Back in the throes of wintry January, I combed through thousands of travel photos to create a collection of my remote “offices” as a digital nomad from the past 16 years.

My plan was to make a short blog post. But looking through so many photos of warm, happy places proved too much at the time, so I shelved the project.

SafetyWing (a leading provider of travel medical insurance for digital nomads) recently incentivized the effort, so I decided to resurrect this monster.


Digital nomad office in Ubud, Bali

Working in Cafes

Finding a place to work remotely as a digital nomad is easier than ever before, but it’s still a skill that gets honed with time. Long-term travelers develop an instinct; they have an inner Admiral Ackbar ready to warn them if needed.

Not all cafes and guesthouses that advertise Wi-Fi do indeed have usable Wi-Fi. It’s a trap! Proprietors in a few struggling places have learned they can increase business substantially by putting up a four-letter sign. Wouldn’t you?

I’ve consumed at least 2 million optional calories over the years by ordering a drink of some sort (the fee for working in a cafe a few hours) only to discover the place hadn’t been blessed by an 802.11 signal in months.

Or if a signal existed, the connectivity hadn’t improved since US Robotics 56K modems screamed and squealed to seal a handshake.

I’d finish my drink, pay, then move on to another cafe where I’d be forced to order another drink in my desperate search for connectivity. And possibly diabetes.

The all-too-familiar “hmmm…we’re having trouble finding that site” screen below says it all (Kuala Lumpur, Malaysia).

Digital nomad office in a cafe

But there are exceptions.

In places such as Bali, cafes really have to step up their game. Competition is fierce, both for good coffee and fast Wi-Fi.

Stuart from introduced me to Nook, one of the best cafes in Bali (in my opinion). Milu in Canggu is another notable option. Both frequently served as my remote office while in the area.

Nook cafe in Bali

Crowded Connections

Sometimes a place with decent Wi-Fi turns out to be an oasis for meeting digital nomads. These cafes draw us in like wildebeests, anxiously crowding into a muddy, crocodile-infested watering hole for a drink.

While exploring new towns, I became conditioned to look for travelers sat behind open laptops.

But once saturated by too many connection-seekers, the Wi-Fi often gives up. Or the staff flip the switch on the router (I’ve seen it done) to clear out customers who have loitered too long.

Meanwhile, at guesthouses, good connections often crumble in evenings after travelers return from excursions. Their iPhones connect automatically without intervention and begin uploading 4,000 selfies to the iCloud. Thanks, Apple.

Many people are unaware of this unique challenge for digital nomads.

Working From Anywhere

Glamorous stock photos of influencers sitting on beaches with laptops perpetuate the myth that you can work anywhere.

While this is partially true, my eyes generally can’t see a screen well enough in bright sunlight to stay productive. And equatorial heat is hell on both the laptop and the user of said laptop.

More importantly, my laptop is the second-most valuable possession with me on the road. The mighty passport comes first, of course, but my laptop is a magical machine that provides the ability to pay for pad thai.

I don’t need sand and water destroying it just so I can brag about working on a beach.

That said, my very first remote office as a digital nomad in Acapulco, Mexico (a rental house), did have a pool desk. Pretty cliche, but it happened.

Nowadays I would never risk my laptop to one bozo’s errant cannonball splash. But as a newbie in 2007, working in a pool seemed much more interesting than my IBM cubicle.

Digital nomad works at a pool desk in Acapulco, Mexico

Working in a swimming pool

Digital Nomad Offices on the Beach

As mentioned, getting any serious work done on the beach isn’t easy, despite what you see on Instagram.

Regardless, I have built several travel websites and written hundreds of thousands of words while enjoying a nice view, often from my bungalow porch or a beachfront cafe.

Here’s one of my favorite writing spots on the island of Koh Tao, Thailand:

A beachfront cafe in Thailand

And below you can see the challenge of LCD screens in tropical places. This was taken in West Sumatra while working offline on my book about meeting travelers.

Small ants scurried in and out of the keyboard as I typed. Slightly distracting. Those same ants traveled hundreds of miles with me as tiny stowaways.

Digital nomad laptop on a bungalow porch

Despite my best efforts to baby them (laptops, not ants), hardware gets put through a lot on the road. Sometimes the sand, humid air, and foul language from luggage handlers are just too much.

On one trip, my power button (ironically, the button pressed the least but arguably the most important of all) unexpectedly popped off! The laptop was still under warranty, but I was deep in Sarawak, Borneo, and far from an Asus technician.

