Thailand Won’t Make You Happy

For many aspiring entrepreneurs (especially readers of Tim Ferriss’s 4HWW), the “digital nomad” lifestyle is the holy grail. And it sounds great – globetrotting, living on a beach in Thailand, working a few hours a day from your laptop, running your business through a 4G modem. And I must admit that I spent a few years of my life trying to do the same thing. But there’s one thing I’m finding out as I mature as an entrepreneur and a human being – our digital nomad culture often focuses too much on building a lifestyle, rather than a life.

Yes, Thailand is gorgeous. It’s an incredible spot for a vacation, it’s comparatively cheap when you earn in USD, and you can post pictures on Facebook that will make all your friends ultra jealous. But for most, Thailand isn’t a permanent lifestyle – you’re going to land in Bangkok, go sit on a beach, and two weeks later you’re going to realize that you’re still you. All your challenges, your aspirations, your demons – your life is sitting right there next to you on that beach.

Hiking in Cinque Terre, Italy
Hiking in Cinque Terre, Italy

I think as an entrepreneurial community, we are selling people a dream that’s partially hollow. “You too can create an affiliate website and then move abroad and be happy forever! Just buy my e-book…” And for sure, the digital nomad lifestyle is FUN! A lot of fun. Thailand is fun. Globetrotting is fun. But I think it’s about time for some real talk about the difference between fun and happiness. As my friend Dave Craige says, “Happiness and contentment do not come from external things like parties and beaches. They come from the inside.”

Last year, I spent 3 weeks traveling through Italy with my family. It was easy to do – I brought my Macbook Air, grabbed wifi where I could, and the business continued to run without a hiccup. But by the end of those 3 weeks, I was ready to be back home. Not ready in a homesick way, ready in an excited way. I had meetings scheduled with other awesome entrepreneurs, had a factory visit planned, and dinner with my friends at our favorite local sushi joint. These are things you don’t get when you’re a digital nomad.

For me, I’ve realized that you don’t need to move abroad in order to be “doing it right” as a location independent entrepreneur. Being location independent for me is becoming more about having the freedom to do the things I want to do and go the places I want to go, while still having a home base here in the USA.

Sailing with my brother off the South Carolina coast
Sailing with my brother off the South Carolina coast

I feel like the digital nomad community dramatically undersells the US as a place to live. Beyond the basic amenities like unlimited clean drinking water and excellent hospitals, we have some of the most incredible geography in the world. In just the past year, I have: spent three weeks on a remote beach in South Carolina with 4 entrepreneur friends, hiked to the top of Angel’s Landing in Zion National Park, skied some of the best terrain in the world at Telluride, listened to live jazz in New Orleans, climbed to the top of the Empire State Building, and sipped wine in the hills of Sonoma. No passport needed, and I’m still around enough to nurture relationships with my family and my friends. And it’s hard to put a price on that.

So to all the current and aspiring digital nomads and 4 hour work weekers out there – let’s shift the conversation and weave “happy” into our aspirations together with “fun”. Let’s stop chasing ghosts around the globe, and give ourselves permission to build lives in addition to just lifestyles.

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  • Now you are falling into that trap yourself, assuming everybody is like you. We aren’t. All with different motivations in life, Thailand will actually make some of us happy. Travelling is a life style for many of us, I myself can truly say that i need to be home from time to time, except for me home is not a location, it is where I can close the door and where I have a kitchen. Travel is not something I do “to do something different”, and get away from work and party. I live a similar life wherever I am, but the scenery and the people changes.
    That’s also why I can’t ever comprehend the question “when do you go home”. I go home every night (almost)… Regardless where I am in the world, and I have meetings, interact. Cook. Work

    • Hi Ann-Katrin,

      Thanks for your comment. I think you’re definitely right – everyone is not like me, and I’m really glad you’ve found happiness for yourself. But the reason I wrote this post is that it’s also true that not everyone is like you. I think the general narrative in the digital nomad community is so pro-expat that it’s easy for people to forget that’s not the only way to be happy. I wanted to provide a bit of a counterpoint for people who haven’t found the fulfillment they were looking for through travel. Still, I’m glad you’ve found a lifestyle that works for you!


