Remote Working Digital Nomads

The Pros and Cons of Remote Working in Paradise


Waking up to the sound of tropical birds cooing and chirping outside, it’s clear I’m a long way from home again. I picked an Air bnb room in a house (which turned out to be a mansion) in the Manoa valley area, a little way out of town from the touristy Waikiki beach. The guy who rents it is in the US military, and says that doing Air bnb works out so well that it covers his rent. The key-code on the front door means that when you book the room you get emailed the door code, so that he doesn’t even need to be there to give you the key. Now there’s an example of smart automation in action!


Looking through the blinds I can see tropical plants and mist covered hills. The sun is out but it’s also raining. This is why it’s called the rainbow state. Take a hike into the hills and you’re bound to see one as we did yesterday in the light and refreshing rain. So where am I? Oahu, Hawaii of course. This place, with lush volcanic valleys and paradise beaches and Jurassic park jungle trails has been an obsession of mine since I had a little taste of it last summer on my honeymoon, and couldn’t stop thinking about it.

The reality of Remote Working

The concept of remote working is now a reality, thanks to the increasing internet speeds in most developed and developing countries worldwide. The freedom of travelling whilst working on a laptop in exotic locations is a dream lifestyle that I put into practice exactly one year ago. I moved with my wife, who’s Burmese to stay with her family in Yangon, Myanmar (Burma) for 6 months to escape the English winter. Birds migrate for the winter to warmer climes, so why can’t humans?


Remote working is becoming a growing trend, and the movement for people who live this way are called ‘Digital Nomads.’ Because working remotely is dependant on internet, digital nomads can usually be spotted in coffee shops and co-working spaces around the globe, and it’s been truly noted that these people travel thousands of miles to sit in Starbucks. 


The Dutch designer, programmer and entrepreneur Pieter Levels set up the website Nomad List as a great resource to track the best countries to work remotely in. The top world cites, ranked by cost, weather, air, fun, safety are Chang Mai (Thailand), Taghazout (Morocco) and Las Palmas (Gran Canaria), out of a list of 484 places. The local cost of living, from the price of an Air BnB apartment to a Cappucino are detailed. Levels has no fixed address. Instead, he lives out of a single backpack and works from coffee shops and co-working spaces around the world.



The social media tool Buffer is company that has sewn this idea into the heart of its company ethos. Its career page reads: “work in the place that makes you happy, that inspires you daily, and helps you to become the person that you wish to be. You will work daily with team members scattered around the world and across time zones to build a better culture and product.” 


“In the future every knowledge company could have a distributed workforce” – Matt Mullenweg, co-founder of WordPress


Scott Stohler, the travel blogger of Roamaroo describes his travelling lifestyle as ‘Vagabonding’ – which I thought was a hilarious modern twist on the phrase. A vagabond is a person with no fixed home. Swap the coal faced Dickensian urchin of Victorian London with a beach dwelling freelance programmer in Bali and you have a very modern vagabond!


Why travelling makes me feel alive

So why do I do it? The answer is simple. When I travel to new places I’m not on autopilot. I’ve stripped away the repetition and clutter of my home life in London and I’m forced to reinvent, learn and survive in a new environment. Everything’s different – an even the day to day mundane things become interesting. I find even going to the supermarket in a foreign country is exotic, particularly in flip-flops.




Comparing prices and finding new foods to take back to your temporary home feels a bit like camping, but with the added luxury of a real bed, bathroom and desk space. Living in someone else’s house is like being in someone else’s shoes for a while, before things become routine.


Making the remote working lifestyle ‘work’

I’m currently experimenting with this lifestyle, but I cannot yet claim that I’ve cracked it. I do get itchy feet every few months, and like seeing what it’s like to live in a new place, but I’m not one for travelling for extended periods. There must be very few Digital Nomads who can stay on the road for years without feeling homesick, exhaustion from moving around and the inevitable ‘beauty fatigue’ that hits you’ve seen all too many spectacular beaches, mountain ranges and waterfalls. Simon Fairbairn & Erin McNeaney are a Digital Nomad couple who manage it – they have been travelling around the world since 2010! They run a great travel blog called neverendingvoyage, in which they write about the locations they have lived in and share info on how they make a living.


“There must be very few Digital Nomads who can stay on the road for years without feeling homesick, exhaustion from moving around and the inevitable ‘beauty fatigue’ that hits you’ve seen all too many spectacular beaches, mountain ranges and waterfalls.”


What are the difficulties? 

You’ll need some cash saved up for the first part of your journey. Some people sell all their possessions in order to travel around until they have got their online business setup and bringing in revenue, which can take a year or more. If you’re moving around a lot, you will spend so much time researching, planning and getting from A to B, since everything will be unknown. In a foreign country, just getting a single thing done, such as printing out and sending off a CV (resumé) might take you a full day or more! It can also be lonely, and doubts will hit you early on in your journey. Our minds like security, and yours will be saying things like: “Where the hell have you taken me? What is your big plan now?” If you’re like me you’ll also be asking yourself if you deserve to be in such paradise! Shouldn’t I go back and brace the winter like everyone else? You’ll need to push through these kinds of thoughts constantly. If you’re in a relationship, this will need both of you to be happy with moving your stuff from place to place, and that isn’t an easy thing to balance. 


The next issue is the type of work you’ll be doing. If you’re lucky enough to have a steady flow of client work, then your issue is simply to be in a place where you can get the work done in time over a good wi-fi connection. In this case it helps to be in a time zone ahead of your client (e.g work in Asia if your client is in europe or the US). In my case I’m mostly self employed, so my issue is keeping up the motivation – which is very hard to do in a hot weather country. I’m used to cold and rain, and when there’s nothing much to do outside I think that may be the reason why I turn to creative projects in the first place. So if that doesn’t put you off and you’re up for trying something, then read on. Depending on where you choose to live, your experiences will be wildly different to mine..


