Table of Contents

Introduction

Chapter 1 - A Month in the Life

Chapter 2 - Home and Away by Rolf Potts

Chapter 3 - Getting Started

Chapter 4 - Outdated Perceptions on Cost and Risk

Chapter 5 - Social Aspects of Nomadic Travel

Chapter 6 - Go Deep by Derek Sivers

Chapter 7 - Crazy Flight Deals

Chapter 8 - Flight Tricks

Chapter 9 - Loyalty Programs

Chapter 10 - Travel Cards and Programs

Chapter 11 - Airport Lounges

Chapter 12 - Credit Cards

Chapter 13 - Currency Conversion and Management

Chapter 14 - Banking

Chapter 15 - Jet Lag

Chapter 16 - Visas

Chapter 17 - Funding a Nomadic Lifestyle

Chapter 18 - Where to Stay

Chapter 19 - How To Meet People While Traveling by Todd Iceton

Chapter 20 - Getting Around Cities

Chapter 21 - Phone Service

Chapter 22 - Traveling with Children by Leo Babauta

Chapter 23 - Empire Housing Method

Chapter 24 - Las Vegas as US Home Base

Chapter 25 - The Cruise Hard Sell

Chapter 26 - Travel Gear

Chapter 27 - Checklist

Chapter 28 - Troubleshooting

Chapter 29 - Two Cities To Visit

Forever Nomad

By Tynan

Table of Contents

Introduction

Chapter 1 - A Month in the Life

Chapter 2 - Home and Away by Rolf Potts

Chapter 3 - Getting Started

Chapter 4 - Outdated Perceptions on Cost and Risk

Chapter 5 - Social Aspects of Nomadic Travel

Chapter 6 - Go Deep by Derek Sivers

Chapter 7 - Crazy Flight Deals

Chapter 8 - Flight Tricks

Chapter 9 - Loyalty Programs

Chapter 10 - Travel Cards and Programs

Chapter 11 - Airport Lounges

Chapter 12 - Credit Cards

Chapter 13 - Currency Conversion and Management

Chapter 14 - Banking

Chapter 15 - Jet Lag

Chapter 16 - Visas

Chapter 17 - Funding a Nomadic Lifestyle

Chapter 18 - Where to Stay

Chapter 19 - How To Meet People While Traveling by Todd Iceton

Chapter 20 - Getting Around Cities

Chapter 21 - Phone Service

Chapter 22 - Traveling with Children by Leo Babauta

Chapter 23 - Empire Housing Method

Chapter 24 - Las Vegas as US Home Base

Chapter 25 - The Cruise Hard Sell

Chapter 26 - Travel Gear

Chapter 27 - Checklist

Chapter 28 - Troubleshooting

Chapter 29 - Two Cities To Visit

Introduction

I wrote my first book on travel, Life Nomadic, six years ago. Fresh off of a few years of nonstop traveling for the first time in my life, I was starry eyed and felt like I had to shout from rooftops, “there’s a whole other world out there! It’s even better than I thought! Come see!”

It felt as though I’d travel forever, I so preferred it to normal life. And then the downsides of constant travel, namely social distance and high mental overhead, started to kick in. I convinced myself that I would stop traveling so much.

I quickly realized that stopping wasn’t possible. I’d made friends all over the world and I wanted to spend time with them. Different places had different things to offer, and I didn’t want to miss out. I’d figured out how to get impossibly cheap flights, and I had a tough time saying no to them.

For a few years I oscillated, always feeling as though I should travel less, but never regretting any of my trips. I eventually accepted that there was no cure for the travel bug, and that if I was going to keep traveling constantly, I ought to figure out how to do it in a way that worked and wasn’t filled with tension.

I didn’t realize it when I started traveling in 2008, but I was one of the first real digital nomads. I learned from my predecessors, the backpackers, and along with other people at the time, blazed a new trail. We cracked the code on how to live a life without an address, beyond just escaping life for an extended vacation or gap year.

In addition to the tricks and principles I uncovered, the travel world changed around me. Airbnb started, credit cards started dumping mounds of miles on their holders, and technology advanced to a point where global internet access has become easy.

My aim in this book is to bring you into our world, and to describe to you a lifestyle which I suspect most people don’t realize is both possible and within reach. I’ll share the broad strokes as well as every single tip and trick I’ve figured out along the way, a good chunk of which cannot be found anywhere else.

This is a lifestyle that, like every other lifestyle, includes sacrifice. I won’t paint it as a perfect life that’s ideal for everyone, because no such life exists. By the time you finish the book you should have an idea of what the nomadic life is like, what it takes to live it, and how exactly to do everything. You may feel a stirring to jump in and see if it’s the right lifestyle for you, and I hope that you do that. It’s a risk worth taking.

I will also discuss a new style of traveling which I’ve pioneered, and which I believe is the future of long-term travel for digital nomads. It may sound so outrageous that you will be tempted to dismiss it out of hand, but I’d encourage you to sit with the ideas and really examine them objectively. Using them, my friends and I live better lives than I could have imagined when I first started traveling, and we do it for less money than most people with normal lives spend.

Chapter 1

A Month in the Life

As I looked over my past month, I realized that it was a good illustration of what a permanent nomadic life looks like. I hesitate to share the details for fear of coming across as though I’m trying to brag, so let me begin with a disclaimer. The whole point of this book is to live an exceptional life more inexpensively and easily than conventionally considered possible. By the end of the this book, even the most extreme aspects of this month should make sense and seem within reach, should you choose to reach for them.

This time last month I was in Las Vegas, where I own an apartment. Normally that’s my time to hunker down and be productive, but a friend from New York was in town, so I was busy showing him around and trying to convince him to move to Las Vegas as well (I will also attempt to convince you in a later chapter).

On the same day he left, a friend from Japan flew into town. I met him ten years ago, when I first began traveling, and we’ve become better and better friends, seeing each other a few times a year, mostly in Japan. I picked him up from the airport, gave him a whirlwind tour of Las Vegas, and then we both headed to the airport to fly out together six hours later.

Our red-eye flight took us to Halifax, Nova Scotia, where we own an island with a few other friends. One of the other owners showed up shortly after. Earlier in the summer I built myself a cabin with an office upstairs, so for the first time ever I had a productive week on the island. During the day I’d nail shingles onto the cabin or do other projects, and then at night I’d sit at my desk and write or do coaching calls. In Las Vegas the only nature available is rock and desert, so it’s nice to get out into the forest and smell the leaves and soil.

After a week of work, manual labor, hanging out around the fire, and very nearly losing our boat due to a severed rope, I headed back to the airport and began a journey to London. There aren’t a lot of Halifax to London routes, so I ended up having a nine hour layover in St. John’s, Newfoundland. Because my life is so geared towards travel, I was able to catch up on phone calls and get a full work day in, so it wasn’t much of an inconvenience.

I landed in the morning in London with no jet lag. I booked the flight several months prior and had failed to notice that I had another very long layover in London. I texted a British friend to see if he was around and free, and he was. For logistical reasons we bought him the cheapest flight out of the airport so that he could get through security and meet me at the airport lounge.

He joined me in the Gatwick No. 1 Lounge, one of my favorites anywhere in the world, and we had a nice breakfast for free. Afterwards I made him some tea that I had picked up in China the previous month.

He walked me to my gate and I hopped onto a short flight to one of my favorite cities ever, Budapest.

Upon arriving, I power-walked a familiar route through security and customs and to the airport bus stop. I bought a ticket for a few dollars and boarded the bus. In just over half an hour I was at the city center stop, which is a quick five-minute walk from the flat my friends and I bought there. I used my key to get in and responded to emails for an hour while I waited for my sister and her fiancé to get there.

In the past year I’ve been focusing on traveling with my family, and that trip was the first time my sister had ever been to Europe. We hit the ground running, visiting one of Budapest’s famous bathhouses and then having dinner before going to sleep. The next day we saw an opera and my brother flew in as well. It was a jam-packed stretch of five days where I got very little work done, but it was well worth it to share my favorite city with my family.

Once they left I snapped into productivity mode and did all of my coaching calls for the month as well as other tasks which had piled up. Another nomad friend who co-owns the flat came in halfway through the week so we spent time catching up, enjoying Budapest, and working. I spend enough time in Budapest that I have a bunch of friends there now, so I also got to catch up with all of them.

From Budapest I took a brutally early flight to arrive at Rome. I met another friend at the train station there and after a quick gelato breakfast at La Romana (check it out if you’re ever in town), we got on a different train and headed for Civitavecchia.

Civitavecchia is Rome’s cruise port. We checked in and boarded our cruise ship, which will have been our home for two weeks by the time we disembark in Puerto Rico. Most people think of cruises as vacation, but we’ve been using it to get work done. I’ve been working on this book every day, with plenty of breaks to eat good food, work out, climb the artificial rock wall, play mini golf, and drink tea while staring out at the sea.

It’s been an excellent month, but not an unusual one. The locations and activities change, but the core components don’t. Having a nomadic life allows me to spend quality time with my friends and family, experience the best that the world has to offer, and get important work done, all without hassle or stress.

Your ideal month may look nothing like my month, but that’s the point. Using the techniques and ideas in this book, you can figure out what your ideal lifestyle is and then make it a reality with as little friction as possible.

Chapter 2

Home and Away by Rolf Potts

Rolf Potts is a legend within the nomad community, having influenced everyone in my generation of nomads, either directly or indirectly. His book, Vagabonding, is absolutely required reading for the modern nomad.

Years ago, while I was trying to finish writing a book about the philosophy of long-term travel, I ran into a problem while outlining the final chapter. My intention in this chapter had been to speak to the importance of—and difficulties inherent in—returning home after an extended, life-altering journey. The problem was that I had not yet returned home myself—I was writing my book in a residential hotel room in southern Thailand, and the very notion of "home" was, for me, at the time, vague.

Yet, somehow, I had intuited that returning home—or, perhaps, finding a new sense for home—was a key part of the travel process. By that point in my life I'd been traveling through Asia, Europe, and the Middle East for nearly three years. Add in the two-year expat stint I had spent teaching English in Korea, and it had been five years since I'd lived in the United States for any extended period of time. Since I'd found steady work as a freelance travel writer, I could have extended my overseas journey another five years—but somehow I knew the point of a long-term journey isn't to travel indefinitely: the point is to travel in such a way that it enhances your life in a way that is unique to your own way of being in the world.

In many ways those three years of wandering across distant continents gave me the best experiences of my travel career, and I've never quite traveled with the same existential intensity as I did back then. The book I wrote in that room in Thailand, Vagabonding: An Uncommon Guide to the Art of Long-Term World Travel, has since been through dozens of printings in several languages worldwide, and I've visited dozens more countries on every continent on the planet. I've driven a Land Rover across the Americas, sailed the Aegean Sea, hosted a Travel Channel special, started a summer writing workshop in Paris, lectured at Penn and Yale, lived multi-month stints in New Orleans and Havana and Rio, written three more books, and—in a test of extreme minimalism—traveled around the world for several weeks with no luggage or bags of any kind. These new adventures were all great, but they couldn't really compare to that first overseas vagabonding journey because they were happening to a person who was already used to traveling. The thrill of traveling long-term for the first time is a singular joy by the very nature of its freedom-rich novelty, and the more you travel, the more your relationship to it changes.

This needn't be a bad thing. The more you travel long-term—and the more you realize that long-term travel is cheap and accessible enough to do again and again over the course of a lifetime—the more it becomes an integral part of your life. As travel becomes more integral to your life it also becomes less novel, of course—but it also becomes deeper and richer, slower and more nuanced. One of my favorite travel acts in the years since I wrote Vagabonding was getting a home of my own on 30 acres of prairie near my family in north-central Kansas. On the surface living in a home-place where you can be still and centered would seem like the opposite of travel, but in a way my many years of travel have made my time at home seem that much more satisfying—and being there is not separate from, but very much a part of the greater journey.

Everyone travels in different ways, and I think every experienced wanderer balances the idea of home and travel on his or her own terms. But one amazing thing that travel teaches you is that coming home—or finding home—after a long trip doesn't spell the end to your wandering; it just deepens your relationship to the adventures yet to come.

Chapter 3

Getting Started

If you’re already somewhat nomadic, you can skip this chapter and dive into the rest of the book. On the other hand, if you’re new to this sort of travel, let me offer some advice on getting started.

Choose a place and a date, read the chapter on getting good flight deals, and book a flight.

There is never a right time to drop everything and go on a big trip. It’s even more impossible to find the right time to sell everything and become a full-time nomad. Accept that there will be conflicts, but book a trip anyway.

If you don’t know where you want to go, jump ahead to the chapter on my two favorite cities, Tokyo and Budapest, and choose whichever one appeals to you more. Both offer a very wide range of reasons to visit and are very accessible.

Once you book your flight, read through the rest of the book. It will be a lot more applicable when you look at it through the lens of an upcoming trip. Some of the advice will fit your situation exactly, and other bits can be left for a later time.

My goal isn’t to make you an expert immediately upon reading this book. It is to accelerate your learning curve, maximize your chances of enjoying life as a nomad or semi-nomad, give you some ideas for the future, and help you avoid some of the mistakes I had to make.

At the same time, you will have your own trials and tribulations. You’ll book a train for the wrong month, show up at the wrong airport, get horribly lost just as your cell phone dies, and accidentally visit an island during monsoon season. You’ll never totally eliminate those sorts of mistakes, and I’m not sure you’d want to anyway. Some of my best travel stories have come from the dumbest things I’ve done.

Using this book you’ll be able to make your path through those mistakes as comfortable, enjoyable, and efficient as possible.

Most excuses for not traveling or delaying travel stem from fear rather than legitimate concerns. If you can’t afford it, even with all of the tricks in this book, it’s probably best to return the book, save up money, and circle back to travel once you’re in a better financial situation. If your hesitation is due to another reason, examine it very closely and make sure it’s not just fear inventing an excuse for you to stay within your comfort zone.

Chapter 4

Outdated Perceptions on Cost and Risk

Just twenty or thirty years ago, traveling was very different. Flights were much harder to find deals on and were generally much more expensive. Rather than book a flight in minutes on your computer, you might have to deal with a travel agent. How would you know which hotel was good, or even which area was good? You had to read guidebooks, which were only as accurate as the recency with which they were printed.

I suspect that traveling was much safer than people thought it was back then, but it was certainly more dangerous than it is today. Violence levels in nearly every aspect have declined in the preceding decades, and it’s far easier to get up-to-the-minute information on what’s going on in a city and whether or not it’s safe to visit.

In other words, travel used to be a pretty big deal, and it was expensive.

These days travel is remarkably safe and inexpensive. Many people like myself travel around constantly with no regard for the cost, simply because we know that it costs almost the same amount to travel as it does to stay put.

If you feel as though travel is too risky, too uncertain, or too expensive, think about where that belief actually comes from. It probably comes from either outdated experience, or from “common knowledge”, which hasn’t been updated with the conditions of today.

The truth is that, done right, a life filled with travel is no more expensive, dangerous, or stressful than one without it.

Most people would tell you that it’s more expensive to travel than it is to stay put, but that’s an idea rooted in the fact that most people overpay for convenience and “luxury” on vacation and assume that the costs of constant travel would be similar.

Maybe the most powerful factor of permanent nomadism is that you can scale your spending up or down on the fly to match your financial situation as well as other factors.

Let’s say that you run an online business and are spending time in Tokyo. Tokyo isn’t as expensive as most people believe it is, but it’s not the cheapest place in the world to stay. Suddenly a situation comes up with your business that has squeezed your income and will require a month of your time to fix. You can hop a cheap flight to Thailand, live rather well for a few hundred dollars for a month, and then go back to Japan or somewhere else.

If you don’t travel a lot now, this may seem like a big uprooting, but when you travel a lot, such transitions are trivial. Maybe your travel day would be a little less productive than usual, but the next day you’d be right back on track.

Most people in normal living situations have almost zero flexibility in their monthly expenses. They have to pay rent, bills, and maintenance on all of their possessions. A stationary lifestyle is seen as safer than constant travel, but this is one way in which it is not.

Especially among internet entrepreneurs, it is extremely common to move around to vary costs. Even if there’s no cause for decreasing costs, you can oscillate between high and low cost places to live an average cost life that’s anything but average.

Chapter 5

Social Aspects of Nomadic Travel

Worldwide Friends

Those seeking isolation can find it while traveling, but it is by no means part-and-parcel with the nomadic experience. Nomadic friendships, however, are different from stationary ones, and the differences deserve some explanation.

Maybe the biggest difference is that the well from which you draw your friends becomes much larger. Whereas before you may have primarily made friends with people only in your city, a nomad can make friends with people from all over the world. I have good friends I see regularly who are clustered it at least ten different cities.

You also tend to get the cream of the crop, if you define that as people who are open-minded and adventurous. I once told a traveling friend from New Zealand that I always loved Kiwis. “No,” he said, “you love Kiwis who travel.”

He was half-joking, but there’s some truth in that. The people who travel, and thus the fellow travelers you meet, are often pretty interesting people. They’re open-minded enough to explore new cultures, brave enough to leave their own, and have the benefit of the sort perspective derived only from long-term exposure to the world.

The downside, of course, is that you won’t see them as often as normal friends. This is a real downside and can never be fully mitigated. I found that it bothered me a lot less as time went on and I had so many traveling friends that I wouldn’t be able to see them all very often anyway. Now there are many I see several times a year as well as many more I see every year or so.

I’ve found that these friendships have all become the sorts of friendships where you just pick up where you left off, and it feels as though no time has elapsed, even if you haven’t seen each other in a couple years. I don’t know exactly why this is, but I suspect that all of us nomads have just learned to pick right back up because it’s the path to having successful friendships.

I Do The Work

An attitude I’ve adopted and found very helpful in maintaining international friendships is that I always do the work. In other words, I’m the one who has chosen an unconventional lifestyle, so I believe that it’s my responsibility to bear most of the burden of maintaining the friendship.

What this looks like in practice is that I go way out of my way to see my friends, even if they’re in different cities or countries, and that I don’t expect them to do the same for me.

For example, some of my dearest friends are in San Francisco, a city in which I no longer live. Since they all have businesses and jobs there and can’t travel as much as I can, I make sure to go back all the time. I even have a standing policy of flying from Vegas to San Francisco any time anyone invites me to anything, even if the cost doesn’t really make complete sense.

I consider that extra cost to be like insurance, a small cost I pay in order to have a good long-term outcome.

I also organize trips for friends, since that’s something that is easy for me and somewhat difficult for them. I’m comfortable doing the work to make things like that happen because of the ease differential, because I like to share my world with them, and because it’s another way for me to see them more often.

I even extend this principle to communication, though I admit I’m not quite as diligent about this one. I try to text or call my non-traveling friends more than they text or call me, since I’m the one who made the decision to not live in the same city as them.

Intense Short Friendships

There’s an interesting type of friendship that you experience frequently as a nomad, but that has no analog in normal life.

You meet someone or a group of people, and you end up hanging out all day for a few days or weeks. Maybe you even make plans to go to another city or country with them. And then when you part ways you never see or speak with them again.

This probably sounds extremely weird if you haven’t experienced it, but it feels very normal when you travel. If I’m in one of my home cities, my bar for making friends is high. They have to be people that I really respect and share a lot of values with. I have these standards because I know I only have so much quality time to devote to friends, so I want to make sure those slots are filled with really amazing people.

When I’m traveling, though, I know that there’s no expectation the friendship will last. Everyone has something to offer and a different perspective, so traveling is a good opportunity to get to know someone without any pressure. You can lower your barriers, do activities with them, and never see them again.

I once stayed in a hostel in Qatar with my friend Todd. The only other occupant we met was a sixty-something solo traveler from Australia. On a whim we invited him to come ride 4x4s with us in the desert. We were shocked that he accepted, but we had a great time with him then and afterwards. We probably wouldn’t have ever gotten to know each other in normal life, but it makes sense when traveling.

And, of course, sometimes these friends evolve into more. I have very close friends in Tokyo who I initially expected I’d never see again after my first visit. When you meet people as you travel, be aware of this common type of friendship, and embrace it. It will probably be responsible some of your best memories on the road.

Dating and Traveling

If you’re a woman, then you are in luck. Most nomads are men, so you will have your pick of the litter and can date someone who has a compatible lifestyle. Other aspects of being a woman are a little harder while traveling (though certainly not prohibitively so), so I’m glad they get that big bonus.

Men, on the other hand, are most likely going to end up dating someone who travels less, at least until the gender ratio evens out, which I hope will happen one day.

To be completely honest, dating is the most difficult part of being a nomad. I can’t tell you how many times I’ve gone on a promising first date, seen some confusion when I suggested we next see each other six weeks later, and returned to find out that she’d begun dating someone else. That’s par for the course.

The best solution I’ve found is to stay in one place long enough to date normally and find a girlfriend who also likes to travel. Then you can plan trips with her during her vacations and long weekends, and work visiting her into your schedule.

