Being able to work from anywhere you want in the world is as amazing as it sounds. You get to earn a living while meeting new, exciting people in stunning locations across the globe. You get to try new foods, go on adventures and can spend weekends exploring a different city. But behind the fabulous selfies of people with laptops on crystal clear beaches and the Instagram photos with views to die for, there is a lot of effort involved to make it all work. It isn’t as easy as it seems, and it can be downright overwhelming at times
Working from another country takes planning, which is not my strong suit. I would argue that a lot of people who choose this kind of lifestyle like the free nature of it all and being able to go wherever you please whenever you want. Digital nomads value their freedom above all else, but the actual lifestyle isn’t as carefree, fly by the seat of your pants that is often imagined. You need to choose your destination, figure out your flights, find out the visa process and apply for a visa, plan how long you want to be there, sort out where you want to stay, find the best neighborhood to stay in, look into coworking spaces (if you prefer working from them) and so on. So, without further ado, here are the ups, downs, the highs and lows of working remotely from another country:
While you can travel to most countries on a visitor’s visa, depending on your residency, there are times you may need to pursue a work permit. If you plan to work from a country long-term, a visitor’s visa won’t work for you, but there are tons of options. Germany offers a freelance visa that can be extended up to 3 years. Czech Republic and Spain offer year long visas you can apply for and Mexico even offers a temporary resident visa that allows you to stay for a year and renew for up to three years. There are many more countries offering long-term visas, and even quite a few that have developed visas specifically for digital nomads. While the process of applying for a visa can be daunting, it is a necessary part of working remotely. Keep in mind that some countries have significantly longer visa processes than others, so don’t wait until the last minute to apply for one.
As a freelancer, filing taxes can be a very complicated process. A lot of things factor in like how long you were out of your home country, which countries you worked in, the type of work you do, your residency and more. This is one of the greatest pain points for digital nomads and you’ll often see it as a topic of discussion in remote work and travel groups. While the process can be a headache, having the support and advice of a group of fellow digital nomads can make this process a lot easier. We have frequent discussions on finances while abroad and quite a few tax experts in the WiFi Tribe group, which I have had to lean on more than once, that can help ease you through the process.
There will be times when you get to a brand-new country, get settled into your apartment, and realize that the internet speeds aren’t efficient for your work needs. Or that there are rolling blackouts in the area. Or that your new sim card doesn’t work well. A lot can go wrong with connectivity, which is the lifeblood of remote workers. Seasoned travelers will make sure to bring back ups, like MiFi devices, so they’re never truly disconnected. This is also when traveling with a remote work and travel group is super beneficial. They can warn you of upcoming blackouts, which happened daily while I was in Cape Town, and provide those extra MiFi devices for free when needed. I wasn’t aware of the power outages when I got to Cape Town, so it was hugely helpful to be traveling with WiFi Tribe to have a backup whenever I needed. One less thing to stress about!
As a digital nomad you kind of have to be comfortable with a level of uncertainty. A lot of freelancers and remote workers don’t have a typical salary paid job, meaning that their pay isn’t going to always be the same from week to week. It can be difficult and stressful to have fluctuating work and can make you enjoy the whole experience a lot less. If you are one of those people who aren’t guaranteed a certain paycheck each month, it’s helpful to choose countries with a low cost of living and to try and build some savings to fall back on for those slower times. I will admit that I am someone who transitioned to freelancing without savings to back me up, and my experience was ten times harder because of it.
Working through weekends and holidays and feeling utterly swamped often comes with this lifestyle. You definitely see both sides of the coin when traveling with other remote workers. There are full-time workers who are employed by a company and have set hours, but get holidays and benefits. Then there are freelancers who work flexible schedules, but aren’t able to take time off and have to pay for benefits out of pocket. To avoid burnout, make sure you take the time to enjoy the place you live! Even if it’s just enjoying a quick sunset between calls, taking some time off work to explore and enjoy is the reason we all love this lifestyle, so take advantage of it.
This is a big one. If you are going to be working and traveling long-term, it’s important to invest in good health insurance. You want to be covered for any accidents, as well as routine health concerns you may have throughout your travels. Luckily, travel health insurance tends to be very affordable and can offer great coverage depending on your specific needs. When I know I’m going to be traveling for a long period of time, I tend to do my physicals and any necessary exams before leaving to avoid the hassle, but plenty of plans cover those visits while traveling if needed. Do the research and find a plan that suits your coverage needs and the countries you plan on visiting.
An Ever-Changing Office
Working from a gorgeous beach, fun cafes and rooftop bars is one of the most brilliant parts of being a digital nomad, but it’s not always conducive to every kind of remote worker. I am one of the unlucky ones who has a decent amount of work calls each week, and therefore have to have a very reliable connection and a quiet place to take my calls. This tends to leave cafes and bars out of my scope and instead I tend to take my work calls from coworking spaces or my apartment. I have had times where I had a call fast approaching and was frantic to find a good place for a call. Cusco, for example, created some big problems for my workflow. My apartment didn’t have a very good connection, but the local cafes were too loud or lacked wifi for a solid call. I ended up spending my first week scouring the city for the best cafes that were a little more subdued and offered wifi and had to spend most of my workday in those spots in order to get all of my work done. It can be a gamble finding your new “office” in a foreign country, so doing some research beforehand and reaching out to fellow travelers who have already been there is a great way to get on top of it before problems arise.
Working remotely requires a lot of self-motivation. You need to be able to juggle your meetings, deadlines and work while also exploring a totally new place. There will be times when you have to work late and will miss that incredible happy hour at sunset, or times when you have to pass on a weekend trip to meet a deadline, and it can be tough for people who aren’t used to so much autonomy. You also might be working in a different time zone, meaning that you work late nights or super early mornings. You need to be able to make sure you’re waking up on time and accommodating the hours your work needs. It’s helpful to be traveling with other people working in a similar timeframe so you can have support and company during your long nights or early mornings.
Moving from country to country every month, or even every few months, can make some people feel a little lost. You may find it hard to make lasting connections when you’re always on the move and can miss the feeling of having a place to call home and feeling somewhat settled. Most digital nomads thrive on the unknown, but if you travel long enough you will experience some feelings of loneliness at some point. I have traveled while working by myself for months at a time and it can be tough. You can join groups, tours, cooking classes, coliving spaces, coworking spaces and the list goes on and on in order to meet some new people, but after a while even those can get old. I would recommend coupling solo travel with months where you travel with a group. It’s a great way to get the best of both worlds. You can experience the excitement of being alone in a foreign country and balance it out with the comfort of traveling with likeminded people who can become lifelong friends.
These are all things that can cause stress and make you feel overwhelmed when planning your next trip, but they are all also easily manageable! You just have to put in the work and research beforehand. If you truly hate to plan or find some of the above too difficult to navigate, you can always travel with a remote work travel group. I often travel with WiFi Tribe and find those trips to be a lot easier to enjoy and tend to do the most exploring when I’m with a group of people who are also working while traveling. It is also a great way to learn even more about the country you’re visiting since you have 15 people looking into the best experiences in the area. However, you choose to travel, whether in a group or solo, your remote working experiences will be some of the most valued memories in your lifetime and its certainly worth the research (and headache) that sometimes comes with it!