Where Are You Moving To?

You’ve made it to the point of almost no return. You’re ready to move abroad but you haven’t completely chosen where. Why not? Because you don’t know what life will actually feel like when you’re there on a rainy Tuesday with a sick kid, a broken washing machine, and a homesick heart. If you’re in the “mid-pivot” phase, a.k.a. past dreaming but not yet settled, narrowing down where to go is often the decision that keeps you stuck the longest.

So instead of asking, “Where would be amazing to live?” try the more useful question:

“Where would be sustainable for the life I actually have?”

Start with constraints. Constraints are clarifying, while fantasies are paralyzing. Your visa options, budget, work situation, family needs, language ability, and tolerance for bureaucracy will eliminate far more places than Instagram ever will.

Visa pathways alone can shrink your map overnight. Portugal, for example, looks idyllic from afar because of its mild climate, beautiful coastline, and relative affordability compared to much of Western Europe, but staying long-term requires navigating specific visa routes. Remote workers might qualify for Portugal’s digital nomad pathway, while others rely on passive-income visas or local employment. Many people fall in love with the idea of living in Lisbon or the Algarve before confirming whether they can legally stay beyond 90 days.

Next, anchor your decision in money. Not just the cost of living, but cash flow stability. Portugal is often labeled “cheap,” but that depends heavily on where you land. Housing costs in metro areas have risen sharply, deposits can be high, and local salaries are generally lower than in the U.S. A place that is affordable on paper can still feel financially tight if income doesn’t translate smoothly. Ask yourself: Could we handle six months of surprises here? Because there will be surprises.

Healthcare deserves its own line item. Portugal’s public healthcare system is widely respected and far less expensive than in the United States, but access can involve wait times, language barriers, or the need for supplemental private insurance, especially early in residency. If you have children or ongoing medical needs, understanding how you’ll navigate appointments, prescriptions, and emergencies matters more than whether the country ranks highly on quality-of-life lists.

Then consider education, even if you don’t have school-aged kids yet. International schools offer English-language instruction and familiar curricula but can cost tens of thousands per year and often have waiting lists. This single decision will shape your daily routine, finances, and community.

After the logistical filters, shift to lifestyle alignment, and remember that “best lifestyle” is not the same as a compatible lifestyle, which is much more important. 

Ask practical questions:

• Do you need a car, or is public transit reliable? (Example: Lisbon’s transit is strong. You’ll need a car if you’re not in the city center, a mistake we made when moving.)

• How important is walkability?

• Do you thrive in dense urban energy or need physical space?

• How much sun do you realistically need for your mental health? (Example: Portugal has long sunny stretches, but winters can be gray, damp, and surprisingly cold indoors due to limited insulation.)

• Are you comfortable being visibly foreign every day? In many Portuguese towns, you may stand out for a long time.
  

Climate, in particular, is often underestimated. The Algarve’s beaches are stunning, but summer crowds can be intense and winters quiet. Northern Portugal and Porto are more lush and green and much rainier. Your nervous system lives there, not your vacation self.

Language is another pivot point. Many Portuguese people speak English, especially in cities, which makes daily life easier at first. You’ll cruise through a recon trip on English. But full integration, such as dealing with government offices, healthcare paperwork, and school communication, often requires at least basic Portuguese. Living somewhere where you cannot communicate independently creates a constant low-grade stress. Some people find this invigorating. Most find it exhausting.

Community is harder to quantify but just as critical. Portugal has sizable international communities, particularly in Lisbon, Porto, and parts of the Algarve. This can ease the transition but can also create a bubble if you never connect locally. Isolation is one of the most common reasons moves falter, even more than finances and paperwork.

At this stage, it helps to shift from endless research of locations to a shortlist of three. Not “everywhere that seems nice,” but three places you could realistically see yourself living for at least two years. For example: Lisbon for urban life, Porto for a smaller city feel, and a coastal town for slower living. Different regions within the same country can feel like entirely different worlds.

For each location, run a “Tuesday Test.” Imagine an ordinary day:

You wake up. Are you in a compact Lisbon apartment or a house outside the city?
Do you get groceries by walking to a neighborhood market or driving to a hypermarket?
What language are you speaking most of the day?
Where do your kids go during the day?
What happens if you need urgent medical care?
Who do you text when something goes wrong?

If you can’t picture the mundane details, you don’t know the place well enough yet.

Whenever possible, do a reconnaissance trip that mimics real life rather than tourism. In Portugal, that might mean staying in a residential neighborhood instead of the historic center, riding buses or trains during rush hour, visiting local supermarkets, pharmacies, and parks. Try something mildly inconvenient, like getting a sim card for your phone or asking about school enrollment. Test drive the bureaucracy you’ll eventually face.

Finally, remember that no choice will eliminate uncertainty. Every location involves trade-offs. Portugal offers safety, beauty, and a slower pace of life, but also lower salaries, administrative complexity, and housing pressure in popular areas. You will not find the perfect place, so find a place where the trade-offs feel worth it to you.

If you’re stuck right now, here’s an actionable step you can take today:

Create a “Non-Negotiables List” of five items your future home must have. Examples might include:

• Legal residency pathway within one year
  

• Access to affordable healthcare
  

• Walkability or strong public transit
  

• English-friendly services (or your target language)
  

• Specific climate needs
  

• Proximity to an airport with direct flights home (Lisbon’s airport, for instance, offers many transatlantic routes but no direct flights back to Atlanta, where we moved from.)

Anything that doesn’t meet all five drops off the list immediately.

Decision-making becomes dramatically easier when you stop trying to maximize happiness and start minimizing regret.

Moving abroad will not be choosing the most extraordinary place on Earth, but choosing a place where you can build routines, relationships, and a sense of belonging over time.

And perhaps the most comforting truth in the mid-pivot phase: your first choice does not have to be your forever choice. Many successful expats didn’t land in their ideal country first. They moved, learned what mattered most to them, and adjusted.

Maybe you can break the cycle and get it right the first time.

Until next time,

Benn (+ Melissa)

“How To Move Abroad and Not Torch Your Income” Early Bird Pricing

Did you attend the Lightning Lesson last month about keeping your income during your move abroad? Melissa is about to launch the full Maven course in March on just this.

Six weeks, live, done-with-you, real numbers, real frameworks, real intel.

She’s also offering a discount for the first session. Interested? Reach out!