How To Become A Digital Expat: Expectations, Criteria, Transitioning, My Experience

A “digital expat”, is a term for an entrepreneur who makes money online and moves to a country with better opportunities. I’m talking about moving to a cheaper country, say in Asia, and taking 2 to 4, cheap vacations a year.

It’s most definitely not for everyone, 1% of guys at most, but it can be a great lifestyle for some guys when you set things up properly. You can:

  • Live in a cheaper country (and geoarbitrage your online income)
  • Living in a more fun, relaxed and safer country
  • Low to no taxes
  • Live in a country with better dating prospects (sexual market value arbitrage)
  • Live in a warmer country
  • Take cheaper and more frequent vacations
  • I’ve been a “digital expat” for 3 years now and in my quality of life has gotten a lot better. And it’s a lifestyle that’s available to you too, if you want it. Honestly though, I don’t like the term, it’s just another identity you don’t need.

I use the term as a reference point for you, in reality, I’m just an entrepreneur who moved to a place where I can have a better quality of life. But it’s the lifestyle I’m talking about, not the identity.

You don’t need to run around calling yourself a digital expat. And you definitely don’t want to identify as a digital nomad. Becoming a digital nomad is nothing to aspire to, the same way you wouldn’t aspire to be a hobo.

You just can’t make money going from one country to the next every two weeks. You can’t make money working only a few hours a week. And you definitely can’t run a business from the beach, it’s too damn hot and the internet doesn’t work.

Even if you’re young and want to see the world, being a nomad is not the move. When you build an actual business, you can live anywhere you want, and take a vacation to anywhere, at any time, for the rest of your life.

When you don’t you blow all your money on mediocre girls and third world hostels only to have to come home to mom’s basement, get a job and try to scrape together some more cash.

Why You Shouldn’t Aspire To Be Digital Nomad

  • The more you travel, the more things can go wrong – visa problems, immigration etc.
  • Travelling is unfun, uncomfortable and stressful
  • Travelling costs money: hotels and plane rides will eat whatever you save in taxes and living costs
  • Constant travel will fuck up your routine – your health, fitness and peace of mind will suffer
  • You cannot build and expand a business without a base and a routine
  • Being a nomad, and having a bunch of stamps on your passport is nothing to be proud of

I don’t want to be too harsh on the nomad community, a lot of nomads are young guys doing their best to create a better lifestyle for themselves.

There are also some exceptions to the rule, great guys like:

All those guys are legit guys, who travel a lot, and still take care of their business, but they’re the exceptions to the rule. And I’d be willing to bet all those guys don’t define or align themselves as digital nomads. In reality, guys who can make it happen are entrepreneurs first and foremost.

And again, don’t think being a “digital expat” or living in one country for a long period is something to be proud of either. Again, it’s just for your reference, in reality, you’re just an entrepreneur who chose to move to take advantage of better conditions and create a better lifestyle for yourself. And you’d be shocked at how much better your life can get, when you do it the right way.

How To Become A “Digital Expat”

The first thing you need to do, before you even think about moving, is get serious. From your fitness to your daily tasks, to your budget, to most importantly – having a thriving business already built. I’m talking about building a business first, and then moving to work on and expand that business, not :

“I’m going to Thailand to try and start a dropshipping business and hope my money lasts.”

I’m also only talking to guys with proven discipline, meaning for at least the last two years :

Because it’s a big move, and it takes a certain guy to be able to make that move, here what you can expect:


  • You’re cutting off your social circle and your family
  • You’re living in a foreign culture with a foreign language
  • Your new home doesn’t have the human rights standards or political stability you’re used to
  • You have to get used to living 100% of your business income with no safety net
  • You have to force yourself to work every day while it’s sunny out and cheap beer and hot girls are waiting
  • A weak, transient expat community with many untrustworthy expats and sad old guys
  • You have to adjust to the floating feeling that comes with total anonymity and freedom
  • Very dangerous driving and strong police presence

This among a lot of other adjustments, it’s no joke, don’t believe the hype, you need to be serious.


Before you make the move you should have the following things on lockdown:

  1. You’re Over 25: With a few exceptions I can think of, being under 25, means you won’t have the income and discipline needed to win
  2. Upper Middle Income:  This means for at least the last six months you’ve had consistent income to put you in the upper middle class of your new country. For Asia, that’s 2k a month.
  3. Solid Financial Safety Net: I’d like to see you have 20K saved before you come out. Combined with consistent revenue will leave you comfortable.
  4. Solid Psychological Foundation: No recent history of major depression or anxiety
  5. Have A Burning Desire For Business Success: You need to be in it to win it


