Four ways to live as a Nomad, from expat to perpetual traveler to digital nomad

Written by Andrew Henderson

Last update: October 26, 2017

Dateline: Hong Kong

Ever since I first came to Hong Kong, I’ve been in love with the place. The city is bustling, the weather is perfect, and the scenery is a mix of urban chaos and an odd sense of Asian calmness. On top of that, Hong Kong has some of the world’s best restaurants, amazing shopping, and one of the most stable banking and business jurisdictions on the planet and ranks #1 on our Nomad Quality of Life Index in 2017.

But I’m going to let you in on a little secret: I couldn’t stand staying here that long.

No, it’s not because one of my companies is based in Hong Kong and my living here would cost me more money. And no, it’s not because of the living expenses. (Despite the fact that it took me weeks to find an apartment as large, well-located, and luxurious as the one I had in Kuala Lumpur… and the rent was $42,000 a month.)

The reason I couldn’t spend my entire life in Hong Kong — or even a significant period of time — is because doing so would ruin it.

There’s something magical about Hong Kong in the way that there’s something magical about Las Vegas.

When I was a young kid starting my business in Arizona (and briefly in Southern California), I often frequented Vegas for business and leisure, or ”bleisure” as the cool kids are calling it now. Driving over the mountain and finally seeing the lights of the Las Vegas Strip was as exciting the 25th time as it was the first.

However, whenever I would talk to a group of European guys at a craps table or Middle Eastern girls in the lobby, I was astounded when they would tell me they were visiting for two whole weeks.

What the hell is there to do in Las Vegas for TWO WEEKS? The magic wears off in a few days! It’s best to leave after a long weekend, just soon enough to want to come back and do it all over again.

Now, I don’t spend time in Las Vegas these days — Macau is far cooler for the more mature me — but I do understand that the Nomad Capitalist lifestyle is one that must be adapted to the person living it.

For some people, that means living a life of nothing but proverbial visits to Las Vegas, where you leave just as soon as the magic wears off.

For others, that means finding a new home in one of my New Safe Havens and settling down in a permanent home there in traditional expat style.

For others still, it’s something in between.

Whenever I hear people talk about digital nomads or perpetual travelers, I often hear certain stereotypes thrown around. For example, when I reference how I spend time in 25 countries a year, people may assume that I don’t have a home of my own and merely live in hotels.

Likewise, someone might assume that a digital nomad bounces from Airbnb to Airbnb, and co-working space to co-working space.

But that’s not always true.

I started out as a young guy with a business, living in the United States and wanting to travel. I began with one trip and then quickly got up to many trips in a year. Before I knew it, I was traveling more than I was at home.

Soon enough, I left the United States for good to become a full-time perpetual traveler, dragging an oversized Tumi bag behind me.

Now I have settled down to the point that I have places that I call home, places that I feel at home in, and places that I am still exploring. Each of these parts of my strategy fits into my goals to not only explore but also to find new opportunities and make investments.

With these years of experience, I’ve come up with four different ways to live a Nomad Capitalist lifestyle. These four strategies present different ways you can live your life based on how much time you want to spend in any given place, how much time you like being away from home, and whether you want a home at all. I’m open to hearing your ideas if you have more and would like to add on to what I’ve observed.

Four Ways to Live as a Nomad

Ready? Let’s take a look at the four strategies:

1. The Perpetual Traveler Strategy

This is the way many digital nomads live. It’s how I lived once I started spending my entire life on the road. The perpetual traveler has no permanent address and no permanent home, choosing instead to live life out of a suitcase.

For example, I spent the second half of 2013 traversing most of southeast Asia, making connections and investigating deals in each country. In order to do that, I gave myself one month in most countries, which I eventually shortened to 2-3 weeks. I started in Vietnam and continued to Cambodia, Thailand, Laos, Malaysia, Indonesia, and then the Philippines.

Then, the first half of 2014 was spent in Eastern Europe, starting in the Baltics and working my way down to the Balkans at a slightly faster pace.

There is no perfect strategy for being a perpetual traveler. The system I used back then could work as well with shorter trips, or with more extended trips.

For example, several friends of mine commit to three months in each city, giving them plenty of time to get accustomed to their surroundings. Most of the freelancers I collaborate with through Hubstaff ( a well-recommended platform we use for hiring talented remote workers) choose to live like this.

