The Rule-Follower’s Guide to Failing at Immigration: When life hacking doesn’t work

The Rule-Follower’s Guide to Failing at Immigration: When life hacking doesn’t work

I moved to Toronto and Lisbon thinking the world was a board game I could win by simply learning the rules. I wanted flexibility, adventure, and a ‘fresh start’—but I didn’t account for the soul-crushing friction of being a perpetual applicant. From Kafkaesque tax audits in Canada to the chaotic residency systems in Portugal, this is why the ‘optimized’ expat life is often a trap of high-level anxiety, and why the easiest move you can make is the one where you stay put.

Visiting Ilha das Flores in the off-season

Visiting Ilha das Flores in the off-season

It baffles me that people don’t visit Flores in the winter. In fact, all of the places in the Açores that are mobbed with tourists in the summer are empty in the winter. This, despite the fact that the temperatures are in the low 50s to mid 60s (10 to 19...
How I travel full-time without losing my mind

How I travel full-time without losing my mind

Traveling full-time is one of those things that seems very complicated and mysterious because we don’t have realistic examples of how it works. In reality, it’s not necessarily more or less complicated than living in one place. When I’m feeling...
How to move to Portugal as a remote worker

How to move to Portugal as a remote worker

It seems like everyone is talking about moving to Portugal. Is it inflation? Rising mortgage rates? The continued chaos of US politics? The media coverage planting seeds in our minds? For me, it was two years of various stages of lockdown in Canada. The winter weather...
It’s a real hassle to move to Canada

It’s a real hassle to move to Canada

Far more people talk about moving to Canada than actually make the move. This is true, despite the high likelihood that there’s a way for many Americans to legally move to Canada. If you have a US passport, you could probably be living in Canada a few weeks from...
I probably spend less on travel than you do

I probably spend less on travel than you do

In The Sum of Small Things: A Theory of the Aspirational Class, Elizabeth Currid-Halkett quotes an elite travel agency saying that the normal traveler spends $10k a year. I was pretty sure that their idea of a normal traveler is a skewed. I was also certain I spent...
That thing I packed and never used

That thing I packed and never used

Somehow, no matter how much I travel and how light I pack, I always end up with something I never ended up using. Often, the item that’s indispensable on one trip ends up being totally unnecessary on another. Other times it’s a product of hope — the...
Adjusting to life at home after traveling

Adjusting to life at home after traveling

It’s no secret that it’s a challenge to adjust to life in another country or life on the road. However, many people assume they’ll be able to pick up right where they left off when they return home. Nope. It can be just as challenging to get back...
Quarantine reads to embrace staying home

Quarantine reads to embrace staying home

People are eagerly sharing tips on how to “travel without leaving home.” What about accepting where we are? Is travel about finding the “exotic” or is it a way of seeing the world? As Jonathan Franzen reminds us, “The first lesson reading...
Staying home when going home isn’t an option

Staying home when going home isn’t an option

The news is listing off a daily COVID-19 death toll. The world has shut down to prevent the spread of SARS-CoV-2. Everyone is frantically learning to adapt to working from home, homeschooling kids, living without cleaners, personal care assistants, and someone else to...
Who I am in the beds of strangers

Who I am in the beds of strangers

I have stayed in a lot of different homes. I spent three years subletting apartments in Prospect and Crown Heights, Brooklyn in an era before AirBnB. I have stayed in well over 100 homes through CouchSurfing and the personal networks that have sprouted up through the...
Washington DC: A digital nomad’s guide

Washington DC: A digital nomad’s guide

Sure, any tourist knows what to see for a weekend in DC. But what about those of us who aren’t just any tourist? As a nomad we have time to explore, but we’re there for a lot longer than the typical tourist. While I’m free to spend an afternoon in a...
How to retire in Canada

How to retire in Canada

By Rachel Hartman IF YOU’RE INTERESTED IN heading north for retirement, it’s important to think through the implications the decision can bring. “Many Americans assume that moving to Canada is easy and that there’s a special pathway for Americans, since our two...