Being a nomad necessitates having flexibility in one’s lifestyle, and that flexibility can be positively applied to dating. For example, I see my girlfriend roughly every three weeks, and when I do, I do no work. Then when we’re apart I do a lot more work, not having the distraction of having a girlfriend around.

My girlfriend already had a trip to China planned for a month from now, so I changed my plans to meet her there for ten days. Last weekend I had a trip to Mexico planned, so I helped her find tickets so that she could come along.

Some people do find partners as they travel, but it’s difficult, especially if you’re looking for something serious. In my experience it’s better to find someone local and merge lifestyles, rather than hope you’ll find someone as you go. Unless you’re a woman.

How to Not Be Obnoxious to Locals

One of the pet peeves of seasoned travelers, not to mention locals, is seeing travelers come in and act like idiots. I suspect this happens usually not because the travelers are bad people, but because they don’t yet have the experience to understand how to be respectful to locals.

When travelers are disrespectful of or oblivious to local culture, it creates a hostile relationship between the two groups. This encourages a race to the bottom where locals see travelers as walking wallets, and travelers see locals as one-dimensional play actors in their “dream vacation”.

A good relationship between travelers and locals can create a sum-is-greater-than-its-parts situation where each party is both enriched by and enriches the other. Part of the joy of traveling is learning about the culture and trying to understand it, and there’s no better conduit through which to do so than locals. So even if you don’t really care about fostering a good relationship between travelers and locals as a group, your personal experience will be better if you treat locals and their culture with respect.

The first step is to understand that when you’re in a foreign country, you should adopt their customs rather than expect them to bend to yours. Consider it “house rules”. For example, if you’re in a Muslim country that dictates modesty in dress, you should dress modestly. You may be tempted to dress in your normal style to “make a statement”, but that’s not an appropriate time to make one.

If you’re going to be somewhere for more than a few days, make an effort to learn key phrases of the language, even if you have no intention of learning more than that. Just using those key phrases is a big indicator that you are interested in learning about a country. It shows that you don’t expect everyone to learn English for your convenience. When locals see this, they will treat you better. This is especially true of places where culture is routinely trodden (Thailand), the language is difficult (Japan), or is extremely obscure (Romania).

Ask locals what most tourists miss that you ought to see. This gives people a chance to open up about their country, and allows you to see things you’d never otherwise see. There’s nothing wrong with seeing the major tourist attractions, as they’re usually big attractions for a reason, but seeing the things that locals recommend will give you a wider appreciation for what the country is all about. Think about what you’d show someone in your own city, and how much it differs from what guidebooks recommend.

Chapter 6

Go Deep by Derek Sivers

Derek Sivers is best known for founding CD Baby, his TED talks, and his book Anything You Want. As I’ve gotten to know him, though, what I find most remarkable is the way he travels. He’ll move all the way across the world and live there like a local until it becomes too familiar, at which point he flies across the world to somewhere totally different and repeats the process.

If your top priority is comfort, family, community, or stability, then you can stop here, because this advice doesn’t apply to you.

But if your top priority is intellectual growth, let’s continue.

You are the way you are because of what you’ve experienced.

Your country, family, town, random circumstances, and friends shaped the way you think. If you grew up on the other side of the world, you would have a different set of values and thought patterns.

But if you keep experiencing the same things, your mind keeps its same patterns. Same input, same response. Your brain, which was once curious and growing, gets fixed into deep habits. Your values and opinions harden, and resist change. If you don’t flex, you lose your flexibility.

You only really learn when you’re surprised. Unless you’re surprised, everything is fitting into your existing thought patterns. So to get smarter, you need to get surprised, think in new ways, and deeply understand different perspectives.

With effort, you could do this from the comforts of home, but the most effective way to shake things up is to move across the world. Pick a place that’s most unlike what you know, and go.

This also keeps you in a learning mindset. Previously mindless habits, like buying groceries, now keep your mind open, alert, and noticing new things. New arrivals in a culture often notice what the locals don’t. (Fish don’t know they’re in water.)

Don’t think of yourself as visiting. Say that you’ve moved here, and mean it. Commit. Immerse. Go native.

Form deep friendships with locals. Ask lots of questions. Ask them to explain everything, and show you how it’s done. When they state a fact, ask how they know. When they state an opinion, ask for examples.

At first, their values and methods will feel wrong. You’ll feel the urge to tell them how it could be better. (Meaning: more like what you know.) But try to understand a perspective where they are right, and you are wrong. Eventually you’ll realize that your beliefs are not correct—they’re just the quaint local culture of where you grew up. You are a product of your environment.

Every country has a shared and working philosophy. Dive in and really try to understand it. This is one of the best things you can do for your brain. Stay immersed at least until you feel yourself saying “we” instead of “they”.

Then, if you want to keep your brain actively learning and growing forever, keep moving across the world and immersing like this for the rest of your life.

Chapter 7

Crazy Flight Deals

Sometimes you want to go to a specific destination at a particular time, and your task is to find the best way to do it. But other times you don’t really care so much where you go, as long as the price is right. Or there are a handful of destinations that have been floating around in your mind, and you’d jump on any deal that was going to one of them.

The good news is that such flights do exist. I’ve flown round trip to New Zealand for $240 (including earning about $400 in miles as a result), round trip to Tokyo for $315, and from San Francisco to Jordan and Hong Kong for $180. These deals aren’t typical, but they’re not as rare as you might imagine. In any given month, one or two deals of this caliber will pop up and many more that are almost as good will show up as well.

Sometimes these deals are the result of excellent fare sales, usually through inter-airline competition on a certain route, but more often they are mistakes. Airlines have hundreds of routes, thousands if you include stopovers, and they are priced in the least straightforward way possible. That means that once in a while the automated system misprices them.

If you find a mispriced flight quickly, you are in luck. You can book it and it will most likely not be canceled (I’ve only ever once had had one canceled on me).

Before I discuss sources for finding these deals, it’s important to discuss what to do when you do find one. Most people mess this part up and end up not getting to go.

The most important thing to do is to book the flight immediately. Don’t check your calendar, don’t see if your friends can go. Just book the flight. Any airline which has at least one flight to the United States (which is most of them), will allow you to cancel within 24 hours of booking, as discussed elsewhere.

As soon as you get one flight booked, start digging in more to find the best dates. Check your schedule, talk to friends, and rebook. Every time you rebook, cancel the previous flight. Or book several different dates and spend the next twenty-four hours figuring out which one to keep. The best deals disappear within an hour, and most good ones are gone within a day. Don’t miss out on going somewhere you’d really like to go because you were a perfectionist and waited too long.

When deals disappear, they usually fade away rather than vanish instantly. The first thing you’ll notice is that there are fewer dates on which you can book the flight. Next you’ll notice that sometimes when you go to check out you’ll get an error. Sometimes the site will stop working when you search for the deal.

Once this starts to happen, look for other sites through which to book. Try Orbitz, Expedia, Travelocity, Priceline, and Kayak. Very often it will work at one of the sites longer than the others. Sometimes errors are the result of too many people trying to book and will disappear if you just try the search again. It pays to be tenacious.

If you search for a lot of these flights, you will sometimes find them yourself. Most of the time, however, you will find them on flight deal sites. These change, but the best as of this writing are Secret Flying, The Flight Deal, and Airfare Watchdog. If you check these sites frequently, you will eventually find great deals that you can use.

There are also paid services that will notify you proactively when good flights match your criteria. The one that I use is built by my friend Todd and is called Flymor.com. Finding just one great deal per year makes it an excellent value.

Chapter 8

Flight Tricks

Some of these tricks may be familiar to you, but I’d guess that many are ideas you’ve never heard of, or at least never tried. They are designed to make flying as inexpensive, comfortable, and efficient as it can be. When you become proficient in them, you’ll find that the friction involved in taking a flight drops to just about nothing. I remember years ago when booking a flight seemed like a big deal to me. Now I frequently book international flights and forget about them by dinner.

No constant element of your life can be “a big deal”, or your lifestyle will stress you out. Using these tricks makes booking and taking flights easy and painless, which is essential to truly being a permanent nomad.

Secret Pricing on Discount Airlines

Spirit Airlines has a big beef over the high tax rate on flights. Some of the taxes are fixed per segment or flight, so they are a proportionally higher for discount airlines. Spirit even shows the tax rate as you check out so that you will be angry that the government taxes you so much.

They’ve also found a clever way around some of these taxes, but in the process have created a loophole which you can use to get your flights significantly cheaper. I’ve even gotten some that were better than free, where the ticket price was negative before the taxes.

Airlines aren’t required to charge tax on fees that they assess, like baggage fees. The catch is that any fee they charge has to be optional, otherwise it counts as airfare. So Spirit has snuck in a “Passenger Usage Fee”, which is a fee you pay to use the web site or phone to book a flight. It’s a fixed cost of $18 per leg of the flight. In order to not count as airfare, there has to be a way to avoid it, and there is. If you buy a ticket in person at a ticket desk, you won’t be charged the fee.

Allegiant airlines also does this. Buy at the counter and you save a similar amount per flight leg. You don’t need to say anything special or ask for this discount, it will just be applied automatically. Somewhat shadily, they tend to heavily restrict the hours during which they will sell flights.

Sometimes, and I don’t really understand why, the discount will be even greater than the expected $36 round trip. In one case I got a $149 flight for $88.

If you live in a city where the airport is really close, like Vegas, you can go buy tickets yourself. In other cases you just keep a list of the flights you need and buy them every time you hit an airport that has spirit. Or if you have a friend who’s at the airport you can get him to buy one for you.

Weird European Travel Agencies

Just when I thought I knew every trick in the flight-booking book, I found a site called http://momondo.com. At first glance it looks like every other run-of-the-mill flight search engine, but the results reveal something different.

Most of the time, especially when booking flights to Europe, the prices are considerably cheaper than other flight search engines, including Google Flights, which is the gold standard. Upon further investigation, you realize that all of the cheap flights are through strange European travel agencies no one has ever heard of.

The booking pages all look fairly sketchy, but the agencies are legitimate. I’ve booked a bunch of flights through them and have never had any issues. I don’t know how they have such cheap prices, but they often undercut the prices everyone else has by 10-30% for the exact same flights.

It’s always worth including Momondo (the main flight search engine that links to the agencies) in your searches, especially when booking European flights.

Free Assigned Seat

These days airlines nickel and dime passengers for just about everything, like getting on the plane early, bringing a bag, and choosing a seat. Luckily there’s a way to often get around the last one.

Take a randomly assigned seat. If you don’t like what you end up with, go to the check in desk before your flight. If you want window seat, say:

“Is there any way I could be moved to a window seat? Being able to see outside makes me feel less nervous about flying.”

If you want an aisle seat say, “Is there any way I could be moved to an aisle seat? I have to pee a lot, and a I hate disturbing other passengers.”

All agents have the ability to move you to any seat within your category for free, and are generally happy to do it as long as there’s space. Sometimes the plane is full and there’s nothing that can be done, but this works about eighty percent of the time. If the check-in desk won’t do it, try again by asking the agent at the gate.

Intentionally Missing Connections

Due to the complicated and merely semi-logical pricing schemes of airlines, odd situations often arise where it is more expensive to buy a single leg of a flight than it is to buy a longer flight that uses that leg. For example, when I was helping my brother buy a flight from Los Angeles to New York recently, the cheapest way to get there was to buy a flight to Boston that connected in New York and to simply not take the second leg from New York to Boston.

It probably goes without saying that you cannot do this if you have any bags checked. Your bag will make it to its final destination without you, and you’ll have to work with the airline to get it back.

Airlines don’t like it when you do this, but they can’t stop you and have no way of knowing whether you actually missed the flight or if you decided not to take it. There’s an excellent site for finding these flights called http://Skiplagged.com. They were sued by United, but the court found that there was nothing wrong with encouraging people to take only the legs of the flight they needed.

One slightly gray area cherry-on-the-top bonus to doing this is that on the rare occasion that your second segment is heavily delayed or canceled, you may be able to get a refund of the full ticket even after you’ve flown the first segment. I’ve never done this personally, but I know people who have.

Southwest Airlines

Southwest Airlines deserves special mention in this section because you can use it very strategically in ways that you can’t use other airlines.

The key to using Southwest is to understand their cancellation policy. You can get a full refund of any flight at any time, including minutes before boarding, for any reason. If you pay with points you will just get the points back, and if you pay with a credit card you’ll get the money back as a credit for future travel.

It’s best to have some Southwest points, which you can earn through flying, getting their co-branded credit card, or by transferring Chase points. Even if you don’t use points, though, you can just keep refunding flights and using those credits to buy future flights, which you may also refund.

Let’s say that you were considering going to Boston next week, but weren’t entirely sure. No problem! Just book it on Southwest. If you find out that you will have to go for sure, immediately check to see if there’s a cheaper flight than Southwest. If there is, book it and cancel Southwest.

You can book these flights as backups to ensure that prices don’t go up. I recently needed a flight from Puerto Rico to Las Vegas, but I wasn’t ready to make plans and commit to a specific day. So I picked the most likely day and booked a Southwest flight. It’s a good thing I did, because when I checked a couple weeks later, the prices had gone up by five times.

You can even use Southwest bookings to make sure that you pay the best price on Southwest. Book the flight you want way in advance, and check once in a while to see if the price has dropped on Southwest. If it has, you can cancel and rebook, pocketing the savings.

It used to be possible to book multiple Southwest flights for the same city pair on similar dates, but they recently started canceling plans that looked to be very similar to others. However, I suspect that you could still do something like BOS-LAS on 1/1 and BOS-LAX on 1/2, giving you some flexibility on where you’d go after Boston.

Using Southwest like this is very powerful and will most likely not last forever, as Southwest is, in a way, paying for you to insure your flights. If you use this strategy, use it responsibly by canceling flights as soon as you know that you won’t need them, so that Southwest can sell them to someone else.

The Free Layover

Most airlines have rules which allow stops of up to twenty-four hours in connecting cities for free, as long as the city is one in which they usually connect for that route. For example, say that you are flying from Tokyo to Chengdu, and have a one-hour layover in Beijing. Usually you can extend that to 23 hours (or as close as the airline’s flight schedule permits) for free.

Doing this allows you to see an extra city you wouldn’t otherwise see, and makes a one-stop flight feel like two direct flights. I generally do this any time I can and use it as an opportunity to check out a new city or to have a day visiting friends before moving on.

The problem is that search engines hide long layovers because most people would prefer shorter ones. To get around this, use Google Flights to search and scroll to the bottom. Click the area that says “Show longer or more expensive flights”. Then scroll back up and look and see if there are cheap ones that have good layovers. In general this will show all possible routes with that airline.

If you don’t see anything you like, go to the website of the company which has the cheapest price with a layover that you like. Instead of searching for a one-way or round-trip, search for a multi stop and include the layover city as a stop.

One-Way vs. Round-Trip

A long time ago, round-trip used to sometimes be cheaper than a single one-way. This isn’t always, or even often, true anymore, but it is definitely worth checking. Even if it isn’t cheaper, the price of adding a return leg may be very inexpensive. If you don’t need the return leg but it’s very cheap, try adding it for six to twelve months in the future, at a time when you might want to return. If it’s $100 extra, but will save you $500 if you come back to the same city, it may be worth booking even if there’s a good chance you won’t want the return flight.

On the other hand, buying two one-ways is often cheaper than buying a single round-trip. This is mainly because flight pricing varies wildly by airline and often different airlines will have much more expensive or inexpensive one-ways than others. Buying two one-ways is a hassle, but it provides the additional benefit of being able to cancel or miss the first leg and not have the second leg automatically cancel. For that reason I will even book two one-ways with the same airline if it’s the same price as a round-trip.

Sometimes search engines will show flights that book on two separate airlines, calling them “Hacker Fares”. It’s always best to search for yourself, though, because I’ve found that they don’t always show every option. Make sure to include Southwest in your manual searches, as they don’t show up in searches on other sites.

Refunding Non-Refundable Tickets

A couple years back I was a little too trigger happy about flight deals and ended up booking way more flights than I was actually intending on taking. I had four international tickets that I didn’t want to take, none of which were refundable. I thought I’d try anyway.

I called and said, “I’m thinking about not taking this flight. If I cancel now, could I get a refund?”

I wanted to make it seem as though I might take the flight anyway, reasoning that if they knew they could get me off and sell it for more, maybe they’d be tempted to refund. Two gave me a full refund, one gave me about half, and one didn’t give me anything. I’m not sure if I got lucky or if my wording helped, but I was surprised to be able to get a refund.

Some airlines, like Spirit, will give a token refund of $10 per flight so that they can resell the seat. It may not be much, but it’s better than nothing.

Even if a ticket says it’s non-refundable, it’s worth calling and asking. I don’t know why it works, but you can often get a refund.

Twenty-four Hour Refund

This isn’t so much of a trick as much as an airline rule that many people don’t know about. By law, any airline that services the United States must grant you a full refund within 24 hour of booking a flight, as  long as the flight is more than a week from the booking date. Some airlines also allow you to cancel within a week, but you need to check your specific airline to make sure.

You can even cancel the next day and then immediately rebook if the price dropped (and could, conceivably, do that every single day).

Knowing this is particularly valuable when a good flight deal comes along and you don’t want to miss out on it, but aren’t completely sure you want to take the flight. Just book it and take 24 hours to think about it before being locked in. Or you can do what I often do, which is to book several different dates with the deal, and then cancel some of them the following day once plans are figured out. Sometimes I’ll even book for a friend and then ask them if they want to go before deciding whether to cancel or not.

Cheapest Days to Travel

Though not true in every case, flights that depart on Tuesdays and Saturdays tend to be cheaper than others. This is especially true of short domestic flights and less true on complicated international itineraries that span multiple time zones and days.

If you have to be somewhere on a certain day then this isn’t valuable information for you. If you have some flexibility, though, planning trips around these days of the week can reduce your flight costs significantly. If you’re going somewhere for a week, always try to fly Tuesday to Tuesday or Saturday to Saturday. If you have control over your work schedule, try to make your free days coincide with cheap flight days.

Holidays are also very inexpensive days to travel. I’m constantly trying to convince my family to delay our observance of Christmas to one day later so that we can all fly in on Christmas, which is often half the price of the day before or after. New Years and July Fourth are also good days to travel.

The Nested Round Trip

If flights were priced as taxis are, flat fee per mile traveled, there wouldn’t be many travel deals to be had. In reality flights are priced exactly the opposite, following arcane rules as well as supply and demand that isn’t always apparent to the consumer.

One key pattern to understand is that a primary driver of flight cost is the number of people who fly that route annually, especially for business travel. This is why it’s usually cheaper to fly from Los Angeles to New York (2500 miles) than it is to fly from Los Angeles to Santa Fe (700 miles).

Say you wanted to fly from Las Vegas to Zurich. You could search for flights between those two airports, but there’s also another way to complete this route that may cost less and give you some cool perks.

Las Vegas to New York is an extremely common route, which makes it very inexpensive. Often flights are just $99 each way. New York is the US hub with the most connections to Europe, so flights from New York to Europe are often disproportionately inexpensive.

To take advantage of these cheap routes you can book a round trip to New York, and then book another round trip from there to Zurich. Prices constantly change, but at the time of this writing the combined two round trips come in at around $700, while a round trip from Las Vegas comes in at $900. Because there are no direct flights between Vegas and Zurich, both options leave you with one stopover.

Doing this also grants you some flexibility. You can nest the flights such that your layover is just a few hours, or you could leave a day or two on one or both sides so that you also get a free trip (or two!) to New York. Because you will usually be doing this between cities that are busy, there should be enough flights that you can make just about any schedule you like.

For flights to Europe, check New York, Boston, and Washington. For flights to South America, check Miami and Houston. For flights to Asia, check Los Angeles, Las Vegas, and San Francisco. Make sure that you leave at least 3-4 hours between flights to account for delays and terminal changes. I tend to leave much longer layovers and spend the time in an airport lounge so that I can get a free meal, take a shower, and get some work done.

Chapter 9

Loyalty Programs

Until you understand how they work, it’s very easy to dismiss frequent flyer programs and not bother with them. But a little bit of familiarity with them can reap enormous benefits, as you can get at least 10% back in value on all money spent on flights, and sometimes even more than 100%.

Most airlines have partnerships with other airlines. These partnerships have all sorts of forms, but the upshot of them is that they allow you to earn and redeem miles on airlines other than the airline on which you’re flying. A simple example is that Delta has an alliance with KLM. If you are collecting Delta points, you can fly on KLM and credit them to Delta. That way you don’t have a useless amount of points in dozens of different programs, and instead you can concentrate them in the programs that work best for you.

In the past these programs were very simple. For every mile the flight was scheduled to fly, you received one point. This was very generous, so most (but not all), programs switched to a dollar based scheme, giving you a certain number of points per dollar spent on the ticket.