To me, such a long stay doesn’t really feel like I’m a “perpetual traveler”, but rather an expat with several homes. That said, if you bounce from one Airbnb apartment or hotel room to the next with nowhere to leave your belongings, that counts.

On the other hand, some PTs and digital nomads bounce from place to place at lightning speed; I believe my record was 30 countries in one year.

Pros of being a perpetual traveler:
  • It’s a great way to try on different cities before committing to a more permanent strategy
  • You get to experience more places
  • It can be part of a global investment strategy
Cons of being a perpetual traveler:

2. The Base Cities strategy

As the years I’ve spent away from my home country increase, the more I crave a base. I’ve done the full-on PT routine, but my penchant for decorating and the fact that I own a lot of suits and carry-on luggage means that I prefer to have a base these days.

My first base was Kuala Lumpur, Malaysia- one of my favorite cities in the world ( read my recommendations for living in KL ) where I have based myself for almost a year. It is a great base, especially because it gives you access to two airlines that fly everywhere very affordably, plus quick access to Singapore for even more options. KL is also a great base because you can bank and store your assets in neighboring Singapore while living in the more interesting and cost-effective Malaysia.

However, having one foreign base can start to look a lot like being a traditional expat if you don’t travel much. That’s where the idea of multiple bases comes in.

Perhaps you never want to deal with winter. Or maybe you’re like me and just can’t sit still. When I’m in Asia, I start wondering about what’s going on in Europe, or vice versa. Having multiple base cities simply means that you have homes in different cities, usually relatively far apart so that you can travel to nearby places from each base.

Let’s take a look at some examples of this strategy:

Example #1:

You love the warm weather and opportunities in Asia, but you miss Europe from time to time and love the quiet summers there. In this case, you could rent an apartment in Singapore and own a home in Belgrade- my Balkan base city. Both cities are well-connected, so it’s easy to travel back and forth. It’s also easy to travel around the region when you have business trips or want a weekend off.

Example #2:

You’re a lifestyle real estate investor who likes owning different types of properties. Perhaps you buy a condo in the sky in Kuala Lumpur, a beach apartment in Montenegro, a house with a yard in Panama, and your original home in the city you left to do all this traveling. You could easily bounce between all of your properties, always having a place in each part of the world to call home without having to stay in a hotel.

Example #3:

You’re a true nomad who wants to be connected to all three major parts of the world: the Americas, Europe, and Asia. You could buy homes in Medellin, Colombia and in Malta, then rent a place in Bangkok. Medellin has food and culture, Malta has relaxation and access to the rest of Europe, and Bangkok has the hustle-and-bustle and start-up culture. You move around as you see fit.

The list of possibilities is endless. Of course, base cities give you access to more regional travel. For example, I’ve had bases in Malaysia, Georgia, and Belgium. From there, I’ve easily been able to get anywhere I want without hassles.

Tbilisi isn’t the best-connected city, but it is close enough to get around Eastern Europe, including borderline-frontier markets like Ukraine or Armenia. Northern Belgium is small enough that it’s easy to get to Brussels airport (or Amsterdam, or Paris) from anywhere by train, and from there to anywhere in the world. And KL can get you anywhere in Asia, Australia, or Europe.

This is my current personal strategy; I like the flexibility of being able to have several homes set up the way I want. While I love staying at five-star hotels, I like the option of feeling at home without having to stay at the often-dreadfully decorated short-term rentals in the countries I visit.

A base cities strategy also allows you to enjoy a lifestyle buffet: the big city, the small town, the beach, and whatever else it is you’re after. And if you choose your countries carefully, you can get second residence permits and eventually passports just for buying property. Just make sure that you follow the tax rules in each country so you don’t accidentally get sucked into a tax net.

Pros of the base cities strategy:
  • Your life is less stressful as you have each home set up the way you want it
  • You can manage parts of your business, or multiple businesses, in each place
  • You can travel between multiple homes for business or leisure without wondering what to expect
  • You can manage a real estate portfolio around the world for your own benefit
Cons of the base cities strategy:
  • You have multiple properties to maintain and, if you rent, leases to pay even when you don’t live there
  • You might feel pressured to spend more time in one of your homes “because it’s there”
  • Owning properties in multiple places can blur the distinction between a home to live in and an investment

3. The Base City + Focus Cities strategy

This strategy is similar to the Base Cities strategy, but it involves one base and a number of “focus cities”. In case you’re not familiar with the term, focus cities are what airlines call the cities they serve with great frequency, but that aren’t full-fledged hubs.

