Living & Working Remotely Abroad (Part 1): The guide to making it happen
“Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did.” — H. Jackson Brown Jr.
You’ve seen the Instagram posts in your feed: a digital nomad in Bali. Someone giving their apartment tour living in Paris. Laptop on a beach in Cartagena. It looks effortless.
It’s not… but damn it’s worth it if you can.
I haven’t been a digital nomad, but I’ve been fortunate to have done a few one-month stints abroad (and 5 months studying abroad, which doesn’t really count here). I’ve worked remotely from Argentina, spent a month in Medellín through Remote Year, and turned what was supposed to be a week in Mexico into a month-long stay.
Today I want to map out a framework for the journey to making this happen - because it seems intimidating but actually isn’t that bad. And it’s so rewarding.
This is about the logistics: deciding when and where and how, prepping for the move, handling the unsexy details. Nothing about actually being there yet - that’s Part 2.
I talked to two people who’ve done this: Steven Winkelstein, a long-term digital nomad who stays 1-3 months at a time (although announced last week that he’s settling back home in the US!), and Katie Van Deinse (full disclosure: my partner), who has done structured month-long remote work trips, plus close to a year-long US road trip. Katie, Steven, and I all met on the same remote work program in Colombia 😎
Their perspectives, plus mine, will guide you through this one.
But first, like many of these posts, I need to acknowledge that I know not everyone can do this. Job constraints, visa limitations (which a lot of my friends are feeling right now), financial realities, caretaking responsibilities - these are all legitimate barriers. This guide is for those who can make it work and are trying to figure out how.
1. “Is this even possible for me?”
Some companies explicitly allow international remote work. Others have a “don’t ask, don’t tell” approach. Some will fire you if they find out.
Permission vs. forgiveness: Some people ask. Some people just go. If you ask and get told no, you’ve closed a door. If you go without asking and get caught, you might get fired. Weigh the risk.
Types of jobs that work well: Jobs with flexible hours, project-based work, freelance/contract roles where output matters more than hours, situations with awesome + trusting managers.
Both Katie and Steven have that flexibility. I was fully transparent, and had some flexibility, but my past couple of roles when I’ve been traveling were not fully remote. I made sure to be in office when I was home in Austin, and made sure it didn’t impact the output of my work.
If you’re in back-to-back Zoom meetings 9-5 EST, this gets harder (but not impossible; more on time zones next).
2. “Where should I go?”
This isn’t about a pretty Instagram picture. You’re working there.
Steven’s criteria: “I look for places that feel exciting and affordable, and I really prefer somewhere walkable. I need my coffee shops, some LGBT+ community spots, a gym, and decent weather.”
Key factors:
Time zones (a critical question):
South/Central America: Easy (aligned with US)
Europe: Challenging
Asia: Very difficult, needs to be the right work setup
Katie’s experience: South America was easy. Europe meant “wake up in the morning and do all the exploring, then work from my hotel or a coffee shop starting at about 3pm until late. It was difficult some days but so worth it.”
Cost of living + infrastructure: Research rent (are you also paying rent or a mortgage on an empty place back in the US?), food costs, internet reliability, safety, healthcare access.
Steven’s Tulum lesson: “It was expensive, way too hot, and there was very little infrastructure. It just wasn’t easy to live there day-to-day.”
Beauty doesn’t mean livability, and for more than a week that really matters.
For me, the three individual months I’ve spend working abroad all had common themes: US-friendly time zones, relatively affordable with US dollars, and good weather. Spanish-speaking was a bonus, so I could practice!
3. “How do I legally do this?”
Disclaimer: This isn’t legal/tax advice. Do your research.
Most digital nomads work on tourist visas (90 days in most places). Technically, many countries don’t allow remote work on tourist visas - this is a gray area with varying enforcement.
Your options:
Tourist visa: Easiest, usually 90 days in 180-day period
Digital nomad visas: Portugal, Spain, Mexico, etc. Legal for 6 months-2 years, but require applications, fees, income proof
Visa runs: Leave before 90 days, re-enter on fresh visa (some countries frown on this)
Taxes: US citizens pay US taxes regardless. Some countries tax based on 183+ days physical presence. If doing short stints (1-3 months), tourist visas are probably fine. Longer? Talk to a tax pro.
4. “Where will I live and work?”
Steven’s approach: “Mostly Airbnb. If I want to travel with other people, I’ll use programs like Nomad Nest or WiFi Tribe.”
Options: Airbnb (easy, flexible, but sometimes frowned upon by locals), coliving programs (built-in community), Facebook groups. And don’t sleep on local rental sites!