      • Actually, with the experience I have and with all the different people I have met, that live all over the world, I’d say the majority of the expats are just like yourself, they like to come home; Most after considerably longer time than what you mention though – it is not after three weeks in Italy they find out, but rather after a few years. Most of them have kept a connection to where they came from and consider that their home, and live their lives accordingly, they plan for eventually returning. It is true what you say; They don’t build a life, they build a life style. Then there are those of us who actually build a life out of it. I assume how you grew up also plays a role, I have always had family and friends all over the world, and I don’t go on holiday; I live my life in different locations. If I was on holiday for three weeks or even two, I would quickly grow tired of it. I can do that for a long weekend, have the parties, eating out, the “holiday life”.
        I do like your blogpost, just saying it feels it fits in on most people, not a few.
        Still, it is very good, in this era of entrepreneurship, to understand why you do it and what motivates you, as well how entrepreneurship works. Unless you are in the party organising business, parties will be the exception; There are perks with entrepreneurship, but there is also a LOT of hard work, in many ways much harder than being employed; You can’t just switch off your phone and log out…

  • Admit it, all you want is cheap high quality workforce staying in murica, from which CEOs benefit.

    • I thought about removing this comment, but I’m leaving it since I find it kind of unintentionally hilarious.

      In case the original “anon” ever comes back to read this – this post was written to inspire people to live wherever they want and decide for themselves what makes them happy. Most of the folks I employ actually live full time outside the USA – in our global world, great talent can find work from anywhere. I don’t care where folks live as long as they do good work…

      • Ha, glad you didn’t delete it – I love laughing at the completely irrelevant and mysteriously ambiguous troll comments on articles like this. Next thing you know, you’ll be tied to the Big Pharma and have a penchant for killing puppies in your free time. Bad Bill.

        To contradict the title of your post, I think Thailand CAN make you happy if you’re bootstrapping a new business and it’s the only location you can afford to live in on your current income (especially when the alternative option is moving back in with your parents!).

        For some, Thailand is actually a great entry point. When you’re just starting to build a business, it’s handy to live in a place where you can comfortably live for under $1k a month (eg. Chiang Mai).

        But once your business is making more money and you no longer NEED to bootstrap (ie. the necessity of living in a cheap location is removed), that’s when other criteria kicks in.

        And if Thailand doesn’t have what you’re looking for, you’re totally right – it won’t make you happy. Once you’ve gotten through the “bootstrapping due to necessity” phase, you start to have more rigorous criteria about where you want to live. You might not be comfortable living in a country where you don’t speak the native language. Or where you can’t buy grass-fed meat at the grocery store. Or where you have limited dating options. Etc etc.

        As with any location, everywhere has its flaws. Whether somewhere will make you happy has nothing to do with whether you were born there, and everything to do with what you’re looking for in your ideal location.

        In most digital nomad hotspots, particularly Chiang Mai and Saigon, day-to-day life ISN’T “parties and beaches”. It’s actually pretty similar to anywhere else in the world. You wake up, go to the gym, work out of a cafe or coworking space, meet up with other entrepreneurs for coffee, have a few glasses of wine or beers in the evening. It’s just cheaper. And depending on where you’re originally from, nicer weather.

        If you go a step further and live somewhere English speaking like Kuala Lumpur or Singapore, there’s a good chance you’ll end up feeling entirely settled there. It becomes home very quickly.

        I’ve been living in Asia for the past 4.5 years, but don’t consider myself as having been “travelling” in that time (with the exception of a few long weekends away).

        Technically I fall under the digital nomad category, having been based for various lengths in Kuala Lumpur, Chiang Mai and Saigon. But in reality I’m not actually a nomad. I’m just quick at adapting to new environments and making them my new home. At the moment, I’m based in Saigon because there’s such a great community of entrepreneurs here. It’s great to have so many similarly minded people around me that I can learn from and cowork with.

        Does Saigon feel like a permanent location? No. Because it doesn’t fit all my criteria. But for now the benefits I get from living here (particularly being plugged into an entrepreneurial community) far outweigh the benefits I’d get from living anywhere else.

        When my business hits my next target milestone I’ll be relocating back to Kuala Lumpur, because KL ticks all my boxes for what I personally want in a permanent location. Just because I wasn’t born there doesn’t mean that by living there I’m simply building a lifestyle rather than a life.

        And I have to strongly disagree with this point:

        “I had meetings scheduled with other awesome entrepreneurs, had a factory visit planned, and dinner with my wonderful girlfriend at our favorite local sushi joint. These are things you don’t get when you’re a digital nomad.”