These points can be redeemed for flights, but simultaneously dictate the status you have on an airline. If you earn a certain number of points per year, usually around 25,000, you will gain status on the airline for the following year. That status entitles you to seat upgrades, free bags, and a multiplier on points earned, as well as other small perks. The multiplier can be very valuable, as it can reach or exceed 100%.

Most programs charge 25,000 miles to travel round-trip in the United States, and around 65,000 to go to Europe. These numbers do vary, but I mention them as a point of reference.

When looking for a loyalty program, what you should care most about is how many points you will earn for any given flight. A program with a mile-based earning scheme rather than a dollar-based earning scheme will always earn more points over the long run.

You should also care about which airlines credit to that airline. If it’s just one obscure airline, the points won’t do you any good.

Alaska Airlines

As I write this, the best program by far is Alaska Airlines, even if you never actually fly Alaska Airlines. They still credit per mile, even on partner airlines (though often at a discounted rate), and they have a good partnership with American Airlines, which is often the best airline to fly within the US. They also bought Virgin America, which is even better than a partnership, as all flights are credited at the full rate of one point per mile.

In addition to those two strong domestic options, they have a number of good international partners, making it likely that international flights you take can be credited to them.

At their first tier they introduce a 25% mileage bonus, which is standard, but at their second tier they offer 100%, which is much higher than most programs offer in the second tier. That means that you can fly and not only get credited based on mileage, but receive double the mileage you would normally receive. This makes it easier to earn free flights, and also easier to qualify for the following year.

American

American isn’t the best program out there, but it’s the easiest one to gain status on without doing a ton of flying. And once you get status on it, you can then get another airline (Alaska, for example) to match it for the following year, thus giving you over two years of status for one short outlay of effort.

The reason American is easy is because they offer a really cool challenge. You pay $200 to sign up, and if you earn 12,500 qualifying miles within 90 days, you will have Platinum status for the rest of the year. If you do it after June 16th, you get the rest of the current year, the whole following year, plus two months of the year after that. That’s nearly 18 months of status.

The number of miles you earn per flights varies, but that 12,500 mile bar can be reached on just one or two long flights. Flights on partner airlines also count, though sometimes at reduced rates. When I did my challenge, I did it with one awkwardly routed trip from San Francisco to Hong Kong, plus a short one-way between Las Vegas and San Francisco.

The best way to approach this is to be looking for good qualifying fares and to plan one for the second half of June. Then call on June 17th and enroll in the challenge. Make sure that you credit all flights to American— it won’t work if you credit them to, say, Alaska.

To sign up, call +1 800-882-8880 and say you’d like to do the Platinum challenge. They also have a Gold challenge, but it’s not nearly as good of a deal.

Status Matching

If you get status on any airline, you are most likely able to status match to another airline. A classic match is to go from American to Alaska, as American is the easiest to earn, Alaska is the most valuable, and Alaska is easy to match to.

Once you finish your year with Alaska, you can then match to someone else again, thus continuing the cycle until you run out of airlines. Occasionally you’ll requalify for status the next year and won’t need to match. This happens often on Alaska because they have such a good program.

To find out how to match to specific airlines and whether they’re likely to approve or not, go to http://StatusMatcher.com.

Where to Credit

It’s impossible to keep track of all of the different (and constantly changing) airline alliances and the various conversion rates at which they credit, but luckily there’s one site that keeps track of all of this information and makes it easy to look it up. The site is called WheretoCredit.com.

To use it you must know the fare class of your ticket. This will be a single letter (F, J, Q, Y, etc), and is often a little bit difficult to find, especially before you’ve made the booking. Often it’s found under fare terms or “more details”. If you search Google for something like “How to find fare class United”, you’ll be able to find current instructions per airline.

Once you know the fare code, simply enter it with the airline into http://wheretocredit.com. The site will return a list of every airline to which you can credit your flight, along with the conversion rate, in miles or dollars.

For example if it says 25% to Alaska, that means that if you fly 1000 miles on your flight, you will earn 250 Alaska miles if you credit there. Other times you might see “$5 per USD”, which means that if you’re paying $150 for the flight, you’d earn 750 miles for it. To figure out how many miles your flight is, simply plug the airports into http://gcmap.com.

Worry more about the loyalty program than how many miles you get. For example, if I get any reasonable amount of miles for doing so, I’ll credit to Alaska. Because miles generally do you no good if you have fewer than 12,500, there’s no point in crediting to another program if it won’t be followed eventually by many more miles. So I’d rather have 300 Alaska miles than, say, 1000 Air Ethiopia miles.

It’s good to have a few backup programs, though. I tend to credit a few flights per year to Air Canada, since they have a decent program and I do end up flying them once in a while. It can even be worth crediting to bad programs once in a while as long as you have a bunch of other miles there, usually from credit card signup bonuses.

Chapter 10

Travel Cards and Programs

The US government has rolled out a number of “trusted traveler” programs available to all US citizens. Some, like Nexus and APEC, are available to citizens of certain other countries. These programs are inexpensive, and often reimbursed through top-tier credit cards. If you are gearing up for travel, it’s worth getting a good credit card first, and then doing Global Entry, which also comes with PreCheck. That will save you $100 and give you most of the program benefits.

All of these programs require an in-person interview, scheduled through the web site where you apply. In most cases there will be a multi-month wait for an appointment. If you set an appointment date, you can always change it, so you may as well pick one in advance. Sometimes last minute spots open up, so you check and try to reschedule sooner.

You can also just show up when you don’t have an appointment, and if you’re prepared to wait, maybe for hours, you’ll probably get fit in. Interviews are very short and there are frequently no-shows.

Global Entry

Global entry allows you to skip customs lines going into the US and primarily interact with a touchscreen rather than a human. Average time to pass through customs is approximately 30 seconds, instead of 5-60 minutes. Besides saving a tremendous amount of time over the course of the five years the card is active, having a consistently quick experience allows you to book short connections that you would otherwise not be confident you could make.

When Global Entry was first introduced, it was limited to a few major airports. Now it’s in just about every single international US airport, as well as many sea ports.

To apply for Global Entry, just visit the site https://www.cbp.gov/travel/trusted-traveler-programs. Pay for it using a credit card which reimburses Global Entry fees (notably, the top tier Amex, Citi, and Chase cards) and make sure to apply for it instead of PreCheck, since it will also give that to you for free.

PreCheck

If you travel at all, you’ve probably seen PreCheck. It’s a special lane in the airport that allows you to skip much of the hassle of security screening.

You can keep your shoes on, your laptop in your bag, your belt and light jacket on, and your liquids in your bag. You also go through a metal detector rather than a more invasive millimeter wave scan. The line for PreCheck is usually far shorter than the normal line, and always moves quicker. Additionally, it tends to be full of more seasoned travelers, eliminating frustration you might experience watching people completely botch the screening process, slowing everyone down.

PreCheck lanes sometimes close earlier than normal lanes, but even when that’s the case you’ll receive some special treatment in the regular lane. PreCheck requires participation from airlines, so you won’t always get to use it. Almost every domestic airline supports it, as do a few foreign airlines.

When you book a flight it will ask for your trusted traveler number. That will be provided by PreCheck, and you’ll only get the benefits of it if you fill it in. If you forget, you can go to the check-in counter and have them add it for you.

To apply, go to https://www.cbp.gov/travel/trusted-traveler-programs, but it’s better to just apply for Global Entry, which also includes PreCheck automatically.

APEC

APEC is a program that stands for Asia Pacific Economic Cooperation and is available to citizens of countries in the Asian-Pacific area, like the US, Mexico, China, Japan, Chile, Thailand, and many more. The program is watered down in the US, with the only benefit being that you can use the diplomat lane for customs in participating countries. Like Global Entry, this can save a lot of time, especially in congested airports like Bangkok.

For citizens of countries other than the US, it also allows you visa-free travel in all APEC countries besides the US, eliminating the need to apply for visas in advance.

To apply for APEC you are supposed to have a legitimate business interest that would cause you to travel to those countries. I do, but it was never verified other than an afterthought question in the interview where they asked, “Oh, and what’s your business?” I suspect it would be easy to get even if you didn’t have a real business.

APEC is $85 for 3 years, which is only really worth it if you travel to that region a lot, as their processes are often fairly efficient even without the diplomat lane. Also, it will expire before 3 years if your passport expires in that period of time.

You apply by going to https://www.cbp.gov/travel/trusted-traveler-programs, but you must already be enrolled in Global Entry or NEXUS.

NEXUS

NEXUS is a program created by the US and Canada which allows Global Entry-like transit between the two countries.

It may seem silly to get a special program just for one country, but Canada is generally accepted as having the worst immigrations process amongst developed (and most undeveloped) countries. For no reason at all I was once interrogated for 90 minutes and accused of being a “drug dealer or child pornographer”, which was coupled with a very invasive search of my computer and belongings. Several other times I’ve been detained for over an hour, also for no real reason.

When I told my friends and other travelers about this, I found that many other people had similar issues. I went through the process of getting my NEXUS card and haven’t had any issues since then. If you plan on going to, or even transiting through (as they will interview you in either case) Canada, I’d suggest applying for the card.

The one caveat with NEXUS is that it requires an in-person interview at a US/Canada border. The interview itself is short and pleasant, which was a surprise after my experiences with immigration.

NEXUS costs $50 for approximately five years (depending on your birthday).

Second Passport

A less well-known program offered by the United States is the ability to get a second valid passport, to be used simultaneously with your first one. Sometimes you have to send your passport off to embassies to get visas, but also need to travel internationally at the same time. It’s because of this that I first got a second passport, and I found it immensely useful.

To apply for a second passport, you fill out the form at https://pptform.state.gov and submit it like a normal passport along with your existing passport. You can also use a passport agency. You will need to write a letter describing why you need one. If you say that you travel a lot and need to send it away for visas, plus you may travel to the Middle East, your request will be granted. Some countries in the Middle East won’t allow you entry if you’ve traveled to others in the region, so you can silo certain stamps to one passport.

The downside of the second passport is that it costs the same as a regular one, but is only valid for two years. For this reason it’s best to send your main one away for long-term visas, and travel on the second one. When I’m not shuffling visas, I like leaving one passport in a pocket in my backpack so that I never have to worry about forgetting a passport.

Clear

Clear is another travel card which you can sign up for, but it is through a private company rather than the government. It can be combined with PreCheck or used alone, and in either case will allow you to cut the line and travel domestically without showing an ID.

When you have Clear, you walk up to the Clear kiosk and scan two of your fingerprints. The system then prompts you to scan your boarding pass, after which you will get rushed to the front of the line and past the TSA agent who would have otherwise checked your documents.

The agents are so committed to getting you through security quickly that I’ve had to suppress laughs a few times. It’s never taken me more than fifteen seconds to use Clear to get from before security to the baggage X-Ray and metal detector.

My favorite thing about Clear is that it makes security time very consistent. My US home base is in Las Vegas, which means that once in a while there is a big convention or show in town that I didn’t know about, and even the PreCheck lane is long. But with Clear I get to be at the front of it every time.

Clear costs $179 per year, which is a tough sell. Luckily I have a couple ways to get it cheaper. The first is that if you sign up for Delta’s loyalty program, it will knock the price down to $99 per year. Also, up to three additional users are $50 each and do not have to be related to you, so you can get four people total for $250, or $62.50 per person per year. It’s well worth that price.

The initial signup process is also extremely quick. In my case it took about 3-5 minutes for them to register my fingerprints and send me through security, so you can just bundle in the registration process with your next flight.

Sign up using the Delta link at https://www.clearme.com/delta. You can also get two months for free by registering at http://refer.clearme.com/share/clearme2 instead (this also gives me two months).

Chapter 11

Airport Lounges

I love seeing people’s reactions the first time they go to a good airport lounge. The typical experience at an airport is hurried, noisy, and possibly stressful. Lounges are secret oases within airports which provide the opposite experience, plus a host of amenities that can’t be found anywhere else in airports.

Bare minimum you can expect good internet, comfortable seating, some sort of snack, and quiet. Some of the best have gourmet meals, showers, and spa treatments, all for free.

Lounges typically charge day rates of about $60, which is never worth it. Almost no one in the lounge is actually paying that, though, as most gain free access through credit cards.

There is a free app available for Android and iOS called LoungeBuddy. With it you can input all of the credit cards and status that you have and it will tell you per airport which lounges you can access. Keeping track without this app is very difficult and will result in you missing out on lounges you could otherwise visit.

Within LoungeBuddy you will find the location of each lounge, including the terminal and gate. In excellent airports like BKK, LAS, and IAH, you can get from any terminal to another without leaving security. This makes it very easy to access the lounge no matter which airline you’re flying. At other airports like SFO and LAX, you can only connect through certain terminals without leaving security.

If you have a lot of time, you can almost always enter the “wrong” terminal for the sole purpose of going to the lounge. If the TSA agent tells you that you’re in the wrong place, just tell them that you’re going to the lounge first. While this should work all the time in the United States, it doesn’t always work internationally, as they sometimes segment their airports differently.

Once in a while a lounge will be “pre-security”, which means that you will have to exit security to visit it, or go there before you go through security if you’re not on a layover.

There are three types of lounges of note:

American Express Centurion Lounges

Centurion lounges are consistently the best lounges, and are currently expanding around the globe. They always have showers and great meals. They don’t advertise it, but if you ask the people at the desk, you can also get free toiletry kits.

The only way to get into Centurion Lounges for free is to have a platinum or black card from American Express. If you have a gold or lower card you can pay for access, but it’s probably not worth it.

Currently Centurion lounges are available in most major airport hubs, and new ones are opening all the time. My favorite is the Dallas lounge, as it has great barbecue and guacamole.

Additional users on the Amex cards also currently get access to Centurion lounges. As of this writing, the cost is $175 total for up to four additional cardholders.

PriorityPass Lounges

PriorityPass is a network of over 1000 lounges all around the world. All of them are operated by third parties, including some airlines, but having a PriorityPass allows you free access.

The most basic lounges, typically European lounges operated by air service companies like Menzies, are pretty basic and barely better than sitting outside. Some, like the one in Dubai, are truly exceptional and have even better food than Centurion lounges. There are even a few restaurants, like one in London Gatwick, that give you a free credit for food just for showing your PriorityPass.

If there’s more than one lounge in an airport, I’ll go into each one to check it out before choosing one to sit in for a multi-hour layover.

Several credit cards will give you unlimited access to PriorityPass, including top tier ones from Chase, Citi, and American Express. Not every PriorityPass is the same, though, at least when it comes to guests. As of this writing, American Express and Citi allow two guests, and Chase allows unlimited.

If you cancel the credit card that gives you the PriorityPass, it will immediately cancel the PriorityPass as well, even though the expiration date of the Priority Pass card may be far in the future.

Worth noting is that many credit cards charge very little for additional users on the credit card (sometimes as little $50-75). As of this writing, every credit card that gives the main cardholder Priority Pass also gives a Priority Pass to additional users.

Branded Airline Lounges

Most major brands of airlines operate their own lounges. While American Express currently allows you into Delta lounges when flying them, this perk may not last. Typically the only way to get into an airport lounge is to have high levels of status and be flying that airline, have a first class ticket on the airline, or have the expensive credit card endorsed by the airline.

Domestically in the US, these lounges tend to be amongst the worst. They’re busy and offer the bare minimum for food. I find that it’s not worth jumping through the hoops necessary to gain access to them.

Chapter 12

Credit Cards

Credit cards are a powerful tool in the nomad’s arsenal, and not because of the spending power they give you. In fact, if you are racking up credit card debt, my suggestion would be to stay put until you pay it off, and then to start to travel once you build up a buffer. Credit cards offer a tremendous amount of perks to the traveler, but they are only able to do so because many of their users succumb to the siren call of debt and end up financing these perks for the rest of us. Don’t be one of those people, and if you’re concerned you might become one, don’t get a credit card.

If, however, you are the type who will only spend what he can afford and will pay his balance in full every month, you can take advantage of the perks offered by credit cards to gain far more value than you pay in annual fees.

There are three primary ways in which you can benefit from having a good portfolio of credit cards.

Cheap Access to Money

Did you know that almost every bank and credit card charges you a 3% surcharge to withdraw or spend money when you’re in a foreign country? They don’t mention it anywhere you’ll actually see it and you won’t notice because the exchange rate masks their cut. Top tier cards tend to not charge for this, including Amex Platinum, Discover, Capital One, and any card that is either Visa Signature or World Mastercard.

If you spend $20,000 a year and travel for half the time, avoiding that fee can save you $300 per year.

Speaking of which, many POS terminals in foreign countries ask if you want to be charged in your home currency or the local currency. You should always choose the local currency. Scam may be too strong of a word, but a common “hustle” perpetrated by local financial institutions is to charge a horrific exchange rate. Even if you don’t have a card without foreign exchange fees, you’re better off paying a fixed 3% than to submit yourself to the mercy of payment processor’s exchange rate.

Miles and Points

Most people know that you can get one mile per dollar you spend on a credit card, which can later be converted into a free flight. This is valuable and worth doing, but most people don’t spend enough to get more than one round-trip flight per year. So how are nomads like myself constantly flying around for free?

Sign-up bonuses.

When you sign up for a new credit card, the company will often award you a bonus for doing so. Usually you will be offered a fixed amount of points, say 50,000, in return for spending a certain amount, maybe $3000 in three months.

Points are typically worth around 1.5 cents each, which gives you a value of $750 for spending $3000. Who needs 1% cashback when you’re effectively getting 25% back by doing these bonuses?

A general strategy is to start with the best offer, complete the spending, and immediately switch to a new credit card, completing the process again. Using this method, someone new can earn between 250,000 and 1,000,000 points in their first year. That’s enough for five to twenty free international flights.

A common concern is that doing this will cause your credit score to drop. It will drop very slightly in the beginning, but will then rise slowly and consistently. This is because the inquiries ding you a little bit, but having lots of credit available (and not abusing it) helps you a lot. Everyone I know who does this has a score above 750.

Unless there are no good offers, which is unlikely, start with Chase cards. They care the most about how many cards you apply for, so it’s best to get them out of the way first. They offer some of the best cards and best bonuses anyway.

If you are ever rejected for a card, which may happen often, call up the reconsideration line. In my experience combined with my friends’ experience, this will result in an approval over 90% of the time. Google “BANK NAME reconsideration line” and call the number. When you get an agent, say, “I saw that I was recently denied for a card I applied for. I have good credit and always pay my bills on time. Could you consider approving me for this card?”

Calling the reconsideration line has worked every time but once for me, even before my credit score became really good.

When deciding which card to get, think a lot about what sorts of free flights you’d like. Southwest is the best choice for most domestic flyers. American has discounted off-peak rates to most regions of the world. United has the best availability, but highest mile cost. Delta is generally horrible. Chase Ultimate Rewards points can be transferred to multiple airlines, including Southwest and United. Some cards give you points which can be converted to dollars to spend on flights.

Never redeem miles for anything other than flights. Flights are always a good value, and everything else is a bad value. As a rule of thumb, you are getting 50% of the value of a point if you spend it on anything other than a flight (like cashback).

Keep track of the credit cards you sign up for and their respective bonuses on a spreadsheet. This will seem like a big hassle at first, but remember that you will be receiving approximately 25% cash back on all money you spend. If you spend $20,000 in a year, that’s worth $5000, which certainly warrants a minimal amount of time spent on tracking.

Perks

High end credit cards come with perks, and many of them are aimed at frequent travelers. It’s impossible for a book to list all of them and stay up to date, but I’ll mention my two favorites which are active at the time of this writing. When you apply for a credit card, make sure to dig through the benefits and take note of useful ones.

One of my favorites is US Bank, which gives you eight gogo inflight wifi passes per year. I save these for when I’m on long transcontinental flights. I also bring a small travel router which is powered off of USB and allows me to use multiple devices on the same connection. To see examples of that and other gear, go to http://tynan.com/gear2018. If you read this after 2018, you can put in the current year instead.

American Express gives you a free unlimited Boingo subscription, which gives you fast internet access in most airports, including those which have throttled or time-limited connections. Whenever you log in to wifi, especially in an airport, look for “partner login” and find Boingo. You’ll generally get the best connection available that way.

Chapter 13

Currency Conversion and Management

As mentioned before, the best way to convert from your home currency to a foreign currency is to withdraw from the ATM. But this is a one-way conversion, so you still need to figure out what to do with the extra money you have left over.

If you think it’s likely that you’ll return to the country, just keep the money. I buy small zip-loc bags that each hold one country’s money, coins, transit cards, and extra tickets. Whenever I get home I put them all in a box, and then grab the ones I need before I head out again. It’s a lot easier to do this than to have a giant mess of these things that usually just gets ignored and left at home.

