Expat Diaries | #298
May 26th, 2025: Greetings from Thailand! As we’ve recently moved abroad again, I’ve been meeting people from all over the world and decided to write up a post about Expats. I’m always fascinated by the range of stories from people I meet. I did a little survey and am sharing some of the responses here.
Every Expat is Different
The internet broke the link between work and place, and more than that, it enabled people to stay in touch with people “back home.” I remember being shocked when reading Green Island, a historical fiction book about Taiwan, which shared the journey of a couple that was emigrating to the U.S. in the 1960s. As the family said goodbye, everyone understood that this may be the final time everyone would see each other. Now with FaceTime, text instantly, and ubiquitous air travel, the costs of moving somewhere else have fallen.
I’ve been thinking a lot about what it means to be an “expat,” especially as Angie and I move abroad again. It is an imperfect label, one that captures a wide range of people. It includes people who are escaping crises at home and people who simply enjoy being “from nowhere,” as Sachin shares below. Expat has been a term used to describe corporate workers who do 2-year stint abroad in an effort to fast-track their careers. But now, with remote work and growing self-employment, people don’t need HR permission. They can “expat themselves,” and go wander.
The reasons for such decisions vary radically, as I’ve found in my discussions over the years. In the examples below, the reasons range from study abroad programs that accidentally turned into decade-long adventures to "rage quitting" jobs to live on a Thai beach before digital nomadism was cool, from following love to fleeing burnout to simply discovering that quality of life is better when your money goes further and you can make friends more easily. It also includes people who moved abroad with their parents and never wanted to go back.
Despite demands from people back home, many of these people don’t have a good answer that ever satisfies why they stay abroad. They enjoy the rootlessness or lostness of such an existence, have fallen in love with a second home, or simply are “somewhere, for now, until visa rules change.”
This post was fun to pull together as I scratched my curiosity. I’m not sure if I’ll continue to write on this topic, but happy to hear more from people, so please share!
Note: LLM tools helped me to create the initial draft of the summary of survey results, but the final version is human-crafted, fact-checked, heavily edited, and meets my own standards for what I want to send. Enjoy.
#1 Kirill: Early accidental digital nomad, embracing many home bases with his family
Original Country: USSR/Russia
Current / Past Countries: Czech Republic (12 years), Germany (4 years), UK (1 year), Singapore (6 years), global nomading (3 years)
When They Left / Years Abroad: Left in 1999, 26+ years abroad
"I consider myself a citizen of the world with a Czech passport, residence in Singapore, and many temporary bases and HQs where I can live, work, and experience life with my wife."
“For the first 3-4 years, I was confused and had a fear of not being able to return. But as my life went on, after year 5, I had a fully autonomous life of my own in a different country that was welcoming me with all its color and experiences.”
"I rage quit my job to move to Thailand and live in Ko Samui for 6 months before digital nomadism went mainstream, and just exploring with the youthful naivete was one of the best things I've done in my life."
Kirill So expat journey began when his parents moved from Russia to the Czech Republic in 1999, but what started as a forced relocation became a lifelong adventure across continents. He eventually renounced his Russian citizenship and became Czech, explaining, "As life was stabilizing, and I was creating new social circles being young, learning the language, and integrating culturally, made me cherish the opportunity to live elsewhere." His journey took him through multiple countries before he became an early digital nomad pioneer. He notes that many expat relationships "break at the 3-year mark" due to people "not trying to be friends with locals, only hanging out with expats and not trying to integrate."
To read more, you can find more on his website
#2 Blake: “Europe Was More Livable”
Original Country: United States
Current / Past Countries: Argentina (2017), Germany (2018, 2020), New Zealand (2019), Europe (2022 onwards)
When They Left / Years Abroad: Increasingly abroad since 2017, hasn't been back since 2023
"Quality of life is simply better in Europe. I can thrive without a car. My money goes farther. I find it easier to make friends. I have more success with dating."
"With all the craziness happening in the USA, people seem to think that I consciously planned my escape. It was just fortuitous timing."
Blake Boles move from the US to Europe wasn't a dramatic escape plan but rather a gradual realization that life simply worked better for him abroad. Starting with travel-heavy stints within the US, he began exploring internationally in 2017 and found that Europe offered everything he valued: walkability, affordability, easier social connections, and better dating prospects. His main fear about returning is "being able to afford housing" rather than social reintegration.
