Going Remote: Preparing to Work For an Extended Time Abroad

by Kaitlan Whitteberry on August 25, 2017

Flashing back to December 2016, I was diving deep into this relatively new world of working while living abroad after reading an article by The Remote Nomad. I started feverishly researching companies like Remote Year and Hacker Paradise, increasingly curious about how working and living abroad for months at a time could even work. I took a leap, and with iOFFICE’s blessing, was accepted by We Roam, signing on to work 3 months in Europe during the summer. I was filled with both elation and anxiety. Exactly what did I sign up for? Here’s everything I wish I had known before hopping on my one-way flight back in June. 

Prepare Yourself for Working Remotely

For some of my fellow travelers on the trip, this was their first attempt at working abroad. Ever. Some didn’t even tell their employers they were going on the trip (don’t worry your secret is safe with me). As an experienced remote worker with four years of working from home under my belt, I felt confident in my ability to continue to perform while abroad – and yet even I had a bit of trouble adjusting.

If this is your first time working away from a traditional office, it might be a good idea to ease slowly into the remote working lifestyle. Try working from home a few days per week, and then give yourself a test run a few months prior to planning a big trip. The worst thing to happen is to get half way around the world and realize you need your supervisor sitting next to you to do half of your job, or that you can’t get anything done unless you have your favorite desk next to the window. Working remotely means being flexible with where and how you work, and that often takes practice.

Prepare for Unexpected Costs

So you’ve booked your flights, and your housing, and budgeted x amount of dollars for food, fun and frivolous expenses. Now take that budget and add an extra couple hundred to it, per month. It’s true that certain things cost less when traveling abroad, but certain things definitely cost more.

For example, European airlines often don’t list the cost of baggage fees or seat selection until the very end of your reservation. So the initial price looks low, but you end up paying a normal rate in the end. If your laptop battery dies or your converter breaks, it can be costly and time consuming to have one sent to you. If you plan to rent a car, know that all the insurance in the world still won’t cover the fee for a flat tire. And in some countries, like Sweden, you have to pay a fee to just enter the city in a vehicle. Know your bank’s cash withdrawal fees and percentage charges before you leave, and it might even be worth switching banks to avoid a surprise bill when you return home. Leaving room in your budget will ensure you can still get your work done while avoiding the stress of living within your means.

Prepare for Healthcare Setbacks

No one likes to be sick at work, and it’s looked down upon if you show up to the office with a hacking cough. However, in the states if you do get sick you likely would stop by Walgreens on the way home, pick up some medication so you can get through the symptoms and do your job.

While abroad, it isn’t that simple. Your body is going through serious changes from time-zone shock to consuming a new breed of tap-water and ingesting street kebabs that looked rather questionable (don’t ask). Even healthy people are bound to feel the pains of travel, and it’s not as simple to bounce back as it is back home. Bring with you all the medicine you think you might need, plus any you believe you might not use but know would be nice to have. Have the location and numbers of the nearest pharmacies and hospitals in every country you’re staying in on hand.

Prepare for Loneliness 

This is a topic many people shy away from, mainly because it’s sensitive. However, it’s something that everyone should prepare for when traveling alone. While working from home can often foster feelings of loneliness, adding a foreign country to the mix only intensifies this feeling. It’s not just the people back home you’re going to miss, but not being able to speak to the grocery cashier, not hearing familiar phrases and sounds and seeing English text on ads can heighten the feeling of isolation even more. If you’re not traveling with a group like Remote Year, consider joining Meetup or another online site to find fellow freelancers to hang out with.

Aside from feeling lonely in your personal life, working remotely abroad can make it difficult to feel connected to your team back home. Even through video chatting apps like GoToMeeting, and applications like Slack, nothing beats face-to-face contact. It can take serious effort to stay on top of everything going on at the office to avoid sounding like you weren’t paying attention during the last call. Know that when working remotely, it’s your responsibility to fill yourself in on what’s going on back home, and this can be a challenge for some people.

Prepare for an Experience Unlike Any Other

Would I do this again? Absolutely. Have I learned more about myself in three months than I have in the past three years? Absolutely. Is this for everyone? Absolutely not. Choosing to travel while continuing to work is now a choice many employees have the privilege of making. While it doesn’t make sense for every person, it can definitely be worth the effort for others.

I feel so much more capable as an employee and as an independent person than I ever have before.

Things go wrong, and you are forced to fix them, often alone. You meet some of the most fascinating people, and some of the most kind, generous, selfless people. And, unfortunately, you also meet some of the most malicious. It allows you to appreciate all the opportunity you have back home while also showing you ways of doing things that other countries do better. It reminds you that though people can be so different, yet somehow they can also be the same. It presents the world in a way that no book, blog post or movie can. It truly shows you. And I hope everyone has the opportunity in their life to see that.

Photos courtesy of Alex Martin with We Roam. 


Kaitlan Whitteberry

Kaitlan Whitteberry is a Magna Cum Laude graduate from the University of Missouri's journalism program, and currently focuses on iOFFICE press releases, software updates and related news.

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