In some cases, I’ll intentionally retain money or train tickets. For example, the Budapest airport sometimes has a very long line for the two ticket machines for the bus. The machines are a little finicky about which cards they use and some travelers aren’t great at using the machines, so I’ve missed several buses in a row before while waiting my turn to buy tickets. Now I always make sure I have a couple tickets on my way out, buying extras if I don’t already have them.

Even if I don’t keep money or tickets on purpose, I’ll usually keep whatever I have left over if I think there’s a reasonable chance I’ll return. It saves me the hassle of converting money and lets me hit the ground running.

If you have a significant amount of money or don’t think you’ll be returning, you can convert it. If you’re going to another country, convert to their currency in whichever of the two countries is less touristy and developed. For example, if you are going from Vietnam to Tokyo, you should convert in Vietnam because they want their local currency but will have enough Japanese tourists that they can have a competitive rate. If you try to convert in Japan you’ll find that you’ll pay a bad rate as no one will want the Vietnamese money.

The easiest way to find out the “correct” rate is search google using currency codes. For example, if you had 1500 Japanese yen left, you could search “1500 JPY in USD”. If a currency exchange place isn’t offering you within 10% of that amount, you’re probably getting a bad deal. If they’re offering you more, it’s probably a scam.

A good shorthand way to figure out how good of a deal a conversion place is offering is to look at how close the buy and sell prices are. For example, if a company is buying a Euro at 1 US Dollar each, but selling them for 1.5 US Dollars per Euro, that’s really bad. If it’s 1.12 vs 1.20, that’s a lot better.

If you need to transfer large amounts of money from a US bank account to a foreign bank account, use TransferWise.com. They have the best rates, are reputable, and are easy to use.

If you have transit cards like the Oyster card in London, it probably includes a refundable deposit in the ballpark of $5. If you won’t return to the country, you can go to an office to get a refund. If it’s a big line and not worth the hassle, give it to someone in line so that they don’t have to pay the deposit.

Chapter 14

Banking

As a nomad, the majority of the money you’ll spend throughout the year is going to be drawn from a bank in your home country, not a local bank account. The vast majority of banks and credit cards charge you at least 3% to access your money in a foreign country. That applies to ATM withdrawals as well as credit and debit card purchases. Many banks also charge an additional flat-rate surcharge for using foreign ATMs.

There is one debit card which you’ll see in most serious nomads’ wallets, which is a Schwab debit card. Schwab has an account called the High Yield Investor Checking account which is excellent for all travelers. It has no monthly fee, no foreign exchange fee, and rebates all ATM fees (though this doesn’t always work automatically for all international ATMs). You can apply and open an account over the internet.

If you happen to live in the San Francisco area, I like the SF Fire Credit Union even better. They have all of the same benefits as well as no limit for mobile banking check cashing, instant crediting of all transfers, the ability to increase your ATM limit, and excellent customer service. Plus they have physical branches if you need to deposit cash.

There are a few other credit unions around that have similar deals, but for most people Schwab will be the best choice. It’s very common for frequent travelers to have both a Schwab account and a local bank account, and to just move money between the two as necessary.

Chapter 15

Jet Lag

When you fly dozens of days per year, whether you get jet lag or not is a big deal. Without jet lag, you can hop between continents without concern, keeping up your normal routines. If you suffer from jet lag, you’ll never be able to maximize the benefits of traveling all the time.

I remember the worst time I had jet lag, nine years ago. I didn’t do any of the things in this section, and I ended up being miserable for the entire first week I was in Japan. Friends would come over at 5pm to see if I wanted to go out, but I’d still want to sleep more. It was then that I decided I’d attack jet lag and figure out a solution.

The first thing to realize is that anyone can beat jet lag, and that it’s not that tough. I never get jet lag and have taught many others to avoid it as well. I recently had five family members fly east (the more difficult direction) from the US to Europe and none of them had jet lag because they followed my simple method.

Much of what people believe is jet lag is just dehydration. The air on airplanes is very dry and you aren’t served enough water to compensate for it unless you constantly bug the flight attendants. Drinking alcohol can further dehydrate you. Boeing 787 airplanes, better known as Dreamliners, humidify the air so that this is less of a problem, but they still dehydrate.

To compensate, drink a ton of water before you get on a plane, bring water with you in a water bottle, and always ask for water whenever the flight attendant offers you a drink.

Beyond hydration, jet lag comes from a shortened or lengthened day, coupled with incongruent lighting.

When planning for jet lag, understand that the most important factor is whether you wake up at a normal time in your target city, having slept 6-10 hours within the past 24 hours. If you do this, you are 75% of the way towards eliminating jet lag.

For example, next month I will fly from Beijing to Las Vegas. My flight leaves at 2:45p local time in China and arrives at 12:10p local time in Las Vegas. Ideally I would sleep as soon as I got on the flight and wake up a few hours before I land.

Of course, it’s not easy to go to sleep at 2:45p. So what I’ll do is make sure I don’t sleep very much the night before, maybe just four hours. I’ll stay up late and/or set an early alarm. What this does is compress the time when I’m not at my best into just a portion of the travel day, rather than force me to suffer through it for a week after I return to Vegas.

As long as I sleep only four hours the night before, it’s almost impossible for me to get jet lag. Maybe I’ll sleep early in the flight and sleep for most of it. Maybe I’ll stay up for a few hours, nap on and off for a few more, and then be up for a couple hours before I land. Either way I will have slept 6-10 hours in the 24 hours preceding landing and will be fairly awake when I land. On good days I’ll feel great and fall asleep at a normal time that night. On bad days I’ll be a little sleepy all day, will go to bed early and will wake up maybe a bit early the next day.

As soon as you get on the plane, you want to act as though you’re in the new time zone. Set your watch to the new time and adjust the lighting to reflect it. I wish that airlines would do this, but I’ve found that they do a poor job of timing their signals. If it’s bright in the cabin and should be dark according to the target time, I’ll throw a sleep mask on and listen to a podcast (current favorite is Noah Kagan Presents). Usually once a long flight gets going they turn off the lights so that everyone can sleep.

When it’s morning at the destination, I blast all of my lights. I open the window if it’s bright out, which it typically will be, turn on any overhead lights I have access to, turn on the TV in front of me, and turn my laptop on the brightest setting. Other passengers may find this annoying, but it’s actually helping them with jet lag even if they don’t realize it. This is also the time (and the only one, at that), where you should drink tea or coffee. Every signal you can control should be telling your body that it’s morning.

Using this method, just about anyone should be able to beat jet lag. It takes a bit of discipline to stick to, but that’s easier than suffering through several days of bad sleep patterns. If you’re one of those people who “just can’t sleep on planes”, it’s probably because you aren’t making yourself tired enough beforehand.

Chapter 16

Visas

I get a lot of questions about how visas work. They work a bit differently for every pair of countries (your citizenship and the place you’re visiting), so they can be confusing.

The short version is that you only have the absolute right to be in your own country (there are some exceptions, like the Schengen area of Europe). In order to visit another country, you need permission. The main reason for this is that countries don’t want you hopping a flight over and moving there, possibly becoming a drain on society.

There are always limits on how long you can stay, and often you have to apply for a visa, which is how the country determines whether or not you are worth the risk.

In practice, many countries have “visa free travel” agreements. That doesn’t mean that you can stay in that country forever, only that upon arrival you will be given permission to stay for a certain amount of time as a tourist. These agreements don’t cover other visiting purposes, like being a student or working.

Some of these limits are fixed length, but can be had in any quantity. You may have heard of “visa runs”, which is where someone gets, say, a 30 day visa upon arrival, but when it’s about to expire he hops across the border to another country, only to return immediately to reset the 30 day clock. This is very common in Thailand.

Other times there are cumulative limits. For example, US citizens can visit the EU for 90 out of the preceding 180 days, on a rolling basis. That’s a lot harder to keep track of, and generally they don’t actually check that closely, but gross abuse of it would certainly be caught.

Some places, like China, have even more complicated rules where you can stay for just a few days as a layover, but only if you’re coming from or going to a different country in between, and with different limits per each airport.

There are also programs called “Visa on Arrival”, which means that you can’t travel visa-free, but that you can instantly get a visa when you arrive. Countries that support this scheme use it primarily as an income source and don’t always universally apply it across all border points. Usually you’re only able to do it at the major airports.

If none of those situations apply, you have to get a visa. Like every other aspect of this process, procedures vary widely by country. But in general you can either apply in person at an embassy or consulate of the country you’re visiting, or you can use a service where you mail your passport and they do the work for you.

Going in person is sometimes possible at any embassy of that country, but other times only possible at the embassy that serves your region. When I needed a Brazilian visa, I tried to get it in New York when I was visiting there, only to be told I had to get it from my local embassy near my residence. Another time I was going from Thailand to Vietnam, didn’t realize I needed a visa, and got one last minute at the Vietnamese embassy in Bangkok.

For US citizens, getting a visa tends to be a straightforward process. You fill out a form, bring in a passport-sized photo, pay a fee, and you’ll be approved in 5-30 days, depending on the country. Some other nationalities face more scrutiny and have to prove that they can support themselves.

I generally do visas myself, but will occasionally use a visa service if I don’t have the time or bandwidth to deal with it.

You should generally apply for a visa as late as possible while still being sure that you will get it in time. If they say it will take 30 days, for example, I’d apply 45 days in advance just to be safe. Visas are usually issued for a specific duration of time, so if you apply right before traveling you may be able to go back to the country six months later on the same visa. If you apply nine months in advance, your window to re-enter is much smaller.

There are two main types of visas: single entry or multiple entry. A single entry can be used exactly once, a multiple entry can be used a fixed or unlimited amount of times, depending on the terms.

Always apply for the longest visa term possible if the price difference is negligible or non-existent. It’s important to research this in advance, as it’s not always obvious what the maximum possible duration is. For example, the longest duration on the Chinese visa application is a one-year multiple-entry, but if you write in ten-year, you will be approved for it and it costs the same amount as a one year.

The reason visas of different lengths often cost the same amount of money is because the fees can be charged based on reciprocity, i.e. countries charge you whatever your country would charge their citizens. The US usually charges about $140, so that’s what it will often cost a US citizen to get a visa in another country.

Chapter 17

Funding a Nomadic Lifestyle

When I ask for feedback on travel topics, one of the perennial requests is for information on how to make money while traveling. This is a tricky topic, since there’s no one-size-fits-all method. When I wrote my first travel book, I was making very little money and there weren’t that many established avenues for doing so. Now I make a fair bit more and the options for earning money while traveling have grown exponentially, so I have a bit more to say on the topic.

Expect that you will be trading something for the privilege of traveling. I could earn a high salary in San Francisco as a programmer, but I’ve forgone that in favor of the freedom of traveling. For many years I made far less as a result, but it was always worth it to me.

Keep in mind that while traveling you have much greater control over your costs, so your critical requirement for income decreases. My suggestion for a strategy would be to save money up in advance, start in an inexpensive city, and focus on building up to earn enough to live there. If you have few possessions and live in, say, Southeast Asia, you can reliably live for $1000 a month or less.

Vegas, as mentioned elsewhere, is also a great place to drop costs. You may even be able to Airbnb your place out as you travel and make a profit, thus traveling for free.

Bait and Switch

For anyone who prefers a corporate job, becoming a remote employee may be the ultimate goal. There are many companies who now hire remote employees and reap the benefits of happy employees who can self-manage and often don’t require as much compensation. Some, like blogging giant WordPress, are completely remote.

On the other hand, many companies have a fear that if they give their employees too much freedom, they’ll take advantage and not get as much work done.

It’s fair to say that there are pros and cons to both arrangements, but no one can deny that there are many remote workers doing excellent work and enjoying their lifestyles.

If you can get hired to a remote team, then you’ve reached your goal. But what if you work at a company you like and they don’t allow remote work? It just so happens that this is the starting point for some of the happiest remote workers I know.

The first step is to become an excellent employee. I hear from my business-owning friends all the time how hard it is to find and retain good talent. If you are a top performer at your company, they will do just about anything to keep you there, especially if it doesn’t cost them anything.

Once you’re an excellent employee, start taking your vacation time. Travel far away, but keep working even though you don’t have to. Your boss will notice, but so will your coworkers. One of the top concerns for bosses is that if they let one employee travel, they have to let everyone travel. If it’s commonly known that you work while you’re on vacation, you will be seen as different.

After that experiment goes well, suggest another one to your boss. Say that you love your job, but that it’s preventing you from traveling as much as you’d like to, and that you’re trying to think of alternatives. Suggest that you do a two to four week trial working while traveling. Say that if it doesn’t work out, the company can count it as vacation time. Hinting that you are looking for alternatives can make your boss worry that you might be thinking about leaving and will motivate him to agree.

During the trial, do a ton of visible work. Don’t aim to keep up your previous pace, aim to exceed it. Having full control over your time and schedule should enable you to work more efficiently than before, so this shouldn’t be too difficult. It’s important to make the trial such a huge success that there’s no reason for your boss to object to you traveling more.

From there you can negotiate your next steps. Maybe you agree to be in the office for ten days per month. Maybe you work fully remotely but agree that if the company becomes dissatisfied with your work at any time that they can revoke the agreement. Make sure that along with your upside comes only positives for them.

If all else fails and remaining an employee is not an option for you, try to quit. Talk to your manager and make it clear that you like the company, like the people, and like the work, but that not being able to travel is a deal-breaker. I have friends who have done this and gotten great deals as a result. One got his hours cut in half and was allowed to travel 100% of the time for the same pay. He did that for five years until his division got shut down. He then moved to a company with “unlimited vacation”, which most people don’t ever use. He used a lot of it, but always worked while traveling, so they never complained.

At the end of the day, the quality of your work is what companies care most about. If you are doing a good job and contributing to the bottom line, they should be willing to allow you to travel. The key is to take the risk upon yourself and prove to them that it will be a good decision. It’s not fair to force them to make the initial leap of faith when you are the one who is in control of how it will work out.

Writing

It shouldn’t come as much of a surprise that a guy writing a book on a cruise ship would suggest that writing while traveling is a good way to make a living.

The secret of the travel writing industry is that travel writing isn’t valuable enough to fly writers around the world to write the stories. The economics just don’t add up. So almost all travel publications are filled with stories written by freelancers who have paid their own way and are writing articles to help keep them moving.

I used to write for Gadling.com, which was at the time one of the biggest travel publications. They didn’t pay a ton, but they paid fairly and I could submit as many or few articles as I wanted to. Just as I could scale my expenses by traveling, I could scale my income by writing more or less for Gadling.

You can also write your own books. One of the great triumphs of recent years is that independent people have access to huge markets. Now I can write a book and make it available to millions of people using the same laptop on which I wrote it. That simply wasn’t possible fifteen or twenty years ago.

If you want to write your own books, there are two things you need to focus on. First, you must have some way to get at least a couple hundred people to buy the book within the first few days. If you do that, it will percolate through the recommendation engine and you will sell a lot of copies. Most importantly it will create longevity. I still make money on books I’ve written many years ago.

The second thing is that your book needs to be good. Only books with good reviews stay in the recommendation engine, so most of your longevity will come from quality. This may be a good time to mention that if you leave me a review for this book, especially a five-star one, I’d be extremely grateful. Readers generally don’t realize that they can help authors far more by leaving a good review than they do by paying for the book in the first place.

When searching for a topic, think more about what you’re uniquely suited to write about than what the market wants. I once wrote a book about living in an RV, solely because I had a friend who was interested and was typing all the information out for him anyways. I put the book on Kindle and it ended up earning me over $10,000 total. Not bad for the ten or so hours it took me to write it.

Once you write a good book and have a way to get a few hundred people to buy it initially, publish it on Amazon through Kindle Desktop Publishing for Kindle and CreateSpace for paperback. Also consider recording it through ACX for Audible, which also shows up on Amazon. In some cases I make more from audio books than I do for paperbacks. Kindle always sells the most, though.

UpWork

Upwork is a sort of hybrid between having a job and having your own business. It allows independent contractors to connect with people who need work done. I’ve seen people learn HTML and CSS, which are the easy-to-learn building blocks of web pages, and immediately start their own contracting business through UpWork. You won’t start off making a ton of money, but it’s pretty cool that within a few months of self-study you can learn the skills to earn enough money to travel to inexpensive places.

From there you can improve your skills, build a portfolio, and charge more. If web design is an area that interests you, it’s a perfect fit for this lifestyle. UpWork has jobs for everyone though, ranging from customer support to technical writing.

For Sale By Amazon (FBA)

FBA is a route that a lot of nomads are taking because it allows them to access the huge market that Amazon services, but without having to manufacture and warehouse items themselves. The gist of it is that you contract someone in China to manufacture your product, either something you’ve designed or something premade. You can find these products and vendors on AliExpress.com. Then you arrange to have them shipped directly to Amazon, and you create a listing there for the products. Give away some free ones to get reviews, and if you’ve chosen a good product and marketed it well, you can have a recurring source of income. The difficult part is finding a product which has a large market but not a lot of competitors.

When I first started traveling it seemed like SEO and affiliate marketing were the big things nomads did for money, but now FBA is becoming much more prevalent.

Starting Your Own Company

I can’t tell you what type of company you should start, but I can tell you that there is no time in history when launching your own business has been so easy. In particular, starting a web-based tech business is particularly well suited to a nomadic life.

There are many reasons for this, but they center around the ability to control the length of your runway, especially in the early stages where your primary expenses are your own living costs.

Unless you are fundraising, I believe that the benefits of living in a tech hub like San Francisco are overrated. There is value there in having a culture that fosters tech businesses, but that culture comes at a very high price. If you travel through inexpensive places while starting your business, you’re able to do so with less stress and more freedom. You can hire remote employees, which will be far less expensive than employees in tech cities.

Additionally, the level of success you need to achieve to sustain yourself as a traveler is far lower than it would be if you were in an expensive city. Getting to $1000 per month of revenue in San Francisco or New York isn’t much, but it can be enough to keep yourself living a good life in Bangkok or Budapest.

I ended up starting a business called CruiseSheet while I traveled. I’ve programmed from Airbnbs, cruise ships, trains, and capsule hotels. Sometimes I’d hunker down and make tons of progress, other times I’d focus on the cities I was in while the money continued to come in. I’ve had other income streams going at the same time, but even if they didn’t exist, that one little site would be enough to keep me traveling.

Set a goal of building a business that earns $1500 per month. That’s not a ton and shouldn’t require any employees. You can save up money in advance to fund the beginning of your trip, and then you give yourself 6-18 months to have money coming in. If you build a decent business and keep maintaining it, that short period of time spent creating a business could keep you in the air (and on the sea) indefinitely.

Chapter 18

Where to Stay

Where you stay while traveling can have a large impact on your experience in that place as well as how you feel about the city in general. In other words, choosing somewhere to stay is important and warrants some time spent on it.

Location is extremely important. If you can’t afford to stay in a good location somewhere, even in basic accommodations, I’d suggest traveling somewhere else first. It’s better to have a good experience in a place that’s your second choice than to have a bad experience at your first choice.

If you can be in an area that’s walkable to restaurants and places you’re going to visit frequently, it will make a big difference. If you can’t, you should at least be near a stop on a major train route. If you have to rely on ridesharing or taxis every time you leave, there will be too much friction for you to make the most out of your trip and still be relaxed.

My criteria are first basic cleanliness, then location, then niceness. I’d rather have a very small and basic place in the center of town than a fancy hotel suite on the outskirts.

Hostels

Often the best values are private rooms at the top rated hostels. You’ll have privacy and probably your own bathroom, but the room will be small and you’ll spend time in a big common area. Even if you plan on staying somewhere else eventually, this is a great way to get to know other travelers early in your trip. Hostels tend to fall into a few different categories; choose the one that best reflects your interests and you’ll maximize your chances of meeting people you’ll be interested in.

Maybe the best known type of hostel is the party hostel. They’ll have big bars, DJs, and a lively atmosphere. Perfect if you want to party, but terrible if you want to work (or care much about your sleep quality).

The next type of hostel is the budget hostel. These tend to be very bare bones, but as long as they’re well rated on booking.com or hostelworld.com, they should be clean. With a budget hostel you’ll get to save more of your money for doing activities and will meet other frugal people.

Last is the upscale hostel. These might be unique experiences, like a converted countryside schoolhouse or a series of cabins in the woods, or just a nice normal hostel. They tend to have good food and great common areas for reading and working. In my opinion they offer a lot more than similarly priced hotels in terms of experience and attention to detail. They also tend to provide memorable stays.

One really unique feature of hostels is that they are very likely to have inexpensive rooms with 4-10 beds. If you’re traveling with a group, everyone can stay together for very little money.

Airbnb

Airbnb covers a wide variety of stay options, ranging from a room in someone’s house to a giant private villa that can sleep twenty. That variety means that you can usually find an Airbnb that matches well with whatever your needs are. The downside is that the check-in experience varies a lot. Sometimes you have to coordinate schedules with the host to find a time to meet them, but other times they have an electronic lock or a lockbox.