More Here:
I also recorded a podcast with Blake on his podcast which I reshared on mine:
#3 “Godwin”: Intellectual freedom in Canada
Original Country: India
Current / Past Countries: Hong Kong (age 1-18), Canada (age 18-24)
When They Left / Years Abroad: Left at age 1, 23 years abroad
"One reason to be in the west is that it enables more freedom of thinking. I can feel the difference in the calmness (and, thus, the divergence/quality/etc) of my thinking when I'm 'back home' in Hong Kong vs when I'm in Canada."
“If your goal is to stay in the West (and your implicit goal is to have exposure to the kinds of creative, non-linear careers that the west tends to spawn more of), it *can* be strategically more optimal to study in Canada than the US, because it's typically easier to immigrate to Canada. This might be changing literally as of this writing, but at least it's been ~true until ~now.”
Godwin's story begins with his father's job relocating the family when he was just one year old, but his decision to stay abroad has become deeply intentional. Growing up, he “strongly railed against” any potential move back to India. After university, he chose to live and work for his mentor-boss, someone he believes he was “fated to meet.” He strongly resisted any prospect of returning to India during his youth, feeling that "the pressure-cooker environment of India would just have crippled me." Now 24, he champions Canada's underrated tech scene and values the "freedom of thinking" that the West enables. His biggest fear isn't about going back—it's about not being able to stay.
Preferred to remain anonymous.
#4 Sachin: Embracing rootlessness
Original Country: India
Current / Past Countries: United States
When They Left / Years Abroad: Left in 2017, 8 years abroad
“I love being in cities and places where it feels like people are from nowhere. The tension that rootlessness and a quest for novelty creates is something I enjoy a lot and find inspiration in. For example, recently I've been observing how immigrant communities use public spaces in ways that I don't see born and raised Americans do, like huge Hispanic family gatherings at the park or old Middle Eastern men having tea by the creek near me.”
"I needed some distance from everything that I was familiar with and I think this eventually helped me do the things that I wanted to do, such as publishing a book."
Sachin moved to the US with a green card in 2017, having never visited before, but his motivation wasn't economic. He said “I needed some distance from everything that I was familiar with and I think this eventually helped me do the things that I wanted to do, such as publishing a book.” He finds inspiration in immigrant communities and rootlessness. His family was "moderately to severely upset" that he didn't settle in Houston's Indian townships, where immigrants can live comfortably without even speaking English. The distance from familiarity enabled his creative work, including publishing a book. He hasn't returned to India since moving and admits this is "a real fear I have not faced yet."
+ I’m actually reading and enjoying Sachin’s book, Thinking About Leaving, which is a collection of essays chronicling the year before he became a U.S. Citizen
He writes "storyworthy moments in the mundane every day" here:
#5 Emily: Finding a Better Life Formula Abroad
Original Country: United States
Current / Past Countries: Mexico, Spain, various European countries
When They Left / Years Abroad: Left October 2020, 5 years abroad
“I think there are lots of people who assume I prefer living abroad simply for a more advantageous cost of living, which, sure, is an added bonus that I can't deny to have benefited from. I won’t pretend that paying $17 for a latte and a bagel in NYC wouldn’t take some of the joy out of that element of my morning routine.”
"The pandemic provided the perfect 'silent escape route' — since so many people's daily lives, routines, jobs, future plans were completely flipped upside down, nobody really batted an eye at what I was doing."
“Some people also probably think I’m "lost", but in reality it's quite the opposite. Particularly during the last two years, I've made very deliberate choices about where/how I spend my time, prioritizing living in places and doing the things that bring me most happiness.”
Emily Ann Hill’s expat journey began as a planned 6-8 month remote work trip in 2020 that has now stretched to five years. Through trial and error living in various places, she developed a specific list of non-negotiables, including warm weather, beach access, walkability, and reasonable costs, criteria no US city meets. Learning Spanish has been "one of the coolest things I've accomplished in my adult life," and she's never felt homesick. The pandemic timing worked perfectly as a "silent escape route" since everyone's lives were disrupted anyway. Her main fear is being forced to return to the US for family or work reasons and having to "give up the incredible life I've spent the past five years building," and admits to having “reverse culture shock” when she goes back now.
