The Expat’s Dilemma: When Do You Know It’s Time To Go Home?

I’ve lived in Thailand for approximately four years.

Like many expats, when I initially moved here, I only planned to stay a year or two. But then, as I’m sure many of you can relate to, the Land of Smiles grabbed a hold of me, and hasn’t let go since. I’ve been back to my home country (the USA) three times in my four years, two of which I planned far in advance, but the most recent of which I planned at the last minute.

In the four years I’ve been here, I’ve missed eight of my friend’s weddings, my aunt’s funeral, a big 80th birthday celebration for my stepfather who raised me, and my best friend’s father’s sudden funeral, among numerous other memorable occasions.

One of the most frustrating things about being an expat is missing all of these milestones, both celebratory and somber.

I was particularly upset I couldn’t be there for the two funerals, but given my locations at the time (on an island in the South of Thailand and in rural China), making it back in time would have been nearly impossible and extremely cost prohibitive.

A few things help me get through these difficult moments. For one, I love my life here, and I wouldn’t trade it for anything in the world. Secondly, as an old adage goes, “you can’t make choices for other people, so don’t let other people make choices for you.”

Related to that point, with regards to the numerous weddings I’ve missed, I take solace in the fact that while a few of my friends have visited me in Thailand over the last four years, many have not, including the eight whose weddings I missed (though they all attended my wedding in the States).

For my most recent visit back to the States, however, it was a culmination of factors that led to it.

For one, it was my wife’s 30th birthday, and while we were debating several different options in Bangkok, the rest of Thailand, and even other parts of Asia, none of them were particularly jumping out at us. The driving factor that led us to take the trip home, however, was when one of my two favorite sports teams made it to their championship series, a feat that hadn’t happened since 1945. Furthermore, that team, the Chicago Cubs, hadn’t won a championship (the World Series in baseball) since 1907. It’s the longest championship drought of any of the four major professional sports in the US.

Suffice to say, it was a huge deal in my city, Chicago.

returning home as an expat

In fact, my stepfather, who’s 81 years old and is the biggest Chicago Cubs fan I know, has never witnessed a championship for his favorite team, and the last time they got to the championship series he was 10 years old.

In terms of historical perspective, the relevant figures in America during the last time the Chicago Cubs won the World Series were Al Capone and Teddy Roosevelt. It was also around the time that Albert Einstein discovered the theory of relativity. So to say this opportunity doesn’t come along very often would be a huge understatement. Thus, when it arose, I knew I couldn’t pass it up.

Although I wasn’t too keen on spending $1,500 for a trip back to the States when my wife and I were just back there this past summer, I figured if I was still living in the States, I undoubtedly would have purchased a ticket to the game, the cheapest of which were going for $2,500 (for standing only; no seat), so $1,500 actually seemed like a pretty good deal. While I wasn’t planning to attend any games, I just wanted to watch with my friends and family and be in the city for this historic event.

returning home as an expat

One of my few concerns about returning for the World Series would be what my friends and family would think of my decision to return for this, but not for one of the many aforementioned events that equally could have justified a trip back home. But then I remembered the old adage I alluded to earlier, and made peace with my decision.

All of this brings me to the crux of this article: the life of an expat is often one of difficult choices and almost impossible trade-offs.

Do we go back for a wedding but not a funeral, the birth of a nephew/niece but not a sibling’s graduation, a job interview that you might not even get?

These are the difficult choices we have to make, and each individual person has to make their own choices.

In doing so, if the purpose of going back is for a particular person, I often like to ask myself, would the person I’m going back for do the same for me, and if the answer is no, to me, it’s a no-brainer. If the answer is yes, it’s a little more difficult, but ultimately, the choice is yours, and yours alone.

For me, besides the unexpected championship appearance for one of my two favorite sports teams (I mean, honestly, who could have ever foreseen that something that hadn’t happened since 1945 would happen in the few years I’ve been gone?), when I left America, I told myself the only two circumstances under which I’d return home for an unexpected visit would be either an unfortunate health circumstance with either my or my wife’s parents, or one of our siblings’ weddings.

And that’s it.

