Thinking About Living Abroad? 8 Questions to Ask Before You Make the Move

After more than 20 years of travel, Charles and I have spent a lot more time outside Canada than the average vacation allows.

We spent about five months in Australia, months at a time in other countries, and long enough in places like Spain, Portugal and Costa Rica to settle into some pretty ordinary routines.

We’ve rented apartments, bought groceries, worked from kitchen tables, figured out public transportation, hunted down laundromats, and occasionally spent far too long trying to find something completely mundane.

We’ve never permanently moved abroad, though, and I think that distinction matters.

What those longer stays have given us is a pretty good sense of the questions we’d want answered before we ever did.

Because liking somewhere on vacation and wanting to build your everyday life there are two very different things.

Once you start thinking seriously about living abroad, the questions change. Suddenly it’s less about beaches, restaurants and what you can see in a week, and more about rent, visas, healthcare, work, groceries, transportation and whether you’d actually enjoy an ordinary Tuesday there.

If living abroad has been rattling around in the back of your mind, these are some of the things we’d think about first.

1. Can You Legally Live There?

This one isn’t nearly as fun as browsing apartment listings, but it probably needs to come first.

Before you fall too hard for a destination, figure out what actually gives you the right to live there long term.

That might depend on your citizenship, employment, income, retirement status, family connections, education or relationship status.

Some countries have digital nomad visas. Others have retirement programs, work permits, investor routes or ancestry-based residency options.

And sometimes your relationship determines which route you need to explore. In the UK, for example, someone joining a qualifying partner may need to look into a civil partnership visa as part of planning a longer-term move.

The key is to figure this out before making major plans.

Visa rules can change, requirements can be more complicated than they first appear, and being allowed to visit somewhere doesn’t automatically mean you can live or work there.

2. Can You Afford Everyday Life There?

A place that feels inexpensive on vacation isn’t necessarily cheap to live in.

When we travel, our spending looks very different from normal life. We might pay more for a short-term rental because it’s convenient. We eat out more. We don’t have utility bills, local insurance, furniture expenses or a year-long lease.

Living somewhere means looking at the whole picture.

That can include:

• Long-term rent
• Electricity and other utilities
• Internet and mobile service
• Groceries
• Transportation
• Healthcare or insurance
• Taxes
• Banking fees
• Visa and residency costs

Currency fluctuations matter too.

A destination that looks inexpensive when your home currency is strong can feel very different a couple of years later.

Before deciding somewhere is affordable, we’d want to know what a realistic monthly budget actually looks like.

3. How Would You Actually Earn Money?

This is a big one for us because working while traveling has been part of our lives for years.

Having an online business has given us a lot of flexibility, but working abroad still isn’t as simple as opening a laptop somewhere sunny.

There are practical questions.

Is remote work permitted under your visa? What happens with taxes? Can you reliably get fast internet? Are your clients awake when you are?

Time zones can be surprisingly disruptive. Working from Europe while most of your clients are in North America can mean late afternoons and evenings. Working from Asia can flip your schedule even more dramatically.

If you plan to find a local job, there’s another set of questions.

What are salaries like? Is your profession in demand? Do you need local qualifications? Are you legally allowed to work? The dream version of moving abroad tends to focus on location.

The practical version needs to include income.

4. What Would Healthcare Look Like?

Healthcare barely crosses our minds when we’re planning a short trip unless we need travel insurance or have a specific medical concern.

It becomes a much bigger consideration if you’re thinking about living somewhere.

Some countries allow residents to access public healthcare fairly quickly. Others require private insurance, have waiting periods or offer different levels of access depending on your immigration status.

If you take regular medication, you’ll also want to know whether it’s available locally and what it costs.

And if you’re moving with children, healthcare becomes an even bigger part of the equation.

You don’t need to understand every detail before you start dreaming about living abroad, but you should have a reasonable idea of how healthcare would actually work before you pack everything you own.

