Reasons to Expatriate… Even Just for a Little While

To expatriate is to choose a life of flexibility and freedom that maximizes the professional, tax, and cultural opportunities offered around the world.

February 6, 2023

B​y: Bobby Casey, Managing Director GWP

T​he world has become a smaller place because of common-man accessibility to any place on it. Can we take a moment and just appreciate that nearly anyone can just buy a ticket to jump on a plane? A luxury once only reserved for the affluent.

E​very new thing started off as something only the rich could have though. Plumbing was like that. Computers were like that. Cellular phones were like that. So was travel. Now, here we are with all sorts of ways to travel the world, one continent, one country, one province… whatever the scope.

I​ think expatriation and the nomad lifestyle is starting to coming into this space now where it’s no longer just retirees and independently wealthy celebrities. The average person can really have this for themselves.

T​here are plenty of advantages to expatriation and the nomad lifestyle.

Professional Opportunities

T​he overall work environment has become more globalized. The days of everything being born, cultivated, made, and sold in one place are done. In the past, companies were restricted to whomever was proximate to their offices as their only talent pool. You would see hubs crop up in large metropolitan areas like Los Angeles, Tokyo, and London.

Naturally, people flocked to those cities because that’s where the hubs were. There was prestige associated with having an office in these cities, there was some job security in that if one company laid off, another was hiring.

Property prices followed the demand, and soon the companies that were growing were in places that had sprawl out as far as two hours.

I​t’s like the pandemic just took a cue ball to that whole cluster and broke it all up.

N​ow, the brain trust can spread out across provinces, countries, and continents. Companies are looking for people with a fresh point of view, a different approach to work streams, different insights. Even if you aren’t an entrepreneur or contractor, you have new opportunities in other countries to bring your inherent expertise to another country!

I​f you are coming in from Asia or Latin America, those are markets many companies in Europe are trying to break into and understand. If you are coming from Europe or the US, there are companies in Latin America and Asia who would love the inside scoop on those markets.

Even if you are just fresh out of university, getting experience working in different countries is a great way to build your curriculum vitae (CV). Think of it as a study abroad program, only instead of a student of university, you’re now a student of life, building work experience in the process.

T​he robust experience and diversity is a massive selling point for anyone either looking to enter a career or start a business.

Improvement in lifestyle and affordability

Needless to say, if you’re coming from a place like Norway or a city like New York, it’s not difficult to point anywhere and find a cheaper cost of living.

I​f you can just make a lateral move on your salary, and then move somewhere where your cost of living is a fraction of what it currently is, you’re putting money way, investing, and living a more comfortable and financially secure life with very little compromise to the lifestyle you’re accustomed to.

We’ve discussed the tax benefits involved in expatriation from some countries, especially from the US. If you play your cards right, you can keep all the creature comforts, and just not pay as much for them.

I​f you’re coming from a less costly market, you could very well tap into a higher earning potential through expatriation. There are affluent markets to be tapped that would be happy to share that wealth to anyone bringing a worthwhile idea or skill set.

W​e all stand to win here. The brain trust isn’t dependent on the supply chain as physical goods are. The more we can share ideas across borders the better off all of humanity is. The free exchange of ideas, the diversity of thought, those are things are under heavy attack. Breaking out of those stagnant pools of large juggernaut domestic tanks is the future.

M​ore and more, the decided winner will be the willow over the oak. If you can adjust and move with where life is taking you, the better off you’ll be, the greater the opportunities and potential gains.

Between the potential financial gains, tax benefits, and quality of life enhancements, that alone is worthy of investigation if not pursuit.


T​here are so many aspects of culture to enjoy and you’re not meant to like it all. That’s totally fine. I think some people are discouraged by aspects of culture they wouldn’t like, and think that’s unto itself a deal-breaker. It really isn’t.

I know someone who lived in Japan. She loved so many aspects of the culture while understanding there were parts she could do without. The trains, the food, the ease with which she could navigate the cities was all fantastic. The people were great, the cities were clean, the customer service everywhere was far better than anything she knew in the United States.

S​he made some great friends, learned a lot about herself and others, and had some fantastic memories she’d never trade away.

T​he whole point of the expat and nomad life is to break away from the sense of permanence or obligation to one place. If you find a spot on the map that is ideal for you, stay! If you find places that have their charms, but they wear thin after a while, leave!

I​n the meantime, you’ll have an enriching experience meeting different people from different walks of life, maybe pick up a few new languages, try foods you never knew could be as good as they are.

A​voiding the Downsides

Good planning and preparation goes a long way in avoiding pitfalls.

  • Getting all the paperwork you need for your visas in advance prevents any sort of misunderstandings when getting your application sorted out. Have a solid checklist and get all the information and documentation you need up front.

  • Doing the research on the tax agreements between your country and your desired destination to avoid double-taxation; as well as researching what steps you can take to have the most tax-advantage experience abroad. Consult a good offshore tax professional who works with expats and knows the ropes.

  • G​et involved in some expat communities and discussion boards to get the lay of the land in your country and city of choice. Nothing like a firsthand account of what it is like for an expat in those places just to ground your cultural expectations and even tap into some local resources.

  • Consider learning some basics of the local language. You’ll pick up more as you go out there and immerse yourself in it, but a good faith effort goes a long way culturally.

Like I said, I’ve been an entrepreneur my whole life. I don’t have “crappy boss” stories or “corporate culture” nightmares. I have a bachelors and MBA, but honestly, the stuff that has always lead to success were the things I learned along the way, not the stuff I got from a classroom. As an entrepreneur I didn’t really need those degrees to qualify for my work. I needed real world experience in the fields I got into.

I met someone through Fiverr who was 19 years old. I asked what his qualifications were. He said he didn’t think college was for him, so he decided to take an online certification course to learn how to place ads on social media and Google.

T​hat kid was 19. He was netting $50k per year after fees and taxes, roughly. Whenever we spoke, he was in a different location. This is him at an entry level on Fiverr. He has no reason to believe that a degree and a fixed employment gig with one company will yield something better for him than this.

And he would be absolutely right!

Every time I touched base with him, he was on his way to somewhere, or in a different city. He’s probably of legal drinking age now, and has over 5 years work experience with nothing more than a couple hundred dollars in online coursework and a work ethic. The world is his. He can get an RV and just drive around. He can get a passport and fly all over. He works on a diverse range of business… and he’s probably charging much more now for his hours than when he was starting out.

Like I said, this life isn’t just for retirees and the wealthy. It’s for young people who don’t want to take the traditional path their elders laid before them. It’s for people in the middle of their careers who want more from life than what they’ve got. It’s for families who want to raise their kids in something better than their local public schools. AND it’s for retirees who want their pensions to go further as well as the wealthy who never needed to be told they could travel.

Sometimes we need to give ourselves permission to just opt out. Consider the sunk costs as the price of the lesson you learned.

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