Though I hold my friendships dearly, in my view, once you start coming back for friends and extended family, then you’re left picking and choosing between them. Fortunately for me, my very best friend is actually getting married this month, but he’s having a family-only wedding, in the middle of the week, in a remote destination. Had he had a more ‘normal’ wedding (at least by American standards), I would have had (another) very difficult choice to make.

And so as I extrapolate this topic to a related, ultimately more important life decision, one question my wife and I are facing is if, and when, we ultimately return home.

As suggested earlier, when we first left the States in July 2013, we were initially only planning to stay a year. But for anyone who’s read some of my other articles likely knows, we enjoy our lives here far more than we did in the US. Back home, we both worked 50-70 hours a week, 50 weeks a year, at an office job (I was a lawyer, my wife was in marketing) we typically didn’t enjoy.

Now, in Thailand, we work 20 hours a week, get four months’ vacation a year, and genuinely enjoy what we do (teaching English and law at a private university in Bangkok, in addition to having time for several other side projects like writing for this magazine, blogging about our travels, starting a new business, and just generally our enjoying our leisure time).

If it weren’t for our families, there’s a decent chance we’d spend the rest of our lives here (or somewhere else abroad), particularly when we can come home every summer for up to three months. But on the other hand, we do miss our family and friends, and we also feel as though we sort of owe it to our parents (particularly mine who are on the older side and thus can’t travel here as easily as we can travel back to the States) to return home at some point.

These are the difficult choices we face as expats, but as suggested earlier, I’ll take these choices any day of the week over the lack of choices I had when I lived in America.

For example, with only two weeks’ vacation a year, you basically get one holiday a year to look forward to (typically over Christmas/New Year’s for me as that was the slowest time at my office).

Compare that to the twelve months of traveling my wife and I have done over the last four years. If I had stayed in America, it would have taken me twenty-four years to get that much vacation time. By then, there’s no way I would have been able to do so many of the wonderful things we’ve done in the last few years like hike to Mt. Everest Base Camp, climb Mt. Rinjani, hike the Inca Trail of Machu Picchu, ski in the Andes mountains, swim with whale sharks, sleep in the Amazon jungle, just to name a few.

So in terms of trade-offs, to me, it’s been a no-brainer. Although that doesn’t mean it still doesn’t hurt when we miss a wedding, funeral, or other milestone for someone we love.

But we only have one life to live, and it’s our life, not anybody else’s. The only people we owe anything to, in my opinion, are the ones who raised us. Everyone else is just gravy. But in making your choice, remember, would they do the same for you?

And as for my beloved Chicago Cubs, who obviously would never travel to Thailand for me (once in a lifetime experiences are another category altogether), it ended up being the best result I possibly could have imagined.

returning home as an expat

Not only did they win the World Series, but the Series went the maximum seven games which allowed me to spend as much time as possible watching them with different friends and family. And the final, seventh game, an epic battle where they blew a three run lead late in the game and had to wait out an unexpected rain delay which may have very well been their savior, was considered one of the greatest baseball games ever played.

On top of that, my wife and I were interviewed on both national television and the local news about our dedication in coming all the way back from Thailand for the Series. After they won, the city celebrated with a parade of over five million people.

By one account, it was the largest gathering of people in the history of the Western Hemisphere, the seventh largest and the largest non-religious gathering in recorded human history (though many would argue that baseball, and the Cubs, for some, are religion). Considering the city of Chicago has approximately 10 million people, roughly half, myself included, showed up for the parade.

Having crossed this item off my bucket list, I’m happy to say my wife and I are now back in Thailand and already planning our next adventure (a ski trip to South Korea and Japan over the winter holidays).

Valuing life experiences over material possessions, and making decisions solely based on our own best interests and nobody else’s save our parents and maybe siblings, has allowed us to live this incredible life. I hope this piece can inspire others to lead similarly fulfilling lives.


All photos (except featured image) courtesy of David Rosenfield



About Author

After practicing law for eight years at two of the largest firms in the world, in July 2013, David and his wife decided to take an extended honeymoon through South America and Asia, ultimately settling in Bangkok where he’s been teaching law and English at an international university ever since. David has visited over 50 countries on 6 continents and continues to practice law while also teaching and running his blog. Follow his adventures at The Stave Diaries, on Instagram and on Twitter.

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