If you’re looking for an Airbnb in advance, it’s a good idea to send a message to the host and ask them for a discount. Even a simple message like, “Hi, I’m considering a few Airbnbs in the area and yours is a little more expensive than others. Would you consider a discount for these dates: _____” will get results more often than not. If you’re going for weeks or months you can sometimes get a very significant discount. Find 3-5 Airbnbs that you’re interested in, ask them all for discounts, and take the one that ends up being the best value.

Hotels

The main advantage of hotels is that they’re very quick to check in and out of and they provide a consistent experience. If I’m staying somewhere for just one to three days, I’m most likely to stay in a hotel to avoid dealing with the uncertainty of Airbnb.

My favorite site for an overall hotel search is trivago.com. They have a huge variety of hotels and search many different booking sites, which often have big differences in price. If you’re very particular or want a specific hotel, Trivago is the best site to search.

Usually I end up booking hotels through Priceline Express Deals and Hotwire, though. Both sites work the same way: they allow you to choose your criteria, such as location and star-rating, and they will give you a hotel with price and user-satisfaction rating, but without revealing the name of the hotel before booking.

This model allows hotels to sell extra inventory inexpensively without ruining their premium image, so it works best for 4 and 5 star hotels. I’ve had overwhelmingly positive experiences with it, often staying in 5 star hotels for around $100 a night. The key is to only choose hotels with an 80% or higher user rating. When they’re lower than that, the hotels often have very major problems like loud construction or are in disrepair. If you are traveling by yourself, make sure you search with both one guest and two guests. Sometimes the price is more or less expensive one way or another, even though you’ll get the same room either way.

There’s also an app called HotelTonight which has last minute deals and is a hybrid between Trivago and Hotwire. It only works for stays beginning that night (for any duration), but the pricing is similar to Hotwire. If you like the idea of knowing exactly where you’re staying before committing to a hotel, it might be the best choice for you.

Chapter 19

How To Meet People While Traveling by Todd Iceton

Todd is one of my closest friends, and a frequent travel companion, including on the very first multi-country trip I did. He has shaped my travel experience as much as anyone else has. I asked him to write this chapter because he’s the best person I know at making friends while traveling.

Many of my favorite moments with Tynan have been in the company of people we’d never have encountered at home, and some of my most treasured friendships began on the road. It’s the humans that make the world feel small, and travel is an ideal opportunity to meet new ones!

You’ve already taken the first step. Navigating new surroundings requires more sensitivity than staying home, and that naturally makes you more receptive to connection. What else can you do to make the most of it?

Travel Alone (Sometimes)

The essence of travel is a destination, but the surest way I know to meet new people lies in traveling companions, or lack thereof. Imagine landing alone in New York City, walking through the airport, taking a bus to Grand Central Station, and walking down to the subway. Imagine all the faces you’d see! Now imagine the same path if you were traveling with a group of friends. How much of your attention would be diverted? You’ll meet more people with one less layer of insulation between you and your unfamiliar environment. Others find it easier to approach you when you’re alone, too.

On the other hand, one of my most independent friends calls from exotic places all over the world to tell me about his latest adventures. Whether it’s motorcycling across a lush country, or sleepless nights with someone cute in a tropical paradise, he follows every experience with a hint of lament that a good friend wasn’t there to share it. It would make it more real, he says.

Tynan and I stumbled across a solution years ago when I left Singapore a few days ahead of him to meet my cousins in nearby Thailand. When he arrived, we realized we’d met a lot of people in our time apart, and that a block of solo time in a shared trip could be the best of both worlds.

Travel With a Group (Sometimes)

Traveling with a group can also increase your opportunities to meet new people if you’ll be among other groups, like at a music festival or in Las Vegas. It’s also helpful if others in the group are more social than you.

Get Introductions

Even if every stranger is just a friend you have yet to meet, some are closer than others. Friends and family who’ve spent time in your destination often know local people to whom they can introduce you.

Choosing Destination Size

In Los Angeles, where people and interactions between them are plentiful, strangers passing on the street greet each other less than they would in a small town. Hikers on the Pacific Crest Trail, who may only see a handful of people a day, will always say hello. A destination with fewer people eases connection based on location alone.

A destination with more people helps with meeting people who share less common interests. Attending events like conferences or festivals specific to your interest helps too!

Opposites Attract

You can often make more connections in a destination full of people very different from you. You’ll have more to learn from each other, and novelty will be on your side. I’ll never forget walking past a schoolyard in a small town in Aomori with Tynan. The children were thrilled to see visitors from a strange land, just as we were excited to meet kids we don’t normally see, and though we couldn’t communicate much, we were all grateful for the chance to interact.

Create a Temporary Routine

An everyday routine like taking a walk in the morning, visiting the same coffeeshop, or having lunch in the same cafe can provide the repetition and familiarity necessary for deeper relationships.

Pursue Your Interests

Within a larger trip, I often take smaller trips in search of tea, not because I’m a diehard enthusiast, but because a purpose will take me outside typical tourist activities. Plus people who share your interests are among the most likely to become friends!

Allow for Serendipity

It’s tempting to rely on Yelp for restaurants, Maps for directions, and Facebook for events, but you’re more likely to meet people by examining your environment closely instead. Ask locals for recommendations -- even for silly things! Locations you’d find online may also be less receptive to new people than ones you find wandering.

Keep in Touch

Even if you don’t know someone well, default to asking them to connect on social media. You never know what mutual friends or interests you might have, and you’ll have more context next time you visit!

Tynan and I met an American girl at the top of a mountain in Yakushima in 2008. She lived in San Francisco, so when I moved there years later, she invited me to a party at her parents’ house exploring solutions for the nutria rat invasion in Louisiana swamps. Now we’re all close friends and I can’t imagine what would have happened had we not kept in touch on Facebook!

When in doubt, connect! Happy trails!

Chapter 20

Getting Around Cities

There are many ways to get around once you’re in a new city, but the optimal strategy is to travel as locals do, plus add in ridesharing, which locals don’t always do.

If you’re in the US and live outside New York, Boston, or DC, you may not use public transportation very much. For most places in Asia and Europe, however, this will be your best bet.

Most systems allow you to purchase one-time tickets, unlimited use cards, or stored value cards. Unlimited use cards are almost never worth it (the huge exception being the JR Pass, which covers all of Japan), as much as I’d like them to be. One-time tickets are great, because you won’t have leftover credit to deal with, until you hit rush hour and have to wait twenty minutes to buy another one.

In general, if a stored value card is available, it’s the best way to go. You pay a small deposit of around $5, load on more money to pay for fares, and just tap it in and out every time you use transit. These cards also handle transfers between buses and trains automatically, and in some cases, like in London, will cap the amount you can spend each day and convert it into an unlimited day pass if that would have been better.

As I’ve mentioned a few times, it’s important to reduce friction while traveling, and buying a stored value card is a good way to do so, even if you end up with a few dollars of leftover credit at the end.

Taxis are a bad deal in all but the poorest countries, and in those countries they tend to be cheap only if you know how to avoid the scams. I spent a good deal of time in Panama when it cost 75 cents flat rate per ride anywhere in the city. If you handed your quarters over as you exited the cab, there would never be an issue, but if you asked the price, you’d be quoted $5 or so. Some cities, like Prague, have mafia-like taxi cartels that employ a host of fascinating schemes designed to rip you off.

Ridesharing is usually a better bet. Uber has expanded to more cities than you’d expect, and the experience is consistent everywhere. Lyft has started as well. Some places don’t have either, but they have their own alternatives. Even in cases where they’re just fancy apps to call taxis, they tend to circumvent the scams and make payment easier.

When I’m first in a new city, I bias myself towards walking, usually doing any distance up to three miles on foot if I have the time. I naturally have a poor sense of direction, but walking seems to counteract that and allows me to get the lay of the land better than I’d be able to any other way. It also gives me the chance to discover places by chance, which is how I’ve found many of my favorite restaurants all over the world. Once I get used to a place, I tend to shrink my walking radius to 1.5—2 miles.

Notice how locals get around. Since this is where they live, they’ve already figured out the most efficient ways to get around, so you may as well copy them rather than reinvent the wheel. Just substitute ridesharing for car ownership and taxi riding.

Chapter 21

Phone Service

The availability of international phone service, particularly internet service, has exploded since I first began traveling. Whereas before you’d have to scramble to get a SIM card your first day in a city, now there are a few phone service providers which offer free roaming in all countries. Of all technological advances, this one may be the best for the permanent nomad.

Of course, this information is perhaps the most likely to become outdated. So use it as a starting point, but make sure to do your own research if you didn’t buy this book shortly after it was released in 2018.

If you are a nomad, you probably want T-Mobile. They have long been at the forefront of global roaming, and will likely continue to be for quite a while. As of this writing they offer full-speed data in both Mexico and Canada, as well as unlimited throttled data in foreign countries. That rate is 128k or 256k per second, depending on your plan.

Those speeds are fast enough for maps, sending and receiving pictures, or making phone calls with Skype or Google Hangouts. They are not really fast enough for any sort of video. The speed bump from 128k to 256k is significant enough that it’s probably worth paying for the upgrade.

Sprint has rolled out a similar plan, but is only 64k a second, which is not fast enough for reliable audio.

Google Fi, which only works on a few specific phones, offers even faster speeds (full speed in most places), but is a bit more expensive.

I no longer recommend buying individual SIM cards in different countries. Even as a programmer and power user, I find these reduced speeds to be fast enough for most activities, especially when wifi is as ubiquitous as it has become.

All carriers charge for phone calls, but you can also make them for free or cheap through Google Hangouts, Skype, WhatsApp, or even T-Mobile wifi calling if you have wifi. Of all the options I’ve tried, Skype seems to have the highest audio quality and the fewest issues. It’s the only service I use for voice calls.

Chapter 22

Traveling with Children by Leo Babauta

The most impressive thing about Leo Babauta, author of the ultra-popular blog ZenHabits.com, is how he manages it all. He has a family with a wife and six children, runs his own business, and still finds time for his friends and to travel. Sometimes just the two of us will travel in search of great tea, but every year he travels with his entire family as well.

One of the more common excuses people give for not traveling is that it’s too hard with children. Leo is a living example of why that’s not a valid excuse.

Having kids doesn’t have to be the end of your world-traveling lifestyle, nor does traveling with kids have to be a stress-filled affair.

Traveling with my six kids has been one of the greatest pleasures of my life, and I’d love to share what I’ve learned to make traveling with them a joy.

And yes, I said I have six kids. I’ve had lots of different kinds of trips with them:

- Trips to Europe, Japan, Mexico, Hawaii and the U.S. with all six of them.

- Trips with just me and one of the adult kids (when they turned 18) to Iceland, southeast Asia, New York City

- Trips when they were toddlers, elementary school age, teenagers, and just-turned adults

And all of these have been wonderful! Let’s talk about the things that made all the difference in the world.

Learning Mindset Through Traveling

The first thing we taught the kids, on our first trip to Japan with them, was to think of our trip as an adventure. That means that things might go wrong—they probably will, actually—but that’s all a part of the adventure.

We might get lost, but that’s OK, because it’s an adventure! We might miss trains, miss a plane, have plans go awry… and we’ll just have to figure out how to deal with it, and have fun while we do. That’s the adventure mindset.

Traveling, then, became an opportunity to teach them good approaches to life:

- Be patient. Things might go wrong, we might have to wait in lots of lines, nothing goes as planned. Again, all part of the adventure. But it’s also an opportunity to learn patience, and to figure out fun things to do when waiting is something you can’t control.

- Be curious. Every place, every experience, is a chance to learn something. You can learn about a different culture, learn about history, learn about science and technology and much more… just by being curious and paying attention, asking questions.

- Explore with openness. You can go into a trip with a set plan, but that doesn’t allow for unexpected experiences. It’s often better to just head out and explore a city on foot, not knowing where it will take you, and allowing yourself to be open to whatever might happen. This is a great way to travel through life, too.

- Travel light. I talk more about this in the next section, but it’s not just about what you bring in your luggage. It’s about a mindset—traveling lightly is about being flexible, not being weighed down by a lot of things, which allows you to easily change directions, adapt to new plans.

These are some examples of what we try to teach our kids as we travel, talking to them about it before the trip but also while we’re on the trip. It’s a great way demonstrate these ideas through your own example, and to allow them to practice it in a fun way.

Travel Light

This is the only way we travel now, and we taught it to the kids early on. We bring a small backpack each (20 liters or less) and no checked luggage, no other carry-ons, no roller bags. This is incredibly important when you’re traveling with kids.

First, we have them take their own backpack. That means they carry their own stuff. We did that even when the kids were as young as three years old (OK, we carried a few things for them, but they still carried their own tiny pack). This is so important, because it 1) lowers the burden of what we, as parents, need to carry and 2) teaches them to be responsible for their own stuff.

We also have them pack their own stuff (with our supervision when they’re young). At first, we taught them the essential things to bring (two changes of clothes, a few toiletries, a lightweight rain jacket, passport, a book and/or device). But eventually they could do it on their own without our help. We just made sure they had their passports.

We taught them how to wash their own clothes in the sink or shower, and to pack clothes that dry easily.

The kids have learned the value of traveling with a light pack, not only through airports but running through train stations, riding buses, moving from one city to another. It helped us not waste our energy, and makes traveling together much more enjoyable.

Travel as a Learning Method

I’ve discussed teaching them the right mindset, but travel is a great opportunity to learn all kinds of life skills as well. We try to teach them to take over the responsibilities of traveling, a little at a time:

- We have them help plan. We all vote on the itinerary (which cities we go to, what we want to do in each city) through various online polls. The older kids now help look for Airbnb apartments, book trains, find good flights. This allows them to be able to do this on their own, later in life.

- We let them navigate. The older kids, once they were in their teens, would each have days where they figured out where we were going, and led the family to those places. That means using Google Maps, but also figuring out opening hours for museums, how to navigate the mass transit system, how to look for landmarks so they can navigate without the map, and more.

- Have the older kids watch the younger kids. We do this at home too. It makes it way easier than having to keep an eye on all six kids, when the older ones can share that responsibility. On our first trip to Japan, we had one older kid (or parent) in charge of one of the two younger kids at all times, and had a system of clearly passing responsibility to another person (you had to get confirmation). This way, the younger kids never got lost, and the older kids were learning how to be responsible.

- Teach them democracy. Again, we planned by voting in online polls, but we also made decisions out on the field by vote—everyone but me closes their eyes and raises their hand to vote. “Who wants to go to the Louvre?” (No one raises their hand.)

We also teach them to push into their discomfort zone a little at a time, trying new foods, navigating our family in a strange city, trying new experiences, meeting new people. This is a key skill in life, and travel is a great way to teach it.

Making It Fun

Travel, for us, is not all just about learning and responsibilities. It’s about fun! We want them to enjoy our travels as much as we do. Of course, we have our conflicts and bad moods, being human, but we do our best to make things fun:

- Gelato. The kids will walk all over town, go to museums, and basically be happy doing anything if we buy them gelato during the day. This was a tradition we started in Italy and continued elsewhere (with variations based on the country, of course).

- Museums should be short and fun. Eva and I enjoy going to museums, but the kids can get tired of them. Museum fatigue is a thing. We learned a lot from our friend Nick of Museum Hack, who made a business out of delighting people with amazingly fun museum experiences. So we keep our museum visits short, and look for interesting stories and fun experiences.

- Always have activities or books. There’s always time when we’re hanging out in a train station, lounging in a park, on a long bus ride, etc. … so it’s important that they have something to do. A good book is always a good default, but we also have games we like to play together (like Ultimate Werewolf) that we can play anywhere.

- Don’t try to do too much. We’ve made the mistake of trying to cram too much into each day … it results in everyone being too tired and cranky. That doesn’t make for a fun trip. Instead, we do fewer things, and have more fun doing them.

- Lounge somewhere cool and shady. When it’s hot, it’s important to take lots of rests, drink lots of water, and find somewhere cool to lounge around. And eat gelato. And play games.

In general, we try to make a game of a lot of things, like racing and playing charades and asking “would you rather?” and so on. Skip along on the sidewalk, see who can walk the weirdest, dance in the middle of a public square, tell really bad jokes.

Other Tips to Make Things Easier

Traveling with kids can drain you of some energy, so other than traveling light, we’ve learned some ways of making our family trips easier:

- Stay at Airbnb apartments. With a big family, we would need to rent several hotel rooms. That makes an Airbnb apartment, with three bedrooms (or two with some couch beds), more cost-effective for our family. But in addition, there’s usually a kitchen, so we can at least eat breakfast at home and keep things refrigerated; there’s a living room we can all hang out in, and usually a washer and dryer where we can all wash one or two big loads for the whole family. So in general, for us, a short-term apartment stay is cheaper and more convenient than a hotel, and we all get to hang out as a family.

- Get Global Entry/TSA Precheck. This speeds you through airport security, which is especially convenient if you are traveling as a family. My wife and I and all our kids have Global Entry, and so traveling together is a breeze.

- Teach them to get through security with ease. Other than Precheck/Global Entry, there are a few things you can do to make going through the airport security easier on your family. First, as I’ve already said, don’t check luggage, which makes airports a hassle. I also don’t recommend roller-bag carry-ons, because it’s just a huge hassle dragging a whole family’s roller-bags around airports, cities, trains and buses.  Just a light backpack carry-on. Next, have them prepared with their passports and boarding passes (mobile or paper) when entering security. Put everything in their pockets in a backpack pocket, so they don’t have anything to mess with when they get to the security scanner. Go through, and you’re done. Go a little early when traveling with kids, just to have a bit of cushion so you’re not too stressed. Breeze through security, get there a little early, and you’re all relaxed and happy.

- Start slowly when you get to your destination. I’ve found that my family is usually pretty tired when we get to our destination. I like to walk around a bit to stretch out, stave off any jet lag, and get a feel for our destination. But I try not to force them to overdo it for the first couple days, because otherwise everyone gets tired and grumpy. So walk around a bit the first day, try to stay awake until night (if applicable), but take it easy. The next day, don’t try to do too much—explore, but rest a lot. This makes the trips a lot more enjoyable.

In the end, traveling with your kids can be a non-stressful, enjoyable time, but also an incredible learning experience that can prepare them for life. I’ve loved every trip I’ve had with my kids, especially now that they don’t cry on airplanes (well, it’s down to a minimum).

Chapter 23

Empire Housing Method

The two major pain points of having a nomadic life are dating, as discussed elsewhere, and productivity. As someone who likes to work a lot, the hit to my output while traveling has long been an issue. I’ve come up with routines and habits to compensate, but there’s no denying the benefits of a familiar workspace, a reliably ergonomic desk and chair, an extra monitor, and a familiar routine within which to fit work.

It’s this productivity hit which, for years, made me second-guess how much I was traveling and made me wonder whether being a nomad was worth it at all.

Whenever I’m faced when this sort of dilemma, and I have the presence of mind to remember the process, I think about what the ideal outcome would be, and then I work backwards to figure out how I can wrangle it for myself. In this case the answer seemed obvious: I would want to have houses or apartments all over the world with great work setups, and would come and go as I please. A tall order. No one I knew had a situation like this.

Then a strange thing happened: a friend realized that islands in Canada weren’t that expensive. I became obsessed, and I organized a group of ten of us to buy one together. I would have preferred to have it all to myself, but I couldn’t afford it without help, so we ended up buying it as a group.

The story hit the internet and doom and gloom was predicted near universally. We would hate each other, we would fight, and some of us would certainly be killed by dead trees falling over.

Incredibly, the opposite happened. We became better friends, we never had a single argument, and many of us felt like the island was the best purchase we’d ever made. At first we camped in tents, weathered hurricanes, and were happily miserable, but since then we’ve built it up a bit. Now we have power, internet through a cell connection, and a place to sit and work.

In the meantime we have made similar purchases elsewhere. We bought up part of a neighborhood in Las Vegas so that we each had our own neighboring condos. Last summer we bought a small flat in the center of Budapest and we’re currently looking at the Caribbean and Tokyo for the next two.

My favorite trips are ones which span multiple cities where we have a place. It’s a great feeling to land and, within an hour, be back “home”. I’m now just as comfortable and productive in Budapest as I am in Las Vegas. I don’t have to figure out lodging and I don’t have to deal with Airbnb check-in procedures. I know that my bed will be comfortable and clean, and I already intimately know the area in which I’ll be staying. The experience is far better than renting an Airbnb.

Having multiple places also creates gravity in those locations. We originally bought the island only for itself, but due to proximity I’ve gotten to know the city of Halifax quite well. It turns out it’s a great little seaside city with a lot of cool day-trippable towns nearby. I’ve made friends there and am even a sort of “regular” at a couple of the restaurants. The same goes for Budapest, a city definitely worth getting to know as deeply as possible.

