personality trait that is infuriating in ‘real life,’ because it gives others little in the way of predictability, and when you’re living in a more standard societal structure, a little predictability is quite welcome.
On the road, though, plans often go awry. Seldom does everything go as planned, and being able to go with the flow doesn’t just save your blood pressure, it also saves the day. Rather than being frustrated over a schedule change, why not embrace it? Find a new opportunity in the moment, and give that a shot instead? You’ve got a reservation across town, but you likely won’t make it, so maybe go check out the little corner deli where the people you just met are planning to eat.
It’s not just dinner plans and other reservations that tend to be disrupted while traveling; sometimes traveling itself becomes the frustration. Planes are late, mucking up your connecting flight schedule. Buses break down. Sometimes the trains are oversold, and you’re stuck at a station in the middle of nowhere with just your bag and your thoughts for company.
The type of person who excels at long-term travel embraces these situations, and sees them as opportunities. They’ll do what needs to be done, whether that means pulling new plans from thin air, hopping on another train, or finding someone with a car heading in the direction they need to go. Finding a solution to the problem that’s arisen, no matter what.
If things go completely sideways and nothing is working out, this type of person is able to salvage the day. Nothing will stop them from having an interesting, enjoyable time.
This is what I mean when I say a traveler knows how to roll with the punches. It may be helpful to know, too, that if you are not this kind of person yet, there’s no reason you can’t become one. Being resourceful is a matter of being put in tricky situations and figuring out the best solution given the circumstances. If you travel long-term or full-time, trust me, you’ll find yourself with plenty of opportunities to be resourceful. More than you’d like, at first, probably.
There was a time in my life when money was the only metric by which I judged my success. I knew there were other units of measurement out there — folks who were more cause-oriented than I was, for example — but to me, money was king. My goals were measured in its terms, my lifestyle geared toward acquiring more of it.
There’s nothing wrong with money. I like money. Money helps me do what I do, and from a philosophical standpoint, I much prefer a world where money exists, because the alternative is likely a world run by those with the biggest guns.
A focus on money to the exclusion of everything else is, like any other extreme viewpoint, missing something. It’s a flat view, lacking the roundness of a full, healthy, exploratory experience. Money is the preferred metric for so many people because it ostensibly displays how well we’re doing at the game of life; each number just another point earned by working the right job and climbing the right career ladder. The digits in our bank accounts clicking ever upward, flying toward that high score and a chance at the leaderboard.
I see money differently these days. Today, money is an enabler. It’s a means to an end, not an end unto itself. Money allows me to do what I do without worrying that I’ll be pulled away from the work and experiences and people I love, forced to do something else in order to keep a roof over my head and food on my plate. Money in my bank account is a sign that other people find value in the work I do, and are willing to pay for it.
Money, in short, is something you should be concerned with just enough that it gains you the freedom to live how you want to live. To a person lacking dreams and causes and imagination, money is just another expensive bottle of liquor or VIP seat at the club; borrowed dreams from generations of advertising. For them, dollar bills are just peacock feathers.
For those with purpose beyond showing off, money helps build a better world; whatever that might mean for them and their sense of morality. I’m not saying you need to be a philanthropist or saint to use money well, but you do need to have something to spend the money on; something to work toward. Some sense of self; something that makes you ridiculously happy and fulfilled. This could be collecting experiences, or it could be collecting unicorn statuettes. Either way, unless you have a cause, you’re spending in hopes that the spending will make you feel something. It’s no accident that people who win the lottery often implode, not to mention the young celebrities who find themselves with massive bank accounts but with little purpose beyond consumption.
If you want to make travel a part of your lifestyle, you’ll want to see money the same way you see oxygen: it’s something you’ll miss if you don’t have enough of it, but not something you need more of than you’ll ever use. You need some money in order to keep going, but if you’re approaching it the right way, you’ll always have plenty and never need to think about it.
When it comes to earning money while traveling, there are a few main methods to consider.
There’s remote working, which means you work for someone else, earn a paycheck, and have a normal job the same as anyone else; the only different is you work that job from anywhere. This generally involves interacting and submitting files and attending meetings online, and is a solid option if you can find a job that allows you to travel the way you like and doesn’t keep you stuck in an office all day. Being stuck in an office all day, even in another hemisphere, is probably not what you had in mind when you decided you wanted to travel.
Then there’s entrepreneurship, which means you start a business of some kind, earn money from your service or product, and travel using the profits. Some people are able to combine their travels with their entrepreneurial activities, while others keep them separate. Either way, this model is a little riskier than remote working (there’s not necessarily a steady paycheck), but it also tends to be more liberating. You may work longer hours, but you can work them when you like, and the more work you put in, the more money you tend to make.
You can also find a job locally, wherever you happen to be visiting. This is a model many people use while enjoying a gap year, or while taking time to travel after years and years on the job. Folks who choose this option sometimes teach their native tongue to people learning it as a second language, work as nannies or au pairs, work at resorts or ski slopes or on cruise ships, or sometimes do something more specialized (design work, copywriting, tour guide, etc). There are a lot of jobs available for foreigners in most countries, and it’s a good idea to figure out what advantages you have (speaking perfect English, for example) and make use of that. There are sometimes hurdles to doing local work, however, so be prepared for paperwork, or to figure out a way to work unofficially (I’m not encouraging you to do anything illegal, but in some places, ‘black market,’ off-record jobs are more common than the alternative, and may be viable options).
Whatever path you end up pursuing, I highly recommend starting what I like to call a ‘freedom business’ along the way.
A freedom business is an entrepreneurial endeavor that, over time, will earn you time, which you can then spend on whatever you like. I say ‘time’ here rather than ‘money’ because the point of this type of business isn’t to make you rich, it’s to pay for your necessities.
For example, I ran a design studio back in college, through which I would design gig posters, websites, and billboards for local businesses. I worked long hours for little pay, and gave up my weekends, mornings, and nights in the tradeoff. This is an example of a business, but it wasn’t a freedom business.
When I was in New Zealand, on the other hand, I found myself short on reliable internet access, but flush with time and energy. I took some of that time to write a book on networking, taught myself how to design and publish and market such a book, and then put it online for people to buy. Within the first week, I earned enough to pay for my food and rent for the remaining three months I was in the country. The book wasn’t itself a business, but it was in-tune with the freedom business mentality: it was an effort that freed me up to pursue whatever I wanted for months. Those next three months were wonderful. I didn’t have to worry about money, and I was able to spend more time learning about the publishing world while traveling New Zealand extensively.
A freedom business is ideally centered on something that, like the book I wrote, requires initial effort but delivers a long-term payout. It’s an investment that becomes an asset (something valuable that you own), rather than a liability (something that drains you of resources).
I currently make most of my income from the library of books I’ve written and have available for sale. I don’t earn much from each sale, but added together, I make more than I need to survive and travel whenever I want. I know other people who do the same, but instead of writing books, they build downloadable online courses, apps for smartphones, movies for YouTube, or other types of long-term earning assets.
It’s possible to save up a fortune while traveling, but that’s beyond the scope of this book. What I want to emphasize here is building something that will allow you to sustain your lifestyle and maintain the quality of life you want to enjoy, so that you can take away as much as possible from every new location and experience. The best possible situation is one in which you aren’t burdened with worry over how you’re going to pay rent and afford a ticket home, so you can spend more time exploring New Zealand or learning how to say ‘keep the change’ in Swahili.
How to Indie Publish an Indie Book
If you’re keen to get involved with publishing, and perhaps make a living from your work, this is a great place to start. My business partners and I, all three of us professional authors, outlined our exact process for publishing books, and even recorded podcast discussions about the details, each step along the way. This is available completely free of charge, and I hope you find it useful.
I’ve been running businesses since I was 19, but I still learned a lot the first time I picked up this book. Josh Kaufman really knows his stuff. If you want to get a fundamental overview of what it means to run a business, along with a lot of detailed advice and strategies that only seasoned professionals know, check out his reading list and consider reading his book of the same name, where he summarizes the important points from the books on the list.
Making Money Overseas
Nomadic Matt has put together a great guide to making money overseas. Follow the links to get more specifics on the different paths available.
When I moved to Kolkata, I didn’t know a soul. I’d never met anyone from the area, and the hand-painted airport signs gave me little direction in terms of making it from the terminal to the front door, much less how to make it from the front door to a part of town where I could rent a roof and a bed.
Thankfully, a girl named Nisha arrived in a taxi shortly after I made it through customs. In Bengali, she negotiated a rate into town with the driver, helped me rent a three-wheeled ‘auto’ (called a ‘tuk-tuk’ in some parts of Asia), then helped me rent a bike-drawn rickshaw which took us to her home on the far side of town. Nisha aided me in acquiring a SIM card for my phone; she allowed me to borrow one of her family’s spare Nokias after the phone company lost my paperwork for the third time. She took me to an internet cafe, where we perused rental listings, before hopping in more autos and rickshaws and taxis, hopping around town, looking for a place I could rent for the four months I was planning to be in the city. She helped me call the owner of the rental I liked, and helped me negotiate prices. I stayed at Nisha’s house the first night, her family insisting I take the only bed, which they usually shared, and she helped me find a guesthouse where I could rent a room until my flat was ready for me to move in.
In short, Nisha helped me navigate from being a confused foreigner to having a life, a place to live, and a fundamental understanding of the city in just a few days. All of this, and I had never met Nisha until I arrived at the airport that day: she contacted me via Twitter, after I announced I would be moving to the city for a while.
Twitter is a platform I’ve spent a lot of time on over the past several years, because it allows me to share interesting things with others, but also gives me the opportunity to (sometimes quite passively) make connections with amazing people like Nisha.
A platform is a jumping-off point. A place where you can set your things and kick your feet up. It’s a means of communicating with the rest of the world, and one of the best ways to ensure the world sees the real you, rather than a random quilt of ‘likes’ and drunken college photos.
For the purposes of this book, ‘platform’ refers to your website, your blog, and your social media profiles. Through these platforms, you have the opportunity to shape what people know about you and how you’re perceived. Each and every one of them is an opportunity, so long as you’re willing to put a little bit of effort into ensuring the image you’re projecting is both accurate and purposeful.
A good metaphor for this type of platform is real estate. You can upgrade real estate over time and it becomes more valuable as a result. You can fill a home with things that represent you, and if you do it well, people will know who you are just by stepping inside. The same is true with your blog and your Facebook profile. The things you don’t include say as much as about you as the things you do, and a well-manicured, public-facing profile that shows up when people search for your name is key in telling the world (even people you haven’t met) who you are, but also in validating everything you do.
Of course, platforms can be the opposite of helpful if left untended. Better to have no blog than a derelict one; the equivalent of a home left to dilapidate, the yard overgrown, rats infesting the attic. This is why the key to a well-managed set of platforms is ensuring you don’t overextend, and don’t bite off more than you can chew. Start small — a Twitter account, perhaps — and grow from there, if warranted. If not, that’s fine, too. Make that Twitter profile the best you can, and let it be your official home base.