This strategy is for someone who wants a home but also wants the perpetual traveler lifestyle without the surprises. It’s perfect for someone with less cash to invest or cash to spend every month on rent.

Here’s how it works: you have a home in one base city that acts as your personal hub. This is where you keep all of your stuff and the place from which you travel. However, unlike a traditional expat, you have a list of cities that you know well enough to feel at home in.

While you don’t have a technical base of operations in your focus cities, you know how to get around, know where the best restaurants are, know where to get your dry cleaning done and know how to get back to the airport without wasting time. You FEEL at home without HAVING a home there.

Then, you simply determine how long you want to spend in each focus city, or group of focus cities, before returning to base. You’ll never deal with the feeling of new-ness in a city.

The benefit of having focus cities is that you can develop habits there. For example, I’ve been to Singapore enough times that I know exactly where I want to stay depending on my spending preference that trip. I know where to eat and how to get around. And, most importantly, not only do I know people there that I can call and meet, but there are other people and businesses I’d like to get to know.

A focus city can also be a city where you hold assets, have bank accounts, or have other flags planted. After dozens of trips to Hong Kong and Singapore, I feel extremely comfortable in both; partially because I’ve made the mental connection of having part of my assets there.

We’re also structuring Team Nomad to work from their choice of my base cities, or traveling to a new city every three months together. In that case, my focus cities could become the places where the team works, giving me a greater reason to visit those places or develop new ones.

Building your list of focus cities takes time, so this is a strategy that is best used by recovering perpetual travelers, or people who are willing to visit a rotation of cities frequently enough to get used to them. It’s taken me almost a decade to develop my list of focus city candidates: Dublin, Warsaw, Brussels, Riga, Tbilisi, Istanbul, Panama City, Kuala Lumpur, Hong Kong, Singapore, and Phnom Penh. Maybe I’m missing a few.

(Of course, I could be at home in any number of US cities, but I choose not to spend time there.)

Pros of the Base + Focus City strategy:
  • You will always feel at home, without the discomforts of being in an unfamiliar place
  • You can visit focus cities without ever getting bored of being there
  • It’s a great excuse to check up on banks, assets, or employees in a fun way
Cons of the Base + Focus City strategy:
  • You don’t get the benefits of storing your stuff in another city, which could make longer trips difficult
  • You still have the costs of living as a tourist, which in cities like Singapore could be expensive

4. The Expat strategy

Being an expat is pretty straightforward: you settle down in one city in a country different than where you’re from. While this way of living doesn’t particularly suit me (at least yet), for some reason it tends to be shunned by many in the Nomad community as being boring.

The funny thing is that, while traveling and living overseas is supposed to be all about breaking the rules and living life your own way, some people fall into the same rut of “follow the leader”. Instead of living life their way, they only attempt to replicate the same nothing-but-a-suitcase lifestyle they see others living.

It’s your life. If you want to live as an expat, you should do it, regardless of how “awesomesauce” some digital nomad blog says perpetual travel is. Being an expat doesn’t mean you’ll never leave your new city; the same way you aren’t tied down to the city where you currently live. You can be an expat and travel, too.

Being a full-time expat is best suited to families or those who want the stability of one place most of the year. Expats can still travel on summer vacation, or take trips whenever they please, of course. It just means that they tend to make simple, Point A – Point B – Point A trips that return them home.

Pros of the expat strategy:
  • Having one permanent address makes opening bank accounts, starting companies, and obtaining travel visas much easier
  • Spending a longer time in one country may qualify you for a second residency or second citizenship
  • You may feel comfortable if you’re used to living in and traveling from one place, particularly if you are a family with children
Cons of the expat strategy:
  • Living in one place for most of the year may subject you to tax, depending on the country
  • You may get bored if you’re used to adventure
Andrew Henderson
Last updated: Mar 12, 2020 at 10:39AM

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1 Comment

  1. Abraham

    Thanks for your work to put his together. I have a similar relationship with Hong Kong, which is what initially made this article catch my eye. I’ve been in the perpetual traveler mode for the past 3 years. I love the adventure of always moving on, but as you wrote it gets lonely and the lack of rooted social connections, arranging accommodation, flights and visas is wearing on me. I haven’t been that strategic in the way I’ve traveled, which I think has led to burn out and could be the key to continue what I’m doing more successfully. Also, I haven’t yet made the mental comittment to one city as a base, which could make a whole lot of difference. Thanks again for giving me some fresh ways to think about it all.


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