Over the past 3+ years, I’ve gotten rid of most of my stuff and have been living around the world.  I’ve lived in six different countries:  Taiwan, Thailand, Indonesia, Spain, Mexico and the US.  I’ve lived out of AirBnBs, sublet apartments, signed a lease in Taiwan, lived with my parents and crashed with friends who had spare bedrooms.

Prior to that I lived a pretty normal life, working full-time and signing year-long leases.  At the age of 32, driven by dissatisfaction and curiosity, I decided to take steps towards a different kind of life.

Many people have this yearning but it is quieted by an offsetting fear of the unknown. Exploring this unknown has become a central theme of my writing. I want to help people make sense of life off the default path.

With a global pandemic forcing many people to work from home, lives like mine have become a lot less weird and many people are re-assessing their priorities and dreaming up new possibilities for their life. 

I’ve received more questions in the last nine months about my life and how to work remotely than expected so I decided to write about many of these questions I received. I’ll publish this on my blog and keep it updated and make edits as appropriate, but I’ll dive into some of the following questions:

  • How do you think about travel?
  • How much should you work?
  • How do you bank and get access to money abroad?
  • How do you make friends and deal with loneliness?
  • What should you bring with you?
  • How do you handle visas, healthcare & taxes?
  • How do you pick where to live?
  • What do things cost?

Without further ado:

How to think about long-term travel?

When you are living nomadically, travel shifts from something that can be consumed to something that you are living every day.  The preferences you think you have will shift because you are no longer traveling within tight time constraints or in an attempt to escape from work.  Travel is your life.

This can be a pretty wild mindset shift at first and can leave you feeling a bit detached from reality, not to mention disconnected from your friends “back home.”  One of the best things I did to deal with this was to journal and write about the experience.

In addition, I also recommend reading books about travel. Reading about what you might expect before and during the initial travel can help you make sense of the experience. Here are some books and writing that were useful for me along the way:

  • The Field Guide To Getting Lost: Her quote “That thing the nature of which is totally unknown to you is usually what you need to find, and finding it is a matter of getting lost” helped me make sense of wandering into the unknown when I arrive in Taiwan in 2018.
  • Vagabonding: This book by Rolf Potts is a must-read for anyone embarking on long-term travel.  In his terms, “Vagabonding is about looking for adventure in normal life, and normal life within adventure. Vagabonding is an attitude—a friendly interest in people, places, and things that makes a person an explorer in the truest, most vivid sense of the word .”
  • The Four-Hour Workweek: This book is a bit outdated with its resources but still valuable in how Tim thinks about the relationship between time, work and money. The title often confuses people as an attack on work but really this book helps spur the imagination for the possibilities of one’s life in powerful ways.
  • Being an Illegible Person: This older post from @vgr on Ribbon Farm is still very relevant to someone not following the default path of work:“nomadism has almost nothing to do with the rooted-living behavior it nominally resembles, travel.”

How does one actually make the shift and how do I tell my loved ones what I’m planning?

As you simplify your life and look forward to spending your new wealth of time, you’re likely to get a curious reaction from your friends and family. On one level, they will express enthusiasm for your impending adventures. But on another level, they might take your growing freedom as a subtle criticism of their own way of life. Because your fresh worldview might appear to call their own values into question (or, at least, force them to consider those values in a new light), they will tend to write you off as irresponsible and self-indulgent. Let them. As I’ve said before, vagabonding is not an ideology, a balm for societal ills, or a token of social status. Vagabonding is, was, and always will be a private undertaking—and its goal is to improve your life not in relation to your neighbors but in relation to yourself. – Rolf Potts, Vagabonding

The aspiration to live abroad or test out remote working often emerges slowly.  For me it emerged over a period of six months period while working on a remote project in the US and during a month of travel in Asia.

I didn’t have a reason other than a general curiosity pulling me towards living abroad but as I shared it with others I realized this was not good enough for others. When you are starting to tell others what you are thinking you need to think about their process of becoming comfortable with your move. They may see it as dramatic and it can be useful to give them the same space that you needed in the first place.

Thus it can be practical to start with “I’m thinking of doing this, what do you think?” before progressing to “I’m doing this…” Similarly, if you are trying to get your employer to let you work abroad frame it as a one or two month experiment before asking to make the move permanently. The norms are changing fast but living and working abroad is still quite new and strange to most.