If you’re traveling frequently, a well-tended online platform is a valuable asset. I have a newsletter I send out to subscribers’ email inboxes once or twice a month, and that gives me the opportunity to share information about the projects I’m working on, and my new steps, travel-wise. Twitter and Facebook are two ways I share where I’ll be and when, so I can meet up with folks who have similar interests, or who might be able to help me get set up in a new location. Instagram is a platform I use to share my experiences with others, which is valuable to those who see it, but also another means of connecting, via taste or geography.
Online platforms are a wonderful means of keeping in touch with folks you meet around the world. People you meet randomly in a train station or coffee shop can connect with you online, and you can learn even more about each other over time. I’m thrilled to have sites like Facebook available, because even though there are gobs of clutter to wade through, with the proper filters, it makes keeping up with the exploits of those you care about dead simple, and keeping others in the loop about your own exploits just as breezy.
It is possible to take tending to your platforms to an unhealthy extreme. If you’re writing a blog and have nothing to talk about, for example, you may want to get back out into the world and experience some things before hitting the keyboard again. Likewise, if you’re regurgitating online content without adding anything in the process, you’re not really using your platforms to their full potential; going through the motions of ‘being active on social media’ probably won’t give you the results you’re after.
Put in some time here and there and build something you can easily maintain alongside all the cool stuff you’re doing. If your platforms start to get in the way of the life you’re living, shove them aside a little, or come up with other ways to integrate them. What you want is for them to fit in seamlessly with how you live your life, not to be one more responsibility or something cumbersome that you dread. Use your best judgement and use these platforms wisely.
It’s worth noting that knowing a bit about social media and websites/blogs is also a very marketable skill, if you take it a few steps further. Pick up a little HTML/CSS/PHP and not only will you be able to build your own, custom blog, you’ll also be vastly more hirable. Learn how to promote your work via Twitter, and you may find yourself capable of promoting the work of other people or companies, as well.
Facebook / Twitter / Instagram / Tumblr / WordPress
These are my favorite platforms, and all of them are free to use (the links above go to my page on each service, so you can see how I’m using the platform in question).
Codeacademy / Learn to Code the Hard Way / Treehouse / Coursera
Here are some of my favorite tools for learning to code. I’m no whiz-kid developer, but I know enough to work professionally as a web developer, and am more than capable of building most of the things I need to build for my own projects, as well.
Each of these resources takes a slightly different approach to teaching similar topics, so try them out and choose the one you like best to start. From there, you should know enough to pursue more education moving forward (most of which is also available online, cheap or free).
When I started streamlining to prepare for my new travel-based lifestyle, I thought I’d reduce down to a certain scale, pack most of what I owned away into storage containers, and take the rest with me. I wanted to travel light, but I also wanted the benefits of having all that other stuff I’ve accumulated on-hand if needed.
It didn’t take long for me to realize storing all those possessions would be incredibly inconvenient, expensive, and ridiculous. What was I going to do, come back in a few years and unpack all those computers? They’d be obsolete before then! The clothing might not fit; might not be my style anymore. The furniture may not be to my taste, or I may never own a place long enough to warrant moving it in again, so would I just keep paying for it in perpetuity? What was the point?
I started by going through my closet and pulling out all the clothes I hadn’t worn in a month, made a big pile on the floor, and donated it all.
I repeated the process with my electronics. My books. There were little caches of possessions I was hoarding all over my townhouse, and the more I went through them, the more I realized these were things that were occupying my space — things I was essentially paying to store, by paying rent for the space they occupied — but which were bringing me no value.
It’s nice having books on the shelves, but I hadn’t picked up a physical book in ages. It was nice knowing I had all those clothes to choose from, but I wore the same couple of pairs of pants, the same suit jacket, and the same handful of shirts over and over again. As soon as I accepted that it was okay to discard things, the floodgates broke and my number of possessions dropped drastically. It took me a full four months to get rid of everything I no longer needed, but it was time well spent.
Minimalism is not a competition to see who owns the least, no matter what some blogs or newspaper articles might have you believe. It’s not about counting your stuff and comparing that number to other travelers, and it’s not about denying yourself anything you really want. Minimalism is about prioritization. Knowing what you want, what makes you happy, and putting yourself in the position to get more of those things.
If collecting baseball cards makes you happier than anything else, don’t buy a big screen TV: spend that money on baseball cards. Likewise, if traveling or pursuing memorable experiences make you happy, why waste your time accumulating more stuff? Spend your time, energy, and resources (including money) on plane tickets. Safaris. Hikes to the top of volcanoes. Minimalism is about this kind of focus, and if you want to travel, that means eschewing consumption for the sake of consumption and focusing your efforts on the things that help you to get where you need to be and to do the things you like to do when you get there.
I’ve changed careers numerous times already, and I’ll no doubt do so again in the future. Every time I change, I start fresh; not at the bottom, perhaps, but lower than I was before, by many standards. I can afford to make such changes whenever I like, though, because my needs are few, and my cost of living is low. By subtracting all the things I don’t need or want — the things that don’t make me happy, that don’t add value to my life — I was able to cover my expenses even when I was just starting out in the publishing world. The money was a small fraction of what I made doing branding work, but I was able to throw myself into it and get better, faster, because I had fewer bills to pay, and fewer possessions to store, maintain, and protect.
In short, focus on quality over quantity when it comes to possessions, and if you intend to travel, make sure you apply your energy, money, and time to your pursuit of adventure, not getting the most fashionable whatever.
Set your life up in this way — focusing on lifestyle rather than possessions — and you’ll be giving yourself a lot of room to make mistakes, and will travel much lighter. We’ll talk next about what you must have on your packing list and it’s not very much; the lighter you can travel, the more you can enjoy where you find yourself.
I’m a huge proponent of packing super light when traveling, but even I acknowledge that there are some things that make the whole experience approximately thirty-seven bajillion times better.
That in mind, here is a short list of things to consider when putting together your packing list. What’s nice is that you don’t really need anything beyond this, but it’s also a good default from which to start. Then, you can add a few additional items based on taste and need.
Not just any bag. You want something sturdy. Rugged. This bag is going to be your home, your significant other, and an extension of your body in some circumstances, which means it’s got to be something that you love.
It needs to be comfy, reliable, and good-looking (according to your stylistic taste). You’ll want something that doesn’t stand out too crazily — one of the best ways to be targeted by scams and thieves is to stand out as a backpacker or tourist — but if something too humdrum and conventional will bore you, opt for a little non-standard; it’ll be a tradeoff worth making.
When I’m looking for a bag, I like darker, earthen tones, hearty materials that will get better with age, and something that makes me look like I live in the city I’m walking through, not visiting. That means a style that reads as ‘day bag,’ not the ‘my life is in this bag’ kind of luggage. If you’re going to be doing a lot of outdoorsy stuff, and want to be able to just throw your possessions into a big rucksack, aim for something repairable; I’ve seen a lot of backpackers scrambling to collect their belongings from the middle of bustling streets, because an errant zipper came loose, or a seam frayed at the wrong moment.
It’s also worth considering size relative to what different modes of transportation will allow. I carry two bags: one laptop bag, and one that’s more like a small duffel. When flying, I can stuff the former under my seat, and the latter fits in the overhead bins of every airplane I’ve ever been on. This is incredibly convenient, and means there’s little chance my bags will be misplaced/stolen/loaded on the wrong plane. Consider how often you’ll be traveling in what type of vehicle, and plan accordingly.
It’s not difficult buying clothes for travel, but there are a few things to consider that you may not otherwise think about.
First is that you should generally avoid obvious ‘travel-wear.’ These vests and jackets and shirts are marketed to people who want to carry an arsenal of gadgets or feel travel-ish while still ostensibly looking classy, but they very seldom actually read that way. Usually it makes the wearer look like someone who’s going on safari. That is to say, it’s a great way to look like a tourist, and looking like a tourist is a great way to pay higher prices, be targeted by grifters, etc. Avoid this.
Next, make sure that you’re ready for everything, if only a little bit. What I mean by this is that instead of packing a massive winter coat for your trip to a Caribbean island in the summer time, pack a hoodie and maybe a light sweater. My strategy is to always have a handful of things that, when worn together, layer nicely into a thicker, warmer outfit. I can buy gloves and a hat on location if I need to, but having clothing that will warm your core can be a lifesaver if you find yourself making a stop in Iceland and wishing you could go explore for a day, but find yourself with nothing but beach clothing. Versatility is the name of the game here: each piece can be worn separately or together, ideally with every other piece.
Finally, make sure the clothing you bring is clothing you’ll wear. There’s little point in having an amazingly practical jacket if you can’t stand to be seen in it. I know, I know, when you’re out of your comfort zone, you should just bite the bullet and wear the best clothing for the climate, but if you’re like me, you want to be social and go out and meet people. You want to be able to attend parties, go on dates, have meetings, and not be the person who looks like they just got off the bus. Aim for clothes that will last and get better with age, but failing that, bring articles of clothing you can afford to wear out quickly; clothing you will actually wear and be comfortable in.
The point of all this is to be yourself while favoring stuff that will pack well, travel well, and provide suitable coverage and climate control no matter where you end up. For me, this means I have a few pairs of jeans, a pair of pants, a half-dozen tshirts and polos, a few button-downs, and a half-dozen each of underwear and socks. I also have two light sweaters, a windbreaker-style jacket, and a hoodie. Simple, easy to pack, and all of it easy to dress up and down as necessary. Occasionally I’ll buy something specific — gloves or sunglasses, or a massive jacket if I’ll be in Greenland for a while — if they’ll bring sufficient value in a country I’ll be exploring. Otherwise, what I’ve got by default is perfect for any climate.
Internet Accessible Device
This isn’t something I thought I’d need to have when I started traveling, and indeed there have been times when I’ve gone without. But all the same, I’m going to highly recommend you bring along some kind of pocketable, WiFi-accessible device, because it’s a versatile means of connecting with the outside world, finding data about where you are now, and even keeping yourself entertained during long, uncomfortable flights and rides.
This device could be a smartphone, though if that’s the case, it may be smart to have a backup battery with you (so that you don’t find yourself phone-less after a flight-length marathon of Angry Birds). I usually carry a separate device, though, so that I can safely listen to music for the entirety of my trip, check my email when I arrive, and take notes as I need to, all without needing to have my phone turned on. If you have a device with apps (like an iPod Touch), you also have a calculator, currency converter, notepad, camera, and numerous other tools at hand when you need them. A very, very useful gadget.
The main purpose of having headphones is that they allow you to listen to music, watch movies, and generally engage with your computer, phone, or other device audibly without annoying the people around you. Wearing headphones is also the international sign of ‘don’t bug me, I’m in my own world’ at coffee shops and the like, which is useful in places where you might otherwise be hassled for handouts constantly.
