When I was younger, I was eager to optimize my life and have lots of adventures. My old posts confidently talk about how you can navigate the rules to ensure a fun time and a stable future. While I can’t say I haven’t had a fun time, it has been nothing like the carefree life people imagine I must being. And not just because my work involves studying the experience of critical disability and death in different cultures.
People debating a move abroad often worry about what to do with their things and how to spend time with their family and friends back home. Transporting anything other than sentimental and specialty items isn’t worth the hassle. I thought having a place you could rent out while you traveled, including spending weeks at a time with family and friends, was the perfect solution.
I moved to Canada and then Portugal specifically because each country offered a relatively easy pathway to citizenship. I chose Toronto because, as someone without a car, it was just as easy to get back to my family in NJ from downtown Toronto as from Brooklyn. Even if it was an extra $150 each round trip, it was a nicer experience. First, because this was before Porter tried to copy Ryanair’s vibe, and because when you’re visiting from another country people will prioritize you in their schedule. No one was excited when I took the train from Brooklyn, even if it was a far less pleasant trip that took just as much time.
While I wasn’t sure if I’d actually stay in Portugal long enough to get citizenship, that option was the reason I moved there and not somewhere else. I had a Europe specific research project, which gave me a lot of choices for my home base. Portugal gave me an easy residence permit and I knew that pathway to citizenship would motivate me to actually study the language and learn the culture in a way that a non-renewable permit would not. My research would benefit from my being embedded in the culture. Plus, living in Portugal for 5 out of 15 years would make me eligible for citizenship, so it didn’t mean I had to abandon my life in Toronto.
It’s hard to say how I would have done things differently, since so much in my life has changed since I made these choices and I can’t imagine how else it might have gone. However, back when I was writing on here more regularly, I had this understanding of the world as a something like a board game or programming. I could learn the rules and then follow them in a way that would predictably lead to obtaining my goal — flexibility, adventure, future options.
Alas, that is not how life works. The rules are not carried out exactly as written. And I can’t even guess at how many times both written policies and their unwritten interpretations changed while I was trying to optimize my way through them.
I originally left the United States because I viewed its systems as fundamentally fragile—a landscape of inadequate social safety nets where one stroke of bad luck could dismantle a lifetime of work. I moved to Canada and then Portugal chasing the promise of institutional stability, believing that these more robust societies would provide a “floor” that would allow me to navigate life’s changing circumstances without a constant, underlying fear for my future. I thought citizenship was the ultimate hedge against uncertainty. Yet, I’ve found that the peace of mind I anticipated remains stubbornly out of reach. Despite holding a Canadian citizenship certificate and being married to an EU citizen, I am still mired in a different kind of instability. Between shifting international tax laws that have turned my retirement account into a “toxic asset,” a Toronto home that feels less like an investment and more like a ticking financial time bomb, and an international life that attracts a permanent layer of bureaucratic scrutiny, I haven’t escaped anxiety—I’ve simply traded one flavor of systemic failure for another.
You’re not supposed to travel for six months
In a lot of ways, it’s easier to be away for six months than six days. The same transportation costs seem a lot less expensive. Instead of paying for a hotel or trying to find a perfect match on Home Exchange, I can string together some house sits and rent out my apartment. My friends are a lot more excited to see me when I get home. And if I’m visiting family, spending a few weeks or months there is a nicer experience than trying to cram a years worth of Quality Time into a few days.
However, the world is not set up for this. While no one comes out and actually says I must be some sort of scam artist, that’s how people behave. People at the coffee shop are generally happy to make a temporary friend. It’s the bank, medical insurance, and property management that act like something shady is going on, even if everything you’re doing is technically permitted.
The first time it comes to their attention, they let it slide. But when you’re traveling every time someone interacts with you (or every time they log your IP), you face stonewalling. They lock your account. They ask for extra layers of documents that aren’t normally required. They add extra steps to delay every process.
You have to prove yourself constantly
Despite having flown many times in my life, I am still that person who feels anxious when going through airport security. Being treated like I’m probably smuggling cocaine makes me feel guilty and ashamed, even though I know beyond a shadow of a doubt that there’s nothing verboten in my bag or on my person. I feel similarly overcome with shame and doubt when they bring out the bag sizers, even though I obsessively travel with a personal item that would fit into the sizer. While I suspect I’m the only person who measures their personal item, or is even aware of the size limit, I don’t think this feeling guilt when my guilt is presumed is unique to me.
Immigration law requires me to prove my good character. Of course, I can’t just include a note from a rabbi and a minister. I have to demonstrate this by getting numerous police checks, of which there are numerous kinds, which need to be verified, and they all expire within six months. I also need to show my ethics by showing I’ve filed and paid my taxes. This is where my desire to follow the rules is insufficient, because Canada audits me every year. In fact, since they audit each portion separately, they audit me more than once a year. I have no idea how many ongoing tax audits I have going on right now. We play a little game where they disallow my foreign tax credits, I pay, they reinstate them, I get refunded. The CRA agents are all quite pleasant to chat with, making this a surprisingly pleasant experience despite its Kafkaesque nature.
I struggle to spend more time in my own apartment because I’m offered so many opportunities to do things that sound super cool. I’m in a niche of a research niche, so people invite me to weird research opportunities. People invite me to stay in their homes and take care of their pets because when you google me, I seem like a certified Good Person. There I am, the director of a nonprofit for caregivers. There I am, involved with my dad’s nonprofit to teach kids STEM. I’m not a rabbi, but I have an old 403b with the rabbinic pension plan.
