The Ultimate Guide to Working Remote

Digital Nomadism
November 19, 2018
For an increasing number of people, the 9-5 lifestyle just isn’t cutting it. With more and more jobs requiring only an online presence, rather than a physical one, adventure seekers around the world no longer have to settle for travelling on their long weekends or days off. You can have it both ways – you can see the world and earn a living – at the very same time. Life on the road, it’s a dream coming true for more and more of us.
Working remotely, also known as “digital nomadism” is something we have discussed a good deal on this blog, but never before have we put together a comprehensive guide. Normally, we advocate for packing a few merino wool t shirts and pairs of underwear, and landing a cheap flight (both still a great idea), but here we thought we would go a bit more in-depth, offering you a start-to-finish guide for working remotely.

How to Work Remotely

Which Jobs Fit The Lifestyle?

Flexibility is key when finding a nomadic job, and so the lifestyle tends to attract people who work in design, tech, or an adjacent field. Enter a coffee shop in Chiang Mai and you will probably meet a couple web or app developers, maybe an SEO analyst, a software tester or a freelance writer.  Really, any job that allows you to work from home should allow you to work remotely.

Where Can You Find Remote Work?

Given the online nature of digital nomadism, it should come as no surprise that the conventional way of landing remote work is – you guessed it – online. There are a number of job and recruitment websites that cater primarily to remote workers, but the best ones are (which deals exclusively with remote work), Flexjobs, RemoteOK and AngelList (which deals mainly with startup work, an often overlapping job market to digital nomadism). If you have other suggestions for finding remote work, leave them in the comment section.
The Pros And Cons
Once you’ve ascertained that you can, in fact, find a remote job, the next logical question to ask yourself is “Should I take it”. The digital nomad lifestyle is not for everyone. 

On the “pro” side,
you get to see far-flung parts of the world, unmoored by a fixed address, and can move freely between countries and cultures that interest you. You don’t have to dress up to go to the office, nor are you required (often) to work at set times. If you are someone who feels their best when free of constraints, this is the lifestyle for you.

On the “con” side,
it can feel structure-less at times, and unless you make a concerted effort to meet others, it can feel lonely. Often times, you’ll also need to be scrappy and drum up your own work. If you’re someone that likes structure, and isn’t going to put yourself out there to land gigs, working remote may not be ideal. 


Where To Go

What Makes A Good Destination For Working Remotely?

Where working remotely is concerned, not all destinations are created equal. When choosing a country or city, some popular criteria for digital nomads are as follows: affordability, weather, an existing digital nomad community, an interesting culture, and ease of housing. For example, an expensive, cold country with little to do on the weekend, and a convoluted visa process might not be your best choice.
Lucky for you, we’ve spoken to countless nomads and compiled a list of favorite places to work and live remote. Here is a list of popular digital nomad destinations (by no means comprehensive), along with a brief note about what makes each a desirable city for working remotely:

Chiang Mai

Northern Thai culture meets laid back vibes in this very popular choice for digital nomads. As with the other Southeast Asian options, it is cheap and balmy. 


The Thai capital is inexpensive relative to anywhere in the west, with a massive nightlife and plenty of other expats to befriend. You are also never too far from a beach – just be sure to pack a merino t shirt because the summers get spicy.

Ho Chi Minh City

Another popular Southeast Asian hub, this Vietnamese city is a food paradise. Just be careful when you’re crossing the street.

Johor Bahru

A slightly lesser known destination, this Malaysian city is popular with digital nomads for its – you guessed it – warm weather, great food, plenty of shared work space and cheap prices.


Relative to Western Europe, the Hungarian capital is fairly inexpensive, and it is full of interesting culture, architecture and things to do. It gets cold in the winter, but not “Baltic countries” cold – pack a couple pairs of warm, merino wool boxers and The Compact Travel Hoodie and you should be fine. 


Warm weather, stunning beaches, good food and fast internet make this coastal Spanish city pretty popular with remote workers.


There is always something to do in Berlin, as we’re sure you have heard tall tales about the round-the-clock nightlife here. It’s also much less expensive than it’s pricier Euro counterparts like London, Paris, and Rome.


The Croatian capital is a foreign friendly and inexpensive part of Europe. The positioning is great: you are close to the Balkans here, as well as Northern Italy


The Chilean capital is a safe, affordable and beautiful part of South America. The average cost for a 1 bedroom, at the time of writing, was less than $300, which is real good.


While not the safest entry in this list, the Colombian capital all but makes up for it in charm, nightlife and affordability.