        Yes, you do get these as a digital nomad! If anything, you get MORE of these things:

        * In Saigon and Chiang Mai, I’ve been surrounded by more awesome entrepreneurs as peers and mentors than I ever was in London. It all depends on your personal network.

        * The proximity to China means that it’s very easy to visit factories if you want to manufacture goods in Shenzhen – arguably the manufacturing capital of the world.

        * There are loads of great sushi places in Saigon/Chiang Mai/[insert Asian city of choice] plus they tend to be cheaper than in the US / UK which means you can frequent your local favourite more often. Oh and yes, if you don’t already have a boyfriend/girlfriend to go with, Tinder has in fact reached this side of the world 🙂

        So to summarize, although I totally agree with you that the USA may indeed be an overlooked destination for digital nomads and that the ol’ “sipping coconuts on a beach is THE LIFE” myth should be busted, I disagree that choosing to live in Asia is all about globetrotting and lifestyle.

        As with any city, whether it’s NYC or Chiang Mai, it’s entirely what you make of it. They all have their upsides and downsides, you just have to find the location where you feel happiest.

  • I agree with the first post, you are assuming we are all the same.

    My biggest motivation is to not spend the winter in the depressing weather of the UK, I also love travel and meeting new people so the digital nomad life is awesome for me and I would be sad to lose it!

    • I definitely understand the desire to escape UK winter weather 🙂 I mostly wanted to provide a counterpoint with this post – to show people that there’s a way to use your freedom while still staying attached to a local community, family, and friends. I think the prevailing discussion in digital nomad circles is that everyone is the same in that travel is the end-all-be-all, but this post was written to speak to the people who have tried that yet still feel like something is missing.


  • um, I COMPLETELY agree. The choice to go out on my own was about getting to live and work on my own terms, according to what’s best for me. If living in a developing country is what I want to do, then I want to be able to do that. But, if living in USA or Europe is what I want, then I want to be able to do that too… If someone is so sold on the “digital nomad” hype that they start using its mantras as a club to beat me over the head with so that I conform to industry standards (whatever those are), then I call their bluff, say they are full of sh*t, and go on living my life the way I always do – what I want, when I want, how I want. Plus, Thailand is not all its cracked up to be IMHO… the depravity of some social problems there is absolutely and fundamentally appalling. I don’t understand why everyone keeps going / saying to go there despite the huge stinking white elephant in the middle of the damn living room.

    • Glad you liked it Lillian – hopefully it provides some reassurance for people to know that “living the dream” can mean whatever they want it to!

  • Very good post, So many people are selling the hype of the lifestyle business and so many people are buying in to it, but is it what they really want? Yeah you can live a great life style for a little bit of money in SE Asia but I prefer to build a solid business and live a great lifestyle in the US. To each his own.

    We have so many great places to visit in the US. Last summer I took my family on a trip to Glacier National Park it is by far one of the most beautiful places you can visit.

  • It’s great to have the opportunity to live/work in other places whether it’s within the United States or abroad. For someone like myself that has lived in various locations, I found living in the UK for a year a huge eye-opener. Not a lot of entrepreneurism, a disdain for Americans, horrible food, bad health care, lack of freedom, lack of choice, cigarette smoke everywhere, high prices for everything and miserable weather. I love being American and never took it for granted, however, I have an even better appreciation for my nationality having this experience. Going abroad for a vacation will be a “yes” in the future, but living in another country again I will never do.

    • Bad health care? The NHS is completely FREE! In America you have to pay extortionate amounts to see the doctor and have treatment. It’s absolutely shameful, especially when many families can’t afford it.

      And while I agree there are many things to dislike about the UK having lived here for 28 years, our health care – especially in comparison to the draconian US – is not one of them.

      • My comments are to shed some light on what seems to be better in other countries versus the reality of the situation. Life abroad is not better than the USA. Yes, there are issues and life is not always perfect in the United States, but, you do not want to be living anywhere else.

        The healthcare in England is awful. Yes it is “free”, but actually it costs Brits a high percentage of their income to be covered. Most Brits do not use the NHS because it is highly overloaded with the ill, and, there are a lack of doctors to care for them (wait times are all day – 8-10 hours to get a prescription for 500 mg of ibuprofen). Therefore, there are ill people everywhere, who then infect others because they continue to go to work, etc. And a simple “cold” turns in to an epidemic. Imagine not being able to buy isopropyl alcohol at the drug store! Seriously, a prescription is needed. Over-the-counter medications in the U.S. are a dream. The medical equipment used in the UK is often not as state-of-the-art as in the U.S. and the techs aren’t well-schooled and/or often do not care enough to do the job they are supposed to do. Would you like to strip down for an exam and not be given a gown? Or, sit on the same exam table as the last 1000 patients without a cleansing of the surface first? Want a female doctor or male? Doesn’t matter, you get what is given to you.

