What I’ve learnt after five years working remotely

Then one day I landed a gig for a company based out of Hong Kong. I had been living in London for nearly ten years at that point, working full time, commuting everyday in the grime and rain, and the idea of spending some time outside the city was appealing. At first, my plans were modest. I thought about moving to Brighton to work near the sea. But the more I thought about it, the more I realised I could actually work… anywhere.

I moved to Berlin where I had friends but it wasn’t long until I got itchy feet and travelled to Barcelona, Tel Aviv, Chang Mai, NZ, Australia, Vietnam, Istanbul, Athens, Corsica… but then everything stopped when I moved to Melbourne for a full time role. Long story short—when the pandemic hit, I hit the road once again and since Dec 2020, I’ve been living in Airbnbs all around the world.

It’s not all sunshine and lollipops

Like with every life choice there are trade-offs. Some people live in the suburbs and exchange living a life of variety with safety and uniformity. Many dwell in cities, trading tranquility and clean air for the constant buzz and dynamic environment. The digital nomad sacrifices stability and companionship for the freedom to live anywhere.

Travelling to foreign countries to live like the locals do is great, but for every benefit there’s a flip side. So if you’re thinking about chucking it all in, stuffing your laptop and some flip flops into a single carry-on rucksack, here are some things you outta know first.

Solitude

You need to be comfortable spending a lot of time alone. Whether you’re an introvert or an extrovert, you’re not going to be able to meet up with friends after work every Friday. You need to make new friends and a lot of the time that won’t be possible, so you’ll be on your biff for many days or weeks. Personally I enjoy the solitude and as Hunter S. Thompson said, “We are all alone, born alone, die alone, and—in spite of True Romance magazines—we shall all someday look back on our lives and see that, in spite of our company, we were alone the whole way. I do not say lonely—at least, not all the time—but essentially, and finally, alone.”

Minimalism

There are two types of travel available to you as a nomad. You can flit around from place to place, staying a night or a month, leaving on a whim, as I used to do; or you can settle down and live in a place for a month minimum. Now that I’m in my 40s, this is my preferred lifestyle. When I started working remote many years ago, I had a single carry on bag with a laptop, a change of clothes and not much else, but now I carry a decent sized suitcase because I don’t move that often. Even with a suitcase though, you have to live minimally. It's quite freeing in a lot of ways—not having a bunch of junk around—but wearing the same clothes all the time is a bit of a drag.

Language barriers

When you’re living in places for an extended period, you inevitably have tasks you need to accomplish that are outside of a normal travellers’ experience in a foreign country. On holiday you only have to deal with taxi drivers, café staff and shop attendants. On my travels I've had to see doctors in Japan, find a vaccine clinic in Tbilisi, and file a theft report in Mexico. In all of these situations, no one spoke English. It's difficult in person but once you need to make a phone call, forget about it.

Airbnb

As of May 2022 I’ve stayed in 102 airbnbs. Some have been better than others but overall it's generally been positive and I’ve been lucky enough to spend extended periods in a lot of really interesting neighbourhoods. Here are my tips for renting airbnbs.

Don’t trust reviews

It’s not that people are morons and cannot be trusted, it’s that not everybody shares your values. Reviews are subjective. I stayed in a place that multiple reviews said was quiet—there was a bangin nightclub next door. In my experience, other people’s opinions of a place never align with my own perceptions.

The right neighbourhood

Pick a central neighbourhood with good amenities nearby. You need a supermarket, a gym, a park, some cafes and ideally good transport links. I always use Hoodmaps and it's mostly reliable.

Avoid main roads

In my experience a lot of airbnbs in apartment buildings are on busy, noisy thoroughfares. Even if you’re high up you often don’t avoid the traffic noise. So if you’re a light sleeper, avoid main roads and look for places on quiet back streets.

Washing machine is critical

I don’t use laundromats because the machines are low quality and don’t wash clothes properly, its expensive and it’s supremely inconvenient to visit 3 times (drop off, put clothes in dryer, pick up). Also, make sure there is somewhere to dry your clothes in the airbnb. I’ve stayed in too many places where I had to drape my clothes over the back of chairs.

Kitchen

You need a decent kitchen if you’re going to cook. Look for a proper oven (not a camping stove) and a lot of kitchens on airbnb have no workspace so look out for that. You need space to chop an onion.

Dedicated workspace

Make sure there is an actual dedicated workspace. A lot of airbnb listings say they have one but it’s a breakfast bar. In my dictionary, that’s not what ‘dedicated’ means. You need a proper desk and a proper chair if you’re going to work all day. Avoid round tables, in my experience they are never suitable.