It turns out that buying property with friends is even better than buying by yourself, even if you could afford to do so. Knowing that any unexpected repairs will only burden you with 10% of the cost erases a lot of worry. I don’t want anything bad to happen at our properties, but if it does it’s not enough to ruin my week. We had an unexpected $3500 charge at the island, but each of us only had to pay $350 of that, which was a lot easier to swallow than the full amount.

Maybe the greatest unexpected benefit of buying places with friends is that they have a strong reason to visit there, too. I realized years ago that trips with friends were far more valuable to me than trips I went on alone, and now some of my closest friends have a strong incentive to travel with me to some of my favorite places. Sometimes we overlap by chance, other times because we planned a trip together. The island particularly illustrated this as ten of us were there clearing trails and doing work on the structures we’ve built. That wouldn’t be much fun alone.

Through my experience with these group purchases I’ve come up with some systems and guidelines to help you repeat my success with them with your friends.

Choose the Right People

This system only works because I have great people in each group. The number one criteria I use when choosing to invite people is how cooperative that person is. My ideal candidate is someone who could lead a project like a renovation or a group trip, but who would also be happy to let someone else do that.

Don’t choose someone who will want to make changes to every plan you come up with. Your co-owners have to trust you and each other, despite being capable enough to do things by themselves. A large part of the reason it makes sense to buy these places is because it reduces the friction in your life. That changes entirely if you have to manage a group of people who are fighting and arguing all of the time.

I choose my invitation lists very carefully. I don’t just invite everyone I like, because I know that some people will get along better with the rest of the members of the group than others. As I consider people I think, “would I and everyone else be glad if they showed up to the place and this person happened to be there already?”

It feels a little bit harsh to look at your friends through this filter, but it’s the method which will create a cohesive group. As we’ve had to make decisions and deal with things in our properties, I’ve been particularly grateful to have such a solid group of friends involved in each property. So far they’ve all made the process easier rather than harder.

Not Too Much Money

I believe that the properties I’ve been involved in work because we think of them as permanent purchases, not real estate investments that we may some day flip. This is reflected both in my pitch to my friends and in the agreement that we write up to make sure we’re all on the same page.

For that reason, the amount invested per person needs to be small enough that it is a “big expense”, not a “small investment”. The number that feels right for my friend group is around $10,000 each. That is, of course, a lot of money, but it’s not so much that anyone’s life is going to be screwed if it’s locked up in a property that they aren’t allowed to sell.

Depending on where you want to buy, it’s certainly possible to go as low as $5,000 each. If you and your friends are more wealthy, you could go higher as well. If the amount you’re asking is going to be a stretch for a potential group member, I wouldn’t let them invest, as it’s not going to be a good buy for them if it’s going to cause stress in their life.

Choosing the Place

The primary heuristic I use when choosing a place is: will this place be better than an Airbnb that I would have otherwise rented? If it’s not, there’s really no point in going through all of the hassle just to stay somewhere worse. As much as I like buying these places, I won’t do it in a city where I can’t afford a better place than I’d AirBnb.

There are, of course, extenuating factors. In Budapest the Airbnbs tend to have terrible furnishings and linens, so even if I had bought a place that was on par with the Airbnbs otherwise, it would have been worth it.

Of primary concern is location, of course. When thinking about location, don’t think about miles from any one point, instead think of minutes by most likely mode of transportation.

In Budapest, where real estate is cheap, we bought a flat that is within 1-2 minutes from about fifteen good restaurants. We were considering a larger place, but it would have been a 5 minute metro ride from good restaurants. That doesn’t sound like a huge difference, but we were willing to sacrifice space in favor of increased convenience several times a day.

I’m planning on buying a place in Tokyo in a year or so, and we will be much further away from my favorite areas. There my goal is to find a little neighborhood that has a few restaurants nearby and is within 45 minutes of my favorite area, Shibuya. In Puerto Rico my main criteria is that it has to be within a fifteen minute walk to the beach.

Don’t worry about resale value. Freeing that constraint gives you more leeway in others, and you’ll be structuring the purchase to make it almost impossible that you’d ever sell.

When evaluating a space, don’t think in terms of bedrooms, but rather about likely group sizes and how you can fit them in. In Budapest I decided that the most likely group sizes were 1-4, with occasional larger groups. We got a place with a tiny bedroom, in which we put a bunkbed with a trundle, and a larger bedroom with two twins that convert to a king. Downstairs we have a couch that converts to a queen, giving us very comfortable sleeping for 1-4, with reasonable accommodations up to seven.

Don’t worry about all of your group coming at once, because it will never happen even if you try.

Furnishing

My strong suggestion is to just furnish your place using IKEA. Choose a monochrome palette, go to the store, and try everything before you buy it. There is better furniture out there than IKEA, but none that is as well made for the price.

IKEA has a gray metal bunkbed which I really like that can be expanded upon with a trundle bed which rolls out from underneath it. This is a great way to fit three beds in any room, allowing you more flexibility in the other rooms.

I also recommend the configuration of two twin beds rather than a queen or a king. By pushing the two together and securing them with squeeze-clamps that you can buy from any hardware store, you can turn the two beds into a king sized bed. In addition to the two twin bottom sheets, buy a king bottom sheet as well. IKEA even sells a foam insert to bridge the slight gap between the two mattresses. Use the normal twin duvets, top sheets, and pillows. This prevents anyone from hogging the blankets and is a quite civilized way to sleep as a couple.

Group Size

So far our group sizes have been around 10 people. This may be a reflection of how many crazy friends I have, but it also feels like the right size in terms of making decisions and planning trips together. The important thing to think about is how often the space will be used, how long those visits will be, and how many it can accommodate.

For example, if you were buying a three bedroom beachfront villa in Tahiti, you could probably have a group of over 20, because it’s so remote that people will rarely be there. A place in New York, on the other hand, may need to have a smaller group, as it’s so accessible and easy to spend long amounts of time in.

The Hard Sell Email

I organize my groups the same way every time. I write what I jokingly call the hard-sell email and I send it out to everyone who I think would be a great member of the group.

When I bought the island I was desperate to get a group together because it was an excellent deal and I didn’t want to miss out on it. So I sent the email to a lot of people, including people I never thought would say yes. I was shocked at the turnout. Even my aunt, who I’d never seen in nature before, said yes! So don’t think much about whether the person will say yes or not, just think about whether you’d want them to.

To write a hard sell, think about what each member of the group will be motivated by. I don’t care too much about the beach, but I knew key members of my group are, so I highlighted it in my Puerto Rico hard sell. Same with things like night-life and food. I also include things that I’m personally excited about, even if I don’t think my friends will be excited, because I think that enthusiasm is contagious.

Right off the bat I want to sell the “vision” of the place. This is to make sure that everyone is on the same page and has the same expectations for what the place will be used for. When I pitched the island, I pitched it as a way to reconnect with nature, build things, and to get away to write or program. My worst nightmare was that half of the group would want to turn it into a party island. The vision for Budapest was a common European home base from which we could work and explore the city and neighboring areas. For Vegas it was the ultimate US home base with a community focus. For Puerto Rico it was a cheap and easy weekend getaway for couples or friends.

In the hard sell I outline how much it will cost, and I round up by a bit. Fees can eat away at the amount of money you think you have to spend, sometimes minor repairs are needed, and you can always use whatever is leftover for furniture. I never want to promise that something is going to be $10k, and then find myself in a position of having to collect another $2k.

Part of the reason it’s easy to get friends to buy in now is because I have a track record of finding great places and staying under budget. It’s one thing to ask someone to pledge a fixed amount of money and a different thing entirely to ask for an open checkbook.

I also include estimated monthly costs, and again I round up. If people aren’t familiar with this arrangement they might think that monthly costs will be quite high, whereas they can usually be kept under $50 each.

Keep Taxes in Mind

I bought my first property in Austin, Texas, way before I began to travel. I did it because I was making decent money and it seemed like the Thing You Are Supposed to Do. It was a reasonably good experience, but the property taxes were so high that I decided owning property was a huge scam and that I’d probably never do it again.

Later I learned that taxes varied wildly even within states, and even more so between countries. In Hungary you pay around 4% up front, but then never pay property tax again!

Before you choose a place, check the taxes and make sure they’re low enough that it’s worth buying. Not every place you like will be a good candidate for this housing method.

How to Structure The Group

First step is to open a Wyoming LLC. I like http://awesomewyomingregisteredagent.com/ because they are the least expensive and provide really good fast service. The purpose of the LLC is to create a company that can own the property, because it’s easier to distribute shares of a company than it is of a house.

Choose Wyoming because it has good privacy and is easy and inexpensive to maintain. The physical location is irrelevant.

Start by making yourself the only member of the LLC. This is because it’s much easier to open bank accounts and buy the property if you’re the only one attached. Obviously your friends need to trust you a bit for this.

Open a bank account. Choose one that has low fees, as you’ll need to keep the bank account open, but won’t often use it. I use Wells Fargo because they have a $5 fee which is waived if we have $500 in the account.

Once you buy the place, create the operating agreement. This is where you write the rules and declare who owns what share of the company.

You Won’t Airbnb

We thought that we would Airbnb our spaces, but have since decided against it. The main reason is that one person will end up doing all of the work to make it happen, but will only receive 10% of the profit. You could change that ratio, but the math never really creates a compelling case for someone to deal with it.

On top of that, you lose the ability to leave your stuff there unlocked. I really like having extra laptop chargers, leftover money, etc., in our places, without worrying about people moving them or taking them.

Last, once you have Airbnb guests you have to manage their schedules vs. yours, as well as the availability calendar. If you can’t visit your own place on a moment’s notice because some strangers are staying there, it defeats the purpose. If your friends are already there when you want to visit, that’s probably a bonus.

Chapter 24

Las Vegas as US Home Base

For years I had heard that Las Vegas was hit harder than almost anywhere else by the housing crash. As a frequent visitor to Vegas, my interest was piqued, but never quite enough to take a serious look. I lived in San Francisco, a city I loved, and assumed that high property taxes would make Vegas not worth it.

Eventually, though, curiosity got the better of me and I searched properties and checked into the costs. It turned out that Las Vegas had extremely low property taxes. Better yet, there were dozens of properties for sale for less than $100,000, some for around $50,000. That was about a twentieth of what it would cost to buy a habitable place in San Francisco.

Even though I was in Europe, I immediately began searching and ended up buying a place in Vegas sight-unseen before I returned. I didn’t know exactly what I’d do with the place, but the price was so cheap that I figured I could make something work. Maybe it would be a crash pad for me and my friends, maybe I’d Airbnb it, or maybe I’d hang on to it for a few years and try to sell it for a profit.

I never imagined that I’d end up moving in and making it my primary home base. Even though I visited Vegas all the time, it was always in three or four day sprints. I’d hang out on the strip and play poker, not exactly activities that fit into a daily routine. But as I got to know Vegas better, I came to realize that it’s the ideal US home base for a nomad. Since then I’ve gotten more friends on board and now nine of us use it as a base, with more preparing to do so.

Best Airport

For a nomad, Las Vegas is the best airport to have as a home airport, and I say that as someone who has been to just about every major airport in the US many times.

The best things about it, of course, are the ridiculously cheap flights. I routinely fly to San Francisco for around $15–20 each way. I went to Houston for $88 round trip. New York is usually around $200 round trip. LA is $20 or so each way.

Vegas is so cheap that it’s very often cheaper to go from Point A to Vegas and then take another flight to Point B, rather than to go straight from A to B. I always price it out both ways, and frequently end up with a day or two in Vegas to do laundry and catch up on work.

McCarran International Airport is also extremely close to everything. I once got from my living room to post-security in under ten minutes. Fifteen is probably around average. When you travel a lot, having a short and easy commute to the airport relieves a lot of stress and makes planning easier.

In the airport is an American Express Centurion Lounge, which is the best chain of airport lounges. I prefer some of the other locations over the Vegas one, but it might just be because I eat so many meals there that the food doesn’t seem as special. Also key is that you can walk between all terminals without exiting security, so you can go to the lounge no matter which airline you’re flying.

Las Vegas doesn’t have nearly as many international flights as major global hubs like LAX and JFK, but it has a fair number and is expanding all the time. Even when you have to take a connection, it’s usually just an hour flight away to Los Angeles or San Francisco. Surprisingly, international flights to and from Vegas are as usually as cheap as or cheaper than from major hubs. I’m not sure why this is, but I usually price flights to SFO, LAX, and LAS, and recently LAS has consistently been the cheapest one.

So although it may not be quite as good as some others for international, it’s a strong contender and beats out every other airport domestically.

Low Cost of Living

People are always shocked when I tell them that Las Vegas is a cheap place to live. Most people are used to the high cost of activities on the strip and don’t realize that life even half a mile away from the strip is far less expensive than other top-tier cities.

Besides cheaper groceries and restaurants, though, Las Vegas has very inexpensive taxes. Property taxes are low and there is no personal income tax. If you are a nomad who files taxes in a taxable income state and makes any significant amount of money, you can probably move to Vegas at a negative cost.

As a local, you also get discounts on a lot of things. Some normal Vegas attractions, like the world’s biggest observation wheel, give you more than 50% off. Some of the best restaurants in Vegas offer 10-25% off just for showing your license.

If you sign up for services like Fill-a-Seat and House Seats, you can get free tickets for major Las Vegas shows. I’ve gotten thousands of dollars of tickets for about $3 a month.

You can buy a nice place for under $100,000 or a veritable palace for $300,000. I know plenty of people who pay less than $400 a month for rent.

High Quality of Life

I can’t imagine a higher quality of life for the price anywhere else in the US. Some of the best restaurants in the US are in Las Vegas, and many of them are inexpensive enough that you can go on a regular basis.

Take Lotus of Siam, for example, which is consistently rated as one of the very best Thai restaurants in the US, but where entrées are around $10-15 each.

The weather is always good, though it packs a fierce dry heat during the summer. I love waking up to bright sun every day. Fewer than one million people live in Las Vegas, but it has more to do and see than all but a few other US cities.

Everyone Visits and You Can Host

When I started traveling a lot and making friends around the world, I frequently ended up staying in people’s guest bedrooms and on their couches. I always wished that I could return the favor, but having no fixed home base made that impossible. Now that I have a place in Vegas, I’m slowly able to repay the hospitality of my friends.

The thing about Vegas is that almost everyone visits there at some point, whether it’s for a conference, special event, or a guy/girls’ weekend away. Staying in hotels in Vegas can be expensive, especially now that they charge hefty resort and parking fees, so it’s a great hookup to be able to pick them up from the airport and host them.

Chapter 25

The Cruise Hard Sell

I get excited about opportunities that people should be taking advantage of, but don’t because perception doesn’t match reality. One example is living in Las Vegas. People have fixed ideas of what it would be like to live there, but it turns out that the reality is way better, especially for nomads. Another big example is cruising.

The first cruise I went on was about fifteen years ago. I had a crush on a girl and she found an amazing deal for a cruise, just $199 plus tax, for five days in the Caribbean. It could have been twice that expensive and not gone anywhere, and I would have signed up. I just wanted an excuse to spend time with her.

We went on our cruise and I fell in love... with cruising.

Many of the familiar preconceptions about cruises are absolutely true. They are full of old people. Much of what happens on board is really cheesy. They try to upsell you on stuff. But there was a lot more to cruising than I expected, and it quickly became one of my favorite ways to travel. I like all cruises, but my favorites by far are long transoceanic voyages with lots of sea days.

The food onboard is roughly high-end buffet quality. It’s not prepared by a Michelin chef, and it’s obvious, but it’s all pretty good. You get things like prime rib, lamb chops, and lobster, as well as all sorts of salads, appetizers, soups, fish, and other things. It’s not as good as your favorite restaurant, but it’s almost certainly better than average meals you’re eating at home.

I personally love the food because the variety is so wide that I can pick and choose and just eat a bunch of protein and vegetables.

Your cabin will be on the small side, but nice, if not a little heavy with fake wood veneer. Your stateroom attendant will be uncannily friendly and will clean your room twice a day. Between your room constantly being cleaned and all food prepared, you have no annoying maintenance or housework to do, which is a great feeling.

The ship itself will be enormous, much bigger than you’ll expect if you’ve never been on one. It feels like a small city. Unless you make a real effort, you’re not likely to see all of the public areas on the ship, even if you’re on board for two weeks.

The amount of freedom you have on board is also surprising. You can carry a plate of food from the restaurant to your room and no one will bat an eye. We’ve found conference rooms and set them up as offices to no complaint. You can go hang out in the empty night club in the middle of the day to find a quiet place to read.

While in the past ships had tiny ineffective gyms, new ships have huge gyms with free weights, machines, treadmills, and everything else. I love being able to just go up a few sets of stairs, work out, then go down a level and get some post-workout food. There’s no friction to keeping a great workout schedule.

Staff members are far more friendly and happy than it seems they have cause to be. They work very hard, but are somehow always in a good mood. I’ve gotten to know several of them, and it always turns out that their enthusiasm and positivity is genuine, not just an act they’re forced to put on. Being around positive friendly people all day is a really nice mental boost.

The crowd will be very old, but they’re also the old folks who choose to get out and see the world, which makes them a self-selected group of interesting people. I’ve met a ton of older people on cruises with whom I’ve had many great conversations I wouldn’t have otherwise had.

The real value of a cruise, though, is that it’s a canvas upon which you can paint anything you like. The freedom from daily hassles and distractions combined with all sorts of spaces and activities means that you can make your time on the ship into anything you want.

For example, I always write books on cruises. Having a fixed block of time with limited distractions is perfect for me. I’m on a cruise as I write this and have developed the following schedule:

9:30a—Wake up and have tea with my friend and roommate. We spend a few hours talking and enjoying tea as well as planning our day.

11:30a—Ride the FlowRider surf wave. Because the other passengers are old, we have the thing to ourselves the whole time, and the staff teaches us tricks. If it’s a workout day (every other day), I go to the gym instead.

1:00p—Eat lunch in the buffet. I make a huge spinach and lettuce salad and then cover it with any meats or veggies that look good. Today I had ribs, Thai beef, chicken tikka masala, green beans, cauliflower, and broccoli.

2:00p—Write. I write 2200 words every day from an always-empty room that we’ve turned into our office. It has floor to ceiling windows looking out over the ocean and is a couple floors above the buffet, where I can pop down to get tea or a snack.

5:45p—Dinner in the dining room. Four of us meet up for dinner here and usually bring board games to play while we order and eat appetizers.

8:00p—After dinner we occasionally see a show (juggling and violin have been the best so far), sing karaoke, read, or do the surf wave again. If I didn’t finish my writing, I fit in here.

1:00a—Go to sleep to the gentle rocking of the waves

This schedule is both luxurious and productive. On any given two week cruise I can produce one book, spend a lot of quality time with friends, read some books, get a good gym routine in, and end up on a different continent. The more friends I get on the cruise the more structured we make our days, and the more we customize the trip to our own whims.

If you want a real treat, take a trans-oceanic cruise that goes west rather than east. On these cruises you move your clock back an hour on around half the days, giving you a bunch of 25 hour days, known as Martian days. Forget about spas and fine dining; 25 hour days are the ultimate luxury of life. It feels as though you can wake up late, loll around with your friends, do a bunch of work, stay up late reading or doing activities, and still repeat it the next day. If I could figure out how to live on a ship that constantly moved west, I would definitely do it. Conversely, going east feels like you’re getting robbed of an hour all the time, but it’s nice to arrive in Europe pre-adjusted to their time zone.

It’s worth mentioning that I have a vested interest in convincing you to cruise. I love cruising so much that I built a cruising price tracker which eventually morphed into the best cruise agency out there. It’s called CruiseSheet and it’s at http://cruisesheet.com.

I hope you’ll use CruiseSheet to find an amazing cruise, but even if you book somewhere else, cruising is worth a try for just about anyone. I’ve dragged dozens of friends kicking and screaming on cruises, and all but one have really loved it. And even that one had a good time, but just missed having a big nightlife social scene with people his age. Fair.

To make the most of a cruise, plan it long enough in advance that you can convince a bunch of like-minded friends to join you. You can go for fun, but for me the real value of a cruise is that you can block out a defined chunk of time for work, reading, learning a new skill.

My favorite line is Royal Caribbean because they have FlowRider surf waves, ice skating rinks, mini golf courses, rock-climbing walls and other fun stuff for free. These are great ways to break up the day, especially because you don’t have to travel for to get to them. On the other hand, Holland America and Celebrity are a little bit fancier and have nicer food and décor.

Chapter 26

Travel Gear

Within the travel world, I am perhaps best known for my annual gear post. To the best of my knowledge I am the nomad who travels with the lightest and smallest backpack and never has additional bags. I do this not to try to be the lightest and win imaginary nomad points, but because traveling light has a profound impact on one’s experience. It enables you to do routes and trips that you couldn’t otherwise do, improves every trip, and drastically reduces your stress.