5. Where Would You Actually Want to Live?

There’s a big difference between the best neighborhood for a vacation and the best neighborhood for everyday life.

We’ve noticed this again and again during longer stays.

When you’re somewhere for a week, you might want to be right beside the main attractions.

Stay for a few months and suddenly you care a lot more about whether there’s a grocery store nearby.

You start noticing things like:

• Walkability
• Public transportation
• Traffic
• Noise
• Grocery stores
• Healthcare
• Internet reliability
• Weather
• Airport access

Sometimes the neighborhood tourists rarely visit ends up being the place that makes the most sense.

It’s also worth thinking about climate differently.

Loving a destination in March doesn’t necessarily tell you what July or January feels like.

Before committing to somewhere long term, we’d want to experience more than its best season.

6. How Far From Home Are You Willing to Be?

Distance feels different when you’re planning a vacation.

A long flight can seem perfectly reasonable when you’re going somewhere exciting for two weeks.

It feels different when you start imagining doing that trip several times a year.

• How easy would it be to visit family?
• Could people realistically come visit you?
• How expensive are flights?
• How many connections would you need?

Time zones matter here too.

Living six or nine hours ahead of your family changes when you can casually call someone.

There’s no right answer to any of this. Some people love being far away. Others discover that being able to get home quickly matters more than they expected.

It’s just something worth thinking about before distance becomes part of everyday life.

7. Have You Seen the Everyday Version of the Place?

This might be the biggest lesson we’ve learned from spending months at a time abroad.

There’s tremendous value in staying somewhere long enough to get bored.

• Go grocery shopping.
• Do laundry.
• Cook dinner.
• Work for a week.
• Figure out the bus.

Spend a Tuesday afternoon doing absolutely nothing interesting.

That’s when you start discovering whether you genuinely like being somewhere or whether you mostly liked being on vacation there.

We recently did a similar thought experiment by comparing Portugal, Spain, Costa Rica and Panama as places we could potentially live.

What stood out to us was how quickly the answer changes once you stop thinking about attractions and start considering ordinary life.

Could we get around easily? Would we like the climate year-round? Would the pace of life suit us? Could we comfortably work there?

Those questions tell you something a list of top attractions never will.

8. Could You Try Living There Before You Move?

If immigration rules allow it, this is probably what we’d do.

Spend several weeks or months there before committing to anything permanent.

And try to make that stay resemble real life.

Rent something similar to what you could actually afford long term.

Cook. Work. Take public transportation. Shop at local grocery stores. Don’t spend every day sightseeing.

Our own longer stays haven’t been formal relocation tests, but they’ve taught us a lot about the difference between visiting a country and settling into it.

You start noticing completely different things once the novelty fades.

Sometimes that makes you love a place even more. Sometimes it does the opposite. Either way, that’s useful information.

The Logistics Have a Way of Catching Up With the Dream

There’s usually a pretty big gap between imagining life abroad and actually figuring out how to make it happen.

A Reuters report on Americans considering moves overseas highlighted some of the same practical hurdles, including employment, remote work restrictions, salaries, taxes and visa requirements.

Those aren’t particularly romantic topics. They’re also exactly the kinds of things that determine whether moving abroad works.

Research doesn’t ruin the dream. It helps you figure out whether the dream can actually become a life.

So, Could You Actually Live There?

After more than 20 years of travel, Charles and I still ask ourselves this question.

Could we live here?

Sometimes the answer feels like an immediate yes.

Sometimes it’s probably not.

And sometimes a place is wonderful precisely because we get to visit it rather than make it home.

We’ve never permanently moved abroad, so we won’t pretend to have every answer about what that process is really like.

But spending months at a time living and working in other countries has shown us just how different everyday life can be from the vacation version.

If you’re seriously considering living abroad, start with the boring questions.

Figure out whether you can legally stay. Look at how you’d support yourself. Understand what everyday life would cost and how healthcare works.

Then, if you can, spend some real time there.

The best way to find out whether you could live somewhere might be to stop treating it like a vacation for a little while.