Separate bedroom

Depending on your budget this is a bit of a luxury, but if you’re working in the apartment all day, its nice if you have a separate place to go at night. Eating, working and sleeping in the same room kinda feels like a prison cell.

Light

Make sure the airbnb has big windows. Spending all day in a dark room is not great for your wellbeing.

AC

Air conditioning in warm places is not a luxury if you want to sleep at night.

Internet

Obviously make sure there's wifi but I don’t think there are many listings on airbnb without it.

Nice to have

These aren’t deal breakers, but if a place has them and others don’t, it could tip the balance in their favour:

1. Blender for smoothies
2. Balcony
3. Big TV for movies
4. Lamps
5. Gym in the building. These are always crap but the convenience is great.

How to maximise wellbeing

I was going to write two sections, one on maximising productivity and the other on wellbeing, but I soon realised they are too intertwined to separate. You can’t be productive without looking after yourself.

The three pillars

It's crucial to prioritise exercise, sleep and diet over everything else if you want to live productively. Each affects the other and when one slips, the others won’t be far behind. When you’re exercising regularly, you won’t want to eat junk food because you’ll want to take advantage of your gains and get all your vitamins. When you get enough exercise you’ll sleep better, which gives you the rest you need to train the following day. When you eat poorly, it affects your sleep and when you don’t sleep well, you don’t have the will power to cook for yourself or avoid sugar. It's all a vicious cycle.

As soon as I arrive at a new neighbourhood, I find the nearest supermarket and a do a big shop that includes the basics (olive oil, salt, pepper, spices), and sign up at the nearest gym. Ideally the day of or the day after checking in to establish good patterns early.

Mindfulness

Next time you’re feeling negative emotion, like anxiety or fear—notice what happens next. How long do you stay in the grip of that contracted state of mind? How long is it useful to feel this emotion when responding to whatever challenge has appeared in your life? It’s not that the goal is to never feel these emotions again—they’re signals—something’s worth paying attention to. But how long must we let the alarm bells ring? With mindfulness you see that these emotions begin to evaporate the moment you notice them, and then you can respond to whatever’s happening in the world without being miserable. — Sam Harris, Waking Up App

Routine

It's important to have some stability when everything else is changing. I time-block my day to ensure I set aside sufficient time for deep work, meditation, weight training, running etc. Evenings and weekends anything goes, but during the day I stick to a schedule to make sure I don’t end up cooking lunch for two hours, spending too long in a cafe or just sleeping in. It's easy to waste days when you don’t have fixed start and end times to work.

Some items worth packing

I’ve thrown away more than I initially left with in 2020. In fact the only remaining items are my passport, drivers licence, glasses, and a beanie. Everything else has been replaced or jettisoned in the desire to lose weight or make room for something else. It's probably a good remedy for our culture of commodity where a normal past time is shopping. I don’t spend time worrying about whether or not I should buy a PS5 or a coffee grinder.

I have carried some ridiculous things in the past though. I’ve had a soda stream machine, a blender, mosquito coils and a poncho. But now I only carry what I need. Here are some items I use most and wouldn’t travel without:

1. A sharp knife. Hardly any airbnbs will have a sharp knife and trying to prepare meals without one blows. I used to carry a proper kitchen knife until it was confiscated at Eurostar customs so now I just carry a pocket knife.
2. Moka pot. Small enough to fit easily in a suitcase without taking up too much room and they are made from lightweight aluminium. All you need is a hob and some ground beans and you’re set.
3. Eye mask. Not many airbnbs are fitted with blackout curtains and I spend most of my time in places during the summer so the sun rises early.
4. Barefoot trainers. Small and lightweight, I use these for running and hiking.
5. EDC. Every Day Carry. This is a small kit of emergency items that I carry everywhere. It includes a Swiss Army knife, spare debit card, needle and thread, compede blister pad, small torch, etc.

Final thoughts

Reflecting on my journey from the early days of freelancing in London to a life of constant travel, it’s clear that working remotely has both its challenges and rewards. Over the years, I’ve learnt that while remote work offers unparalleled flexibility, it also demands a great deal of self-discipline, tolerance and adaptability.

Ultimately, the key takeaway from these five years is that remote work, much like any significant life choice, comes with its own set of trade-offs. Yet, by focusing on personal wellbeing and maintaining a structured approach to work and life, it’s possible to create a fulfilling and enriching remote working life. Whether you’re considering a similar leap or are already on your journey, these insights and lessons can help guide you towards a balanced and productive nomadic life.