There are some packable, travel-worthy over-ear headphones, but I usually recommend getting some small, in-ear versions, which take up essentially no space in your bag, and usually have a microphone attached to the cord. This serves the double-purpose of not overloading you, while also allowing you to have a relatively private conversation over Skype, even in a public place. And unless you’re a true audiophile, or are doing work with music or film production, you likely won’t notice the difference in quality.
It seems to be part of the travelers’ handbook to buy the most expensive DSLR one can as soon as one decides to take a trip. Though there are plenty of good reasons to have such a camera (they take the best photos available), there are plenty of good reasons not to, as well.
First and foremost, a DSLR takes up a lot of space in your bag. I think the only thing that maybe takes up more space are massive workout shoes, and I don’t recommend you carry those, either. The body of the camera, the lenses, the padded bag; it all adds up pretty quickly, and most pro photographers bring a completely separate, too-big-for-carry-on bag, just for their photography equipment.
Unless you’re a pro photographer, this is probably overkill. As someone who started out doing exactly this (carrying a camera I wasn’t skilled enough to make full use of), I’ve come to realize that the old saying about cameras is right: the best camera is the one you have with you.
That means either opting for a very small, point-and-shoot camera that fits in your bag without taking up too much space, or just opting for a phone and/or web device with a nice camera built in. The lenses, sensors, and whatnot on the non-DSLRs aren’t as good, it’s true, but I guarantee you’ll snap more photos, and more interesting photos, with a device you always keep in your pocket. You’ll be able to photograph real life, not something posed; not just “Wait, wait, let me get out my camera!” moments.
Carrying a DSLR also makes you a target for theft. If I’m carrying a pocketable camera or phone, no one knows, and it’s trickier for people to tell from a distance how much such a thing is worth. DSLRs are predictably more expensive, though, and comparably easier to steal. They also hang in plain view as you carry them around (did I mention how annoying they are to carry around?). My best advice is to leave the DSLR at home and find the best quality, tiny, or built-in camera you can manage.
I have mixed feelings about phones.
On one hand, I went a year without any phone and got along just fine. It made dating a little weird (in South America at the time, not many people used email, so giving a girl my email address was a little awkward for everyone involved), but it was great knowing I could completely unplug whenever I wanted.
On the flip side, smartphones today are remarkably well-stocked with useful apps and hardware. There’s still plenty I prefer to do on my laptop, stuff my phone isn’t capable of doing just yet, but as the years march on, I leave my laptop at my flat more and more frequently. I’m still able to do 95% of the things I want to do, sans-bulky-hardware.
There are two main ways to approach having a phone while traveling. The first is to go high-tech, just as you would at home. Make sure that your phone is your omni-device, capable of helping when you need to see a map of the area, email a friend or new connection, or figure out how to say “No pepperoni, please” to the waiter.
The other option is to go low-tech, opting for a ‘dumb phone’ that will serve you in an emergency and allow you to chat with locals, but otherwise isn’t going to be used. The kind of phone you can drop into a pool or from the roof of a building and will still work afterward.
I’ve gone both routes, and both are great in different circumstances; I think this is mostly a matter of taste, or determined by what kind of experience you want to have.
In the modern world, mobile devices are central to social interaction, and not having one makes you kind of the odd-person-out (which could be a good thing, in some cases). Alternatively, if you’re looking to see the world from different angles during your travels, the angle of ‘I’m not connected to the world 24/7’ is a truly novel one, I assure you. It might be worth trying out at some point.
If you go the smartphone route, you’ll want something quad-band, which will allow you to use it on most networks around the world. Look for a phone that has an accessible SIM card slot, so you can easily swap in a local one when you arrive in a new place, and avoid paying the generally ridiculously overpriced ‘international rates.’
If you go the dumb phone route, opt for something rugged, reliable, and with a battery that lasts forever. It sounds silly, but a lot of these Nokias made for the developing world also have built-in gimmicks like flashlights that are sometimes incredibly handy, so look for that kind of thing, too, when you’re shopping.
It may not be long before the ‘laptop’ evolves into a series of hybrid tablets or super-capable phones, but for the time being, if you want to get real work done, they’re generally still the go-to device for travelers.
Get something small — 15” is generally way too big, so smaller than that — and something with great battery life. Make sure it’s powerful enough to do what you need to do, though if you’re not doing much writing, video editing, or other processor-intensive work, you could conceivably snag a high-end tablet, instead, and be just as well off. I don’t use tablets, personally, but I carry a 13” Macbook Pro that is my go-to for just about everything (though even the 13” seems a little chunky sometimes, which has me eyeballing the very svelte 11” Macbook Air).
The difference in operating systems is not really important here; I use Apple laptops, but iPhones are terrible for travel, so I opt for Android there. Don’t get caught up in the brand: look at the specs. Brand-loyalty is especially unimportant when it comes to traveling. There’s a decent chance most of the brands you care about are completely unknown where you’re going, anyway, so having a particular logo on your bag or icon on your laptop doesn’t tell anyone anything about you.
One more thing to consider is how light and damage-tolerant your laptop is. Everything you own will have to withstand more drops, bumps, exposure to x-rays, and all kinds of other non-standard situations than most other people’s equipment. Keep this in mind, because the fanciest laptop will be worthless a week into your trip if it doesn’t have a hard drive that’s solid state, or that locks when you drop it.
As you travel, you’ll encounter an impressive array of outlet types. Some will be standard for the region and some regions have old and new types, depending on the place you’re staying. Some seem to be quite random, as if the locals are intentionally messing with you and trying to prevent you from charging anything when you arrive.
Whatever the case may be, I have two suggestions for you.
The first is to pick up a cheap adapter for the place you’re headed before you leave, if possible. In some places, this is quite easily done — in the US, you can order just about anything online, for example, and some places have shops full of cheap-made adapters — and in others, it’s nearly impossible. It’s not the end of the world if you can’t get something ahead of time, or if you’re traveling last minute and don’t have time, or don’t know what to expect when you arrive. It is a big load off your shoulders, knowing you can charge your equipment when you show up, and that you won’t be wandering around, trying to find a place that sells such things before you can settle in.
The second is to carry a multi-outlet power strip, of the travel variety. These little doodads provide multiple outlets (of the kind you use back home), and usually a USB outlet or two, as well. The benefit here is that you only need one local adapter to charge all your stuff. The best ones provide protection against power surges and the like, too. That can be handy in places with shoddy electrical infrastructure. These are really wonderful devices, and don’t take up much space in your bag.
Below is an incomplete list of equipment I use and recommend; incomplete because some items I travel with are now unavailable (like my bags), while others are either hard to come by, very specific to me, or otherwise not useful to know about.
I like PCs as much as the next person, but for the work I do, and the software I use, the 13” Macbook Pro is my ideal machine. There are plenty of viable alternatives out there if you don’t dig Mac OS as an operating system. Aim for something small and light, 13” or less, with a mouse pad that isn’t annoyingly small or unresponsive (a real problem with many of the travel-sized laptops on the market).
I’m currently using a Nexus 4, which is an Android phone produced by LG. Again, the operating system is a personal preference, and there are plenty of other great phones on the market.
I wouldn’t recommend an iPhone for travel, because although it’s a marvelous and beautiful device, it’s also a theft-magnet, it doesn’t allow you to easily swap out SIM cards, and most models are not functional on many frequencies around the world (making them unusable outside your local market).
There are plenty of equally awesome notebooks out there, but most copy the look and feel of the Moleskine. My advice: find a cheap source and buy a few at a time, or find a cheaper knock-off you like the feel of and use those instead.
G2 Mini / Uniball Jetstream 101 Pens
I’ve long loved the G2 Mini, which is a gel-ink hybrid pen, small enough to fit cozily in the pocket of your jeans. I’ve recently switched to primarily using the Uniball Jetstream 101, however; as a lefty, I find it dries much faster than anything else I’ve tried, which reduces smudging.
Both are great options, and make a great mark, whether you’re writing or drawing.
Belkin SurgePlus 3-Outlet Mini Travel Swivel Charger
Long, strange name, but one of the most useful items in my bag. This three-outlet, two-USB-charger hub allows you to buy one local adapter and charge all of your gadgets at once. It’s also useful back home (if you live in the US) in coffee shops with crowded outlets, or on trains and such, where chargers are very finite.
Cocoon GRID-IT! Organizer
I question the all-caps and exclamation point in this item’s name, but its usefulness is unquestionable.
Alongside the Belkin outlet, this thing is one of the handiest objects in my bag. It keeps all my little doodads (cords, chargers, my point-and-shoot camera, my tiny tripod) organized, held in place by elastic bands that can strap down objects of just about any shape or (smallish) size.
There are plenty of third-party alternatives to this one, and I’ve tried a few, but the name-brand Gorillapod seems to be the best quality.
This is a small tripod with adjustable, clingy legs, which you can wrap around things, adjust to create a level shot on an unlevel surface, or even (if you get the right model) attach it to metal surfaces with magnetic feet. Quite a clever little doodad, and handy.
I was skeptical of this wallet when I first bought it, thinking I would never convert from the ultra-minimal Slimmy front-pocket wallet I was using at the time. The Architect’s Wallet won me over, though, in no small part because it still fits easily into my front pocket, and has a built-in notebooks and space pen, to boot.
I’m not a big fan of tablets, but I always carry a Kindle, and the Paperwhite I’m using now is my favorite model ever, by far. It has a light built-in so you can read at night, which is especially handy in transit. It’s also cheap, and you can side-load books, if you can’t find what you want on the Kindle store. The battery lasts approximately forever, too, which is great for long trips where you might not have the opportunity to plug anything in.
I carry a little iPod Touch around for listening to music while traveling, alongside all the handy little apps and WiFi access that comes with it. I don’t advise using an iPhone on the road (they’re major thief-magnets), but an iPod for use while on a bus or flight is wonderful, and plays well with Spotify, which is the service I use to stream music.
TICKETS AND TRANSIT
When I travel, I rent flats or rooms in the countries I’m visiting. It would be inconvenient to do otherwise, living in a place for four months at a time, and it’s a method that works really well for me.
Many people who travel full-time or long-term opt to hop around quite a bit more than I do, though, and instead stay in hostels, short-term rentals, or on couches as they traverse the world. All these options (and any others you can think of) are legit, so long as you have a safe place to lie down at the end of the day, and aren’t putting anyone out as a result.
Rent makes up a decent part of my monthly expenditures, but by far the biggest cost of operation for most travelers is the cost of transit. That is to say, most of a traveler’s money goes toward buying plane tickets, camel rides, boat cabins, and myriad other methods of getting from point A to point B.
If you’re thinking like a business person, this is where you exclaim, “Egad, Colin, that means if I reduce the cost of transportation, I’ll drastically reduce my overhead costs, and can spend more time doing fun things and less time worrying about money!”
It’s true, reducing the cost of transit can reduce your day-to-day costs significantly, and can knock your essential expenses (food, shelter, transport) down by a third. Not too shabby.
If you keep them in mind, there are plenty of considerations that will drastically reduce these travel costs.
