I'll be honest with you — the first time I seriously considered working while traveling, I thought I was being delusional.
I had a laptop, a semi-stable freelance income, and a lot of unused vacation days that I never actually used. And somewhere between scrolling through photos of Bali at 11pm on a Tuesday and staring at my office ceiling the next morning, I thought: why not just... go?
So I did. Not perfectly. Not with some grand plan. I made a lot of mistakes, spent one very stressful afternoon in a Vietnamese café with no WiFi and a deadline in two hours, and learned more about myself in 90 days than I had in the previous two years.
This is everything I wish someone had told me before I left.
First Things First — You Need Income That Travels With You
I know this sounds obvious, but a lot of people skip this step and just... figure it out on the road. Please don't do that. It adds a layer of stress that ruins the whole experience.
Before I left, I had been freelancing on Fiverr for about four months — nothing crazy, just writing and some basic content work. It wasn't replacing my full salary yet, but it was consistent enough that I felt okay taking the leap.
If you're not there yet, that's fine. But get there first. Even a few hundred dollars a month from freelance work changes everything when you're living somewhere like Chiang Mai or Tbilisi, where rent can be $300–400/month.
Remote jobs work too. In 2026, there are genuinely thousands of fully remote positions — customer support, writing, marketing, and development. Sites like We Work Remotely and Remote.co list them daily. You don't need to be a developer to find something.
Just have something coming in before you go. In the future, you will be very grateful.
Where Should You Actually Go First?
This was the question I got most wrong. I thought I'd start in Japan because, well, Japan. Beautiful, organized, safe.
Also incredibly expensive and not the most beginner-friendly place to figure out remote work logistics.
For your first trip, you want somewhere that's cheap enough to give you breathing room, has internet you can actually rely on, and has enough other remote workers around that you don't feel like a complete alien.
Here's where I'd point a beginner in 2026:
Chiang Mai, Thailand — still one of the best. I spent five weeks there, and it genuinely felt like the city was built for people like us. Coworking spaces everywhere, amazing food for almost nothing, and a community of nomads who are weirdly generous with advice.
Bali, Indonesia — more touristy than it used to be, but Canggu and Ubud still have a great vibe. WiFi can be inconsistent depending on where you stay, so do your research before booking.
Tbilisi, Georgia — this one surprised me. Incredibly affordable, visa-free for most nationalities, beautiful city, and the locals are some of the warmest people I've ever met. Less "nomad scene" than Bal, but honestly, that was a relief sometimes.
Medellín, Colombia — year-round spring weather (they call it "the city of eternal spring" for a reason), great coffee, fast internet, and a rapidly growing remote work community.
Lisbon, Portugal — pricier than the others but still cheaper than most Western cities, English is widely spoken, and it has a proper digital nomad visa now.
My honest advice: pick ONE place for your first trip and stay for at least a month. Two months is even better. The people who hop between five cities in 30 days while trying to work always look exhausted when I meet them. Slow travel just works better.
The Gear That Actually Matters
You do not need a lot. I want to push back on the YouTube videos showing people with $3,000 travel setups. Here's what genuinely matters:
A reliable laptop with good battery life. If your battery dies after 4 hours, you're constantly hunting for outlets. Not fun.
Noise-canceling headphones. I resisted buying these for way too long. The first time I used them in a noisy café during a client call, I wanted to cry with relief. Get them.
A local SIM card on the day you land. This single habit will save you so much time. Don't rely on your accommodation's WiFi as your only internet. It will fail you at the worst moment. It always does.
A VPN protects your data on public networks and is genuinely useful when certain sites are restricted in countries you're visiting.
That's really it. A laptop stand is nice for your neck. A universal adapter is necessary. But don't overthink the gear — most things you can buy when you're there if you realize you need them.
Finding Places to Work (This Is Harder Than It Sounds)
Here's something nobody tells you: your Airbnb WiFi is going to be terrible at least a third of the time.
I learned this the hard way. Host says, "Fast WiFi." You arrive. You run a speed test: 4 Mbps. You have a video call in an hour.
Now I always message hosts before booking and specifically ask them to send me a screenshot of a speed test. Good hosts will do this happily. If they don't respond or get cagey, that's your answer.