Making a Preparatory Checklist

You have a job, you’ve psyched yourself up, told your current employer to shove it and you have picked your perfect city. The next thing to do is get your proverbial ducks in a row. Here is a preparatory checklist that you can use to make sure you don’t forget any important documentation or steps:
Ensure you have a valid passport.Make sure that your passport stays valid for the entire duration of your time abroad (or at least a few years, whatever comes first).
Get your visa(s). Different countries have different visa requirements, which can change according to your country of origin. Read all about the different visa requirements as well as how to apply at this helpful website.
Get an un-expiring, universally recognized credit card and notify the bank of your travel plans. The last thing you want is for MasterCard to freeze your card because of “suspicious activity”.
Get Travel Insurance. There is no reason not to, and it could save you a lot of money in the event of an injury or emergency. 
Get vaccinated. Ask your doctor which vaccinations you require for your destination (they are going to ask you how rural you plan to go) and get them out of the way. Keep a vaccination record with you when you travel.
Find your ideal remote office in your destination city(s) so when you land, you’re ready to work in an environment that will keep you focused and productive. This isn’t all fun and games.
Lastly, find a cheap flight. If you can be flexible with your days, just monitor Google Flights and set up price alerts, or sign up for a cheap flight newsletter, like Scott’s Cheap Flights.

What To Pack

The idea here is to pack light. You want to be able to move around unencumbered by a large suitcase, but that can be tricky when you are essentially living and working out of your bag. For a comprehensive packing guide for long-term travel, check out this article, which lists the exact numbers of each garment we recommend. As a basic guide, here are the things you will need:

The Right Backpack – Opinions differ on what exactly makes a great backpack, but look for one with a good amount of volume for its size (i.e. the interior isn’t given over to unnecessary pockets and filling). If valuables are a concern, consider getting a slash-free bag – you can find backpacks with stainless steel wire mesh embedded in the fabric. In our experience, the best choice for an office on the move is the AER Travel Pack.

Merino Wool, Obviously – You can’t travel without the breathable, insulating, anti-microbial power of merino socks , boxers, shirts and sweaters. As travelers ourselves, we can say with confidence that these are must-haves for any remote worker.

Multi-Purpose Footwear – Depending on your destination, this could be comfortable running shoes, hiking boots or flip-flops (or two of the three).

Shorts, Swim Trunks, Jeans – For bottoms, get a pair of comfortable, versatile jeans, and supplement them with a pair of shorts for hot days. Your swim trunks you can probably buy abroad.

Hardware – Pack your work computer, phone, chargers, and external hard drives for backing up work in case of a Wi-Fi outage. BestVPN also put together a list of indispensible tech items chosen by digital nomads, which is worth checking out.

Paperwork – this includes copies of your passport, ID, visas, itinerary and travel insurance, as well as extra passport photos in case you need them for your visa process.

Toiletries – Pack the usual suspects (toothbrush, soap, shampoo, razor, hair product, etc.) but know that you can easily, cheaply buy most of these at your destination, so unless you are very brand loyal, don’t pack a giant bottle of shampoo or extra packs of razors.

Travel Towel – A normal towel will probably suffice, or you could buy your towel at your destination, but a travel towel is great for its small packing size and quick-drying potential.


What Blogs To Follow

Other than this one, here are a few blogs to follow if you still have questions about working remotely (or if you just want to read about other people’s experiences):

Become Nomad – Advertising itself as a resource for those thinking of making the switch to digital nomadism, this blog does offer some good insights into the transition.

Untemplater – Often veering into general career advice (with some personal finance tips thrown in), this blog is nevertheless a good source for digital nomads as it is all about unconventional forms of work and living.

Nomadic Matt – A bestselling author, Matt is credited with popularizing digital nomadism, and his site mixes diary-style blogging with tips about working and living abroad.

Stop Having A Boring Life – As the name suggests, this blog is a call to action. It’s mostly a travelogue, but there are some good tips peppered in, and some awesome photos.

But most importantly, head to:

Reddit’s r/digitalnomad – While not technically a blog, Reddit’s digital nomad community is a indispensable resource for remote workers, and one of the few forums you can visit to have your questions answered and concerns heard instantly.

Other Resources

The book Remote: Office Not Required, by Jason Fried and David Heinemeier Hansson, is required reading for those looking to make the leap into the digital nomad lifestyle. The founders of Basecamp (then 37Signals) Fried and Hansson are great advocators for remote working, and bolster their endorsement with talk about productivity and life balance.

You can always count on yours truly: contact us to learn more about our travel clothes and check out this blog for ongoing guides and updates on an array of travel topics, including remote work.

The podcast As Told By Nomads is a great resource for those who like to get their insights and info audibly. It is a series of conversations with digital nomads from around the globe, and tackles a lot of pertinent topics.

For those who’d rather digest their media in film form, the T+E series New Nomads, while difficult to find online, is an accurate look into the subculture of digital nomadism.  


In Summary

It starts with finding a job, and determining whether this kind of living is really for you. Then the planning starts: spinning the globe and choosing your perfect place, gathering paperwork, documentation, tickets and accommodation. Once everything is “real”, you turn your attention to packing, figuring out how to make the most out of a small backpack. When you arrive at your destination, you consult with any number of resources – blogs, books, podcasts, etc. – to help you make the most out of this amazing experience.

 Working remotely is one of the truly awesome things about the age in which we live. You can see the world and earn a living, perhaps even make a fortune. With some careful planning, big dreaming, and a bag full of merino wool, you’re ready for the adventure of a lifetime.


              Col Forbin
Col Forbin