Nomad Location 1 – The suburbs of Yangon, Myanmar (Burma)

North Dagon


Staying with a friend or relative is a huge help if you have the option, so my wife and I could stay with hr family without worrying about rent. Getting a social visa took several trips to the visa office in the centre of town, which is still without a computer system. In Myanmar, the main hurdle for me was getting used to the extremely poor internet. Picture me walking 20 minutes in the blazing heat to the nearest internet cafe to upload files on a USB stick across an unstable 0.5 meg internet. Life became a constant search for internet, which meant going to 5 star hotel lobbies at first and having to buy expensive coffees! But soon after I arrived, cheap mobile sim cards (which have dropped in price from $2000 in recent years to $1.50!) with pay as you go internet packages were rolled out, allowing me to tether my mobile to my laptop from our home in the Yangon suburbs. Considering the location, it felt like a miracle. 




After 3 months of working for myself, mixed with travelling trips I was pining to get some outside work. I managed to pitch the idea of an ‘App Club’ to a local school, and they agreed, and I then got some great freelance work making video sequences for a Design company fairly near where I lived. It felt like I’d taken a risk and was miraculously rewarded with just what I’d hoped to achieve. Phew! Read more about my Burmese App Club here.


Nomad Location 2 – Air bnbing & Co-Working in Honolulu, Hawaii

So here I am in my next location and settling into my Hawaiian adventure. The most populated island of Oahu has less than 1 million permanent residents, but it has about 5 million visitors each year, mostly from Japan and the US mainland. It’s ethnically very mixed, and is a melting pot of cultures – East meets West, and while it is a US state, the street names are still in Hawaiian, and the original language and ‘Aloha spirit’ still remains. But it’s extremely expensive. Only 50% of residents own their home. The average house is $700,000+ and rents are high. The price of supermarket food is shocking – a loaf of bread is around $5, and 2 litres of milk is $3 or more. A locally grown Pineapple is as much as $8! There are many foods that we just won’t buy here, and it’s actually more cost effective to eat out, rather than cook. One benefit of hot weather countries is we have less appetite, so we eat less anyway. The islands of Hawaii are stunning. There are countless hikes to do on, and of course the islands are surrounded by great beaches:


I’ve been through the usual worries that come with the upheaval of being in an unknown place, and I’m ready to get down to work now. Fortunately Oahu has incredible internet, considering it is brought in through incredibly long undersea cables, stretching from Australia to New Zealand, all the way across the Pacific to Hawaii, to join the mainland USA in a loop. Check out this amazing map of the World’s undersea cables.


Find a Co-working space

Due to being unable to work in my stuffy apartment in the back streets of Honolulu, I’ve joined a slick co-working space called BoxJelly. If features the usual co-working vibe: quiet techies, start-ups, fancy furniture and gourmet coffee next door. Everyone gets on with their work here, so I’ve barely had a chat yet, but at least the music is unobtrusive and I’m getting stuff done (“Get Shit Done” is actually their motto). I’m getting into it.. Let’s hope the local gods of creativity send me a rainbow. 


BoxJelly Coworking Space

The upsides of remote working

  • Freedom and flexibility to work when you want
  • When you work abroad it still feels like you’re on holiday
  • Excitement of discovering new places
  • Taking new risks can make you more motivated
  • Not being online all the time is healthy

The downsides of remote working

  • Internet can be terrible in places (but this can also be a healthy way to cure your net addiction: see upsides).
  • It can be hard to work in a tropical paradise with no air con 🙂
  • It takes time to settle in and find jobs / new clients
  • Flights are expensive if you have to leave for a visa run
  • Having no fixed address means no home deliveries, print-outs and stationary. Be prepared to spend a whole day finding a print shop, post office etc. It takes a lot of time to find your way around a new place, especially a city. 

Tips for getting work in a new place:

  • Sign up to local forums such as Google groups, Facebook work groups etc.
  • Post that you’re new in town, listing your skills and that you’re looking for work.
  • Send out your CV to related jobs. Even if they don’t get back to you, they may forward your CV to someone else. This happened to me.
  • Use to find local groups matching your interests.
  • If you have work to get on with, join a co-working space – which allows you to work with people, coffee and a stable internet connection.

Things to consider when working remotely:

  • What time zone are you on in relation to where your client is? If your client’s time zone is many ahead of you, then this can make things difficult. This is why Asia is a good place to be. When your client starts their day, your previous day’s work is already finished! 
  • There are 2 types of remote worker – the person working for clients, and those working for themselves. The former will need to try out whether their time zone will be an issue, while the latter will face a motivational struggle. 
  • Co-working spaces are useful, but they can feel lonely at first. People are generally there to work, not socialise. The vibe can completely depend on work space and the co-workers who happen to be there at the time. 


remote working in paradise with a laptop


Conclusion – can you really work in paradise?

It’s very difficult. This is an honest blog and I don’t want to peddle a lifestyle that’s not feasible. I’m still very much experimenting with the digital nomad thing. My first two locations were not at all ideal, as I had my own reasons for going there, and if you check the nomadlist site, there are plenty of good, more affordable options. It also depends on where you’re from and whether you can get used to working in a very different climate. I’d definitely recommend trying it over the winter like I have. Good luck to you, and please tell me about your locations in the comments 🙂

Finally, check out my infographic for a Digital Nomad’s backpack. Don’t leave home without it!



I'm a graphic designer, animator and app developer from London, UK. My interests include graphic design, tech, gaming, apps, film, comics and travel. I enjoy travelling and working as a Digital Nomad.

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