In my own case, despite a hunch that my own experiment might be longer than a few months, I framed it as a three-month “trip.” While others saw this as a bit crazy and a risk to my success as a freelancer, I knew I had to go. At the end of the day making people uncomfortable is an inevitable part of live beyond the default path.

How much does it cost to live abroad?

“The more we associate experience with cash value, the more we think that money is what we need to live. And the more we associate money with life, the more we convince ourselves that we’re too poor to buy our freedom” –Rolf Potts

People that live in expensive cities around the world like London, NYC, San Francisco, Sydney, and Hong Kong often assume that apartments cost thousands of dollars, meals cost at least $15 and for Americans, healthcare requires insurance and must be expensive.

Depending on the country you decide to go to (and even parts of your own country) these facts need not be true.  My biggest costs when living abroad tend to be housing, food, and transportation. Here is a sample of some of the costs:

Housing:  The more often you move the more you pay.  If you can stay at least a month in a place prices start to drop dramatically.  At 3-months you can start talking to local brokers about signing a lease and saving even more money.

  • Taiwan: I spent no more than $800 a month staying in shared AirBnBs with local hosts and when I signed a lease with my wife in a 1BR we paid about $533 per month.
  • Bali: I stayed in a 1BR without a kitchen at a hotel with a common area and restaurant for about $700  a month
  • Thailand: We spent a month in Chiang Mai and Pai in December 2018 and spent $20-25 a night on lodging.
  • Spain: We spent about $800-1000 per night living on the canary islands in coliving houses and AirBnBs
  • Mexico: We are spending $800-1200 per month living in shared houses with kitchens
  • US: I lived in shared apartments in Boston for $850 and $800 per month in 2017-2018.  One of these apartments was with 4 other people and 1 shared bathroom 🙂

One note on AirBnBs. They can be a great on-ramp to getting local housing but are often 30-100% higher than a rate you may pay for local apartments. I recommend using AirBnB (or Agoda or Booking) for your first couple of weeks but if you plan to stay you can often find brokers through local facebook groups that are offering monthly rentals.

Food:  The higher the price of food the more valuable it is to have your own kitchen which should factor into your housing decisions.  Eating out in many countries is much more common and lower cost outside the US and especially so in Asia.  In Taiwan, Bali, and Mexico, meals ranged from $2-10 per person per meal.  A few examples:

  • Cheap Meals: In most countries there is a local go-to meal.  Taiwan you can walk out to find bounties of street vendors and get a selection of 3-5 items to share with two people at a cost of about $5-7 a person.  In Mexico you can find great street tacos for $1.  In Thailand you can find a kick-ass Khao Soi for $2-3 and in Bali you can find a great Mie Goreng or Nasi Goreng for $1-3.  In many parts of Europe you can find a local item that is cheap such as the Crepe in France.
  • Nicer Meals: In Taiwan, Thailand, Bali and Mexico you can get a pretty good “western” meal (think instagram friendly with lots of colors) for $5-10.  
  • Fancy Meals: In cities like Taipei that serve as international hubs you have meals that are just as expensive as you might find in Hong Kong or New York City.  In smaller places like Puerto Escondido in Mexico, you can get a filet mignon at the fanciest restaurant in town for $15.

Transportation: One of the biggest costs of travel, especially if you plan on going to many places can be air travel.  This has not been a major expense for us mostly because we have decided to stay in places for 2+ months at a time.  

In terms of local transformation. the most common way of getting around is a scooter or motorcycle.  Some countries require an international driver’s license (or at least the cops will try to extort you if you don’t have one in Thailand and Bali) while others do not (you should be okay with a US license in Mexico)

  • Scooter Rentals: For $75-200 a month you can usually easily rent a scooter in Taiwan, Mexico, Thailand and Bali
  • Bike Shares: Many locations are starting to roll out bike share programs.  This made living in Las Palmas, Gran Canaria about 100 times better as it made the whole city bike-able in less than 20 minutes.
  • Car rentals: I rarely rent cars and this can range in price dramatically but think anywhere between $10-$30 per day

What about healthcare?