Even though I have always been a weirdo and got into my share of mischief, I’ve also always been a nerd who’s followed the rules. Even in my 40s, I have not learned how to operate in this world where I constantly have to try to prove — with utility bills and tax transcripts?!? — my moral worth. The trouble is, as a precocious kid, my documents have never made sense. I took high school classes in middle school and graduated with my associate’s degree before finishing high school. I never stood a chance of having a paper trail that wouldn’t raise red flags.
Strategizing to get the right kind of impersonal documents to prove my value as a human being and facing this impersonal, bureaocratic scrutiny, fills me with a low level sense of shame and dread that clutches my chest every time a notification from a government agency arrives.
Living in another country is exhausting
I loved living in Portugal, but living there involved a ton of extra friction. First, there was the enormous amount of effort required to do an entire lifetime’s worth of life admin in a few months. In the US, I never had to get a residence permit because I was born with the right to be there. I didn’t have to figure out how to open my first bank account or even get a drivers license because my parents shepherded me through the process (my dad would have taken the driving test for me if he could have).
That part of moving to Portugal was annoying but fine, particularly since living with friends saved me from the bulk of the work. But then I was struck by a new level of social anxiety. It was clear in minor social interactions that even besides not knowing the language, I did not know how to behave. As a child I’d been dragged along as my parents ran errands and apparently that taught me how this works. In Portugal, things were just different enough to make me paranoid about doing the wrong things. As a tourist, this is inevitable and acceptable. As a resident, it is not. Just like obsessing about your normally automatic behavior makes it impossible to play a sport, this just made me weirder in every social interaction.
Compliance is not an option
My residence card for Portugal expired in August 2024. Until July 2024, at some point in or after your card expired, you’d login to the SEF/AIMA website, click the “renew” button, pay a fee, and then wait somewhere between 10 business days and a year for your new card to arrive in the mail. That website just never “opened” for August renewals.
I abandoned my renewal process, so I watched in horror from the sidelines. After a year with no updates as to how people whose residency expired could renew their status, they created a new process for people whose cards would expire in the future. The people whose cards were already expired were given a special process to be carried out by a different agency, only appointments were nearly impossible to get. People who somehow got an appointment, often traveling around the country, often had their appointment cancelled without notice or submitted their documents and never got a reply. Then it was switched to a new process with a different agency. Then it was moved back to AIMA. Then it seemed like they cleared the backlog by just sending rejection notices to all applicants.
Most of the people I know whose cards expired at the same time as mine or during the year after still don’t have valid residency documents. While they’re not technically in Portugal without authorization, leaving the country is a real risk. Not having valid documents also leads to fun things like having your bank account repeatedly frozen, being unable to renew your lease, and being unable to renew your driver’s license.
Other fun adventures in trying to follow the rules included Portugal creating a residence permit category for people with remote jobs abroad — including requiring a salary local Portuguese companies would never offer — and then having those people discover that Portuguese employment and tax law made it illegal for them to keep that job once they arrived. They are required to have a high paying foreign salary to renew their permit.
Ultimately, my journey through Canada and Portugal taught me that you cannot hack a sense of belonging. I spent my thirties treating the world like a game of strategy, believing that if I just mastered the mechanics of visas, tax treaties, and residency pathways, I could unlock a life of total freedom.
But there is a hidden tax on that freedom—one that isn’t paid in Euros or Dollars, but in cognitive load and moral exhaustion.
When you live between worlds, you are constantly in a state of “proving.” Proving you aren’t a tax evader to the CRA, proving you aren’t a scammer to the bank, and proving you aren’t a “shady” foreigner to a Portuguese website that refuses to load. You trade the mundane stability of being assumed to be an okay person by your home country for a lifetime of police checks and expiring affidavits.
If you are considering the move abroad, do not just look at the path to citizenship or the flight times to your parents. Ask yourself if you are prepared for the identity of the perpetual applicant. I don’t regret my choices—they gave me my wife, enhanced my career, and a view of the world I couldn’t have gained any other way. But it came at a high cost that I did not anticipate. When you’re living an international life, following the rules and your moral compass is not enough to avoid serious legal consequences.
Adventure is a joy. But there is a quiet, underrated dignity in living somewhere where the bank doesn’t lock your account just because you logged in from a different zip code. Before you move, make sure the freedom you’re chasing is worth the friction you’ll inevitably find.
Things would have been much easier if I had been a serial monogamist and severed ties with my former home each time I moved. However, that’s not very practical or desirable. The easiest thing would have been to never move in the first place and instead just traveled frequently. That, of course, wouldn’t have resulted in my becoming a naturalized Canadian citizen and I never would have met my wife.
While becoming a resident and untangling immigration, employment, and tax law is a huge hassle—particularly since they rarely line up within a country, nevermind when you’re a dual resident, and US citizens are always dual tax residents—being a proper digital nomad is also a huge hassle. Some countries will flag you (and possibly detain or penalize you) for following their rules for tourists to the letter. The US is suspicious of anyone who visits too often, even if you’re well within the rules. While the EU has permitted the Schengen Shuffle, the new border control system they’re rolling out suggests those days might be over.