  • Psychological: Get your self ready psychologically. Get the guilt of leaving people behind and the fear of new experience out of your head. Focus on how much you’re going to be winning in your new country.
  • Visa: Do your research on the Visa you need for your new country, as well as what the long term Visa options are in your destination country: In Asia, a good 1 year visa will cost you about $1000/year.
  • Tax Situation: Talk to a good lawyer and check out for your expat tax and offshore incorporation prep
  • Budget: Find out how much you need to live a comfortable (upper) middle class lifestyle
  • Credit: You want as much credit as you can get, while you’re still in your home country, for emergencies as well as paying advertising on FB/Google (not for going into debt)
  • Travel Notifications: Setup any travel notifications you need to with your bank before you come out. As well as keep your banks helpline in your contacts.
  • Take Out Local Currency: Get local currency before you get to your new country, just in case you have any problems with getting money from your bank. And learn your countries’ currency laws, a rarely (but sometimes) enforced law is that foreigners need 20,000 baht in cash upon entering Thailand.

Country Selection

  • despite the name, nomadlist is the best site for narrrowing down your country selection
  • Numbeo is another great site for comparing the cost of different cities
  • Asia, Eastern Europe And South America are the big 3 (I’d avoid SA for safety reasons)
  • Weather, cost, dating, safety, fun, convenience are your metrics (all found on
  • Asia is #1 in my books, primarily because of cost, which should be your #1 metric
  • Asia, IMO, is also where all the money will be for the next 100 years
  • Eastern Europe, would be my #2 specifically Budapest is another good option for spring and summer (no winters)

Cost Of Living For Chiang Mai

I can’t speak on anywhere else, but I’ll give you a breakdown of Chiang Mai to give you an idea of how to budget. You can also check and numbeo to get a better idea.

  • Accommodation (modern studio): $300
  • Food and Drink: $300
  • Miscellaneous: $40
  • Entertainment: $200
  • Transportation: $40
  • Business expense: $120
  • Total: $1000 (I spend closer to $2000)

Transition 1st Week

For your first week you want to do everything in style. If you’ve saved enough money, and have enough money coming in, and chose the right destination, than you’ve earned the right to travel in style. Your days of scraping by are over, that’s why you made the move, and don’t forget that. If you can’t afford to spend your first week in style, then you shouldn’t be there.

When you arrive to your new home, get yourself a:

  • Nice car from the airport
  • Nice hotel
  • Party for 1 week, meet everyone, say yes to everything, try and stay outside all day, not in your room
  • A nice hotel, and going out all day and night will keep you from culture shock/homesickness
  • Enjoy your first week of total freedom you earned it

Transition 1st Month

After your first week of styling and profiling it’s time to get serious. I went H.A.M. my first month, but that was too much, keep it to a week or maybe 2 and then get down to business. You don’t want to risk falling into the habit of being a partyboy, which is very easy in a cheap tropical climate.

Here’s what you need to do:

  • Get a local bank account for currency hedging and low fees
  • Get as many processors as you can for your orders: I have 2 Paypal accounts and 1 Payoneer
  • Get started ordering your online supplies for the quarter and the year
  • Learn where all the good restaurants are and where to get good groceries
  • Get a top tier phone and internet plan (no bullshit 7/11 phone and internet cards)
  • Set your reminders and implementation for your long term visa plan
  • Get a top tier condo/serviced apartment (cheaper with a 6 month/1 year lease)
  • Get your laundry service and cleaning set up

My experience

I’d never been out of north america until 32. But my plan was Chiang Mai, I put two years into savings, on top of the savings I already had, and a bunch of time and money into RLD before I came over. I chose chiang mai because it’s cheap, warm and safe.

Everyone said I was crazy, both my friends and family, and the “nomads” I met who couldn’t believe I was going to live in one place, and not bounce around like some kind of aimless drifter. In reality, I just moved my workaholic life from Toronto to Chiang Mai.

And I told myself I’m living here, outside of a few small vacations, until I get RLD where I want it to be, which will proabaly be another 2 years of grinding.

And I grind hard here, while everyone else is outside enjoying this beautiful weather I’m here grinding. Just because I’m living in “paradise” doesn’t mean the grind stops. True hustle doesn’t take days off. And it hasn’t been without it’s problems.

Here’s a short list of just some of the things that went wrong since I moved to Thailand:

  • My amazon FBA business flopped
  • My ali express dropshipping business flopped
  • Google cut my traffic in half my down ranking my popular articles
  • Got locked out of my Canadian Paypal and had to create a Thai one
  • Got locked out of my Canadian account from online purchases being flagged at least 10 times
  • Tons of legit orders from iherb seized at customs, until I learned to order no more than $50 at at time
  • Been through ejunkie, samcart and gumroad order processors
  • Lost my debit card and had to get it shipped from Canada
  • Dating is worse than toronto
  • Hundreds of other small problems

Eventually I solved all the above problems from producing more articles, to only buying things online with my Thai card, to getting the right order processors – but there are just things that are going to go wrong, and you have to be prepared. I want you to have realistic expecations.

