One Step Closer: Talk to Someone Who’s Already Living Your Dream
Narrowing down your ideal destinations? Blogs and YouTube videos are great, but you can't beat real conversations with people who are already where you want to be.
In this series, we’re exploring small steps you can take right now to support a fully location-independent lifestyle down the road. At some point in your journey, you’re bound to stop thinking, “I could live anywhere!” and start wondering, “Okay, but where do I actually want to spend my time?”
Maybe you have a list of ten potential destinations, or maybe you’re torn between two very different options. A vibrant city with a buzzing expat scene? A quiet coastal town with a lower cost of living? Somewhere with perfect weather year-round?
Or perhaps you fell in love with a place you vacationed and have convinced yourself it’s the perfect place to start an expat life.
You can spend hours scrolling through cost-of-living breakdowns and “Pros & Cons” videos (I’ve lost an awful lot of hours this way 😁). But nothing beats hearing directly from people already living in the places you’re considering, whether it’s for a month or a longer term stay.
Put on your journalist hat; we’re going snooping
Even if you’re years away from making a move, these conversations can help you refine your list, avoid common mistakes, and discover unexpected opportunities.
There are plenty of ways to explore destinations vicariously through expats and nomads:
Join local expat or digital nomad Facebook groups. Search for “[City/Country] Expats” or “[City/Country] Digital Nomads.” There’s a group for just about every destination.
Lurk first. Read through posts to see what people are actually talking about. Are they raving about the lifestyle or constantly venting about bureaucracy and bad internet?
Post a specific question. Instead of “What’s life like in Lisbon?” ask something more targeted, like:
“How hard is it to find long-term rentals under €1,500/month?”
“Is XYZ neighbourhood in Mexico City safe for Native Canadian solo female travelers?”
“How much of a language barrier should I expect as an English-speaker only in Chiang Mai?”
Message someone directly. If someone leaves an insightful comment, follow up with a polite DM. A simple “Hey, I saw your comment in the group—would you mind if I asked you a quick question about your experience?” can open the door to a helpful conversation. (Or they might have comments from strangers blocked; such is life. Don’t take it personally. Try someone else.)
Now, once you’ve familiarized yourself with the expat landscape, see if one of those people is willing to have a Zoom/Meets/Whatsapp coffee with you.
Consider the source
Not all expat/nomad experiences are the same. A retired couple enjoying leisurely mornings at a Lisbon café is going to have a very different perspective from a digital nomad juggling client calls across time zones or a family trying to navigate international schooling.
When seeking advice, try to find someone whose lifestyle aligns with the one you want to create. For starters, ask yourself:
Do they work remotely, or are they retired?
Are they single, partnered, or traveling with kids?
Do they live like a local, or are they in an expat bubble?
Does it seem we’re aligned financially, or are our lifestyles dramatically different?
You might decide these things don’t matter. But it’s important to be aware of these factors so you understand when their answers, despite being 100% valid for them, are not necessarily for you.
Key questions to ask
Not sure where to start? Once you connect with someone, here are some important things to ask:
Cost of Living
What’s one thing that’s way cheaper than expected?
What’s surprisingly expensive?
If you were on a tighter budget, could you still enjoy life here?
Safety & Inclusivity
Would you feel safe walking alone at night?
How welcoming is the city to LGBTQ+ travelers? (Even if you’re not, do you really want to be somewhere everyone isn’t treated well?)
Are locals friendly toward foreigners?
Have they had any healthcare experiences and how did that go?
Daily Life & Culture
How’s the food? Any must-try dishes? Any foods to avoid?
What’s something about daily life that surprised you?
Is it easy to make local friends, or do people mostly stick to expat circles?
Language & Communication
Can you get by with English, or is it frustrating?
How do locals feel about foreigners who don’t speak the language?
Is it easy to take language classes locally?
Visas & Bureaucracy
What’s one piece of red tape you wish you’d known about?
If you had to do it over again, would you still choose this visa path?
How hard is it to open a bank account or get a local SIM card?
And listen… if someone is willing to give you this time, I highly recommend sharing a warm fuzzy in return. Something useful, like an e-gift card for a book or a coffee shop in their region. If they have a Patreon or Substack, you could show your gratitude that way. Maybe they won’t expect anything from you at all, but it’s a nice thing to do. Maybe you’ll make a friend in your new destination before you even get there! Who knows.
Turn your assumptions into real insights
It’s easy to romanticize a place from afar, but the reality doesn’t always match the dream. I’ve seen people sell everything to move abroad, only to realize a few months in that they hate the food, can’t handle the climate, or struggle more than expected with the language. Others move on a whim and end up finding a deeper sense of home than they ever expected.
It was John C. Maxwell who said, “Disappointment is the gap that exists between expectation and reality.”
The more you talk to people who have been there, done that, the better prepared you’ll be; the more aligned with reality. So, take a few minutes this week to reach out, ask questions, and start turning vague ideas into real possibilities.
Where are you considering? Let me know—I’d love to hear what’s on your list.
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