Travel
                     Alright, here’s the long version — the stuff I usually leave out when someone 
asks this casually.
I freelanced full-time while traveling for about three years. I didn’t start with 
some grand “digital nomad” plan. It was more of a slow drift. I had already 
been freelancing remotely for a while, realized my lease was ending, and 
thought, “If I can work from my apartment, I can probably work from 
somewhere else.” I booked a one-way ticket with a vague plan and a decent 
emergency fund. That was the beginning.
The Fantasy vs. The Reality
Let’s start with the fantasy because that’s what usually pulls people in.
You picture yourself coding on a terrace overlooking the ocean. You imagine 
mornings exploring old streets, afternoons casually shipping features, 
evenings eating incredible food in a city you just discovered. Freedom. 
Adventure. No boss hovering over your shoulder. Your income tied to skill 
instead of geography.
Some of that is real. But it’s layered on top of a lot of very normal, 
sometimes boring, sometimes stressful work.
Most of my days were not cinematic. They were me sitting at a small desk in 
an Airbnb, debugging something that absolutely refused to cooperate, while 
outside it was sunny and people were living their best vacation lives. There’s 
a weird psychological friction in that. You’re physically somewhere exciting, 
but mentally you’re still inside a codebase.
And yet — the backdrop matters. It changes how you feel about the grind.
The First Few Months: Adrenaline and Adjustment
The beginning feels electric. Everything is new. New airport. New currency. 
New SIM card. New grocery store layout. Even the smallest things feel 
slightly adventurous.
But there’s also a constant low-level cognitive load. You’re always adjusting. 
Where do I buy decent coffee? Which coworking space doesn’t blast EDM at 
9 a.m.? How do I say “no onions” in this language?
Meanwhile, your clients do not care that you’re figuring out public transit in a
country where you can’t read the signs. They just want their deliverables.
That was my first big lesson: geography changes, but professional 
expectations don’t.
You still need to show up. You still need to hit deadlines. You still need to 
communicate clearly. If anything, you need to over-communicate, because 
now you’re often in a different time zone.
Time Zones: The Silent Killer
Time zones were one of the most exhausting parts.
If you’re working with clients in the U.S. and you’re in Southeast Asia, you’re 
basically living in the future. I had stretches where my “normal” workday 
started at 7 p.m. and ended around 2 a.m. I’d sleep late, explore a bit in the 
afternoon, then mentally switch into work mode when everyone else was 
going out for dinner.
It sounds romantic at first — night coding sessions, quiet cities — but it can 
mess with your rhythm. Your social life becomes inverted. You miss events. 
You’re tired at odd times. And if you stack multiple clients across different 
time zones, it gets even worse.
The only way I made it sustainable was by setting firm meeting windows. I 
refused to be available 24/7. Early on, I made that mistake. I thought 
flexibility was part of the deal. It led to constant Slack pings and this feeling 
that I was never fully off.
Boundaries saved me. Clear availability. Clear response times. Clear 
deliverables.
The Money Question
Financially, it can be great — or terrifying — depending on how you approach
it.
If you’re earning in USD or EUR and living in a lower cost-of-living country, 
the math can be in your favor. Rent drops. Food costs drop. Transportation 
costs drop. Suddenly your freelance income stretches much further.
But freelancing income isn’t guaranteed. Projects end. Budgets get cut. 
Clients disappear. When you’re traveling, that uncertainty feels sharper 
because you don’t have a stable “home base” to retreat to.
There was a month where two contracts ended within weeks of each other. I 
remember sitting in a tiny apartment thinking, “Okay. If nothing else comes 
in, how many months can I float?” That’s when I realized why people 
emphasize emergency funds so heavily.
For me, six months of expenses was the psychological minimum. Not 
because I expected disaster — but because it allowed me to think clearly 
instead of making panicked decisions.
Also, travel can sneakily inflate expenses if you move too often. Flights, 
short-term rentals, coworking passes, visa runs — it adds up. Slow travel is 
dramatically cheaper and less stressful.
Slow Travel vs. Constant Motion
The biggest mistake I see people make is moving too fast.
When you relocate every week or two, you never settle. You’re always 
packing, adjusting, re-learning your environment. Your productivity dips. Your
stress rises. Your sense of belonging never forms.
I eventually settled into a rhythm of staying at least one to three months per 
location. That changed everything.
You find a gym. You find a favorite café. You learn the grocery store. You 
develop a loose routine. And routine, weirdly, is what makes freedom 
sustainable.
Traveling while freelancing isn’t about constant novelty. It’s about building 
temporary stability in changing environments.
Productivity: It’s Not a Vacation
One misconception is that you’ll somehow work less because you’re 
somewhere beautiful.
In reality, freelancing requires discipline regardless of location. Sometimes 
more.
No boss. No office. No coworkers watching. If you don’t work, nothing 
happens. No one’s pushing you.
There were days when the beach was calling, or friends were planning a trip, 
and I had to say no because a client deadline mattered more. That tension is 
constant. You’re trading immediate experiences for long-term sustainability.
I learned that mornings were sacred. Even if I had a late meeting schedule, 
I’d block a few focused hours early. Deep work before the world intrudes. If I 
didn’t protect that time, the day would fragment into calls and context 
switching.
And not every Airbnb is built for productivity. I’ve worked from kitchen 
counters, wobbly café tables, couches that destroyed my back. After a few 
months of that, I invested in small portable comforts — a foldable laptop 
stand, a proper mouse, noise-canceling headphones. Tiny upgrades that 
made a huge difference.
Loneliness and Social Reality
This is the part people don’t talk about enough.