Emily writes about the realities, quirks, and chaos that come with living abroad, intertwined with her quest for a happy, meaningful life.
#6 Leonid: From Burning Out To Building A Family Abroad
Original Country: Israel
Current / Past Countries: [Not specified in detail]
When They Left / Years Abroad: Left in 2019, 6 years abroad
"My parents gave me all the tools to have a better life. By leaving, I'm following their dream for me and having the better life they intended me to have."
“My culture exploration was worth it, and I actually found a better work culture like I was looking for.”
Leonid Ler left Israel in 2019 seeking a break from burnout and a different work culture, but stayed when he found both love and professional fulfillment abroad. He met his partner and had a son, creating deep roots in his new home while also discovering the better work culture he was seeking. The biggest misconception people have is that "I left my family," but as an only child, he emphasizes he didn't abandon his parents; rather, he's living the better life they dreamed for him.
Leonid writes about his life experiences and, from time to time, gives out unsolicited advice to junior managers
#7 Lyndall: The Australian Serial Expat Planning Her 13-Year Return
Original Country: Australia
Current / Past Countries: America (2002), London (2006-7), Amsterdam (2012-present)
When They Left / Years Abroad: Moved to Amsterdam in 2012, spent most of adult life abroad with breaks back in Australia
"I'm not sure I meant to (stay abroad)! But I created a life here that I loved and didn't want to leave."
“I live in Amsterdam so people think I must love marijuana (I don’t!)”
Lyndall Farley expat journey began with her feeling "stuck in a rut" and wanting more adventure, leading her from Australia to multiple countries over the years. This is normal in Australia, though: “I think Australians understand people wanting to move abroad. It's common for young people to do a stint in London.” Her current 13-year stint in Amsterdam wasn't planned; she simply "created a life here that I loved and didn't want to leave." Unlike some expats, she's always intended to return to Australia and is finally planning that move now. Her biggest concern is about reverse culture shock after so many years away.
Lyndall is a sabbatical coach - you can find out more here.
#8 Kaitlyn: Into the "Pai Hole" for 8 Years
Original Country: Canada
Current / Past Countries: Australia (brief), Southeast Asia, currently Pai, Thailand (8 years)
When They Left / Years Abroad: Left in 2016, 9 years abroad
"I had planned to come here for two days, stayed a week, and just kept extending my stay until a year later I realised it would probably be a good idea to just rent a house rather than living out of my backpack in a dorm."
"Living abroad has shown me what's truly important, and some of the more trivial things people worry about aren't of interest to me anymore."
“I think some people have the image that being an expat in a tropical country is like a permanent vacation. I don't think people understand that life continues to "life" and it can still be challenging (sometimes more challenging, if I'm honest) living in a destination that many choose for a holiday destination. There are more logistical hoops to jump through, language barriers, and cultural differences that can be challenging but if you're willing to adapt and integrate, it can be a really beautiful experience.”
Kaitlyn Ramsay expat journey began after a breakup prompted her to quit her corporate job and book a one-way ticket to Australia, but she never made it a full year there before getting curious about other cultures. She ended up in Pai, Thailand, for what was supposed to be two days and has been there eight years—a victim of the famous "Pai hole" that traps visitors. While she initially fell in love with a man there, she stayed for the pace, kindness, food, and affordable living even after that relationship ended. She's currently preparing to leave Pai after eight years, wrestling with whether to try a new place or return to Canada, worried about the cost of living and faster pace back home.
Kaitlyn writes about real life through the lens of astrology, sobriety, and life as an expat living abroad:
#9 Francesca: Left for University & Stayed In The U.K. As It Became A “Second Home”
Original Country: Italy
Current / Past Countries: UK (mostly), France (1 year), Washington DC (9 months), London (since 2019)
When They Left / Years Abroad: Left in 2014, 10+ years abroad
"If I spend more than a few days back home in Italy, self-doubt starts to inexorably creep onto me, like a horror movie."
"It has to do with 'who am I', and 'where do I belong'. Questions for which definite answers probably do not exist!"