In my first travel book I attempted to make a comprehensive gear list. Within a year or so it became outdated and at this point is almost embarrassing (do you need a recommendation for a good Nokia phone?). This time around I’m going to focus on principles behind how I select gear and for specific recommendations I’ll direct you to my gear post which I publish every single year with the most cutting-edge list of gear. Because I do my own research and take things to an extreme, it’s typically full of gear which you won’t find anywhere else. You can see it by going to tynan.com/gear2018, changing the year to the current year.

Less Hassle

A running theme in my ongoing travel philosophy, and thus this book, is reducing friction. The easier you can make travel, the more you will get out of it, the more you’ll be able to do in the future, and the better your life will be.

Packing light is perhaps one of the biggest impact areas in terms of reducing hassle of travel. Think about finding overhead bin space, dealing with lost bags, waiting at the carousel for your bag to come out, lugging bags around when you don’t know where you’re going next, and trying to find a place to store your bag. These hassles, and many others, disappear when you have one small carry-on bag that fits under the seat in front of you.

There are also small benefits you don’t notice until you start traveling with just one small bag. I am almost always the first person from my flight to go through customs. Why? Because 99% of people travel with a checked bag when they go international, so they all have to wait to get theirs before they can go through. I breeze through, confirm to the confused customs agent that, yes, I really only have one tiny bag, and I’m first through the line.

On the rare occasion that I miss a flight, I have a lot more flexibility. Sometimes I’ll get a flight to a totally different location, something I couldn’t do if I had to track down a bag. I can also get off a flight before my final destination (see the flight tricks section to understand why I’d do this).

Also, I don’t pay any baggage fees, which cuts my flight costs way down, especially on budget airlines. I must save at least $500 every year. I actually love baggage fees because they cause other heavier-packing travelers to subsidize my cheap flights.

More Possibilities

One of my favorite flight tricks is booking an eight-hour layover instead of a two-hour layover. Instead of sitting around at the airport with a suboptimal amount of time, I can actually get into the city and go do something. Sometimes there’s just one museum or shop I want to see, or other times I’d like to walk around and get a preview of a place so that I can decide whether to spend more time there in the future.

What would I do if I had my small backpack and a larger carry-on? My options would be to lug the big bag around the city for eight hours or to just stay in the airport. I’d probably end up staying in the airport.

Every once in a while I organize a big train trip through Japan for a group of my friends. My one rule is that you have to be able to carry whatever you bring all day long without complaints. That allows us to take a train, stop somewhere, climb up a mountain to see a view, and then climb back down and get on the train to go to the next stop. Some train stations have lockers, but in some cases you have to carry your bag.

If you don’t do these sorts of things now, most likely because you’re too encumbered, it doesn’t seem like you’re missing out on much. But once you’re able to do them and incorporate them into your bag of travel tricks, you probably won’t want to give them up.

Buy Amazing Stuff

When you have a lot of stuff, it’s hard to justify spending too much money on it. With just a few items it’s easier to rationalize spending a lot of money on each item. If I have one shirt I don’t really care how much it costs. If I have a dozen, I definitely care.

The best stuff doesn’t always mean the most expensive, but it’s rarely the cheapest. Part of what makes things the best are quality of materials that go into them, and those tend to cost the company a lot of money. The flip side is that besides providing a better experience using the items, they tend to last longer. I have the ultimate travel watch (Breitling Transocean Unitime), which will never become obsolete and will probably outlast me. I get one shirt per year and it lasts the entire year. Same with my pants.

Having stuff that lasts and performs reliably also means that you don’t get into the unfortunate situation of having to replace something when you’re in a foreign country and really need it.

Because this stuff lasts so long, you have a high up-front cost, but very low ongoing costs. Predictable spending is always better than unpredictable spending.

If you’re hesitant to spend money on gear, focus on buying the best for stuff that is either never going to break or become obsolete (titanium water bottle, watch, quality backpack). Save money on things like electronics which you’ll have to replace at some point anyway.

Wool

The reason most people have such huge backpacks is because they pack way too many clothes. I don’t actually blame them, though. If you wear normal textiles like cotton and polyester (even with all of it’s high tech names like “capilene”), you will need to wash and replace them frequently. You’d need at least four outfits.

Every single item I wear which touches my skin is made either entirely out of wool or has wool as one its the major components. This is because wool drastically outperforms every other textile.

Don’t be fooled by marketing spin put on synthetics. They push them because they’re manufactured from plastic and can be made cheaply. Fine wool is an expensive raw material and it pushes margins down.

What makes wool better? The big thing is that it is naturally stain and odor repellent. My current yearly shirt is white with light blue checks on it. I’ve splashed it with soy sauce and dropped chocolate on it. Both of those stains came out just by putting a little water on them and waiting for them to fade. I’ve had the shirt for eleven months now and have only washed it about eight times. It never smells bad, and I even wear it to the gym sometimes.

I’ve tried the same with synthetics and cotton and they smell bad after one gym session or one to two days of normal wear. Wool isn’t a little bit better, it’s in a whole new level.

Wool also dries very quickly. I remember a time when my friends and I dashed through a torrential downpour on a Thai island to make it to a karaoke spot. The two of us who were wearing wool were dry within half an hour. Everyone else was still soaked when we left a few hours later. Wool can absorb a third of its weight in water and still feel dry to the touch. Even when it’s soaked it keeps you warm, like a wetsuit.

My entire wardrobe, even for when I’m home, is one button down shirt, one t-shirt, one pair of pants, one pair of shorts, two pairs of underwear, and two pairs of socks. I do laundry once a month or so and I hand wash my underwear more often in the shower.

If you don’t convert your wardrobe to wool, then you will never be able to pack lightly (and not smell bad). Cotton and synthetics simply don’t perform on the same level, so you require multiple times as many clothes.

You can find specific recommendations on my gear page, but there are a few companies which consistently put out high quality wool products.

- Wool and Prince—These guys make amazing dress shirts, polos, t-shirts, and other items. The shirt I wear every day is one of their button downs, and I wear a tee when I work out.

- Makers and Riders—They make pants out of different materials, but always have at least one good pair of wool jeans. I’ve tried many brands, most of whom make wool pants as a one-off seasonal thing, and Makers and Riders is the only pair I’ve had that make it through a whole year (and longer).

- Smartwool—One of the original wool companies, they make my favorite socks. They have a lot of other stuff, mostly athletic wear, and the quality is very good. They have a good selection of stuff for women.

- Icebreaker—They make athletic stuff with a fashionable twist. I don’t like their socks as much, but everything else I prefer over smartwool. They also have a good selection of clothing for women.

Wool is not itchy like it used to be. It’s not too hot (it actually wicks sweat and keeps you cool in the summer). Put aside whatever preconceived notions you have about wool and buy a high quality item from one of the companies mentioned above so that you understand what good wool is like. If you’re like many people, that will be the first step towards relying on wool exclusively for travel.

Backpack

Your backpack will be one of the most important items you have, as you will interact with it constantly. Small annoyances will magnify and small details that make your life easier will compound as well.

Your backpack also sends a message, particularly to the locals. If you have a giant mountaineering backpack like most nomads, you’re slotting yourself with the gap-year party crowd who have a reputation for trampling over foreign cultures. You may not be that person at all, and it may not be fair that it’s assumed that you are, but it will happen.

You want to have a backpack that’s small enough that a normal resident might carry it around on a daily basis. Then you fit in with the culture rather than stand out. This size also happens to be the size that is always allowed under seats in front of you in airplanes.

Backpack manufacturers largely guess or make up the size of their backpacks, usually expressed in liters, but you want something that’s approximately 20 to 28 liters. Don’t worry too much about every dimension. Bags are soft and can usually be squished by an inch or two in any direction to fit. And if they’re close, airport staff won’t bother checking.

I personally carry a Minaal backpack. I’m now friends with the founders, but I care enough about my backpack that I’d rather offend them and have a better backpack than go with theirs if I didn’t think it was the best one available.

What I like about their backpack is that it’s very nondescript on the outside, fits much more than it appears to, can be used as a briefcase in more formal settings, and is made of incredibly high quality materials. I’ve heard some behind the scenes talk on design choices, and in every case they choose the most durable and high performing component, even if it costs them more.

Whichever bag you choose, make sure it’s small, durable, and comfortable to carry. Bags don’t go obsolete, so you can count on five or more years of service from a good one.

Travel is Not About Gear

I always feel like I have to write this disclaimer whenever I talk about gear. Gear can make your trip better, but it won’t make a bad trip good. In other words, focus on the travel and the people with whom you travel, and let the gear enhance that experience.

If you’re starting out, buy a properly sized backpack, invest in a few high quality things that you know will pay off, wear wool clothes, don’t worry too much about the rest, and let your experience traveling dictate what you buy and what you avoid. I recommend an amazing bluetooth speaker, but if you don’t use the dinged up one you had lying around, there’s no point in carrying it with you, let alone upgrading to the one I like.

The gear that matters most is the gear that you don’t have, thus leaving you with a light backpack. If you’re on the fence about buying something, try traveling without it and see if you miss it. If you’re fine without it, that’s a lighter backpack, more room for snacks and gifts for people, and one less thing you have to worry about maintaining and keeping track of.

Controversial Ideas on Liquids

We all know that you’re supposed to have only 3 ounces of liquid per container, and that all of your liquids are supposed to fit in a one quart bag. In practice this isn’t entirely true, and there are several loopholes to get around those limits.

Before I get to those loopholes, my most controversial idea is one which I’ve exercised personally for the past two years. I don’t bring any shampoo or soap with me and I don’t use any either. The basic idea behind this is that those sorts of products strip the oils from your skin, which causes your glands to overproduce more oils, which in turn requires you to use more products.

The first month or two was a little bit horrifying. My hair became very oily, even after showers, and for a while it became somewhat matted as well. I very nearly gave up, but then I noticed it started to get better. After two months the transition was complete and my hair looked and felt better than ever. In fact, I’ve gotten more compliments on my hair since then than before. I told my barber that I was going to do this and he cautioned me not to. When he saw the results he was so impressed that he said he was going to do it himself.

Shortly afterwards I did the same for soap and noticed no difference whatsoever. I also tried to give up deodorant, but that experiment wasn’t as successful.

I’ve dated fairly actively during this time and girls are always shocked when I tell them, because they can’t tell at all.

At this point I can’t imagine going back to soap and shampoo, mostly because I think I feel and look better without it, plus I never have to worry about packing them. I do use soap on my hands.

The next thing to know is that the actual specification is 3 ounces or 100ml. A hundred milliliters is actually 3.4 ounces. That’s almost 15% more liquids that you’re allowed to carry. I once bought 150ml bottles, sanded off the part where it said 150ml, and was never even asked about them during 40-50 flights.

I never take liquids out of the bag. If they ask if I have any, I say no. I’d say that they notice that I have liquids approximately 2-5% of the time, in which cases I say that I forgot I had them. I don’t believe that scanners can actually detect liquids of that size, though I have gotten caught when I accidentally had my water bottle filled.

I always travel with a full tube of toothpaste which is larger than 3.4oz and have never been asked to throw it away. I keep a tiny travel tube as well as a backup in case they do take it, but it’s never happened.

The reason I care so much about liquids is because I’m picky about the products I use and don’t want to have to buy local ones. If you aren’t as picky, these tips won’t matter too much for you.  You can at least upgrade to 100ml bottles and get an extra 13.3% shampoo for long trips.

Researching Your Own Gear

I’d suggest that you take my gear recommendations because it’s unlikely that you’ll be as compulsively obsessed about gear as I am, so you may as well let me do your research. But what about items I don’t cover, or times my suggestion doesn’t work for you?

Think about what the primary criteria for the gear is going to be. Let’s say that you’re searching for a raincoat. It needs to be waterproof, but the second most important criteria is probably weight and size. In fact, if there isn’t an obvious criteria to search for, try “lightest” or “smallest”. All raincoats are waterproof, so I’d search for “lightest raincoat”.

Skip any lists and try to find individual reviews of items. It’s easy to computer generate “top ten lightest raincoats”, but takes actual knowledge and experience to write a review or a comparison between a few options.

I often think about which field would most require a high quality item and I’ll search specifically for that. For a raincoat I might search for “best ultralight hiking jacket”, because I assume ultralight hikers would benefit significantly by having a lightweight raincoat.

As you find items, write down the relevant stats like weight and price. Often there will be many different items claiming to be the lightest, sometimes through ignorance or shading the truth, but often because more current articles review newer products that have bested the old ones.

I search exhaustively for the lightest of an item and then look for disqualifiers. For example, if a raincoat has only a half zip I’m not interested in it because it’s too annoying to put on and take off and offers a narrower range of thermal adjustment.

You don’t always have to go for the very lightest, but you’d have to have a very good reason not to go for one of the five lightest. Eliminate any option that isn’t clustered amongst the lightest. For example, if weights in ounces were 5.2, 5.3, 5.7, 7.1, and 9, I would eliminate the last two but would treat the first three as if they were the same.

Next read amazon reviews for each item. I ignore one and five star ratings and focus on the two-to-four star ratings. Look for common complaints, and also pay attention to what people are saying about the complaints. It’s not uncommon for people to be complaining about something that they don’t know how to use properly. I have an immersion boiler for heating up water that will self-destruct as a safety mechanism if you take it out of water while it’s plugged in. Everyone complains that they break after a few uses, but mine has lasted years because I know to unplug it first.

Of the remaining contenders that don’t have a critical flaw revealed in the reviews, start comparing the more minor features. Which has the best hood? The best pockets? Does one have an integrated stuff-sack? Sometimes you won’t really know which features matter the most to you before you use the item, but you can take a guess at it and make inferences from how reviewers talk about the items.

You can also find comparable products and good reviews by searching for the product name and the word “vs.” in a web search. This will show head-to-head comparisons.

If you are price sensitive, you should also compare prices at this point. Because I rely so heavily on my gear and carry so few things, I’m inclined to get the best one regardless of price, but you may not have the same requirements.

Last, order one or more. If there’s a decent return policy I’ll order a few different items to test them all. If it’s something really expensive and there isn’t a good policy, I’ll just order the one that looks best and move on to the next if I’m not 100% satisfied with it.

Chapter 27

Checklist

One of the most stressful parts of traveling is wondering whether you have everything you need and whether you’ve forgotten anything. As a human with an imperfect memory, I’ve developed a checklist I look at when I leave, especially when it’s for a long time and the compounded effects of my forgetfulness could really matter.

I know that if I have everything on this checklist that my trip will go just fine. Maybe I will have forgotten to bring something that would have made the trip better, but with this list covered I know I don’t have to worry about anything.

Essentials

Passport

Laptop

Laptop charger

Phone

Phone charger

Underwear

Toiletries

ATM card (check expiration date)

Credit card (check expiration date)

Backup credit card (check expiration date)

Driving license

International plug adapter

Headphones

Less Important

Lounge access cards

Weather specific clothing

Bathing suit

Sunglasses

Boarding pass (can also print at airport, but faster to have in advance)

Location-Specific

Leftover currency from previous trips

Transit cards from previous trips

Visa (if necessary and in old passport)

Pre-departure Activities

Empty trash

Throw away food in fridge that will go bad

Turn off lights (or use home automation)

Turn off circuit to water heater and close valve (don’t worry about leaks)

Water plants

Lock door (double check)

Lock windows

Chapter 28

Troubleshooting

For most people some level of traveling is an amazing and life-changing experience. But that doesn’t mean that it’s always easy. The social media stories people share make it seem like it’s a non-stop party in the most beautiful locales around the world, but the truth is that just like with any other lifestyle, things go wrong and not every day is amazing.

Once you become a seasoned traveler, you generally learn how to roll with the punches and make every day a good day. Today our cruise ship docked in Lisbon and my friend and I went around to three museums and a tea shop— all of which were closed. After criss-crossing the whole city by uber for most of the day, we gave up and went back to the ship. We laughed about it, but I can imagine that if it were back when I first started traveling, that could have been a frustrating and disappointing day for me.

Just as any manual for a product would have a troubleshooting section, I thought I’d include one for the nomadic lifestyle. You will begin travel with some anxiety, yes, but also excitement and high hopes. If it doesn’t initially live up to those expectations, it’s worth trying a few things before deciding it’s not for you.

Too Lonely

Travel can be a very social and fulfilling lifestyle, but it can also be a lonely one at times. The tricky part is that unlike at home, we may not have our same coping strategies available. At home maybe you’d go to a familiar place, call up your best friend, go visit your family, or just retreat to your apartment. On the road none of those things may be options.

The good news is that there are additional options available to a traveler that you may not think of if they’re not in your standard toolbox.

Of primary importance is the fact that most other travelers are away from most of their friends, and thus more open to making new friends. When I’m in one of my home cities I’m very resistant to making new friends because I’d rather fill my time with my existing friends. But when I’m traveling I’m much more likely to chat with strangers and invite them to join me on activities.

One of the best places to meet new people is at hostels. I know of one guy who prefers to stay in nice hotels, but always books a room at a hostel concurrently because he likes to hang out there to meet new people.

There’s a very wide range of hostels, which means that you can choose which types of people are stocked in your pond. There are party hostels, eco hostels, hostels geared towards co-working types, and many others. Just read the reviews and see what people say about the hostel.

When you’re at the hostel, spend as much time as possible in the common area. A recent study came out and showed that the number one factor predicting which dorm residents made the most friends wasn’t their extroverted nature, hobbies, IQ, or anything else; those who were in higher foot-traffic areas made the most friends. So sit where people will walk by.

Start the easiest conversations you can think of. Ask people if they’ve done anything cool in the city yet. Ask them about what they’re reading. Ask if they know if the food in the restaurant is any good. More than any other environment I’ve been in, people in hostels are likely to engage in a real conversation based on any small beginning.

A good strategy is to have a couple ideas for things you might want to do, and then to invite people to join you in a low pressure way. I stayed at a hostel in Singapore once and invited a few people to go to the night-time zoo with me. We ended up having a big group, and one of the people ended up coming to Thailand with me the following week.

Keep in mind that dynamics are different while traveling. It’s not weird at all to invite strangers to random events. If you overhear people talking about going somewhere, it’s not even weird to say, “Hey, I overheard you guys talking about going to Macchu Picchu. I was thinking about going tomorrow, too. Mind if I tag along?”

I don’t mention locals in this section because making friends with locals often takes more time than making friends with travelers. They’d probably rather make friends with other locals who they can continue to hang out with, so it’s not as good of a “quick fix” to the problem of feeling too lonely. Long term, though, making friends with locals is even more rewarding as it creates a concrete link between you and the local culture.

If you find yourself lonely while traveling, it’s probably because you haven’t adapted to your new reality. Embrace the differences between normal life and nomadic life and use them to your advantage.

Too Bored

When you first start traveling, every little thing is exciting and fun. But then you see enough temples that you don’t care if you ever see another one again, you eat every region’s food twice, you realize that the Rembrandts in every great museum are pretty much the same, and all the beaches start looking identical. You’re bored, you feel guilty for feeling bored, and that makes you feel even worse.

I remember when this first happened to me. I was in Beijing and just didn’t want to do anything there. I’d wake up, work, go to a Korean restaurant, go back to my tiny Airbnb to work some more, go to the same restaurant, and then go work some more and sleep. Once in a while I’d make myself walk around the city looking for stuff to do, but none of it appealed very much to me.

This tends to happen to travelers who fall in love with traveling, figure out their routines and tricks, and then a year or two down the road find that it isn’t as exciting before. What happened?

When we get used to traveling, it’s easy to forget exactly what it means to be a nomad. The point isn’t to go to more countries than your friends, to see everything, to stay away from home, or to get some imaginary Digital Nomad merit badge. It’s to expand your definition of “home”, maybe to the entire world.

If you were in your home city, you wouldn’t walk downtown with no purpose and expect that it would be a good use of your time. But because the novelty of traveling is so powerful in the beginning, we forget that there’s no inherent point in going to any one place. We should be traveling for a reason, not traveling first and then trying to shoehorn the experience into something it’s not.

A few years ago I found out that Vermeer had only painted 36 paintings. I like his paintings and decided that this was a unique opportunity for me to see the entire output (minus a stolen one) of one of the best artists ever. At first I went to the easy ones like the ones at the Met in New York, but eventually I started traveling around just to see them. I went to Dublin for two days to see the one that was there, Dresden for 12 hours to see that one (museum was closed... oops), and Dallas for five hours because one was on loan there.

I did a bunch of other cool things in Dublin, but having a reason to go there gave me a sense of purpose and it set the bar. If I went and just saw a Vermeer, the trip was worth it. Everything else was gravy. Most importantly, I knew why I was going.

These days I try to avoid going to new places. I’ve been to seventy or so countries, and that’s enough that I feel like I’ve gotten a decent feel for the world around me. Not a complete one, but enough that coloring in more countries in the map isn’t enough of a reason to get me on a plane.