Healthcare is often a major concern for Americans because our healthcare system is in the early stages of collapse. It was a surprise to learn for me that confusing layers of insurers and unexpected high fees are not a common thing in other places.  I haven’t gotten healthcare everywhere, but here are some things I’ve learned:

  • Insurance:  There are many providers that offer global health insurance.  Last year I had a plan with Cigna that covered catastrophe care helping me to limit the downside if I had to deal with anything serious.  I had about $3 million in coverage for $90 a month and this covered me for up to 3 months in the US.  This didn’t cover normal doctor’s visits but that was not something I needed given the low costs of care in the places I went.  I have not used products like SafetyWing but have heard good reviews from others.
  • Paying Direct for Doctor’s Visits: Taiwan’s healthcare system is one of the best in the world and seeing a doctor is pretty easy.  You can see a doctor and get a prescription for $10-15.  In Spain, I had to see several doctors to deal with a health challenge after a tooth removal and paid about $60-$80 per doctor’s visit.  Prescriptions from pharmacies in Spain were about $2-10 per medication.

Special section on US healthcare

The US is a pain in the ass and this becomes apparent when you start looking at international plans and realize that the only country in the world that raises your premium substantially is the US (really).

If you do need insurance and are planning on going back into the US I suggest that you start the process early. You can access state exchange plans at any time of the year because moving back into the country is a qualifying event. You should start the process before you arrive so that the insurance will start by the time you arrive. Otherwise you will have to fight with them to backdate your start date (which is possible in some states).

I’ve done three stints in the US without insurance and have learned that there are ways of accessing healthcare without insurance (sometimes its even better than if you had insurance)

  1. Most pharmacies have special codes for people without insurance.  This can lower the price of the prescription to even lower than many copays.   You can check sites like GoodRx to get a sense of what these costs might be.
  2. If you don’t use insurance you can also get your full prescription.  I was able to get a full year of my thyroid medication at once because I was using an uninsured coupon code and not going through insurance.
  3. Ask for the price ahead of time always! Many doctors and services have “cash prices” if you pay up front, but it can take a bit of calling around to find them.  These are often lower than the post-insurance price you’ll pay (crazy, I know)
  4. You can often negotiate the price after your care or ask for forgiveness programs.  This is still pretty hard and if you really want to go to battle over the costs, there are probably better resources to find on the web.
  5. In many medium or large cities there are services that offer free care and regular services like bloodwork or basic doctor’s appointments without insurance. Some googling around will usually dig up something. Just be prepared to fill out a bunch of paperwork.

Taxes?

Taxes are a tricky subject and I recommend reaching out to an accountant. I scheduled a paid consultation with Grace from Gracefully Expat who helped me answer 10-15 questions I had in less than an hour. While there are some ways to avoid US taxes, the US is the most aggressive country in terms of collecting taxes from citizens living abroad. I know other countries are much more lenient, but you shouldn’t be taking tax advice from me…

I have a pretty simple business and keep track of all my business spending and income through Quickbooks Self-Employed and use a Chase Business Ink card which has no international exchange fees abroad.

Visas

In many countries you can go work remotely as a “tourist.” Depending on your country this means you can show up and spend 30, 60 or 90 days without a formal visa. While this can technically be a legal grey area because you are “working”, countries like Indonesia and Thailand have softened their enforcement of this and have realized that these workers often stay and invest in local businesses and communities.

Countries are increasingly competing to attract these kind of workers with new kinds of Visas. Fellow remote worker Leandro has a great article from September on the entrepreneur and nomad visas that are being offered around the world.

If you are on a tourist visa you will likely have to do a “visa run” which means you have to leave the country and come back. In Bali, people often do a weekend trip to Singapore before coming back but sometimes people will fly out and back in the same day. It all depends on how strict the enforcement is at the country you are entering.

How to pick where to live?

I recommend three ways:

  1. Follow your curiosity: Is there a place you can’t get out of your mind after visiting or reading about?  There’s probably a reason why.  Go and see!
  2. Use Nomadlist: This site by Pieter Levels was created to help nomads figure out where to live and where others might be living and working remotely.  I’ve met many people around the world through their slack community.  This is also how we ended up in the Canary Islands.  We used the platform to screen places with >20 degrees Celsius in February in Europe and were left with two options: Tenerife and Las Palmas.
  3. Follow one friend: This algorithm has worked pretty well because if you have a friend in one place, they can help you get settled, solve problems and introduce you to friends they’ve already made.  This is what brought me to Taiwan, Mexico and Bali.