With that said, the good things outweigh the bad:

  • Motorbiking up the mountains on a weekday
  • Almost all my expense are what I paid in rent in Canada
  • Accelerated my businesses drastically
  • Quintupled my income by being able to work full time on rld
  • No sales job and therefore no cold calling
  • Live in the sunshine
  • Built a crew of awesome, like-minded guys
  • Live around friendly, polite people
  • Drastically reduced stress and commute
  • Upgraded the quality of my lifestyle
  • Built my youtube channel from nothing to 1.5 million views
  • Cooked chicken breast delivery service (gotta love that)
  • Cleaning and laundry every week for $40 a month
  • Never having to cook

Overall it’s been amazing. Hopping on that plane to Asia was the second best decision I’ve made in the last decade, the first one being starting RLD. But it’s definitely not for everyone. If you do want to move abroad, I want to make sure you have the right expecations.

With that said, it’s a pretty amazing upgrade, when you put all the pieces together, you just have to be smart about it, be disciplined, put in the work and make it happen.

  1. Will, Great article mate.
    May I ask did you use the non-immigrant business Visa or a company such as Thailand Elite (5 years for 500,000THB)?
    Or is there another way to stay long term in Thailand that doesn’t involve volunteering or border runs?
    Keep on grinding mate, your work is valued.

  2. Great article! I’ll be revisiting it from time to time to keep my head straight and focused on the grind.

    Last night, there was a snow storm here in Finland, and I stared out the window, thinking “FFS it’s still October.”

    I also had enormous fun motorbiking up the mountains when I was in Chiang Mai, and I can’t wait to get back. Every day, I’m fighting the temptation to return prematurely. Especially now that temperatures are dropping and everything is covered in snow here.

    But I already did the move completely the wrong way once, so now I’m gonna follow the plan laid out by you and wait ’til I’ve actually earned the right to make this move.

    Thanks for being a voice of reason, Will, amidst all that digital nomad lifestyle porn that’s being pumped out constantly.

    I’m curious though, why you think dating in CM is worse than Toronto?

    I’ve never been to Canada, but I’ve seen a lot of hate online about the dating scene in Toronto.

    My own biggest frustration with dating in Thailand was the language barrier. It was difficult find anyone with whom I could have meaningful conversations on topics that go deeper than “what we gonna eat today” or “what you did yesterday.”

    Whereas, in Europe, it’s not uncommon to meet a girl who is beautiful, feminine, but also well-read in a variety of topics, and capable of forming her own ideas about the world (as opposed to parroting societal programming like most girls in Asia).

    So I was just curious what’s your take on dating in Thailand vs the West. Perhaps you care to elaborate in another video/article?

  3. Thanks Travi, great to hear you’ve got the right plan together.

    As for the dating scene, yep Toronto gets a lot of heat, and I’m sure it’s rightfully so, Europe I’m sure is much better, at least Eastern Europe. But the reason, I put it over Thailand is exactly as you said, any type of meaningful conversation is hard to find in Thailand, so a Thai gf is prob out of the question.

  4. Thanks for the article and continued value. I’ve been following your site and keeping track, as I’m very interested in following a similar life path.

    I just started my expat experience on Saturday here in Mexico City so this was great to read. I’m a programmer from Los Angeles, and was grinding for months trying to get a remote setup, so I could full control of my time (instead of being in an office), be a contractor (control my taxes), and also be able to take advantage of favorable working/lifestyle/dating/tax situations.

    I was able to leverage my productivity with my last company into a remote situation and a higher rate. I spent the last 4 months in Austin to get my routine down and take care of things in the states, and also did a beta test in Colombia to make sure it fit my lifestyle/ability to get things done. I’m not planning on moving around much, mostly staying in Mexico and Colombia, so I can focus. Been to Thailand and Budapest, and especially liked Thailand, but with my current situation and my client, it’s much better for me to be in this timezone. I also need to go back to the US for a chronic medical condition from time to time.

    Now focusing on building an actual business, where my time eventually is separated from the money I’m making. I couldn’t agree more that it’s important. I never want to go back to working for someone. As far as social circle and surrounding yourself with like minded individuals, any tips for how to go about that? I’d prefer to be around ambitious type people, trying to make businesses and grinding, as opposed to digital nomads selling the lifestyle.

    Thanks again for the article.

  5. Nice work Jay, check out my article and video on how to have better friendships. With that said you are limited to your location to some degree, there aren’t too many guys I would hang out with in Chiang Mai, and the ones I am friends with are not part of the nomad seen.

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