What to look for: Dedicated workspace, reliable WiFi, kitchen, walkable location, safety. Yummy food nearby is always a plus 😉
Length of stay: Steven does 1-3 months. Katie never longer than a month. Find your sweet spot.
When to book: 3-4 weeks advance for popular cities, 1-2 weeks for others.
Where will you work?
Steven: “Get a good coworking space, or find a quiet coffee shop with solid internet.”
My advice? Do your research on peer sources like Reddit, and then test spots in your first week.
A disclaimer with Airbnb: certain cities have been negatively affected by digital nomads and the pandemic. Here’s an example that dives into this. Airbnb is a big contributor to housing crises (rising rents, fewer long-term rentals), the loss of community feel, neighborhood disruption (noise, parties) from tourists treating homes like hotels, reduced tax revenue for cities, and a shift from genuine local interactions to commercialized tourism. As much as I love to travel, I’m hypersensitive to this conundrum. When traveling in general, but especially for longer-term, I encourage you to read this article on being a responsible traveler.
5. “What about money and insurance?”
Banking: Get a credit card with no foreign transaction fees. Use Wise/Revolut for better exchange rates. Withdraw larger amounts less frequently from ATMs.
Budget reality: You’ll spend more than expected on eating out, experiences, transportation.
Health insurance: Steven noted “I use Allianz travel insurance, which includes health coverage. And yes, I’ve used it abroad - mostly for respiratory infections.”
Options: Travel insurance (~$50-150/month - Allianz, World Nomads, or Genki who I’ve used and was very easy) or international health insurance (SafetyWing, more comprehensive/expensive).
Do NOT skip this if you’re going for more than a week or two. Medical evacuation costs $50k+ and things happen.
Last pro tip here: schedule any relevant doctors appointment and prescription refills before you go!
6. “What do I actually need to bring/set up?”
I’m not going to regurgitate obvious packing items. Plus, eventually I’ll do a dedicated post for packing hacks. But here are a few packing thoughts and a gameplan leading up to it:
Steven: “Pack as little as possible - you can find what you need as you go.”
Katie’s must-haves:
Portable phone charger
Fanny pack with back pocket for wallet/passport
Snacks - you’ll discover some there but it’s always nice having your favorites from home! (my favorite bar are the S’Mores One Bars)
Pre-departure checklist:
As soon as you know: Book flights/housing, check passport expiration (needs 6 months validity from when you return home)
1-2 weeks before: Set up insurance, download offline maps (very underrated), VPN if needed, refill prescriptions
7. “I’m ready. Now what?”
Mental prep: The first 48 hours will be exhausting. Don’t work a full day immediately, if you can. Sleep, find the grocery store, and walk the neighborhood.
Your first step based on where you are:
Just thinking: Research 2-3 destinations, price out a month
Ready to pull the trigger: Talk to manager or plan quietly, book housing/flights
1 week out: Pack, confirm everything, download maps, get excited
Quick decision tree based on length of stay:
Going for 2-4 weeks: Pick somewhere easy (English-speaking, similar time zone, good internet connectivity). Keep it simple - you’re dipping your toes in, not committing long-term. Airbnb and coworking day passes are your friends.
Going for 1-2 months: This is the sweet spot for testing remote work abroad. You have time to settle in. Research infrastructure (coworking spaces, neighborhoods), check monthly Airbnb discounts, consider time zones more carefully. Join coliving programs or local Facebook groups for community. Budget for the long haul.
Going for 3+ months: Look into digital nomad visas for legal peace of mind. Consider multiple cities/countries if on tourist visas (90-day limits).
If you’re still reading…
As my mom always asks, “how do you eat an elephant?”
“One bite at a time”
Making this happen is less about being brave and more about being organized (but yes, it’s also about being brave).
Steven: “YOLO. Follow your bliss. This is your life - it’s not a dress rehearsal.”
Katie: “DO IT!!!! Prepare as much as possible... You’re never going to ‘feel ready’ to do something like this. It can be scary and take a lot of prep, but it’s so worth it!”
You don’t need to quit your job. You don’t need to sell everything. Start with a month (or a week). See how it feels.
I won’t give the usual ‘travel changes your life’ spiel - by now you get it. As it relates to a stint abroad… if you can do it, you might find it’s not for you but I can almost guarantee you won’t regret it.
Part 2 coming soon: what happens once you land. How to balance work with actually experiencing the place, building community in a month, the parts that suck, and making it all worth it.