This is not always an option, but even if you’re not certain you’ll be going someplace just yet, it doesn’t hurt to take a look at plane/train/whatever tickets early on so you have means of comparison.
The rationale here is that many sites these days allow you to scope out an entire month’s worth of prices, rather than just a day. This means the ticket prices can actually help inform your decision on when to go somewhere, rather than the other way around. This is a big part of why I’m able to travel so cheaply, despite lacking the patience for some of the more complex travel-tricks out there. Time is on my side: I can leave for a new country tomorrow or three weeks from now. Having that freedom to wait (or go right now) often saves me hundreds of dollars.
There are also times when it makes sense to buy a ticket in advance, only to change it later. This especially applies to round-trip tickets, which often can be bought for crazy cheap prices, and cost a small fee (or sometimes no fee at all) to change the return ticket to a later date. This is also quite useful when going to countries that require you to have proof of an exit ticket before they’ll let you in: buy the cheapest round-trip ticket you can find, then change the return ticket to another date after you’re inside.
It also helps to plan ahead because you can take stock of all available options. Not all flight aggregators show all airlines, for example, and it may be that there’s a regional airline that’s much cheaper than the options presented on larger sites, like Kayak or Priceline. You can also take into consideration overland travel, travel by boat, and other alternate options of the sort. Personally, I always opt for overland travel (bus, train, car) over flying when I can, not because I don’t enjoy flying (I love flying), but because it turns the trip into an adventure, and it allows me to see more of the world. There’s only so much you can learn about a place from 36,000 feet.
We live in amazing times, where you don’t have to call around from airline to airline to check on prices. It doesn’t take hours on the phone with an exhausted airline representative to see which days of the week, weeks of the month, and months of the year are the cheapest, most crowded, or any number of other variables that might influence your decision on when to fly.
Instead, it’s as simple as hopping on the net or opening up an app. Some are better than others for comparing different variables, and it’s still worth checking out regional airlines (see ‘Plan Ahead’ above) for options unlisted on some of the major aggregators. In general, there are plenty of options for those willing to put in a little (web-based) footwork.
But what should you be looking at when trying to decide how and when and (in some cases) where to fly?
It’s a good question, and the answer is entirely based on how you prefer to travel. For example, I’m the kind of traveler who can suffer through just about anything. I can sleep anywhere, with any amount of noise, and can cram myself into small spaces for hours and hours, knowing that ‘this too shall pass,’ thrilled that I will have saved some money in the tradeoff (which I can spend on cool experiences once I arrive).
I know other travelers who are not as willing to subject themselves to such tortures, and who prefer their journeys to be comfortable and cozy whenever possible. For these people, finding upgrades where they can, flying on preferred airlines, and opting for routes that are straight shots (rather than loaded with layovers) tends to be the superior option.
There are advantages to both preferences, of course, and most people fall somewhere in the middle between these two extremes. What’s important is recognizing where you fall on the spectrum so that you can plan accordingly and compare options using the right variables and the right resources. Sites like Matrix Airfare are perfect for me, because all I really care about is the price. Sites like Hipmunk are perfect for others, because it takes into consideration the ‘agony’ (yes, that’s an actual variable they measure) of a given flight plan.
Believe it or not, hiring travel agents is still a thing. It looks a little different than it used to, but there are still some benefits, if you’re willing to try something new (and talk to someone about your travel plans, rather than just sitting and clicking things until you see a price you can stomach).
The real power of a travel agent, in my mind, is that they know the ins and outs of all the fees, exceptions, and other little secrets of the travel industry. They also, in some cases, have relationships with folks at certain airlines, have software that helps them display superhuman feats of complex bookings, and can, in some cases, put you in the position to get little perks along the way.
There are other ways to accomplish most of this, and there are even sites like Flightfox that will crowdsource similar benefits at a very reasonable price. These days, it kind of comes down to personal preference: the people I know who use travel agents, and the few times I’ve used them have been because there was a complex problem to solve. Around-the-world trips are a good example, as are trips for book tours, multi-stop holiday visits, and the like. It’s nice to tell someone else (in plain language) what you’re looking for and to have them come back with a handful of valid itineraries, each with a different advantage.
It’s nice, too, when they add a little letter to your ticket that indicates you should be first in line to get bumped to First Class, if there are spare seats to be had. You generally get the opposite indicator on your ticket if you buy through a discount booker; that you paid less than anyone else, and will be first to get bumped off the flight if they’ve oversold.
One last thing to consider is that some travel agents won’t even cost you a cent, though you may want to opt for the ones who do charge a fee. The former won’t charge you for their services because they make money from certain airlines for bringing you to them, which means there’s a conflict of interest because they’ll be more likely to put you on a flight with an airline that pays them more, even if the ticket isn’t the best available. Agents that you pay, on the other hand, may charge as little as 5% of your total ticket price (or something like $40-50 for cheaper tickets), and will definitely have your best interests in mind.
I’m a big fan of one-way ticket travel.
Airlines are keen to grab a double-sale upon purchase of a ticket, and sometimes the prices are so ridiculous that it would be silly not to pay a few extra bucks for a return ticket you can change later for a small fee, but in most cases I very much prefer to buy one-way tickets.
Why? Because of the freedom it allows. With a return ticket, you’ve already paid for a way home, on a certain day, from a certain airport. You can potentially change the day, but you’re still stuck with a tether to that city and that airport, and I like feeling that I can change plans midway through a trip, hopping a bus to another country, then a plane from there to someplace else. By the time my return ticket’s date arrives, I might be halfway around the world, and the money I spent is wasted. Even worse would be changing my plans and missing out on amazing opportunities just so I could be at that airport at the right time. It ruins the point of rolling with the punches, because you’re told where to roll, and how far.
There’s more flexibility in the travel sector in some parts of the world, these days (Europe, for example), and like most of the ideas presented in this book, whether or not this idea is useful really depends on how you prefer to travel and what kind of experience you’re after. If you’re aiming for something loose that will allow you to evolve as opportunities arise, though, one-way travel is the way to go.
I’m not a travel hacker. It’s not because I don’t recognize the value in doing so; it’s more that I don’t enjoy it, and therefore the benefits are less compelling. I prefer to do work I enjoy, find decent prices, and then pay for travel using money earned by doing things I enjoy.
Some folks prefer to play with the travel system, which, when done correctly, can result in cheap, free, or heavily upgraded travel situations. This is called travel hacking, and usually involves accruing mileage and points for loyalty programs, then figuring out the best way to use them.
I’ve included some resources below for people who want to give this a go, though as I write this book, many of the loyalty programs have been changed so their points are less valuable. Time will tell if, moving forward, the travel hacking community comes up with new ways to game the system in the pursuit of better and cheaper travel plans.
This is the software most other airline deal sites use to load up prices. Going directly to the source pays off for me quite frequently, though you do have a few more steps, in that once you see a price, you have to go fetch it at the airline’s site. If you don’t mind the inconvenience, you could save some money.
It’s a toss-up for a given trip, which site will have the cheapest flights, but I like the UI of SkyScanner a lot better than most other options. It gives a range of prices for a month at a time, which is better than the weak or so most sites will give. Great, if you want to go somewhere within a certain period of time but are flexible on the date.
This is by far my favorite travel ticket site, and all that’s keeping it from becoming my most-used travel ticket site is adding more countries and airlines to the roster. They’re doing something completely new, though, allowing users to search using natural language and absolute flexibility. It’s worth checking out, especially if you want to see where (I think) the future of ticket searching is heading.
Kayak / Priceline
I’ll usually check these sites for comparisons, but usually it’s more to establish a baseline than to find the best prices. Every once in a while Kayak will surprise me, but mostly these sites provide end-to-end ease-of-use, rather than the lowest prices or best flights. Keep that in mind, and probably only make use of them if you’re looking for a flight/car rental/hotel combo.
There are myriad little sites out there that somehow end up with ridiculous prices on airlines from time to time. CheapoAir is one such site. There are plenty of others out there like it, too, with equally skeezy-sounding names and websites of dubious quality. Keep them in mind, though, when you’re searching, because you may get lucky and snag a heck of a deal through them (like I have more than once).
When ticket-hunting, be sure to check out the airline’s official website, too. Every once in a while, you’ll find the best prices, or some exclusive deal, there and nowhere else.
How to Be a Travel Hacker / Beginner’s Guide to Travel Hacking / Travel Hacking Cartel
Three of the better-known starting points for learning more about the travel hacking world, and better understanding how it all works. There are numerous online communities based around this idea (some free, some that you pay to join), myriad books written on the subject (some that are worth way more than what you pay, and some that are a waste of money), and many, many blog posts published on the topic.
The folks who produced the pages linked to above have a good reputation in the industry, though, so you can be sure they know what they’re talking about.
I hate hate hate having to deal with bureaucracy. In my mind, the process of becoming an international citizen should be as easy as being born. Drawing arbitrary lines in the sand and differentiating between groups of people is one of the great wrongs governments have perpetrated upon us, as people who just want to visit/meet/learn from other people around the world.
That being said, I don’t have a better solution, so I guess we’ll let things stand for now. Legal issues — paperwork, visas, taxes — are realities of the world we live in for the foreseeable future. Travel, unfortunately, does not make these things easier; it actually adds an additional level of complexity.
There’s a chance you’ll be making long-term travel a part of your lifestyle and still maintain a home address; an apartment you rent out, a home where you keep yourself, etc. If that’s the case, groovy, you’re all set in terms of an official home base.
If that’s not the case, though, and if you’re like me, hopping from place to place, with temporary addresses but no location where you actually ‘live’ in the sense of spending time there, you’ll need to come up with an alternative. Governments, it turns out, like to know where you are so they can send you things and find you if they need to, so you have to have something on the books in order to officially exist.
Sometimes, this can be simple as writing down your family’s address, or that of a good friend. This is where your mail will go, so make sure you tell the person first, before bills and advertisements start showing up at their door with your name on them. Something to seriously consider is a P.O. Box, which will give you a place to send your mail for a very small price; you can’t list it as your official address, but it ensures your mail is received by you, whenever you manage to stop by and pick it up.
There are also services that will receive your mail for you and either hold it or scan it and send it your way. Some people prefer this, especially if they’ll be gone for long periods of time and receive important missives by snail mail periodically. I stop in on the office where I have my mail sent frequently enough that this isn’t an issue for me, but I know several people who have utilized such services and swear by them, so it’s an option, if you’re willing to pay for it.
These days, you have options when it comes to dealing with taxes. If you’re using one of the services mentioned above, that sends you your mail, scanned, via email; or if you stop in on your P.O. Box or other address frequently enough that you’ve got all the tax forms you need handy, you can file using one of the many pieces of software available for such purposes (this is what I generally do, and I’ve never had any trouble with it).
If you’re running a business with more than one person involved, have some kind of unusual tax situation (like living as an expat), or are just prone to erring on the cautious side, it’s worth paying for a certified public accountant (like I do with the publishing company I co-founded). This will likely cost far less than you think, and can often save you money in the long run (not to mention the peace of mind you achieve, having someone else handling your taxes for you).