        If you don’t like this treatment, there is no one to complain to because no one cares. If you try to complain, you have to pay to complain. Yes, you have to pay to call a company to complain, or ask a question or order a product or service. There are no “toll-free” numbers in the UK. Want to order cable TV? You will have to pay several dollars to call the cable company and order it. Got a problem with your Internet or cell phone service? Spend more of your money to call the company to get it fixed, and they may or may not fix it the first time.

        You will wait for everything in the UK because there is no sense of urgency or pride in performance. Almost the entire working population has job security. Sounds good in theory, but the reality is that this type of system keeps really bad employees in their job and lowers morale for the others that do care and do do their job. I watched a grocery store check-out girl berate a customer with “F bombs” because she can get away with it – job security. Yes, she lobbed racial slurs too, at a paying customer, all because she didn’t like her race, and, because she can get away with it. I spoke with the store manager in disgust at the scene and asked why? After several other Americans stepped in to address the issue with the manager, the employee was put on “probation”. Probation is 1-3 months of paid, PAID, leave of absence where the employee is allowed to return to work (to the same position) following her time off, without any consequences. After all, her rage was probably because she hadn’t had enough “holiday” in the first place.

        I could go on and on. I speak not just from my year experience abroad, but, having a 30 year relationship with a British-based family. They are more evolved and progressive than their colleagues/friends/families, and have always spoken openly about the differences.

        We’ve got some issues in the USA, but freedom and choice rule here. The take-away; speak up and do something when you see something you don’t like.

      • Wow, that was quite a rant. I’m no patriot, and nor am I an apologist for the British “work ethic” and our way of doing things. But you’re making the UK sound like an LEDC; having spent a lot of time in developing countries like Nepal for example, I can tell you how OTT your definition of the UK healthcare system is, regardless of its many imperfections. Call me naive, but having seen the situation in countries like Nepal (among many, many others), I’m actually quite grateful for the NHS and for the conditions we have here.

        And even though the NHS has been in disarray for years, and has loads of issues, anyone who hasn’t got an income, is retired, or is working minimum wage jobs, can, at the very least, live here knowing that if they were diagnosed with a terrible disease like cancer, they wouldn’t have to face a draconian system that would leave them unable to pay for their treatment. Regardless of your better facilities and higher quality service, is seriously F-ed up.

      • The reply was not meant as a rant. I am merely outlining my experience.

        In the USA, if you are ill and don’t have $$, you can go to any hospital (and you don’t have to be a US citizen) and you will be treated. Payment is collected after treatment, unlike the UK where funds are verified up front for private care, or, you wait for hours first at NHS facilities. Then a determination for care is made.

        In the USA, you can also file indigent status and there are several options for payment, or, there is payment forgiveness based on individual status. And yes, there are the cases where people are debilitated by health care costs here. This is were you have to lobby for yourself among the choices available. There are available choices. This is the American way.

        For example of an unfortunate NHS circumstance, my friend had a clogged main artery (clearly blue and strugging for oxygen) and went for treatment at a London-based hospital and was told to come back in 3 months, when they would diagnose the issue further to determine if he needed care. Mind you he was unable to breath and had all signs of heart attack. NHS let him lay around for months before the family pulled together the $$$$$ funds to move him to private care. They paid an extraordinary amount of their personal retirement account to have him fully taken care of. And, they’ve paid tens of thousands in British Pounds for NHS that ignored him.

        If you like NHS then that is your opinion and choice. My family didn’t like the UK way of life. And, was surprised to find such a huge difference in the quality of living between the USA and UK. I had no idea it was this drastically different. None. So I’m merely taking the time to share. I would hardly call the USA Draconian, but again, that’s your opinion.

        It was also odd to find movies about Hitler on the BBC every day, several times a week, all year long. Um, it’s 2014, ya’ll right?

        I won’t respond to any further comments, but thanks for playing today.