Using things like Nomadlist and reading travel blogs will help you find more popular destinations.  I recommend starting with those “mainstream” places and then once you arrive you’ll often find other villages and communities nearby that might be a better fit after you’ve adapted to the local environment.  For example, in Bali, Canggu and Ubud are the go-to nomad locations, but once you’ve familiarized yourself you can check out living in other parts of the island.

How do you make sure nothing bad happens?

For people that are used to short vacations you are likely used to paying much more for luxury accommodations and services such that nothing goes wrong. This makes sense. Who wants to waste 3 days of a 10 day trip trying to solve various issues?

With long-term travel you should expect things to happen that make you uncomfortable unless you are willing to pay vacation prices (this likely only works if you are making $100k+).

Anytime we arrive in a new location we plan not to get much work done and to spend the first few days solving issues, for example:

  • Lack of pillows and sheets
  • A shower that had an electric current running through the water
  • Lost ATM card and no other way to get money
  • Ant infestations in our clothes and bags
  • Internet that doesn’t work
  • Broken A/C in 95% humidity weather
  • Shared AirBnbs with people we were not comfortable living with
  • A scam hotel booking that was actually an empty parking lot
  • Lots of noise nearby (busy street or partying)

Growing up we had a phrase when I would go camping with my aunt and uncle that helped us to deal with issues as they arose, “it’s all part of camping!” Now my wife and I say “It’s all part of travel!” and try to laught about the experiences we face.

Once you have enough experience solving these issues you tend to worry less about your accommodations and where you sleep. This has been a game changer because its also enabled us to spent less money on lodging because we have more wiggle room for discomfort.

How Do You Bank Abroad?

The two things you should investigate before leaving your country: a no-fee international credit card and a no-fee ATM card.

For Americans, I highly recommend the Charles Schwab International ATM.  It refunds you ATM fees so all you pay is the transaction fee.  This is vital in the many countries where cash is the only way to pay for many things.

I also recommend signing up for Transferwise.com which is a great way of sending money internationally.  It often has a delay but you can use this to pay for housing or other high-ticket items.

How much do you want to work?

For remote workers with full-time jobs you won’t have as much flexibility as nomads, but probably still have freedom to design your day.  Think about the key elements that give you energy such as eating, socializing, exercise and sleep.  See if you can design your day around those things.  If your work day controls everything about how you’re spending your time, you’ll probably be frustrated with remote work.  I have more tips here (that you shouldn’t show your boss).

For others who are either taking a sabbatical or are self-employed, getting the balance between work, life and adventure can take a while to figure out and my ability to get in any sort of rhythm depends more on the environment and people I’m around more than I expected.

I tend to think about my work in terms of projects.  Recently I’ve been focused on my writing and my goal is to have 4-5 days a week when I spend at least 2 hours writing.  This is the kind of work that brings me alive and it’s the answer to Derek Sivers’ question “What do you hate not doing?

Working for myself has given me an unbelievable amount of freedom.  Once I realized that my ideal life cost much much less than I imagined, I no longer start with the idea that I need to work every day or for a certain number of hours a week or month.  This can be disorienting as you struggle to spend time around people that still design their life around work and it can be incredibly rewarding.

I was able to spend more than eight weeks in full-travel mode with my now-wife in the first six months of dating and later traveling with my Aunt, Uncle and mother during their first visit to Asia.  I imagine in 25 years, these are going to be the memories that matter.

Similarly, I also spent two separate months developing two online courses one of which has taken off in unexpected ways. I wrote about one of these “sprints” and how I shared my progress in public along the way.

Living and traveling abroad while working shifts the imagination in unexpected ways.  There is no “right” way to balance this but it’s important to experiment as much as possible with these without getting locked into the same routing from back home.

How to meet people & make friends?

As I mentioned, I try to pick places where at least one friend is already living there.  However, here are the general approaches we use to make friends:

  • Couchsurfing: Though this has waned as a popular traveler app you can still find interesting events and people in various places.  They have a great meetup tool where you can find others looking to do something right now
  • Nomadlist: Nomadlist has an active slack group with channels by location and country that makes it easy to find others
  • Coworking Spaces: These spaces often have events and other friendly travelers that also want to make friends
  • Facebook: In Asia, facebook is much bigger than in other countries and in nomad hubs, there are often 2-3 groups where locals, expats and nomads share housing, meetups and ask and answer different questions.  Search “location name ” + some combination of “foreigners” “expats” or “nomad” and you should find an active local group,
  • Language Exchange: Many people want to learn English and if you are interested, you can find local language teachers and locals who want to make friends and learn each other’s languages.  
  • Twitter: Increasingly I meet and engage with people on Twitter in different countries.  If you don’t have a big following send me a message and I’ll retweet your request to find people in a specific location to see if anyone can connect you. 