A little super glue from 7-Eleven miraculously fixed the problem.

Power button popped off laptop

But working on the road isn’t always so rough. Occasionally, you’re blessed with a gorgeous view of the Chao Phraya River in Bangkok—and air conditioning!

Working with a view as a digital nomad in Bangkok

My porch in Unawatuna, Sri Lanka, wasn’t too shabby, either! I stayed for two weeks to get some serious work (and play) done:

Working as digital nomad in Unawatuna, Sri Lanka

Digital Nomads and Deadlines

From 2010 until 2021, monthly and weekly deadlines were a part of my life. This inescapable fact often shaped my travels. I could only spend so long in the boonies before needing to return to bigger cities, or somewhere with a semblance of connectivity.

This sounds inconvenient, and it was. But looking at James T Clark’s post about the history of digital nomads, I realize I didn’t have it so hard in 2006 after all!

On a side note, after 11 years of timely contributions, Tripsavvy quiet fired myself and many other writers in 2021 without even a goodbye email.

No more pesky deadlines, I suppose.

The desperate hunt for Wi-Fi to wrangle deadlines brings people together in remote places. Here I am meeting a new German friend in Medan, Sumatra. The Wi-Fi sign on the wall was like a beacon that caught our eyes.

Digital nomads working on laptops

Digital Nomad Co-Working Spaces

Yes, luxurious co-working spaces are an option in many places now. I’ve been in a few impressive ones around Bali, Chiang Mai, and other digital nomad hotspots. But despite having ludicrously fast Wi-Fi, many of the co-working spaces cost upwards of $20 for a day pass.

I, being a cheapskate vagabonding traveler, usually opted to spend that cash on food and drinks in various establishments where fewer crypto bros were trying to tell me about an upcoming airdrop.

Working Offline

Sometimes my digital nomad “office” was anywhere I could scrawl some notes with pen and paper.

One such place was the Xiao Long Wu Yuan Shaolin Temple School in China where I studied kung fu. I scribbled notes by flashlight after “lights out” and then sneaked out of the school the next afternoon by climbing a wall. I’d hitch transport into town and find an internet cafe to make my blog post.

In some of the cafes, more than half the Chinese layout keyboards had broken keys or were gummed up with nicotine. I sometimes competed for bandwidth with dozens of young kids playing games.

More than once, I witnessed actual World of Warcraft “farms” where kids silently played the game while a supervisor paced around behind them. The kids got to play for free, and the adults would sell in-game currency or items for real money.

Colorful street in Deng Feng, China

I’d furiously type what I had written on paper the night before then sneak back into the school compound, with cigarette smoke still wafting from my hair and clothes.

That’s a lot of work for one crappy blog post.

When deadlines aren’t a factor, working offline can be a joy. Without the siren calls of email and social media, you can generate some exciting ideas—especially with a view like this (Tioman Island, Malaysia):

Travel journal with view of the beach

Realistic Digital Nomad Offices

Although the photos of working on porches and in pools are fun, realistically, digital nomads make their offices anywhere they can find a horizontal surface and some connectivity.

Airports, restaurants, hotel room desks—almost anywhere can be productive if you can maintain focus.

More times than I would prefer, I had to simply work on my guesthouse bed while my overheating laptop begged for better ventilation. Sometimes I was beneath a mosquito net.

Here are some last photos of my remote offices as a digital nomad. I got some serious work done in all of these places (and sometimes returned year after year).

The rooftop terrace at the Rainforest Hotel in Chinatown, Kuala Lumpur (Malaysia):

Rooftop at the Rainforest Hotel in Kuala Lumpur, Malaysia

My porch while house sitting for #theYucatanExperiment in Yucatan, Mexico:

Table on a porch in Yucatan, Mexico

And last, my porch in Ubud, Bali:

Working on a laptop in Ubud, Bali

Travel Medical Insurance for Digital Nomads

I’ve talked a little about SafetyWing in the past and how useful they are for vagabonding digital nomads, especially with COVID-19 still a threat. Their travel medical coverage can be activated or paused as needed. Plus, you can purchase a policy once you’re already on the road.

This flexibility is perfect for vagabonding, when you aren’t sure where you’ll be or for how long (often the case). You don’t even have to let them know where you plan to travel.

Even better, the company is run by digital nomads and does a lot to support the remote work community.

Here’s my affiliate link when you’re ready to compare travel medical insurance for digital nomads.

Happy travels!