The Trials and Tribulations of Working Remotely

Christopher Johnson
The Collective
Published in
5 min readApr 20, 2017

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It’s always been a dream of mine to travel the world surfing and exploring, but for many of us, we need to make money along the way. Here you’ll get a few opinions on the upsides and downsides of remote working from an inexperienced digital nomad. Below I’ve outlined a few of the apparent downsides that i’ve discovered about remote working, and how it can affect your work. Don’t worry, there’s always a silver lining!

It’s Not as Cheap as You Think

It seems everyone in the tech industry has a dream of traveling to cheap countries, hanging out, exploring and working to supplement the lifestyle. The goal is make first-world money while spending third-world money, but travel isn’t cheap, and things add up. Maybe the seasoned world traveller can do it on $10 a day, but for us newbies, it’s a bit different.

Flights and Airports Are Expensive

Airline tickets are expensive, there’s no way of getting around that. You can play the points game, and sometimes get lucky, but the cost still adds up. If your going away for awhile, your bags will be heavy. Boom, extra baggage fee. If your traveling with any sports equipment (for me surfboards), absurd baggage fee. I just flew down to the Bahamas, and my extra baggage fees where about the same as my ticket. Hanging out at the airport for a few hours to kill time before your flight? You need to eat, so there’s $15 gone to airport food. I’m sure you can think of other ways to squander your money at an airport, after all, that’s all they’re good for.

Other Transportation Costs Money

Taxi rides to and from the airport always cost a bit, take 2–3 of these a month, and you will see how the cost can compound.

For those of us that see our time as money, it’s important to realize that while living the nomadic life, there will always be 1–2 days a month where you will be in transit and not able to work. Unless you are going to a location with super easy access, you’ll have to allot one full day to transit and getting settled. Hopefully you can plan these days around a weekend, but it doesn’t always work out that way.

Other Costs

One important thing I didn’t take into consideration when going international was my cell phone plan. Once settled, I’m on Skype and FaceTime, but mark my word, there will always be times when you need to turn on cellular on your phone and make a call. Has the internet gone down and you have an important call you need to do? Gotta use cellular. Stuck at the airport with no wi-fi and need to get in touch with someone? Cellular. This is something you need to be super diligent about, but always factor in $20–30 a month for these rare times when you need your phone.

Sometimes Nothing Gets Done

Part of the reason why we travel to such cool places is to gain new experiences. Sorry to my co-workers, but when it’s 85 degrees with offshore wind and a 4–6ft north swell hitting the Bahamas, I’m going surfing. Obviously not everyone is a surfer, but maybe you get invited by some cool locals to go check out a really cool hike that you’ve been dying to do, and they wan’t to go at 2pm on a Tuesday. Looks like your work might take a back seat. One may argue that this is an irresponsible outlook on the concept of remote working, but let’s be real, we are in cool places and want to do cool things. Sometimes our motivations lie elsewhere.

Understanding Things We Take for Granted

Coming from New York City, there was a lot I took for granted before traveling overseas. We find solace in the security that a modern first-world country gives us. More often times than not, it’s the little things we take for granted, but these little things can add up. Below I’ve outlined a few…

Wi-Fi Connection

Many places worth going to have really bad internet connections. Your AirBnB might tell you it has Wi-Fi, but there will be a time when you show up, and it’s a dial up connection hooked up to a router (Hey, it’s still ‘wi-fi’ they say). As a Web Developer, I’ve been able to sneak by, believe it or not, we don’t need the fastest internet connections to get work done. Keep this in mind, and beg your AirBnB host (or whoever your staying with) to be upfront about the connection. I’ve found that asking if they are able to stream Netflix or YouTube is a good indicator as to how good the connection is.

Our Time

Things move at a different pace in different places. Coming from New York City to the islands, I was stuck expecting everything to move at light speed. Boats will be late, stores won’t be open on time, etc etc. It’s important to get used to this, and once you do, you’ll find that you are far more relaxed by relishing your time, instead of trying to move through your day as fast as possible.

It’s Important to Be Resilient

It’s important to roll with the punches on a journey like this. With travel, everything that can go wrong, will go wrong. Keep low expectations! This is supposed to be fun, so don’t let the hiccups bring you down.

A lot of us are trying to do this on a budget, so most likely our accommodations won’t be luxurious. Get used to a few cockroaches here and there, no AC, no laundry for weeks, no workspace at a five star infinity pool overlooking crystal clear Caribbean water, etc, etc. Once you let these things go, you’ll find your world opens up to numerous different, cheap places to stay and explore.

Schedule is Everything

We sacrifice the office, but at a cost. When I used to work at an office, my day was scheduled like a well oiled machine. Wake up at the exact same time, shower at the exact same time, get the same subway every day, and make it to work by 9am on the dot everyday. The rest of the day was not much different. Everyone works differently, but for me schedule is very important. My first few weeks working remotely were spent floating through my day. I ate lunch when I was hungry, and started work sometimes as early as 6am. I quickly realized that this was not a sustainable way of living, and put myself on a somewhat regimented schedule. Needless to say, it’s helped. We don’t have anyone policing us out here, so it’s important to stay diligent and keep a conscious eye on yourself at all times.

…But The Upsides Certainly Outweigh the Small Downsides.

Yes, they do. For a small price, we get to experience so many different things and explore amazing places. Keep low expectations, get your work done, and you’ll see how lucky you can be! Working remote and traveling is a huge learning experience, and I hope to get better at it in the future. Seriously, please let me know if you have any insight into any of this stuff, I’m eager to learn more.

Check out The Collective at:

www.thecollective.io

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Christopher Johnson
The Collective

Designer, developer, and co-founder at The Collective.