Francesca Galli left Italy in 2014 for university and has spent over a decade abroad, primarily in the UK, with stints in France and Washington, DC. She says that some people back home, “seem to assume that I have got it all figured out, that I am on this rising trajectory to some high status places.” But staying abroad "has very little to do with 'status'" now, and instead she sees the U.K. as a comfortable “second home.” Her family has always been supportive, as her parents spent a lot of time abroad too. Friends, however, constantly ask, “When are you coming back?” Her biggest struggle is internal. She experiences profound self-doubt when spending time back in Italy, describing how "a chilled aperitivo with friends telling me about their quiet town life sometimes leaves a bitter aftertaste." She has fears about going back to Italy, but fears “not being able to go back” much more.
Francesca keeps a Substack on her creative experiments, personal essays, and the shiny, odd things she comes across.
#10 Brian: Car-free in Barcelona
Original Country: United States
Current / Past Countries: Spain (Barcelona)
When They Left / Years Abroad: Left in 2018, approaching 7 years abroad
"I'm under the belief that the place you live shapes every other aspect of your life. It determines your work, how you get to work, how you spend your days off, who your friends are, who your neighbors are, how many kids you have, the list is endless."
“My friends and family see it too. They can tell by how I light up when I talk about my life here. So when it comes to staying, I don’t feel misunderstood, I feel supported.”
"Here in Barcelona, I feel like I'm discovering the best version of myself."
Brian Wiesner moved to Barcelona in 2018 after feeling disconnected from his surroundings in the US and wanting to live somewhere he didn't need a car for daily activities. Born in Budapest with an EU passport, he chose Barcelona over San Francisco or NYC after one visit sold him on the city. What started as a one-to-two-year test has become a permanent life change as he fell in love with the city and made deep friendships. His philosophy is that "the place you live shapes every other aspect of your life," and his family and friends support his decision because "they can tell by how I light up when I talk about my life here." He has no intention to return to the U.S. but if he had to, says he’d do it with “a sense of gratitude for all the experiences I've had and things I learned throughout my years living here.”
Brian loves writing about the intersection of places and people, focusing on how density leads to serendipity and what makes places attractive.
#11 Kelly: Chasing adventure and opportunity for 16 years
Original Country: United States
Current / Past Countries: Australia (1 year), Southeast Asia (backpacking), South Korea (2 years), Taiwan (8 years), Europe (3 years)
When They Left / Years Abroad: Left July 16, 2009, 16 years abroad
"One thing led to another and I kept trying new experiences."
"My fears are more around where else can I go that isn't the US if this current place/visa doesn't work out, but I have always figured that part out because one things leads to another."
Kelly Davis 16-year expat journey began with a study abroad program in Australia, but "one thing led to another" as she backpacked through Southeast Asia, taught English in South Korea, spent eight years in Taiwan, and recently moved to Europe.
Her path has been entirely serendipitous, driven by meeting people who recommended new experiences and opportunities. She struggled with family understanding for the first decade, especially when living in Asia. Her parents kept asking her to come home, with “my mom telling me there's a cool job opportunity in our hometown frequently.” This has improved a bit since Europe feels "more desired and normal" to people back home. Her biggest fear isn't returning to the US but rather the financial impossibility of sustaining her lifestyle there due to the fact that she has not prioritized "climbing the ladder" or "keeping up with the Joneses.”
Kelly writes about bold new models of education, the power of student voice, and how learning can thrive beyond the classroom.
Thanks for reading these!
Expat Diaries is great on this topic if you want more!
I’ve really enjoyed following The Expat Diaries: Leaving Home, Finding Home from Vivian which shares more in depth stories on similar themes. Here is a recent story:
Thanks for reading!
Which I’ve been doing since 2015. I’ve somehow figured out how to hack a living doing things like this.
If you like what you read here, you’ll probably enjoy my books The Pathless Path and Good Work:
If you’d like to meet others on “pathless paths”, you can join The Pathless Path Community.
Some things I endorse: Crowdhealth, an alternative to US health insurance; Kindred, a home-sharing app; Collective for handling your S-Corp accounting needs; and Nat Eliason’s Build Your Own AI Apps course
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Very inspirational and catching me at just the right moment. 🙂
I can most definitely see how Pai changed Kaitlin so much
Magical place