Starting My Journey: From ‘Where Do I Even Begin?’ to Finding Our Perfect Expat Destination

I’ll never forget sitting on our couch that Tuesday evening, scrolling through Instagram photos of pristine beaches and colorful colonial streets. My fiancé caught me daydreaming again and laughed, “You know what? Let’s actually do it. Let’s move abroad.” My heart raced with excitement, but then reality hit – where on earth do we even start?

The Reality Check That Changed Everything

At first, my grand plan was embarrassingly simple: find somewhere warm, preferably beachside, where our dollars would go further. Classic American thinking, right? But after joining a few expat Facebook groups and getting some tough love from seasoned nomads, I realized my “warm, cheap, and wifi-enabled paradise” checklist was about as useful as a chocolate teapot. These folks had been there, done that, and bought the overpriced tourist t-shirt.

The Questions That Actually Matter (Trust Me)

• Which countries actually welcome remote workers legally? (Plot twist: it’s a shorter list than you’d expect)
• Can we homeschool where we’re going? With two little ones, this felt non-negotiable at first
• Will the internet actually support Zoom calls, or will I sound like a robot from 1995?
• How much English can we get by with while we stumble through language lessons?
• What’s the real deal with visas – tourist hop or proper residency?

The Remote Work Reality No One Talks About

Here’s where my naivety really showed. I genuinely thought I could just plop down anywhere with my laptop and call it a day. Turns out, working remotely from another country is a legal gray area at best, and straight-up illegal at worst. Some places turn a blind eye (bless them), while others will show you the door faster than you can say “digital nomad.” This eye-opener immediately crossed half my dream destinations off the list.

When the Dominican Republic Started Calling

Then I met Sarah (not her real name) in an online forum. Eight years in the DR and still gushing about it like a newlywed. She painted this picture of morning coffee on her terrace, afternoon beach walks, and monthly expenses that made me double-check my math. “I save 40% compared to my old life in Ohio,” she wrote, “and I haven’t touched a snow shovel since 2016.” Now that’s a testimonial that speaks to my soul!

The School Debate That Surprised Me

I’d been dead set on homeschooling – seemed like the obvious choice for expat families, right? Wrong. A Brazilian mom in one of my groups dropped a bombshell: homeschooling is actually illegal in Brazil. But more importantly, she opened my eyes to something I hadn’t considered. “My kids learned Portuguese in six months just from playing with neighborhood kids,” she explained. “No textbook could have done that.” Suddenly, local schools didn’t seem so scary anymore.

Getting Real About What We Actually Need

Time to ditch the dreamy Pinterest boards and get practical. Here’s what really matters to our family:

• Safe neighborhoods where kids can actually be kids
• Local markets with fresh produce (goodbye, processed everything!)
• Internet that won’t make my clients think I’m calling from Mars
• A few English speakers nearby for those “I can’t remember how to say ‘plumber’ in Spanish” moments
• Clear legal pathways to work without constantly looking over our shoulders

The Mindset Shift That Changed the Game

Here’s the truth bomb that hit me hardest: expat life isn’t the easy way out. In fact, it’s often harder than staying put. One veteran expat put it perfectly: “If you’re running away from problems, they’ll just follow you with a different accent.” We’re not moving to escape life; we’re moving to embrace it – messy parts and all. It’s about collecting experiences, not just Instagram posts.

Our Game Plan (Because Winging It Only Goes So Far)

No more paralysis by analysis. Here’s how we’re moving forward:

• Deep-diving into country-specific expat forums (where the real tea gets spilled)
• Building a mega-spreadsheet of visa-friendly countries for remote workers
• Mapping out education options for each potential destination
• Getting real numbers on living costs (not just “it’s so cheap here!” anecdotes)
• Setting up video calls with expats who’ve been there at least two years

This journey has taught me that finding your perfect expat destination isn’t about picking a spot on the map – it’s about understanding what kind of life you want to build and being honest about what you’re willing to sacrifice to get it. Yes, the research feels overwhelming some days, but every spreadsheet cell filled and every expat story heard brings us one step closer to our own adventure. And honestly? The anticipation is half the fun.