If you do opt for a CPA, make sure they know all about your situation, because there’s a chance you’ll be able to benefit from some serious deductions, living outside your home country the way you do. If you are doing your own taxes, using software or otherwise, do some research, check out expat forums, and make sure you’re deducting what you can. Don’t over-deduct, though; unusual circumstances are warning bells for auditors, and you don’t want to tempt fate even more by under-paying.
When in doubt, it’s probably better to overpay than under. Tax systems in most countries aren’t looking to screw you, but they can do so by default, if you give them reason to. If you’re anything like me, you prefer to just get them done and out of the way, and that means either hiring a professional, or following the instructions of software built by people who know what they’re doing.
During a time when I would have preferred to daydream about my lifestyle shift and relax a little, before hitting the road, I was instead busting my butt taking on extra clients so I could pay off the $30,000-or-so of debt I still had on the books from school. It wasn’t easy, or pleasant, and it sucked to work so hard only to have the money I earned slide right out of my fingers as soon as it came in, but ridding myself of debt was one of the better choices I’ve ever made. I promised myself I’d never have debt again, and it’s been a promise worth keeping.
I say this because debt is insidious: we’re taught that it allows the economy to function, and that it’s fine because everybody has some, but those are habits and myths perpetuated by people who benefit from a debtor system. Rid yourself of debt, and you extract yourself from a system of wage-slavery and coloring inside the lines. Rid yourself of debt and you have far fewer bills to pay, and far more options.
Needless to say, you should avoid accruing more debt as you prepare to travel more extensively, and while on the road. Instead, systematically pay off your debt. I would argue that it’s better to start traveling with less money in the bank and no debt, than to be flush with cash, but with plenty to pay back at some point. Not only does interest build up on that money you owe, but you’re tethered to a place where you owe money. That means you have to worry about how to pay installments, continue to earn money at a rate that allows you to do so, and concern yourself with a string of bills that will keep arriving, even as you change your habits and priorities.
Much better to have the option to reduce your needs and cost of living, should you want to. Much better to be able to untether from the rest of the world should you want to, without worrying that you’ll default on your bills if you do. Much better to cut ties with owing anything to anyone, and to live according to your means.
If you have massive debt, start paying it off now and live in such a way that you can continue paying it off faster than interest accrues. Until you do, someone else owns you, and to a certain degree, determines how you live your life.
In order to travel to some parts of the world, you’ll need to get vaccinations, and carry a record stating that you’ve had them done. For example, to go to parts of South America, you need to have a so-called ‘yellow card,’ which shows that you’ve been vaccinated for yellow fever.
This isn’t just a random precaution: people die of such diseases, and anyone who comes into the country who isn’t vaccinated makes life that much more dangerous for everyone around them, because they become a potential carrier; a gap in the armor of vaccinated society.
Not only that, but they’ll turn you away at the border if you don’t have the right shots, and a record to prove it. So do a little research ahead of time, and get the vaccinations for the place you’re going, and any other place you might go while on the road. Being prepared increases your options in terms of places you can go spur-of-the-moment.
Please note that the costs can vary wildly when it comes to vaccines, so if it makes more sense to get a shot somewhere along the way rather than from your standard health provider, do that, instead. No need to reward systems that arbitrarily up the prices on such things.
The location of your country’s embassy is a useful piece of information to have on hand. This is where you should go if you run into legal trouble and for less serious issues, like adding extra pages for your passport (a real consideration if you become a long-term or full-time traveler). You can also glean information about the local political situation at your embassy (this can generally be found online, but is possibly something you’ll do in person if there is unrest in the streets and you need to better understand what’s up).
Some people check in with their nation’s embassy in every new country they visit, and some have never set foot in one.
I tend toward the latter, but many very well-traveled and intelligent people have suggested this is an error, and that I’d be better served checking in and making sure the authorities know where I’m at and what I’m up to.
The benefit of notifying your embassy of your presence is that, in case of an emergency, they can find you and make sure you’re safe. That means if there’s a tsunami, rioting, or some kind of military activity, your government knows where you are, how to contact you, and can do their best to ensure you make it out alive.
If you don’t visit the embassy, chances are they don’t even know you’re there. And the only downside (as far as I’m aware) of stopping by is that it takes time, and you may have to wait in line. Not a bad tradeoff for a little bit of insurance, should things go sideways.
It’s rare, but there may come a time that you need legal help. Maybe you’re held at a border crossing, maybe you’re being accused of something by a foreign national, and maybe there was some kind of misunderstanding you can’t quite get your head around.
In most cases while traveling internationally, the embassies will help you with these kinds of issues. If something comes up, give them a call/email/visit, and they’ll tell you what to do.
In some cases, the issue will be with your own country, and that will mean getting legal advice from someone who has your best interest in mind. For such cases, it’s a good idea to have a lawyer’s info on hand, just in case.
Ideally, this will be someone who knows at least a little about you and what you’re doing, so visit or call someone before you leave, so you know they’ll be able to help you out quickly if such help is warranted. Most lawyers will give initial consultations of this kind for free, so be polite and don’t take up too much of their time. Hopefully, you’ll never need to use their services, but if you do, you’ll be happy you took the time to make the connection early on.
It’s a good idea to understand how well your government is playing with the local government. Tensions can arise between you and locals (including law-enforcement) if there are tensions on a governmental level. If your country has been involved with unpopular international actions in the area recently (ahem, like the US is pretty much all the time), then it’s worth knowing about it, in case someone approaches you about the matter. This is not a time to put your foot down if you agree, by the way; better to verbally disparage your country in the moment and walk away without a fight.
Earth Class Mail
The most popular option when it comes to having someone else receive and manage your mail, but one that also has a mixed reputation. Do a quick search to see what I’m talking about, but also know they’ve got investors and staying power, which is something some smaller sites may not be able to claim.
Traveling Mailbox / Digital Post Mail / Private Box
Three competitors to Earth Class Mail; all have slightly different services, but serve essentially the same purpose; acting as your physical mailing address. Most are cheaper, but possibly less reliable, based on the size of the companies. I highly recommend doing some personal research before opting for any of these services, since they’ll be handling your mail and you don’t want to have such things sent to strangers without feeling comfortable about the decision.
Turbotax / HR Block
The two most popular tax software options if you’re filing in the US. It’s worth looking around for sales, which tend to pop up in the month leading up to tax season (though the prices increase at the last minute).
CIA World Factbook
Sometimes outdated, sometimes the best place to find useful information about a given part of the world. Worth checking out, especially if you don’t know anything about a place you’re visiting, particularly when it comes to figuring out how the government works and what threats warrant consideration.
To me, the process of moving is an old, familiar friend. After this many years of packing up my life, pulling up my roots and heading out — ready to plant them elsewhere — I know a thing of two about how it’s done.
In the beginning, though, it wasn’t so easy. I distinctly remember leaving Los Angeles when I was first heading out on the road. It was a tough moment; not because I had little to look forward to, and not because I would miss the lifestyle I was leaving behind, but because I was extracting myself from the familiar, the comfortable. All of my habits and goals and friends and everything would change, and driving away, headed to the airport with my bag and my passport, I looked out the window and fought the urge to play the ‘last time’ game.
You know what I’m talking about. “This is the last time I’ll see my post office. This is the last time I’ll see that grocery store I always walked to. This is the last time I’ll see that park. Oh man, I forgot to get a last slice of pizza at that one place I love. Maybe I should stop and…”
We all do it. It’s a natural response to a change in not just housing, but lifestyle. There’s a part of us that wants to make everything sentimental, and if you’re not careful, that sentimentality can really do a number on your resolve. It can make you wonder if you’re making the right choice after all. We can wipe out months of planning and years of desire for the sake of comfortable familiarity. The gravitational pull of habitual norms is something we all struggle against any time we try to pull away.
It gets easier, though. At some point, you become far more accustomed to moving, and the sentimentality largely goes away. It’s not that you feel nothing — I still cherish the memories of all the places I’ve lived since I started traveling — but the angsty part disappears almost completely. Instead, you’re left with a smile and an, “Oh, that place was cool,” smile-inducing memory. It’s an appreciation of where you’ve been, rather than a soul-crushing desire to avoid anything new for the sake of clinging to the status quo.
With this in mind, I’d like to provide some insight on a few specifics of the moving process.
Saying goodbye to friends when you move is tough. It doesn’t actually get any easier, but you can become much better at making the process less painful.
First, remember that we live in the future, and as a result there are no longer ‘goodbyes’, just ‘see you laters.’ After you leave, you will still be in touch with everyone you’re leaving behind, and in some cases, even more than you were in person. I’m in contact with my family far more now that I’m traveling internationally than I ever was while in college, just a few hours’ drive away. This is because of the ease of emailing, Facebooking, and other methods of (largely passive) contact.
Second, try not to make a big deal of it. I say this knowing that most people will still make a big deal of it, and that I sometimes do, as well. The ‘big deal goodbye’ only serves to make things sad and uncomfortable, when you should be celebrating a new beginning — a happy move, a happy trip, some happy goals to achieve. No feeling guilty or sad, because the people who are really important to you will stay in your life, and you in theirs. Not being in hugging distance won’t destroy what you’ve got with someone important.
Finally, come up with a default routine for goodbyes for different types of relationships. It sounds really cold to say it that way, I know, but all I mean is that as you find yourself saying more goodbyes, it helps to know what kind of situation allows you to leave things on a happy note, rather than descending into, say, drunken crying, or angry, friendship-ending arguments. If you find having a glass of wine and quiet discussion is the best way to say goodbye to close friends, make that part of your routine. If a large-scale party with everyone in the same room works better for how you socialize, do that instead. If a quick text message works for you, and you offend no one with how impersonal it seems, do that.
There’s no set way to do goodbyes that will work for everyone, so you’ll have to try a bunch of different methods until you find a few options that allow you to leave feeling happy (and leaving your friends feeling happy, too), while also maintaining the connection with people that you value. A quick goodbye will probably serve for your favorite barista whose name you can’t remember at the coffee shop down the street, but you’ll probably want something more personal and meaningful with your best friend since elementary school.
Establish a baseline for such things, and you’ll be surprised how much stress is removed from an otherwise potentially stressful situation. One less thing to worry about.
If you’re anything like me, you’ll acquire a few odds and ends in each place you live, and most of these things won’t be necessary or practical to carry with you on the road.
That means getting rid of stuff, which warrants a few considerations. The first is to figure out what the local equivalent of Craigslist happens to be, and attempt to sell your space heater, your mittens, or your flip-flops. I’ll do this occasionally, but generally only with expensive items I think I may be able to recoup some of my investment on.