      • Guys, this has gotten a bit out of hand. Why must everything turn to politics on the internet? I’m going to delete these comments in the interest of keeping the thread clean, please feel free to take your political conversations to your local bar…

      • Sorry mate – it does sound like Andrea’s friend had a really bad experience here – but they could easily have gone to better practice/s and acquired a 2nd or 3rd opinion, before paying vast sums. Im my 28 years of living here, I’ve never known of anyone who had anything like those problems. And I know plenty of people with similar – and worse – states of health.

        Like I said, the NHS has been a mess for years, but there are still some excellent doctors here and they’re not exclusively for people who pay $$$. Everything’s relative of course, so I understand why Andrea dislikes it so much. But she should try living somewhere like Liberia, then she might realise why I’m taking the stance that I am.

        No more politics from me! 🙂

  • Great article. I never understood why lifestyle design and travel the world have to go together. Maybe your design is living in the USA. And you know what. Thats ok too!

  • I wholeheartedly agree. I, too, was inspired by the 4HWW and made drastic changes to my business in order transition into more of a lifestyle business that afforded me the opportunity to come and go as I pleased. Initially, I loved having the flexibility to travel where I wanted. I visited at least a half dozen foreign countries and loved my experiences out there. But I also felt an emptiness inside. I think this stemmed from a lack of total immersion wherever I went. I was focused more on quantity (how many countries can I visit?!) rather than quality (immersion into the community and culture). I felt like a tourist, not like I was living life. I loved my travels but I loved coming home even more. I realized that I derive a lot of purpose and meaning from deep connections with my friends, family, and community. Those relationships take time and effort. And while its not impossible to have while living the “nomad” lifestyle, its very difficult. Nomad lifestyle, by definition, is living like a nomad which is the antithesis of the rootedness that I seek. As I get older (now in my mid 30’s), I find that my priorities have shifted. Being a globetrotting world traveler is no longer sexy to me. Being rooted in a community and surrounding myself with like-minded individuals, building and nourishing relationships, finding lasting love and sharing the dumb, little details of my life with a special someone, having meals with good friends, being vulnerable, having a home base in a beautiful town- these are the things that bring me happiness and joy. I’ve traveled to over 30 countries around the world and I dont regret it for a second. But, for me, living in the USA and establishing my life here cant be beat.

  • “I think as an entrepreneurial community, we are selling people a dream that’s partially hollow.” WHOA. There is a LOT of truth here, and I can certainly relate.

    I can also relate to being on vacation and being *excited* to get back to get back to work on my business! Thanks for sharing. 🙂

  • Funny enough I just got back to this post – and there was something that immediately appealed to me, and I forwarded the link to someone. Only afterwards did I realise I read this post two years ago. And commented on it.
    While I still agree to what I said before – we are not all the same and many could be very happy in Thailand or anywhere else, as long as they do it for themselves. I could be happy in Thailand. I could be happy almost anywhere, if I have a kitchen and a door to close behind me. I never bought in to the idea of sitting on the beach/being out skiing all day, but having a change or scenery can be tremendously inspiring. I myself needed a new start, fresh ideas, new challenges, and I needed some distance to myself for that.

    I am, after some “corporate detox” again absolutely excited about the tech world and IT, I have realised what is MY trigger – creativity. I had just forgotten how to be creative in tech, and now, after some time away, lots of studies and meeting interesting projects and working various small projects (including art), I am returning to IT full time – and loving it.

    The beach never WAS interesting to me, so I never did that part of travelling, I just travel to let myself be inspired by the people I meet – and beach or not, breaking free from the corporate world was the healthiest thing I have ever done, it brought back a lot of inspiration and made me a much stronger project leader/product owner (with one foot in arts, something that wouldn’t have been possible, had I continued in the corporate world).

    Would be very interesting to hear what you are doing now!

  • Hi Bill,

    In this matter, I am similar to you. I personally love to be surrounded by family and for my sake, everyone cant have a nomad life. If feel this type of lifestyle makes you lazy, and I personally feel better when I am my home, with my people around. Read number of comments saying that they agree with nomad life and for them home has very few basic criteria like kitchen and all. But for me, being an emotional person, I am connected to my friends and family and I have special attachment to my home in my heart. I believe nomad life can’t be permanent. I crave to be in my hometown to hang along with my friends, my favorite hangouts and my family. Emotional connection with home town. I can ignore millions if they separate me from my family. I love traveling but at the end there is always an urge to go home.


Bill D'Alessandro