Honestly, the phrase going out the country sounds so simple when you're just daydreaming over a cup of coffee. You pack a bag. You grab your passport. You leave. But if you’ve actually spent any time navigating the bureaucracy of a long-term exit or even a complex multi-country hop, you know it’s rarely that linear.
The logistics are a beast.
Most people focus on the flight prices. They obsess over whether they should visit Portugal or Mexico because of some viral TikTok. What they miss is the paperwork that actually keeps you there—or gets you kicked out. Travel has changed. In 2026, the digital infrastructure for border control is tighter than ever. You aren't just a tourist anymore; you're a data point in a global system of ETIAS checks, visa waivers, and tax residency triggers that can bite you if you stay one day too long.
The Residency Trap and the 183-Day Myth
Let’s talk about the biggest mistake people make when going out the country for an extended period: the tax trap. There is this persistent myth that if you aren't a "citizen" of a place, you don't owe them anything.
Wrong.
Most countries operate on a 183-day rule. If you spend more than half a year in a place like Spain or Thailand, they might consider you a tax resident. This means they want a cut of your global income. It doesn't matter if your company is based in New York or London.
I’ve seen people lose thousands because they didn't track their calendar. They thought they were just "slow traveling." Then the local government noticed their bank transfers or their long-term lease. Suddenly, they’re scrambling to prove they don't owe back taxes to a country they were just visiting. It’s messy. It’s expensive. And it's entirely avoidable if you actually read the bilateral tax treaties before you book that Airbnb for six months.
Passports are Not Created Equal
You’ve probably heard of the Henley Passport Index. It’s the gold standard for ranking how "powerful" your passport is. If you're holding a Japanese or Singaporean passport, you’re basically golden. You can glide through most borders with a shrug and a stamp.
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But if you’re going out the country with a passport that requires a pre-arranged visa for every stop, your planning phase needs to start six months out. Even US citizens are facing new hurdles. The European Union’s ETIAS (European Travel Information and Authorisation System) is now a full reality. It’s not a visa, technically, but it’s an extra layer of digital vetting. You can’t just show up at JFK and hope for the best anymore.
Why Your Expiration Date is a Lie
Here is a detail that trips up even seasoned travelers: the six-month rule.
Your passport might say it expires in December. If you try to leave for a trip in September, many countries won't let you in. Airlines will actually deny you boarding at the gate. Why? Because many nations require at least six months of validity beyond your date of departure. They don't want you getting stuck there with an expired ID. If you're planning on going out the country, check your date right now. If it’s got less than a year left, renew it. Don't gamble.
The Health Insurance Gap
Health insurance is boring until you’re in a private clinic in Bangkok trying to explain a kidney stone.
Your domestic insurance—whether it’s Blue Cross, Aetna, or the NHS—usually stops being effective the moment you cross the border. Some have "emergency coverage," but the reimbursement process is a nightmare of translated receipts and international wire fees.
For anyone going out the country for more than a week, you need travel medical insurance. There’s a difference between "travel insurance" (which covers lost bags) and "international health insurance" (which covers surgery).
- SafetyWing is popular for nomads because it operates on a subscription.
- Allianz is better for short-term vacationers who want a traditional policy.
- GeoBlue is the heavy hitter for expats who need full-scale coverage that mirrors what they had at home.
Don't be the person with a GoFundMe because you fell off a moped in Bali. It’s a cliché for a reason.
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Communication and the Death of the SIM Card
Remember when you had to find a kiosk in a dusty airport to buy a physical SIM card? Those days are dying.
eSIM technology has revolutionized going out the country. Apps like Airalo or Holafly allow you to download a data plan before you even land. You turn off your home SIM, toggle on the eSIM, and you have Google Maps the second the wheels touch the tarmac.
But there’s a catch.
eSIMs are usually data-only. You won't have a local phone number. If you need to receive a 2FA (two-factor authentication) code from your bank, you’re in trouble if your home SIM is inactive. I always recommend keeping a low-cost "legacy" line active or using a service like Google Voice to handle your texts while you're abroad. Losing access to your bank account because you can't receive an SMS is a specific kind of hell.
Money: The Hidden Costs of Exchange
When you’re going out the country, your bank is often your biggest enemy. Those "foreign transaction fees" (usually 3%) add up fast. On a $5,000 trip, you’re handing the bank $150 just for the privilege of spending your own money.
Use a Schwab High Yield Investor Account or a Wise (formerly TransferWise) card. Schwab refunds all ATM fees globally. It feels like a superpower when you see those $5 and $10 fees credited back to your account at the end of the month.
Also, never, ever let the ATM "do the conversion" for you. If a machine asks if you want to be charged in Dollars or the local currency (Euros, Yen, Pesos), always choose the local currency. The ATM's conversion rate is a scam. Let your own bank handle the math; they’ll give you a much better rate.
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Culture Shock is Real (and It’s Not Just About Food)
We talk about culture shock as if it’s just being surprised that people eat snails. It’s deeper. It’s the "bureaucracy shock."
In many parts of the world, things just take longer. If you’re going out the country to live, you will face the "Mañana" effect. Whether it's Italy, Greece, or Costa Rica, the frantic 24/7 efficiency of North America or Northern Europe doesn't exist.
You’ll wait three weeks for internet installation. You’ll find the grocery store closed for a random three-hour lunch break. If you fight it, you’ll be miserable. If you lean into it, you’ll actually start to enjoy the slower pace. That’s the real secret of successful international travel: adjusting your internal clock to match the destination.
The Practical Checklist for Your Exit
Forget the "pack light" advice. You know how to pack a suitcase. Focus on the digital and legal tethers that keep you tied to your home country.
- The Digital Mailbox: If you’re going to be gone for months, get a virtual mailbox like Anytime Mailbox. They scan your mail and send you a PDF. You can't manage a life going out the country if your physical bills are piling up on a porch somewhere.
- VPN (Virtual Private Network): Not just for Netflix. Many banking apps will lock you out if they see an IP address from a "high risk" country. A VPN allows you to look like you're still sitting in your living room.
- Power of Attorney: If you own property or have complex investments, give a trusted family member limited power of attorney. If something breaks or a document needs a physical signature, you don't want to have to fly back across the ocean for a thirty-second task.
- Local Laws: In Singapore, chewing gum is a thing. In Thailand, insulting the monarchy is a literal prison sentence. In Japan, certain common over-the-counter cold medicines (like those containing pseudoephedrine) are strictly prohibited. Do your homework.
Actionable Next Steps
If you are serious about going out the country, stop scrolling through Instagram and start doing the "unsexy" work.
- Audit your documents: Check your passport expiration and see if your destination requires a "Yellow Fever" card or specific vaccinations.
- Fix your banking: Open a Charles Schwab or Wise account today. It takes ten minutes and saves you hundreds.
- Test your tech: Download an eSIM app and verify your phone is "unlocked." If your phone is still on a payment plan with a carrier, they might have it locked to their network, making international SIMs useless.
- Map the tax implications: If you’re staying longer than 90 days anywhere, Google "Tax treaty between [My Country] and [Destination]."
Leaving is easy. Staying gone comfortably requires a level of intentionality that most travelers simply ignore until it's too late. Get the boring stuff right, and the adventure takes care of itself.