The alternative, and the method I usually opt for, is to give your stuff away. I know, I know, it seems like a waste, assuming you can get even a little cash for the stuff you’re getting rid of. But when I buy something that I won’t be keeping beyond my visit, I tend to look at it as more of a rental, anyway. That way I can avoid the stress of having to put something up for sale, negotiation, meeting with the person who wants to buy it (if anyone does), and hoping I don’t get screwed in the process. Much easier, I’ve found, to just invest in cheap-but-functional items, then to give them away to friends and people who need them when I leave.
This can actually be a lot of fun, especially when the things you’ve purchased are out of reach for many people in the region; when I was living in Kolkata, for example, items that I considered to be fairly cheap investments were given away when I left, and the people I gave them to were overjoyed. They were things (cooking equipment, a space heater, etc) they would never have been able to justify spending so much money on, but could now enjoy. The cost for me, was relatively small, the benefit for them was sizable. What was essentially a rental for me ended up being a big payoff for people I care about.
One more point on this subject is that it’s best to avoid picking up too many trinkets along the way, lest you are forced to carry around sentimental items that lack any practical purpose. Meaning is in memories and in people, not in objects. If you want something to help you remember a time in your life, take digital photos, instead; they don’t weigh a thing, and are much better reminders than some statuette from a gift shop.
One last moving-related item I want to cover is tying up loose ends.
It’s an immense pain when you leave a country and find there’s still an electrical bill in your name, racking up debt. Even worse is that in some countries, you must pay in cash, and present yourself and your signature in person to close the account. This happened to me in India, actually, when I closed my internet account over the phone. I found, that I was still being charged months after I had left. An email indicating my unpaid status was sent to an email I only use for such purposes, and hadn’t checked because I didn’t have any utilities in my name at the time.
It took the better part of a year, help from a good friend, and way too much money to get that loose end tied up, and it wasn’t even an extreme circumstance.
As a result, I highly recommend that you keep a log of all loose ends that need tying before you leave a country. This means keys that need returning, utilities that need shutting off, routers that need to be unplugged, borrowed items that need to be un-borrowed. Make note of the relevant numbers and names, and how much lead-time you’ll need before leaving to ensure everything is taken care of. You will handle some of these responsibilities the day you leave, on your way to the airport, while others may need to be handled a week or more beforehand.
Whatever the case, do yourself a favor and keep all the information in one place so that tying off these loose ends is a quick task, not a week-long stressor. I can’t tell you how many otherwise happy departures have become gut-wrenching, uncertain situations when I realized I failed to complete some small errand as I boarded a plane. It’s easier to handle these kinds of tasks in person, believe me.
Packing is something that’s been romanticized: you can tell who’s an expert traveler based on how they pack their bag.
That’s true in movies and TV shows, at least. In real life, the level of packing sophistication runs the gamut from ‘incredibly precise’ to ‘just throw it all in there and hope it fits.’ Some people have done both, depending on how fast they’ve had to run for the airport. Others start out on one end, and eventually find themselves on the other (once the reality of travel sets in).
Wherever you might start out on that spectrum, I want to present you with a few packing concepts and considerations over which to mull.
Your packing method will directly influence the style of bag you use.
I personally opt for a fairly organized bag, though one that can be easily adjusted when necessary, and which can be packed very quickly when the need arises. As a result, I use a laptop bag that has a large zipped opening at the top, and a flat bottom. There are pockets alongside a large main compartment, and I use an elastic-band-based grid system to organize my cables, chargers, and other small objects. My main bag is a split duffle, which basically means it’s a little less structured, but has two sides, which fold out from the middle when unzipped. Each side is its own compartment, which allows me to organize in a basic way, but also just throw clothing inside, roughly rolled or folded, if I want.
Other people go the backpacker route, buying a massive, two-strapped backpack, which they fill with clothes, electronics, and whatever else, assuming that the soft bits will keep the breakable stuff from jumbling around too badly. This method tends to be cheaper and easier to set up, but it has some downsides. It’s hard to find what you need in a pinch, for example.
Still others opt for the full-on luggage-style of packing, bringing multiple bags, each one containing one type of possession (this is my electronics bag, this is my clothing bag, this is my bag for souvenirs, etc). I would advise against this for long-term and full-time travelers, simply because it’s more bag-intensive, and requires that you store them somewhere before you can explore. It also leaves you open to both looking like a tourist (not ideal if you’re trying to blend in and really see a place) and being hoodwinked. To each their own, however.
Might I Suggest
One suggestion that I will make, based on my own experiences and those of other travelers I respect, is to prepare for the worst when it comes to packing.
What I mean is that you should pack in such a way that, if one of your bags is lost, you can get by with the other. I make sure that the bag I always have with me, no matter what (the smaller of the two) is where I keep the things I need to function; small toiletries, my laptop, my passport. The other bag has toiletries, as well, and extra clothing. It helps to keep a change of clothes in each bag, just in case you end up having to check something and your other bag disappears.
It’s not easy to determine what you absolutely need when it seems like everything is essential, but you’d be surprised how quickly prioritization can happen when you lack the space to be overly needy. When doing this kind of mental exercise, you also realize quite quickly what you can pick up in a pinch just about everywhere, and what you cannot easily replace. A charger for my laptop is fairly important, and tricky to find at a train station in the middle of nowhere. A toothbrush, on the other hand, can be found anywhere these days (or mouthwash, or some other reasonable replacement).
So keep this in mind while packing: if worse came to worse, would you be able to make it without everything you own? Would you be able to make it with just that one bag that never leaves your side? Or just one of multiple bags, if all of them are at risks of being checked/lost/stolen?
Then follow it up with this mental experiment: if you do find you can make it with just one of three bags, why are you carrying the other two?
There are a few main packing methods I’ve tried and found useful, beyond the broad ‘intentional’ and ‘just throwing everything in a bag’ categorizations I mentioned above.
They are rolling, bundling, folding, and compartmentalizing.
Rolling involves rolling up all or most of your clothes into little caterpillars of cloth, and lining your bag with them. This is the method I use most frequently these days, because tightly rolling your clothing actually keeps them from wrinkling overmuch, and allows you to pack more in the same space. It also allows you to pack your clothing the same way you would stacking bricks: it uses all the space in your bag, and supports it, structurally, so there’s less shifting of clothing in transit (which is part of why there’s less wrinkling).
I find this method doesn’t get your bag searched quite so often as some other methods I’ve tried, too. If searched, or if you’re trying to find something specific in your bag quickly, it’s insanely easy to pick through everything without making a mess.
Bundling is similar to rolling in that you’re aiming for fewer wrinkles and optimal use of space. What this entails is choosing a core (in the past, I’ve used chunky workout shoes, a laptop, and an empty water bottle, at different times), then wrapping your clothing around this core. In bundling a shirt, for instance, you’d put the core on the chest, fold up the bottom of the shirt toward the collar, then fold in both sleeves. The next shirt would wrap the same way, over the first shirt. At the end of the process, you have on big bundle of clothing, all wrapped around each other, with the core in the center.
The two big downsides to this method, though, are that it’s incredibly difficult to pull an individual item from such a bundle, and it makes airline officials crazy. Which makes sense, I guess, because what they see when they’re scanning is a bag full of clothing wrapped around something, which makes them want to take a look, forcing them to undo your bundle, and forcing you to redo the bundle right there at the airport. The anti-wrinkle benefits of this model are undone by this inconvenience, but if you’re not intending to fly, it still has some utility.
Folding is probably the most common packing method folks use, and there are definite pros and cons to using it. In the ‘pro’ column, you’ll find that it’s quite easy to perform, and relatively simple to organize and rifle through, should you need to find something in transit. It also doesn’t look suspicious at all to airline officials when scanned. The downside is that it makes terrible use of bag space, and as a result, most folded clothing tends to shift a whole lot while in transit. This means your organized bag is far less organized by the time you arrive where you’re going, and the clean creases you have from the fold turn into crazy wrinkle factories. That being said, I will still sometimes fold my button-down shirts, because if you can keep the folds clean, they’re much better for more formal types of clothing. I do try to keep folded clothing in place by making sure it’s snug against the rest of my clothing, which is rolled.
Finally, some travelers swear by compartmentalizing their bags to an immense degree. Some bags come with little dividers that help make this work, but most people who do this regularly buy their own dividers, some of them made out of foam, while others are actually bags that you zip and drain of air (this is kind of a hardcore method of packing).
The benefits of compartmentalizing are that you can make sure nothing shifts even a hair, and you’re able to create perfect, custom compartments for what you’re bringing. You can also fill up excess space with dividers, which prevents the bulk of wrinkling. If you’re using airtight bags, another benefit is that you can fit a whole lot of stuff in a very small space; though the downside of such bags is that wrinkling becomes a massive problem. It really depends on how you’re traveling; if you’ll have an iron handy wherever you’re going, and won’t need to change clothes in transit, airtight bags may be worth having to carry twice as much in your bag, despite the wrinkles.
There are plenty of other packing methods, of course, and a quick search on YouTube or the web will teach you far more than you ever wanted to know about the specifics. Find something you think will work for you, try it out for a bit, and then try some other methods. I’ve arrived at my ideal only after years of trial and error, and I’m certain I’ll find even better, more ideal ways as time goes on. The art of packing is a field that doesn’t stagnate, so keep your finger on the pulse and be adventurous.
Here’s a video showing a version of the bundle method.
A video of me packing my bags, recorded by a news station in Missouri.
For many people, arriving in a new home, no matter how temporary it might be, means waiting at the airport/bus station/train platform for your ride. In some cases it might mean hopping a shuttle or light rail into town to meet someone there.
But what if you’re arriving blind, with no one to greet you?
This is how I typically show up in a new country. Though it’s not as breezy a process as having someone to hold your hand and point out the differences from what you’re accustomed to from the get-go, it can be an interesting challenge and a wonderful self-education to try and make your way solo before bringing anyone else in to help. I prefer it this way, in fact, so I have a week in a new place before reaching out to connections in the area. This allows me to think for myself and problem-solve the many issues I run into, while also being able to check what I learned against how things actually are shortly thereafter.
If this sounds like fun to you, congratulations! You’re the same type of crazy as me. Here are some suggestions as to how you can get started.
It’s smart to ensure that you know a little bit about where you’re going; details like what currency is used, what language is spoken, etc. You don’t need to speak the local tongue fluently, but if you can pick up a handful of practical words (like ‘please’ and ‘thank you’ and ‘yes’ and ‘no’), you’ll be in a good spot.
It’s also a good idea to have some kind of internet-capable device handy for when you land. You’ll want to find some kind of accommodation for the first couple days (or longer, depending on how much time you’re intending to stay), until you can get your bearings. I would recommend a hostel over a hotel, because hotels tend to be away from where locals live, so you’ll only see the touristy parts of town, and likely won’t be within easy walking distance of the interesting stuff. Hostels are full of other travelers, which makes figuring out something about the area quite a bit easier. If you can’t find any information online about hostels near the center of town, ask the information desk to help you out, then find a shuttle or taxi into town. Call ahead if you can, to see if they have a spare bed.