You meet tons of people. Other travelers. Other freelancers. People passing 
through for a week. You have intense, fast friendships — shared dinners, 
deep conversations, spontaneous weekend trips.
And then they leave.
Or you leave.
There’s a strange emotional churn to that. Connections are frequent but 
often short-lived. It’s exciting, but it can also feel hollow after a while.
If you’re naturally independent, you might thrive on it. If you crave long-term
community, it can wear you down.
I found that coworking spaces helped a lot. Not just for Wi-Fi, but for seeing 
familiar faces. Even casual acquaintances — the person you nod to every 
morning — create a sense of continuity.
Eventually, though, I started missing deeper roots. Being present for 
birthdays. Watching friendships evolve instead of reset. That craving crept up
slowly.
Identity Shift
Freelancing while traveling subtly changes how you see yourself.
You become hyper self-reliant. You solve your own problems. You manage 
your own schedule. You negotiate your own rates. You handle your own taxes
across borders. There’s a quiet confidence that grows from that.
You realize how little you actually need. A laptop. A backpack. Decent 
internet. That minimalism can be freeing.
But there’s also an identity tension. When someone asks, “Where are you 
from?” or “Where do you live?” the answer becomes fuzzy. You’re always in 
between.
At first, that feels cool. Later, it can feel unanchored.
Work Quality and Career Growth
One fear I had before starting was that my career would stagnate.
Surprisingly, the opposite happened — but only because I was intentional.
Freelancing forced me to level up in communication, scoping, pricing, and 
client management. Those are skills you don’t always develop as deeply in 
traditional employment.
However, there’s a ceiling if you’re not careful. If you only take small gigs to 
keep cash flowing, you can get stuck in shallow work. I had to deliberately 
seek longer-term contracts and more complex projects.
Retainers were a game changer. Stable monthly income from a few core 
clients reduced anxiety dramatically. It also freed me from constantly hunting
for the next gig.
Travel is much more enjoyable when you’re not refreshing your inbox 
wondering if a lead will convert.
The Psychological Arc
Year one felt like expansion. Everything was exciting. Every place was new.
Year two felt balanced. I had systems. I knew what worked. I was making 
solid money and living comfortably.
Year three felt different. The novelty wore off. Airports felt repetitive instead 
of thrilling. I started noticing the cost of constant motion.
That’s when I realized this lifestyle is probably best as a chapter, not 
necessarily a forever plan.
Some people do it long term and love it. But for me, the appeal shifted. I 
wanted stability, deeper community, maybe even a place to put actual 
furniture.
What Made It Work
If I had to summarize what made the whole experience successful, it would 
be this:
1. Emergency fund — Non-negotiable. It buys mental clarity.
2. Long stays — Reduces burnout and expenses.
3. Retainer contracts — Stability over constant hustle.
4. Clear boundaries — Defined work hours and communication 
windows.
5. Portable work setup — Treat your body well.
6. Routine — Even in paradise, you need structure.
Without those, I think I would have burned out fast.
The High Points
Some moments are permanently etched in my memory.
Finishing a big project and celebrating with new friends in a city I’d never 
heard of a year prior.
Taking a weekday off to hike somewhere incredible because I’d front-loaded 
my work.
Realizing I could support myself entirely through skill and a laptop from 
anywhere with decent internet.
Those moments build a deep sense of agency. You feel capable.
The Low Points
There were also rough patches.
Getting sick alone in a foreign country.
Losing a client unexpectedly and recalculating my runway at midnight.
Feeling socially exhausted from constantly meeting new people.
Working from a noisy apartment with construction outside while trying to 
push a critical deployment.
It’s not all sunsets and laptops by the sea. In fact, I rarely worked by the sea. 
Sand and electronics don’t mix well.
Would I Recommend It?
It depends entirely on your temperament.
If you’re adaptable, reasonably disciplined, and comfortable with uncertainty,
it can be incredible.
If you crave stability, consistent routine, and deep-rooted community, it 
might feel disorienting.
Also, it’s important to separate two things: freelancing and traveling.
Freelancing alone is unstable.
Traveling alone is destabilizing.
Combining them doubles the volatility.
If your freelance career is already stable, adding travel is much easier. If 
you’re just starting freelancing and planning to travel simultaneously, that’s 
a high-stress combo.
The Big Question
The real question isn’t whether it’s possible. It absolutely is.
The question is: what do you want your ordinary Tuesday to look like?
Because that’s most of life. Not the epic weekend trips. Not the Instagram 
posts. Just a random Tuesday afternoon.
Do you want that Tuesday in a different city every few months? Or in a 
familiar place where you know the barista’s name?
For a while, I wanted movement. It stretched me. It forced growth. It showed 
me how little I needed and how capable I could be.
Eventually, I wanted roots.
Final Thoughts
Freelancing while traveling gave me perspective. It taught me discipline, 
resilience, negotiation, and self-trust. It also taught me that freedom without 
structure turns into chaos pretty quickly.
I don’t regret a second of it. Even the stressful parts were formative.
Would I live out of a suitcase forever? Probably not.
Would I do another extended stint abroad with remote work? Absolutely.
It’s not a magic life hack. It’s just a different trade-off structure. You trade 
stability for flexibility. Routine for novelty. Long-term consistency for short-
term intensity.
For some seasons of life, that trade is exactly right.
If you’re considering it, my advice is simple: stabilize your income first, build 
a cushion, test it for a few months instead of committing to a year, and be 
honest with yourself about what you need emotionally — not just financially.
It can be one of the most liberating experiences you’ll ever have.
Just don’t confuse “location independent” with “problem free.”
You’re still you. You’re just somewhere else.