Now I base my travel around getting to know more deeply places that I connected with. I’m never bored in Budapest because I love it so much, have good friends there, and am still uncovering new things every time. Same with Japan. My explicit goal in these places is to develop good sustainable routines so that I can be productive there. That’s a goal that’s fairly unique to me, but it’s my reason for traveling and it doesn’t require too much excitement.

If you’re traveling and you don’t know why, you may get lucky and have a great time, or you may get bored.

You must also recognize that as you are exposed to more countries, get older, and have the rest of your life change, your reasons for traveling will change. If you are still traveling for your old reasons, you may become bored or dissatisfied. When I first traveled I went to places for two to three months at a time and my goal was to explore them and get to know the world. Now I like to go for one to three weeks to my favorite places and deepen my roots there. Neither is a better way to travel, they’re just different aims for different times in life.

If you’re bored while you travel, ask yourself why you’re doing it. Why did you start? Are those reasons still important to you? Maybe you need to get back on mission, if so. If they’re not important, is there anything you still want out of travel? Most people who start down the nomadic path find more and more reasons to travel, but not everyone does. Maybe you’re done. Figure out why you’re traveling, work towards fulfilling that goal, and you’ll lose your boredom.

Running out of Money

The default way people travel is with stress. Think about airport scenes from movies; they almost always show someone frazzled because that’s what we, as a society, associate with travel. Part of your responsibility as a nomad is to reduce the amount of stress you have while you travel, because that’s one of the main mechanisms by which you make it more sustainable. If you’re running out of money and have to watch your bank account carefully, you will be stressed out.

The first thing to realize is that there are happy people who live for a couple hundred dollars a month in major cities around the world. If you’re running out of money in an expensive city like London or Stockholm, it’s time to move on to somewhere less expensive. You thought you could sustain yourself in an expensive city, you were wrong, so you take your lump and move on.

People want not only to have everything, but they want to have it all right now, which is exponentially more difficult. It’s best to think of being a nomad as a lifestyle rather than an immediate vacation which must be maximized.

Go to a less expensive place and make it an experiment to see how inexpensively you can live there. Eat where the locals eat. Make a deal with a hostel to get a discount if you pay for a month at a time. Get a room in an Airbnb on the outskirts of the city next to a train line. Then use that setup to focus on income so that you can afford to spend time in the places that most appeal to you.

Realize that for a long time it will seem like every other nomad is living a more glorious existence than your own. A lot of them have been doing it longer, so they probably legitimately are, but it’s also crucial to think about the evidence on which you’re basing your perception.

When I travel, I share pictures of the highlights. No one wants to see a photo of the foldout table in the cheap Airbnb where I eat takeout while I pound away at work. I’m not trying to hide it— it’s just not interesting to anyone. I’m not alone in this. People share pictures and stories of the extraordinary, so you can’t allow that to color your perceptions of what’s normal.

On top of that, like many other communities, there’s a lot of fronting in the nomadic community. People use miles to stay one night at a super-fancy hotel, and then they post a picture that makes it seem as if that’s where they’re staying for a month.

I mention all this not because I think you should be deriving your own satisfaction from how you stack up compared to others, only because it’s important to know what’s realistic. Yes, you can live a higher quality of life for less money when you travel. That’s fairly easy to do. But it won’t come instantly and it’s more like a 2-5x multiplier than a 10-100x, especially at first.

Be happy with your process. If you’re stuck in a shared Airbnb on the outskirts of Bangkok and you’d rather be in a chalet in the Swiss Alps, remind yourself that this is the means by which you get there. You lower your costs now because it will help you earn more in the future. Be grateful that you even have that shot. A lot of people are so burdened by debt and obligations that it will be years before they can be in a position to travel. You’re in it now.

Be grateful for the small things. One of my favorite things about Thailand is the ice-cold fresh coconuts I can get for less than a dollar just about anywhere in the country. I don’t need to have a catamaran in the bay to be grateful to be in another country.

Focus on building your nomadic lifestyle and aim to have it be whatever you dream it to be in three years. Do the hard work now to make it that way. Live inexpensively, focus lots of your time on building an income, and appreciate the things you can afford now. Be glad that you can just hop to another less expensive country to cut down your expenses, as that’s a luxury a lot of people back home don’t have.

Too Stressful

Travel is very stressful to a lot of people, and even to people who love being in transit, this isn’t much of a surprise. Our global transportation system transports over six million people every single day and has to account for weather, mechanical issues, government regulations, computer glitches, and all sorts of other issues. Couple that with cutthroat pricing which leave airlines understaffed, and you’re basically left with a system that is stressful by default.

The good news is that there’s a lot that you can do to remove stress. It’s important work to do, because as a nomad you’ll be exposed proportionally to more of the hassles of travel than normal people.

Travel is most stressful when you first begin doing it. As you get more accustomed to the various aspects of travel there are fewer unknowns. On my first trip I booked all my flights in advance, spent months figuring out exactly what to pack, researched visas, and read for hours about which neighborhoods to stay in or avoid.

These days I might book an international flight the night before, wake up ninety minutes before my flight leaves, pack and head to the airport, all without stress. It’s not because I’m a stress-beating superhuman, it’s just because I’ve done every step so many times that it’s all second nature and I know how to glide through it.

You’ll get there too, but that doesn’t help much for now except to possibly reassure you that, yes, it gets better.

If you get stressed out by the transit part, which is most common, start by going places for a month or more at a time. Pay extra for direct flights, which won’t add up to much since you aren’t flying all that often. Get lounge access through the credit cards I mention elsewhere and make a habit of getting to the airport way earlier than necessary.

Traveling enables you to get a much better value on money you spend through the process of global arbitrage. If your ability to save that money and enjoy the process is threatened by stress, spend more money on things like lounges, uber rides, and noise-blocking headphones to mitigate the stress. If you have to pay $2000 per year extra to live happily in a lifestyle that saves you $10,000 per year (or gives you $10,000 more enjoyment per year for the same cost), then it’s a good investment. And as you get more comfortable with travel, think a bit about tapering off some of those things. I take much nastier flights than I used to, sleeping on airport floors overnight to catch a connection, because I don’t find things like that stressful anymore.

Don’t beat yourself up if traveling stresses you out. It’s supposed to do that. Be proactive and find ways that mitigate the stressors for you, even if they feel a little bit indulgent.

Not Fulfilling

Most of us nomads talk about how fulfilling travel is. I get to see friends all over the world, visit a lot of the great museums every year, catch a good portion of Budapest’s ballet, opera, and symphony season, and am constantly struck by the beauty of the world and the people who inhabit it. It’s one of the most fulfilling aspects of my life.

Travel isn’t fulfilling by definition, though. It’s a great avenue through which to add fulfillment in your life, but it requires you to figure out what you need to be fulfilled, and than using travel to get it.

Some people use travel as a way to perpetually party on the cheap. That can be fun, but it won’t be much more fulfilling than doing the same back home. The same is true even with more “cultural” things like visiting historic monuments. Maybe that’s something that fulfills some people, but if it doesn’t do much for you, you should be doing something different with your time.

The best way to think of travel is to think of it as multiplying your freedom. Your world goes from one or two cities to, well, the whole world. So if there’s something in this world that will fulfill you, you now have access to it.

One common source of fulfillment for nomads is connection to other cultures. I get a lot out of learning more about Japanese culture. Even though I’m not Japanese and can’t claim to have a particularly comprehensive understanding of their history or culture, the little that I’ve been able to absorb has given me a new connection.

Not everyone will be interested in every culture. That’s totally fine and just because you aren’t interested in one doesn’t mean you won’t be interested in another. I have a friend who just loves Amazon culture and is always going off to the jungle there for extended periods of time. That culture doesn’t resonate with me, but it doesn’t matter because I can find another one. That’s the whole point of having a lot of options— to figure out the ones that click with you.

I’m a fairly introverted person and I like being alone, but I find that travel is most meaningful with me when it’s shared with someone else. Then I’m building a connection to a place, but also to another person. Even when things have gone all wrong (like that one time we ended up sleeping on fish boxes in a cave), I felt fulfilled by spending good time with good friends.

The times when travel was least fulfilling for me was when I traveled by myself to places I didn’t have much interest in but “thought I should see”. I analyzed when I felt most fulfilled, when I felt least fulfilled, and made changes to steer towards the former. It’s not travel that is leaving you unfulfilled, it’s the type of travel which you’re doing.

Chapter 29

Two Cities To Visit

I wanted to write a big section here on my favorite places around the world, to create a starting point for people who are looking for inspiration. But of the hundred of cities across 70 or so countries I’ve visited, two of them are really in a league of their own in my book.

And it’s not just me. I’ve recommended these two places to dozens of people and they’ve all loved them. So although it’s a little strange to have a section where I recommend only two cities, I’m going to do so because I think they’re the best places to start in both Asia and Europe, and I think that you’ll find something you love in each.

Tokyo

Tokyo was the first city I fell in love with. I visited there early in my travels and there’s one moment which I’ll never forget. We landed and took the train into the city, getting off at the Asakusa stop. We ascended up the stairs and, through the pouring rain, saw the great red lantern that’s hung in an arch called a torii. To get out of the rain we scrambled up some steps and stood under an eave of a temple.

I distinctly remember thinking, “Whoa. Japan really looks like Japan.”

That’s still my favorite thing about Japan. Not the lantern, although it’s worth seeing, but the fact that Japan is so very... Japanese. In a world where cultures are becoming homogenized and, in many cases, westernized, Japan stands alone. It has retained so much of its cultural heritage and even when it appropriates things from the west, it makes them uniquely Japanese. Case in point: standard Christmas tradition is to order a giant bucket of KFC. You have to order way in advance.

Tokyo is also so enormous that it’s sort of like getting a 20 for 1 deal. Many of the neighborhoods, like Shibuya, Shinjuku, Akihabara, Ginza, and Odaiba are large and distinct enough to be their own small city. Shibuya has young fashion and a beautiful sprawling park. Shinjuku has tiny bars and restaurants clustered in specific alleys, Akihabara is the electronics city with maid cafes and bulk electronics, Ginza is the ritzy shopping area with stunning building facades, Odaiba has theme parks and museums.

The excellent metro system links all of these places, and more, allowing you to take in a tremendous amount every single day. The combination of so many unique and interesting things in one place and the ability to navigate it all makes Tokyo the most interesting city in the world in my opinion.

Because it’s so large and varied, there’s something for everyone in Tokyo. I spend a lot of my day flitting between karaoke, tea, and sushi. You could hike the parks and eat ramen. Someone else might spend a week shopping and eating the weird 2-inch-thick pancakes.

Japan is such a great place to visit and it’s visited frequently by nerds, so there’s a lot of information on it, making it far more accessible than such a foreign place would otherwise be. My best recommendation is Tokyo Cheapo book (https://tokyocheapo.com/book/).

It’s important to know that Tokyo is not nearly as expensive as people think it is, at least not necessarily. While you can spend hundreds of dollars on a meal, you can also go to Uogashi Nihon-ichi and have better sushi than you’ve ever had in the US for about $20. Zoning is lax to non-existent in Japan, so you can sleep in a capsule hotel (awesome!), a manga café, or even a karaoke room. It’s easy to stay for about $40 a night and eat for $5-10 per meal.

To get you started, here are some of my “ten out of ten” places to go:

- Haneda Airport—There are two airports, Haneda and Narita. Haneda is both cheaper (by around $40 round trip) and faster to go to and from the city. If it’s not much more to fly into Haneda, do it.

- Uogashi Nihon-Ichi—This is a chain of sushi restaurants that have excellent quality fish bought from Tsukiji market, but are very inexpensive. Part of why they are inexpensive is because there are no tables. You just stand at a bar and yell out your order. They have an abbreviated English menu.

- Rainbow Karaoke—There are far too many karaoke spots in Tokyo to review even a fraction of them, but I’ve probably been to about as many as anyone else. Rainbow Karaoke in Shibuya is a clear winner. Pay a little extra for the deluxe room or studio and you’ll be blown away at the space you get for very little money. Going in the afternoon gets you a discount versus the evening.

- Onsen O-Edo Mongatari—This is an indoor and outdoor hot springs in Tokyo that is themed like an Edo period red light district. You’ll find people of all ages there, including a lot of teenagers on dates. It has a Disney sort of feel to it, but the baths are authentic. They pump the water from a natural underground hot spring. It’s segregated by sex and you go in the water nude, but there is also a coed foot bath and common restaurant area. You can stay overnight on a mat in a giant tatami-mat room for no extra charge.

- Ippodo Teahouse—There will be several Ippodos in your search results, but only the one in Marunouchi is the only one that actually serves brewed tea (the rest sell looseleaf to bring home). Order either the best matcha brewed thin (usu-cha) or one of the top two gyokuro teas. Or both. If you’re not a tea nut like I am you may be shocked at just how good green tea gets.

- Higashi-ya—This is also a teahouse, and like Ippodo has several branches that don’t actually serve tea. Go to the one in Ginza. Here the thing to get is the best gyokuro they have. If you and a friend both get it they do a cool tea ceremony.

- Ice Cream at 7-11—At home or in most countries I eat no dessert. That changes in Tokyo because they have amazing ice cream at the convenient stores. In a class of their own are the Häagen-Dazs crispy ice cream sandwiches (I’m so obsessed that I stash seasonal flavors in a freezer in Tokyo) and Cold Stone Creamery ice cream bars (not always available).

- Toride Ramen —There are plenty of top quality ramen places in Tokyo, but the one I always end up going to is Toride. I like that they will cook the noodles a little on the chewy side if you ask for it, and their mini-gyoza are some of the best dumplings in Tokyo.

Budapest

For most of my time as a nomad, I wasn’t really a Europe guy. I’d been to most of the countries there and had had good experiences in all of them, but never found anywhere that called to me in the same way that places in Asia did. I loved the museums of Paris, the architecture and history of Rome, the and fjords of Norway, but in each place I was happy to leave after a few days and move on.

Then I stumbled across a flight deal to Tokyo that I couldn’t resist. It was only $180 from New York to Tokyo, but the flight had a five-day layover in Budapest, Hungary. By the time the trip came up I had just done two trips in the preceding two months which went fully around the globe and I was a little worn out. I arrived in Budapest with a middling attitude, ready to move on to Tokyo.

Within my first few hours in Budapest I realized that it wasn’t like other European cities I’d been to. We went to a thermal bath, but instead of the small indoor affairs I’m used to, it was a giant turn-of-the-century palace, complete with enormous outdoor pools. We searched for a tea place and I was stunned to find myself in a place that served actual high quality Chinese tea with the right teaware and water temperature. At the time it was the best teahouse I’d been to in Europe, but now is only my fourth-favorite in the city.

Budapest turned out to be a true under-the-radar gem that continues to be my far-and-away favorite place in Europe. I’ve brought dozens of friends and family members there and everyone else has not just loved it, but wondered how such a great place can exist.

The interesting thing about Budapest is that it is not number one in any category within Europe, except probably thermal baths. Instead, it is top five or ten in just about everything. For example, it has the third best opera house in Europe. It has the second biggest synagogue. The old metro line there is always listed as “possibly the oldest in Europe”. It’s famous for its escape games, but was the second country to have them, not the first. The impressive Parliament building is the second biggest in Europe.

This leaves Budapest a place with few enough distinct claims to fame that it doesn’t attract hoards and tourists of cities like Berlin and Rome, but actually has far better breadth than any of those cities. It’s a place where you can do just about anything, and all of it will be exceptionally good and not very expensive.

The city itself is actually two cities, Buda and Pest, which were are split by the Danube river and were combined into one city in 1873. A series of bridges span the river, the most notable being the stunning (but not quite as stunning as that bridge in Prague...) Chain Bridge. The city is extremely walkable, and you’ll find yourself crossing the bridges by foot in good weather.

Most of the entertainment is in Pest, which is convenient because it’s easy to navigate and very flat. There there are three districts which are worth noting. The 5th district is a sort of moon shape that radiates out from the Danube. As a whole its buildings are in the best condition and it contains shopping boulevards, fancy restaurants, and a few tourist attractions like the market hall. Though there’s a fair amount of local business going on there, it’s where tourists will spend a lot of their time.

The 6th and 7th districts radiate from the ring road that encircles the fifth district. The 6th district is largely a UNESCO world heritage site, extending from Andrassy Avenue, which is essentially the Champs Ulysses or 5th Avenue of Budapest. There you’ll find stores like Louis Vuitton, Breitling, and Rolex, along with the stunning opera house. Andrassy runs in a straight line from Deak Ferenc Ter on the border of the 5th district all the way to Heroes Square, a big plaza dedicated to war heroes. Under Andrassy is the “possibly oldest” train in Europe.

The 7th district, known as the old Jewish quarter, hosts a lot of casual and trendy restaurants and nightlife. It’s the up-and-coming hipster area but is close enough to the 6th district that it retains a lot of the grandeur. Because the real estate is cheaper here, you see a lot of new restaurants, escape games, and funky stores.

There are many more districts, but these, along with the waterfront area on the Buda side, are where you’ll spend most of your time. These four areas are so close that you can walk from any point in one to any point in another. There’s also an excellent metro system (with a slightly annoying ticket system) that can get you around even faster. Deak Ferenc Ter is the station that is where the three Pest districts meet. Find a hotel or Airbnb around there and you’ll be able to walk to everything.

What sets Budapest apart is the quality of life at a very low price. You can go have some of the best tea in the world on the Buda side for around $10. Then you walk over to the seventh district and eat the best salad and sandwich you’ve ever had for $5. You stroll over to the sixth district to see a world-class concert or opera for $20, and then go to a ritzy outdoor café on Andrassy for about $12. That’s under $50 for a truly incredibly day in one of the best cities in the world.

There are far too many incredible things to list in Budapest, but here are some of those that my guests and I have loved the most.

- Rudas Baths—There are a half-dozen excellent baths in Budapest, but if you’re only going to go to one, choose Rudas on the weekend (when it’s coed). Rudas was originally built in the 1500s, but had a modern wing added on in 2014. If you get the full ticket you can access both, getting to soak in a bath that’s been open for hundreds of years, as well as visit the sauna world, and the must-see bath on the roof that overlooks the Danube river.

- Szechenyi Baths—Invariably you will love Rudas and want to go to another bath. Szechenyi has a huge series of indoor baths, but is most known for its spectacular outdoor baths that each hold hundreds of people. They’re open late and it’s most fun to go at night, although the inside baths close earlier. If you time it just right you can do the indoor baths and then move outdoors when it gets dark.

- Zhao Zhou Teahouse—Located right across the Chain Bridge in Buda, Zhao Zhou has one of the most thoughtfully curated selections of tea anywhere in the world. They have an encyclopedic collection of Puerh teas, but even their Japanese greens were amongst the best I’ve had. The staff are some of the kindest people I’ve met in Budapest. Tell them Tynan sent you and ask for a recommendation.

- Bors—If you look up the top rated restaurants in Budapest, they’re all fancy European bistros except for number three, which is this tiny sandwich shop. The name means pepper, the restaurant is heavily Star Wars themed, and they primarily play loud explicit gangster rap. They are most famous for their sandwiches, like the Thai Massage, but I think their salads and soups are possibly better. At roughly $2.50 per menu item, you can try more than one.

- Ket Szerecen—Ket inevitably becomes everyone’s favorite sit-down restaurant in Budapest. The quality of the food is extremely high, the prices are comically low, and it has a great ambiance. If you have more than two people, get the meat or veggie tapas platter as an appetizer. The chocolate dessert is incredible, mainly due to the sour cherries and ginger ice cream. You need reservations for dinner, which can be made same-day, but also try it for breakfast. They have great egg scrambles and the croissant I had there was better than any I’ve had anywhere else, including Paris!

- Fricska—This place is a little bit under the radar, probably because it’s a little out of the way. Go for the lunch special, which is approximately $10, and treat yourself to a three course meal. The presentation of food is among the best I’ve seen in Budapest and each dish is as beautiful as it is delicious.

- Locked.hu—I love escape games. If you’ve never been, it’s a specially themed room or series of rooms in which you have to look for clues and solve puzzles to escape. It feels as though you’re in a video game. I’ve been to dozens of them in Budapest, and Locked.hu is consistently the best. Besides great puzzles, they have the best build quality and design which really immerses you in the game. I’ve done all of their games and am always waiting for them to come up with new ones. Start with the Motel room and try to do it without hints.

- Opera and Mupa—I love the performing arts, but in most cities costs of tickets are prohibitive. Not so in Budapest. The best seats for the best performances at the opera house are $60, and they scale all the way down to $5. However, don’t ever get a seat that is second or third row in an opera box. You won’t be able to see anything. Mupa is a brand new performing arts center that has symphony concerts almost daily. I’ve paid as little as $3 for a third-row orchestra seat. To get tickets go to Opera.hu or Mupa.hu respectively.