This is part 2 of “The Pitfalls of Remote Work + Travel and How to Avoid Them”. Go here to read Part 1. Guest post written by Shira Weitz, traveler, actress and blogger extraordinaire.

We’ve discussed how to be prepared financially for digital nomad life and productivity hacks in Part 1. Now, let’s get on to other common pitfalls and how to deal with them.

What time zone am I in and is this due today or tomorrow or infinity?

One of the most difficult challenges to factor in is working with people in totally different time zones. More than once, I’ve been confused about whether I had more time to complete an assignment, or less, due to the differences. It can be quite disorienting! Especially if you’re constantly changing what time zone you’re in.

How To Avoid:

First and foremost, be upfront with people about where in the world you are and what you are doing so there’s a mutual understanding that it might be more difficult for you to be available at the drop of the hat. I guarantee you that just being upfront will take some pressure off of you from the get-go. 

If your job requires face-to-face meetings, schedule them in advance. If you have several meetings that you need to attend, pick a regular day of the week to make them happen so you can always plan your travels around them. 

Personally, I let people know off the bat that I prefer email to calls or face-to-face, but sometimes there’s no avoiding it. Set alarms on your phone so that you know when the workday is beginning, and you can be on the lookout for emails, Skype and Slack messages, etc. around that time. 

A big benefit of a location-independent job is that you can live on your own schedule, so—depending on the work you do—you have the luxury of getting it done as it suits you, as long as you stay on top of your due-dates.

Loneliness is a long road

One of the biggest unforeseen challenges is that traveling solo can often get lonely. Sure, there are a number of other travelers you will meet along the way, some who you will hit it off with and others who you won’t have the energy to put forth the effort to get past pleasantries.

Despite the dozens of new relationships and your growing international friend base, most of the time you know that they will wind up being long-distance, sometimes never to be seen again. Not to mention, when you don’t have a place to call home, the temporary aspect of your life can make you feel even lonelier.

How to avoid:

I personally like to carve out some time (though not often) to shamelessly stare at my screen and message back and forth with friends and family from back home. During this time, no one can come between my phone and me! Yes, it’s not in person, but it really helps

You can also quench your thirst for connection by staying in one place for a longer period of time. This can be tough for people who like to bounce around a lot, and it’s not guaranteed you’re going to click with someone in a certain place, or that someone you click with will stick around. However, you still increase your chances of getting to know locals, your host, and other like-minded people. 

co-living combats loneliness

If you chose to stay in a co-living space (like seen above) then your living situation basically comes with a new set of friends who are probably on a similar journey. Additionally, if you do work exchange programs, like HelpX, you have the opportunity to get to know people more intimately as they’re letting you into their homes and daily lives. 

It’s not uncommon for digital nomads to meet up for a stint and conquer new places together. It might take a bit of time to establish yourself enough to feel comfortable taking this on, but a like-minded group makes it easier to find longevity in relationships. And, unlike other travelers you’re sure to meet along the way, digital nomads will be able to relate more to your goals, experiences, and struggles, and therefore you can establish meaningful bonds more quickly.

There’s also a plethora of apps, both for dating and for friend-finding, (I like Bumble and Tinder.) Be clear about what you’re looking for in your profile. As the number of digital nomads grows, so do social resources!

Am I packing too much, or too little?

Packing the right amount of the right stuff is TOUGH. If you’re on the road long term, you’ll experience multiple climates and seasons. This begs the question, which is worse? Having to lug around a ginormous and heavy suitcase? Or having smelly clothes, and possibly being uncomfortable?

And also, how am I going to look good in all my photos? 😎

How To Avoid:

First of all, with packing, you’re never going to win this game 100%. You’ll have to make sacrifices somewhere, so be prepared for that. In the meantime, don’t wait until the last minute to pack. Start putting your wardrobe together weeks in advance! 

When you’re wondering how to prioritize, start with comfort. It’s more important to make sure you have all the necessities than to make sure you have three different shades of blue dresses. Make sure you have warm layers for cooler climates.

And, leave room in your luggage for more. It’s pretty much guaranteed that you will be collecting items throughout your travels. This isn’t to say you should wait to pick up necessities or leave important items behind, but you should bring a pack large enough to have the ability to build as you go.

Backpack vs. Suitcase? Everybody will have their own preference, but I have learned that a large hiking backpack such as the Deuter ACT Lite 60L makes it easy to be mobile and doesn’t put too much strain on your back. The buckles around your hips allow you to carry heavier weight while distributing the pounds. Suitcases—even the rolling ones—are good to take the weight off, but when you’re traveling through cities with a lot of winding stairways, or hiking up mountains to find your next spot, it’s going to be a pain.

For long-term traveling, I can’t stress enough the importance of diversity in your wardrobe. If you have any items that only match one or even two other things in your wardrobe, replace it with something that can mix and match which several other items. Trust me on this one.

Practice makes perfect! You’ll learn as you go, but make sure you do a trial run of wearing your packed bag with at least a couple of weeks to spare, so that you know you can manage the weight and adjust accordingly.

I hope this mini-series helps you tackle some of the pitfalls and challenges of digital nomad life. Good luck out there, and feel free to share your tips below!


Where to next? Find flexible month-to-month rentals across the globe on Anyplace.

Shira Weitz
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