What I Wish I Knew Before Working Remotely Around The World

What I Wish I Knew Before Working Remotely Around The World

In the last 14 months, I’ve been home for only two. The other 12 were spent vagabonding around the planet, working on my laptop in Tokyo, Hong Kong, Paris, Barcelona, and more. It sounds wonderful, and I was certainly privileged to do so, but I learned quickly that while rewarding, it also brought real, serious mental and physical health challenges.

Images by Stephanie Lee, BVStarr, Karen Hong Photography, Muffet, and Patryk Kosmider.

For context, here’s a little background: I’m a freelancer and fortunate enough to do all of my work online. Before this, I’ve only ever known Big Corporate Life, and I never thought a life without roots could be possible or sustainable. A little over a year ago, I took the leap and realised I could do what I did pretty much anywhere in the world (as long as there was internet.) So I asked myself, why not in Tokyo? And then I was off.

Actually, it wasn’t that simple: there were more steps behind the scenes. And it just so happened that my own circumstances were right: I had avenues for steady income, but no family obligations, dependents, outstanding debt, or anything that would keep me from taking off at any time. I could pick up and just go, but like any path in life, that has ups and downs.

Sleep Gets Very Elusive, So Learning to Sleep Anywhere Is Indispensable

What I Wish I Knew Before Working Remotely Around The World

We all know how important it is to get enough consistent, quality sleep. But booking it from one end of the earth to the other and the constant time zone changes wreaked havoc on my sleep quality and schedule. When I went to Paris — a 9-hour time difference — the jet lag hit me so hard that I literally only slept once every two days for a week and a half. That’s just one instance of many, and it’s surprisingly easy to brush off these little “setbacks” with so much wanderlust-fuelled adrenaline. In the end, I let this cycle of crappy, disturbed sleep go on for far too long, and my body paid for it: I gained some weight, I got sick three times in a couple of months (versus once prior in a few years,) and I just didn’t feel healthy.

It doesn’t help that I’m a light sleeper. I wake up constantly to use the restroom and little things keep my mind racing. This all meant that having to sleep in unfamiliar places, on different surfaces and bedding, and in different climates made sleep even harder to get. If everything else was going to shift, I realised I needed certain constants to essentially trick myself to be able to sleep consistently well, anywhere.

Enter my “sleep anywhere” kit. It’s nothing fancy and is only three things, but it’s been a game-changer. Basically, I have a sleeping mask (I like this one), a pack of earplugs, and this podcast that tells intentionally nonsensical, meandering bedtime stories to put me to sleep. (I use either the ear plugs or the podcast at a time, obviously.) I try to use them during flights, too, but I haven’t quite mastered the art of sleeping on planes yet, unfortunately.

The Allure of New, Exotic Foods Makes It Easy to Overindulge 

What I Wish I Knew Before Working Remotely Around The World

I’m convinced that you won’t get a full travel experience without plunging mouth-first into Tonkatsu ramen with a perfectly soft-boiled egg in Japan? Hell yes! A fresh baked, buttery croissant in Paris? Uh, of course. It’s like the possibility of never eating it again at this place makes these things all the more irresistible. This is fine in the short term, but long term? Not so much.

Free-for-alls at restaurants two or three times a day are deliciously amazing, but it’s also a good way to limit the variety of your nutrients. For example, getting enough protein takes way more effort. And in Japan, unless you intentionally seek out fresh (or pickled) vegetables, you’d be hard pressed to get them. Few restaurants serve any substantial amount, because they’re so expensive.

Additionally, my overconfidence made my spiral into unhealthy eating even worse. I’ve been tracking nutrition long enough that I knew I could make good choices, wherever I was, and could get back into “proper eating mode” whenever I wanted. Or so I thought. I caught myself thinking, “I can get back on track when I return home…eventually” right before inhaling something tasty.

But that line of thinking is exactly the counterproductive rationalization many failed dieters make. That you can put off starting a healthy eating plan until the next day or week, when you’re confident that future you will be strong-willed enough to actually change, for real. We all know what actually happens most of the time.

In the end, my solution was a return to basics: build a more structured eating plan, one that involves cooking my own food for breakfast and lunch and allowing myself more flexibility with dinner. When you travel, this isn’t easy. I first had to make sure I had access to a kitchen, which I usually emphasised when choosing my place to stay, and often had to get creative with the locally available foods at local markets and street vendors. Once I started, it was a good change, and the cooking saved me money, anyway.

The Changes in Environment Hurt Productivity and Make It Hard to Stick to a Routine 

What I Wish I Knew Before Working Remotely Around The World

When you’re in a foreign place, every day is a fresh series of questions: What will you eat? (Everything!) What will you see? (All the places!) But how will you get there? Will this coffee shop let me work there? Does it have reliable Wi-Fi? All these uncertainties seem exciting, but therein lies the kicker: every unknown variable, every wrench in the works, eventually leaves you feeling drained, or at a loss of what to do next. Put another way, when everything is familiar, you waste less energy on basic stuff in your day to day. When it’s not, you need all of the mental and emotional help you can get.

Being familiar with your environment means you inevitably fall into a routine, something I always took for granted until I didn’t have one. Without a routine, I spent more time thinking about where to get groceries or whether this coffee shop had a suitable working space for me, and less time thinking about what I wanted or needed to work on, whether it was health or job-related.

Even old habits can get lost in a state of flux, so it’s important to adapt your habits to your environment. In fact, I found that one routine somewhere may not work that well elsewhere. These days the first thing I do when I arrive at a new destination is spend a full couple of days scoping things out and setting up my routine. Where can I work that has reliable Wi-Fi? What do my meals look like and where can I get them? How convenient is the transportation? Where can I work out? This initial footwork lays the foundation for every other habit I’d build or maintain, and helps me focus and get things done.

It’s a Lonely Road

What I Wish I Knew Before Working Remotely Around The World

Unless you’re lucky enough to have a partner vagabond with you, a life on the road gets lonely. Don’t let my Instagram posts fool you too much: many of those pictures were shot from janky selfie rigs. And because I’m away so often, I see my parents and the people I hold near and dear just one or two times in the last year. Others I never actually get to see, but still talk to online. That’s kind of the beauty of the 21st century.

I’m painfully aware this problem is not unique, and I understand I’ve chosen to do this. So I have to deal with it, but the occasional thoughts of this trade-off have taken a toll on me mentally.

I’ve seen other remote workers in a similar situation cope with the loneliness with drugs, alcohol, and excessive partying. For me, I cope by keeping myself busy with work, exploration, and fitness, wherever I can find it. I also love sending people postcards because I want them to know that they’re in my thoughts, and that eases the feelings of loneliness. And of course, I haven’t always been technically alone. I’ve been fortunate enough to chat it up with locals and other travellers, hang with friends of friends, and reconnect with estranged family members. Though brief, these encounters have been very rewarding, and hey, there’s always Facebook.

While it’s easy to fall in love with the idea of working from anywhere and going to all of these exotic places for months at a time, it’s not for everyone, and sometimes, I even wonder if it’s for me long term. I continue to do it, though, because I credit it with helping me build humility, discipline, self-esteem, and confidence.

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