How do you deal with loneliness?

The other side of making friends while traveling is that you often have a number of short, fleeting and shallow relationships with people that you may never meet again.  Sometimes these relationships lead to great memories like when a few locals picked me up in Koh Samui and brought me to a private beach for sunset or when I spent the day with some travelers from the Philippines biking around Seoul. 

While I’m lucky now to travel with my wife, sometimes we do get a bit down after feeling like we haven’t built many lasting relationships.  The benefits of travel still outweigh the costs for now but I do wonder how long I’ll want to keep living this life.  

Over the past three years I talk to many friends and family much less because I often spent a lot of time with those people in-person.  Time zones and living in a different country add enough friction that this is just hard to avoid.  Video calls are fantastic, but in-person connection is just so much better as many of us have realized in 2020  I’ve missed out on holidays and birthdays and get-togethers and am not around to see my brother’s newborn start laughing, crawling and talking.  Part of this is because my wife is applying for the green card and she can’t enter the US until she’s approved and part of it is because we’ve decided this crazy life on this pathless path is worth it.

It’s hard to write about these things because I have moments where I feel like I’ve abandoned my friends and family but I also know that I feel bad because these people would do anything for me.  This gives me the courage to keep going and keep listening to this deep drive within me to keep wandering and seeing where life takes me.

I’m also lucky to have found a partner that shares my curiosity and helps me make sense of navigating this amazing, confusing and beautiful life we are living. 

It’s hard to be too lonely when you have that.

How to decide what to travel with?

I’m a pragmatic minimalist.  I’m not against owning a bunch of stuff, but owning a bunch of stuff while traveling makes it a lot more stressful.  The more you have the more complex moving around, flights, packing and fear of losing your stuff becomes.

The most important things to bring with you is not high-tech backpacking gear but things that you will use every day. Things like coffee, tech equipment, equipment to exercise and sleep gear.

Since we try to stay in warm weather locations year round my wife and I don’t bring a lot of clothes. Instead we find things we like wearing a lot and make sure our apartment has a washer in the apartment. Instead of clothes we pack things that make our lives better.

My wife tends to use a lot of space for art equipment and fitness equipment as those are two things she loves doing. I tend to have more space for tech equipment like mics, cameras and recorders because I enjoy continuing to create digital content (you can see my full packing list here).

While it can feel like an accomplishment to travel with very little, it also can be easy to travel with slightly more if you plan on staying in location for a month or longer.

When I first started traveling I tried to get everything down to two carry ons. Since we now try to stay in locations for 2-3 months and rent monthly this is less of a concern. Still we don’t travel with that much. When we arrive in a new place we often take the first few days to take a few runs to the local superstore (e.g. Carrefour, Chedraui) to upgrade our pillows, blankets and home goods as necessary.

How do you travel with kids?

I don’t have kids so I’m not going to chime in here with an uninformed opinion but I have met many parents with kids who are either living abroad permanently or traveling with kids and I can offer their reflections.

Often people who pose this question do it from a perspective of missing out on education or “falling behind.” Most of the parents I’ve met traveling with kids reframe things in terms of the experiences or lessons their family and kids will learn while experiencing a different mode of life. It’s certainly not for everyone, but parents seem to take three aproaches to thinking about education while traveling:

  • Homeschooling / self-teaching: Parents teach the kids and keep up to date with any requirements from the state or governments in terms of reporting. I know several parents who have taken this path.
  • Formal homeschool programs: There are many online services such as Kahn Academy which enable people to do remote learning from many places across the world. I met a 14-year old in Mexico last week that does all his school through Kahn Academy.
  • Enrolling in local international schools: Depending on where you are there are often international schools that you an enroll your kids in. This is what Christine Bader did with her kids in Bali and what Ben Keene did with his kids when he moved to Koh Lanta with three little ones.

It seems there will be a lot more possibilities that emerge with homeschooling an virtual learning over the next decade and I expect to see many more parents take sabbaticals or years abroad with their kids once they no longer have to commute to an office every day.



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