Beyond your accommodation, here's where I actually got work done:
Coworking spaces — worth every penny, especially in the first week when you're disoriented and just need a desk, fast internet, and some structure. Apps like Coworker.com help you find them. Most run $5–15/day or $100–200/month.
Cafés — works great for shorter sessions. I had a few "regular" spots in every city I stayed in. Always order something, tip well if tipping is the norm, and don't park yourself at a two-person table during lunch rush for four hours. Common sense stuff.
Hotel lobbies — genuinely underrated. Many upscale hotel lobbies have great WiFi, comfortable seating, and nobody bothers you if you buy a coffee.
The Routine Thing — I Can't Stress This Enough
This is the part where most people struggle, including me in the beginning.
You arrive somewhere beautiful. You want to explore everything. You stay out late. You sleep in. You tell yourself you'll work in the afternoon. Then it's 6pm, and you've done nothing,g and you feel guilty and jet-lagged and overwhelmed.
I went through about two weeks of this before I forced myself to build a structure.
What worked for me: treat your mornings like they're sacred. I was at a desk — not a bed, not a sofa, a proper desk — by 8am every day. Deep work until 1 or 2pm. After that, the rest of the day was mine to explore, rest, eat, and wander.
It sounds rigid, but it's actually the opposite of rigid. It's what gave me the freedom to actually enjoy being somewhere new without the constant background hum of guilt about unfinished work.
One more thing on routines — if you're working for a company in a different time zone, figure out the overlap before you go, not after. I once had a three-week stretch in Southeast Asia where my calls didn't start until 9pm because of a US client. Once I planned for it, it was fine. If I'd found out on arrival,l it would have been chaos.
The Practical Stuff Nobody Likes Talking About
Visas: Many countries now have official Digital Nomad Visas — Portugal, Indonesia, Costa Rica, Georgia, and others. These let you stay legally for 6–12 months. Always check official government sites for visa rules. Blogs (including this one) can be outdated on visa info.
Taxes: This is the one that genuinely surprises people. If you're a US citizen, you still owe US taxes no matter where in the world you're working. Other countries have their own rules. Please talk to an accountant who specializes in expats or remote workers before you leave. One hour with the right person saves you an enormous headache later.
Health insurance: Your regular plan almost certainly won't cover you abroad. SafetyWing and World Nomads are both popular among nomads — affordable, straightforward, and actually designed for this lifestyle.
Banking: Get a card with no foreign transaction fees. Wise and Revolut are the most popular options. Withdrawing cash from random ATMs abroad with a fee-heavy card will eat into your budget surprisingly fast.
The Honest Part
I want to be real with you for a second.
Some days were genuinely hard. A morning in Medellín where the power went out mid-deadline and I sat in a café absolutely spiraling. A week in Lisbon, where I felt so lonely I almost booked a flight home. Moments where the "living the dream" version of this life felt very far from whatever I was actually living.
Nobody posts those days on Instagram.
But here's what I also know: those hard days were my hard days. I was struggling in a city I'd chosen, in a life I'd built, on my own terms. And that felt different from the specific kind of dull misery I felt sitting at a desk I hadn't chosen, in a city I'd never really decided to live in.
This lifestyle isn't for everyone, and I mean that genuinely — not as a caveat but as real information. If you need routine, stability, and your people around you to feel okay, that's completely valid,d and this might not be the right move.
But if you've been reading this whole thing nodding along, wondering when you're going to stop putting it off — maybe the answer is sooner than you think.
Before You Go: A Simple Checklist
- Stable remote income (or a remote job) sorted before you leave
- 1–2 months of savings as a buffer
- Reliable laptop with a good battery
- Noise-canceling headphones
- VPN installed
- Local SIM plan researched for your destination
- Travel health insurance (SafetyWing or World Nomads)
- Zero-fee travel debit card (Wise or Revolut)
- Visa requirements checked on official government websites
- One coworking space or reliable café is shortlisted for your first week
- A rough daily work schedule in your head
You can always come home. But you might not want to.
If you're just starting your remote income journey, this post on making money on Fiverr with no experience is a good place to begin. Questions? Drop them in the comments — I actually read them.
You can also read my other blogs for more options. Best Way to Make Money Online in 2026: Real Stories, Real Struggles, and What Actually Works.s And I Tried 5 AI Tools to Make Money Online — Most Failed, But One Made Me $42 in 4 Days
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