Expat Journey: Know Before You Go

Research alone won't fully prepare you. Embrace the adventure, but also make sure to tick off all the boxes.

Have you ever thought about buying a one-way ticket and moving somewhere new and exciting?

I've done that - six times by now.

In this first part of my “Expat Journey” series, we’ll look into why research alone won’t tell you if a country is a good fit for you.

I’m unsure if evaluating a country gets better or worse with every move.

You’ll either be super confident with so much experience that you can live in any country or overly cautious and spend years researching every little detail.

I’ve learned that research is only a tiny part of the process. You can spend months diving into every little detail only to be surprised by some puzzle piece you missed once you arrive.

Maybe you ignored an early red flag that, after a couple of weeks, is so annoying that you can’t tolerate it anymore.

Before moving to Cyprus, we spent months researching all sorts of details: costs, lifestyle, weather, groceries, etc.

One of the things we missed was the tourist destination vibe that Cyprus brings.

I don’t mean this in a nice way.

There are large hotels everywhere, attracting tons of cheap, all-inclusive tourists who come to get a tan. However, what looked great on the postcard wasn't so good on the ground. This can be nice on a holiday, but trust me, you don’t want to live amidst a constantly changing crew of tourists.

It's hard to figure this all out upfront.

Say you did a short trip there and spent a week or two on the ground.

For us, these first weeks often feel like a little holiday. Maybe you had a nice Airbnb, the weather was great, and you just got a good vibe that empowered your decision.

Settling in can change that perspective. Once you get back to work and into the day-to-day grind of life, things become obvious that you wouldn't have spotted during a short trip.

Our Naive Settling into Cyprus

Let’s have a look at our move to Cyprus. We only stayed for about five months, which kind of says it all.

At the time, we had very young kids and were somewhat financially motivated to leave Australia.

We packed up after a ton of research and just left to check it out.

Waiting another year and going for a visit first wasn’t an option, so we decided to go.

Naive, you might think, and yes, I agree. For our circumstances at that time, however, it felt like the best way forward.

When we arrived, it was all new and exciting, and we wanted to explore; we had a family visit early on, the weather was nice, and I got some rare surfable waves.

Everyone was happy.

Four weeks later, it was a very different picture.

We discovered all these little annoying things:

• Low trust culture: The most basic example is that markets have no price signs. Everything is haggling. The general transparency is low; you need personal connections and bribes to get through the fraud.

• Touristiness: Who wouldn't want to live in a place others go on holiday to? It depends on where you live. All the nice places near the beach were close to big, all-inclusive hotels. So close you could hear the music of the daily evening entertainment program.

• Food & Groceries: On an island, not much is available. On top of that, if tourists come for the weather, the incentive for good food isn't that high. I remember looking forward to the Greek/Cypriot cuisine. On the ground, it was underwhelming.

• Bureaucracy: Everything needed a bribe or some paid agent that takes you somewhere to get you through the process. If you don’t want to cue up for hours on your residency permit, pay an agent who then bribes the officer.

I’ve talked about the whole journey here on the

The Covered Call Podcast

.

The critical lesson? Despite careful planning, a fair bit of luck was involved in our previous successful moves. Luck that ran out in Cyprus.

You can’t know everything upfront, and sometimes you just have to accept uncertainty as part of the adventure.

If you’re thinking of moving abroad, yes—research thoroughly.

But understand clearly that no matter how prepared you feel, surprises await.

Define your non-negotiables, be mentally flexible, and accept that some lessons only emerge from experience itself.

Have an exit strategy ready if you need to.

We left after just five months and were glad that we hadn’t anchored ourselves too much to living in Cyprus at that point.

We didn’t buy anything fancy, rented a cheap place and were financially flexible to pack up and go thanks to:

What to look out for

In general, here are things I look out for:

1. Purpose of the Move: Understanding your primary motivation will guide other decisions.

2. Legal Requirements: Visa and work permits, what will your passport get you.

3. Financial Considerations: Cost of living, income and employment as well as taxes play a role here.

4. Healthcare: Quality, access and insurance (citizens often have different policies.

5. Cultural and Social Factors: Language, cultural differences (such as a low trust culture) or availability of expat communities.

6. Education: How will your kids go to school.

7. Safety and Security: Crime rate, political stability.

8. Infrastructure: Transportation (public/private), Utilities, proximity to Airports.

9. Climate and Environment: Weather, temperature year round.

10. Legal and Bureaucratic Environment: How easy is it to get registered, start a business etc.