From there, start asking a lot of questions. Make friends with anyone who can understand you, and don’t be afraid to ask for help. Talk to other travelers about their experiences, to locals about which places they prefer to eat, and figure out where longer-term accommodation (if you’re staying longer) can be found. For me, this usually means figuring out what part of town is a desirable place to live, and figuring out where to find rental listings. I generally start with online listings, visiting the area on foot after establishing prices and what kind of amenities to expect. Some areas don’t really have the online infrastructure, leaving most rentals to be divvied out in person. How this works locally is worth figuring out, so find a middleman to help negotiate, if necessary.
Finding short-term housing in a place where you may not even speak the language sounds like a monumental undertaking, but in my experience it usually requires a lot less time than you’d think. I’ve always found a solid place within a few weeks, tops, and in all but a few cases it’s taken less than a week.
Avoid being pressured into a place you don’t like, a place in a bad part of town, or a place that’s in a part of town that’s all foreigners (that aforementioned hotel part of the city). I usually opt for something middle of the road, meaning that it’s not a mansion, but it’s not a slum. It’s the kind of place a young person attending university might live. Such places usually provide the best balance of moderate quality, with low-ish prices. They’re also usually in walkable areas, which is great, since you’ll probably lack transportation for the duration of your stay.
Throw yourself into finding a home base, and explore in between rental-related responsibilities. You might start reaching out to other people in the area — folks you know through the internet or common friends — and get their input before signing anything, but that’s up to you.
I like to have a home base before I start building a network, but that’s because I find I’m a little less apt to start building a social life before I have a place I can retreat to and be alone afterward. For natural extroverts, this probably won’t be as much of an issue.
Arriving in a new place, whether that place will be your home for hours or days or weeks or months, is an important moment. Sometimes it’s a moment loaded with meaning — a new home! I’m traveling! How new and exciting everything is! — and sometimes it’s key in a more practical sense. From the moment you touch down to the moment you take off, you’re taking in information both passively and consciously. The type of information you take in, how you process it, and what you do next, can determine what kind of experience you have in that place; good or bad, round or flat, deep or very superficial.
This is an aspect of travel I absolutely live for. I love arriving in a new place and being so out of my element. I love looking at signs and having no idea what they mean; listening in on nearby conversations and not recognizing any of the syllables; smelling foods that I can’t quite place and have never tasted.
Travel is a wonderful means of achieving the good kind of humility, because you’re almost always going to be the most ignorant person in the room, but you have the potential to learn so quickly. Self-identifying as a student is a very positive trait no matter where you happen to be, but travel forces you into that role. If you’re unable to acknowledge that you may not understand what’s going on around you, and the deeper significance of it all, you’re probably better off sticking to the tourist routes, listening to accented voices speaking your own language, and taking in a whitewashed version of wherever you happen to be visiting.
For everyone else, though, stepping into a world you know nothing about means that you can walk into a grocery store and be completely lost. It’s a strange feeling, being unable to figure out whether something is orange juice or bleach, because the packaging is unfamiliar and the words might as well be cuneiform for all the sense they make to you.
Exploring a new city is more like kindergarten than college. The things you’re learning are generally quite fundamental, and the learning curve is fairly flat. That means, with a little effort, you can pick up a whole lot about a place in a very short time, but just like kindergarten, you need to learn the basics first. Your letters, your numbers, how to tie your shoes (metaphorically, of course). The basics, when you travel, are more about figuring out how society operates. When to cross the street, what signs identify the bathroom, how to say ‘please,’ ‘thank you,’ ‘yes,’ and ‘no.’ Which foods you like and which you’re not too keen on.
You also have to find a place to stay, and once you have a home, you have to be able to find your way there from any other place you go. This sounds like a simple task, and it is, for someone who knows a place like the back of their hand; knows a place like they’ve been learning the streets and back roads for ages. But rent a place in the Medina area of Morocco and tell me the alleys are easy to navigate, for someone who hasn’t been walking them for years. Even after days of focused self-education about the area, I was still getting lost as soon as the shops closed and my landmarks disappeared. I was still hiring street kids to help me find my way back home each day.
Accept your position as a student, though, and the knowledge will come. I was in Morocco for a week, and by the time I left, I could find my way back home unassisted. After living in Buenos Aires for two months, I could tell a stranger how to get to a small street they were trying to find, and do so in Spanish, spoken with the local accent. After four months in New Zealand, I knew the roads that connected the towns of the south island like the back of my hand; I’d woven my way through them so frequently, and attentively.
One exercise I would recommend, which has served me well in all the places I’ve lived, is to get lost intentionally. Wait until you have a home base, then explore the area immediately surrounding your home. Start with learning your block, picking out some landmarks, making sure you know what’s nearby so you can tell a taxi driver or ask for directions should you need to. Then expand your radius of exploration to a few blocks away. Walk and walk and walk some more, and predict in your head what you’ll see when you turn a corner: “This street should open up to the alley that leads back to my street.” Peek down the alley. Were you right? If not, figure out why you were wrong, and correct your mental map.
Continue expanding your radius until you find a few capillary streets (main streets that, if followed, will lead back to a landmark you know) and then go out in search of novelty. Ask for museums or parks to visit, or just wander until you find places of interest. Restaurants. Theaters. Whatever you like. From those points, challenge yourself to find your way back, unaided. You may fail a few times at first, and many times I’ve tried this, I’ve ended up walking for hours, thinking I knew where I was only to find out later I was very wrong. This is a good kind of wrong, though, because it results in the discovery of new areas, and mistakes you’ll never make again. “I took that turn and it took me to that big street with the theater, instead of to the side street with the park.” As a result of my mistake, I’ve learned something important, and that solidifies the discovery, and that portion of the mental map, in my mind forever.
There’s no set time period to continue this exercise, but ideally you continue to do it throughout the time you’re in a new location. Really challenge yourself to become an expert, and you may find you become even more versed in the specifics than some locals. I can’t tell you how many times I’ve known about hole-in-the-wall restaurants with amazing food that locals have never heard of, simply because I’ve walked and walked until I know every little detail of my portion of a city. A normal benefit of exploration is finding treasure. Share that treasure with others when you can.
One more point to bring up is that you should always be as safe as reasonably possible, and you should ask around to figure out which parts of town should not be explored on foot, or which parts foreigners should avoid.
There are less savory places in every city, and you won’t necessarily know where these places are just by looking, so be as informed as possible about these types of hazards. In general, people in the places you visit will be just like you; willing to help someone out if it’s clear they don’t know where they’re going or what they’re doing.
Don’t depend on that if you can avoid it, though. You’ll keep tabs on the local currency conversation rate and which diseases for which you should get vaccines, and you should also figure out which are the rough parts of town and avoid them until you know enough to be prepared.
Networking is either fun or terrifying or boring as hell, depending on who you ask. I tend to view it as the former, but that hasn’t always been the case. I haven’t always understood the benefits of networking, and the important role in plays in the life of a traveler and well-rounded person.
For the purposes of this book, networking means meeting people and establishing relationships. Those relationships will be of all kinds, ranging from business to romance to friendship to the myriad options in between. The concept is that you make contact with folks you don’t know, get to know each other, and figure out what role you want to play in each other’s lives.
Networking tends to involve a great deal of talking, but you have to be a good listener to do it well. You often benefit greatly from having a well-rounded network, and it’s good practice to kick-start relationships by trying to help others. The entire process can be a little counter-intuitive if you’ve never done it before, but there are a few concepts that should make clear why it’s a good use of your time, and how you can jump in without overcomplicating things.
Having an extensive network gives you connections to many different industries, different types of people, and different resources. If you’re well-connected, it’s far easier to accomplish your professional goals, learn about an area, and get a well-rounded view of a culture. It’s also the best way to make friends, which is a benefit that’s harder to quantify, but key to happiness.
I’ve spent a lot of time building a network of people I know, respect, and trust. As a result, I can go just about anywhere in the world and already have connections lined up; folks who are friends of my friends, who know me through my work, who follow me on a social network, or who have been introduced through a mutual business connection. These types of connections are like getting a recommendation for a wonderful restaurant: there’s a chance it won’t go anywhere, but the potential for a solid match, of you and the other person liking and respecting each other, is much higher than if you try to meet people randomly.
One good friend in a new place opens up all kinds of doors. Suddenly, there are people who can introduce you to local customs, holidays, and other things you may otherwise overlook and never know about. They may introduce you to more friends, too. In many cases while traveling, 99% of my network in an area has been the result of one good friend who insisted on introducing me to everyone they knew. The result is a large, interconnected network of friends, all stemming from someone who gets me and knows what kind of people I want to meet.
A network is something we all end up with, one way or another. In many cases it just kind of happens; we build a rag-tag collection of friends, lovers, colleagues, and the like; cobbled together from people we sit next to at work, and people we went to school with a decade before. These are relationships that grow sometimes from a great deal of shared interests and respect, but just as often from coincidence; this person works in the cubicle next to me, so we’re ‘friends.’
A good way to look at networking while traveling is as an attempt to build a life somewhere new. Because you don’t have all those years behind you in which to build friendships of convenience, though, you aim for more ideal relationships; ones that are based on commonalities and the desire to be around each other, to help each other reach goals, and to geek out over something obscure. It’s being able to pick and choose the people you surround yourself with. Definitely worth investing some time to make sure you do it right.
How to Network
So how do you get started?
That really depends on you. If you’re kind of quiet, it’s not the best idea to pretend to be the loud guy at the party, because that will come across as disingenuous. Instead, you’ll want to find people who bring out the real ‘you,’ and who you enjoy being around. Folks who share common interests and goals, and understand you and your worldview.
I’ve got a few networking tips to share that are fairly universal.
The first is to be friendly by default. It sounds like common sense, I know, but you’d be surprised by how much terrible advice is out there about ‘being alpha’ or ‘establishing dominance’ in a conversation. Don’t listen to that drivel; it makes you come across as a jerk, and no one likes a jerk. Be nice. Be helpful. Be interested and curious.
On that same note, it’s a good idea to provide value where you can. What that means is, rather than asking for something from people, figure out what you can do for them. Don’t be all salesy about it, but know that, generally, there’s something simple you can help out with, and in doing so you’re both being a good person and showing this new acquaintance what kind of person you are. This could be as simple as showing interest in something that interests them. It could be offering to connect them with someone you know who works in a field they’re trying to break into. It could be offering advice if you’ve been to a country they’re wanting to visit. Simple things, really. Small things. But things that are quite valuable and happiness-inducing, especially coming from someone who was so recently a stranger. Be the person people like to know, and like to introduce around, and you’ll never have any trouble making, and keeping, friends.
After you’ve met someone you want to stay in touch with, it’s a good idea to follow up in some unobtrusive manner. Social networks like Facebook or Twitter are a great way to do this, because it’s a light touch when compared to exchanging phone numbers. It’s a move that says, “Hey, you’re interesting, I’d like to keep in touch with you,” rather than something more formal, which tends to come across as, “WE MET AT THAT PARTY AND WE MUST BE GOOD FRIENDS SO BE FRIENDS WITH ME IMMEDIATELY!”
Send a friend request, shoot them a quick message, or give them some other equally lightweight means of remembering who you are, having your name and contact information on hand, and knowing that you’re interested in maintaining contact. The level of contact you both want to maintain determines what happens next. There’s a chance you’ll never speak again unless you or they need something that the other is capable of providing, like an introduction to someone else, or information about a country you’ve visited, but there’s also a chance you’ll set up a coffee chat or something else that deepens the relationship. Either way, you’ve politely and cheerfully built a bridge between yourself and someone else; that’s all there is to it, really. That and continuing to be a good (non-jerk) person, which I’m sure you are, anyway.
It’s worth noting that you shouldn’t view people as resources to be used; if you get something from someone — a connection, help with something, knowledge, or a professional leg-up — do what you can to help them, too. Even if it’s years later, it’s nice to make sure others know you’re available if they need you, even if they never take you up on the offer (or vice-versa). Being willing to do what you can for people (within reason, of course) ensures that people are generally willing to help you out when you need it. The value of this cannot be overstated, but the same value dissipates easily if you take advantage, or treat people like debtors who owe you something. Don’t do that.
Being an Ambassador
There’s one more small detail I want to mention, and it’s a twist to the networking thing that applies because you’re meeting new people while traveling.
Because you’re going to be traveling internationally, and because you’re coming in to someone else’s home, it’s best to view yourself as an ambassador for wherever you come from. Like it or not, that’s how people will view you, and if you make an ass of yourself, folks will be telling tales for a long time about the ignorant lout who visited from (insert the name of your country here) and upset everyone. If you get drunk, trash your hostel, and treat the locals like servants, you’re making your country, and everyone else from it, look bad.
Coming from the US, a place with such a mixed reputation internationally, I’m acutely aware of this fact. Our government has a pretty bad record for going to war all the time, and treating visitors to our country harshly, visa- and immigration-wise. That being said, the reputation is balanced slightly by the types of Americans who travel, and who stay in hostels. From what I’m told, we tend to be fairly well-behaved, polite, and don’t get too drunk and rowdy. Some European countries, on the other hand, have the reverse rep: their governments don’t terrorize folks as badly as the US government, but their people have a bad reputation because of the drunken gap-year kids traveling around developing countries, treating entire cities as bars built for trashing.
What really sucks is that it’s probably a very small fraction of the travelers from these countries that are acting so impolite. It could be 1% of them, but because they are ambassadors for their countries, it’s those acts that are remembered, and the well-behaving folk suffer for it.
Don’t be a bad ambassador. Be polite and treat other countries the same way you would treat the house of a friend you’ve been invited to visit. Don’t be the jerk who ruins travel for your countrymen and women. It’s a globalized world we live in, and the bad decisions you make reflect on far more people than you’ll ever meet. Make sure those reflections are good ones; stack the deck in a positive way, not a negative one.
You’re on the road, you’re growing as a person, you’re learning all kinds of things, all the time, and you’re connecting with amazing people.
How wonderful! For you. But what about sharing your experiences — the things you’re learning, seeing, and doing — with others? With folks who haven’t done much traveling? Or those who have and who can’t wait to get back on the road?
Documenting your journey is a good habit to be in, not just for a future version of yourself, for whom the experiences you’re having today might have faded, but for other people around the world. People who can live vicariously through your adventures, learn from your mistakes, and benefit from your insight.
How you do this is completely up to you. Some people set up online platforms through which they can share their tales (blogs, photo journals, social media), while others snap a bunch of photos, jot in journals, and either keep these artifacts for their own future perusal or use them to write some kind of book or publish some kind of album. Whatever the case, it’s worth your time to try out myriad methods of media collection, because some will capture what you want to take with you, while others will fall flat. Some will fit smoothly within your mode of operation, while some will be a wall between you and the experiences you should be enjoying.
I make use of both sides of the spectrum. I share stories as they happen to me, through my blog, and through an email publication called Exiles. I also jot down notes and take photos that I can use later to recall conversations and events later, giving me details I may not have otherwise recalled (especially dates and times) which I can use in stories that populate my books.
I do have a policy about enjoying the moment, however. I’ll tweet or Instagram something interesting when I see it, but will first take the time to experience it myself. If I’m documenting proof of something most people won’t believe, I’ll reach for my phone to snap a photo immediately, but otherwise I hold back, taking in all the details firsthand, then maybe sharing it with others if I feel it’s worth spreading. This not only keeps me from putting a bunch of garbage out into the ether, but it allows me to approach the world like an artist, collecting a moment in sight and sound and smell and taste and touch, before I reduce it down to a flat photograph or movie clip.
Alongside stories and amazing views, insights are frequent companions while on the road, and many will be worth sharing with folks back home. That’s not to say every little thing that comes to mind will be gold, but because you’ll be out of your comfort zone, viewing the world from a novel angle, and probably experiencing things that flip your expectations, some of the questions and quandaries and quibbles that come to you will be worth putting out into the world. Tweet them, Facebook them, blog them, or send them in a newsletter. You can just jot them down for later analysis, too, if you like. It’s worth hanging on to some of these things, so long as they don’t result in piles of physical journals you have to lug around. Thankfully, there are plenty of apps available that alleviate such weight from the traveler’s bag.
Also in the vein of documentation are the answers to questions you might have about yourself, humanity, the world, and anything else. Many people travel and undertake massive lifestyle shifts because they’re looking for something. In my case, I knew what it was to be successful on one possible lifestyle track, and I knew that wasn’t a race I wanted to run anymore. I wanted to know what else was out there, and if my curiosity was warranted. I wanted to know how much I didn’t know (a lot). There were so many things I felt I was missing out on, but didn’t even know where to start in terms of finding out what they might be. These things are part of what I write about; the crazy interesting tidbits that I wasn’t aware I didn’t know.
Scrivener / Evernote
These are my go-to programs for publishing the written word. I use Evernote to write blog posts and takes notes along the way, and I use Scrivener to turn those notes and writings into easily published books and ebooks (the book you’re reading now was published using Scrivener).
In travel and in life, default to safe.
‘Safe’ can mean wildly different things to different people, however, so let me be clearer.
When you’re traveling, do your absolute best to prepare for worst-case scenarios. Meet enough good people that you can avoid getting scammed or hurt, and so that you can be aware of which people or parts of town to avoid. Don’t allow your views to become prejudiced as a result, but know how things work so you can act accordingly (a good example of this are the Romani — gypsies — in Romania; I met some truly wonderful people from this group while living there, but as a general rule, the ones you don’t know will try to rip you off).
Have a few phone numbers you can call in a pinch, should you get lost or in a bad situation. Meet new people in public places, and travel in groups. Don’t get drunk and wander around at night; that’s just asking for trouble. Avoiding taking any substances (legal or illegal) that didn’t come from a close, very trusted friend.
Make connections, and be seen. It’s good to have friends, but it can be equally valuable to be on smiling, waving terms with the guy who runs the fruit cart down the street. I can’t tell you how many times I was prevented from making a dangerous decision by strangers who were kind enough to flag me down.
Lock your doors. Be aware of your surroundings. The best way to avoid a bad situation is to pay attention to what’s going on around you and trust your gut when something seems off. I was attacked by muggers in Buenos Aires, and I saw it coming, literally a block away. I knew I was about to be mugged, but shrugged it off, assuming I was overreacting to the situation. Trust your gut and opt to look foolish rather than falling prey to a preventable tragedy.
Know that 99% of the people you meet won’t mean you any harm, and will do all they can to ensure you feel safe and have a good time in their country. It’s that remaining 1% that ruins everything. Don’t make the other 99% suffer for the bad eggs in the group, though; don’t treat people as if they’re trying to pull one over on you. Just be aware and prepared and don’t let anyone force you into an unreasonably uncomfortable situation. Beyond being firm on that, be willing to say ‘yes’ to new foods and experiences and friends. Being prepared and safe makes you more capable of safely taking risks.
In summary, look at travel the same way you look at flying on a plane. Yes, there’s a chance your plane could crash, but it’s incredibly unlikely. Likewise, there’s a chance something bad could happen while you’re traveling, but it’s also incredibly unlikely. You have a better chance of being hurt in a car than in a plane, and you very likely have just as much opportunity to fall prey to bad people at home as you do abroad.
The reason travel seems more dangerous is the same reason flying seems more hazardous than riding in a car: we understand less about the mechanics of the situation, and drive a lot more than we fly. Similarly, we understand how things work at home, while the mechanics of society abroad seem unfamiliar and scary.
Don’t let that worry keep you from enjoying yourself. Take necessary precautions, but don’t be afraid to get out there and have a meaningful experience. Meet people. Try things. Live.
It’s been said that the world is a book, and those who don’t travel only read a single page. Don’t deny yourself the opportunity to find out what happens next, for fear of getting a paper cut.
These guys have a wonderful reputation, and though I’ve never had to make use of their services (thankfully), I do buy insurance through them in countries where I don’t get coverage by default. A great idea, for peace of mind and just in case.
You’ve just read a very brief synopsis of what it is to travel as a lifestyle, some of the repercussions of doing so, and how to do it best.
There’s far more to be said on the subject and many people with ideas worth listening to. If you’re truly interested in hitting the road and seeing where it takes you, don’t let your exploration stop here. Below is a collection of resources worth checking out. Give them a look, and you may find something that resonates. Note that these are just a few options: there are tens of thousands of blogs and sites dedicated to different aspects of travel, so do some searching, and click around. Take a look at the resource pages to find recommendations and more information on the specifics of how these other people travel.
Travel has been one of the most important, positive influences on my life, and if it sounds appealing, I would encourage you to avoid what I like to call ‘paralysis by analysis;’ never acting on your desire to travel, and instead spending all your time reading and thinking about it. If this is something that you really want to do, get started now. Start putting together your platforms, reaching out to folks around the world to make some initial connections, and planning a first step. It may take time to get there, but the sooner you take the first step, the more likely you’ll actually do something about it.
Feel free to connect with me via one of my platforms, as well. There are links to my other work in the following pages, along with links to my blog, newsletter, and social media accounts. Stop by and say hello, and take a look at some of the other things I’ve written, if you’re interested.
Best of luck with your next steps! They won’t be as easy as the ones taken along well-worn paths, but it’s a lot more fun to blaze your own trail.
ABOUT THE AUTHOR
A great big thanks to the folks who helped me whip this book into suitable shape for publication:
Curtis Scott, Sean Rogers, Dan Bowen, Justin Nozuka, Alasdair Martin, Evie Socarras, Kristen Snider, James Syverud, and Shawn Mihalik.
Any typos or other mistakes are probably the result of me ignoring their damn good advice.
“To travel hopefully is a better thing than to arrive.”
—ROBERT LOUIS STEVENSON
“To travel is to discover that everyone is wrong about other countries.”
That we might all be ambassadors for good ideas, open hands, and a shared human culture.