The last four months I’ve been traveling in South America while working remotely with the help from my best friend called the Internet. As a matter of fact I’m writing this blog post from Cusco, Peru. And so far I’ve picked up a couple of tips and tricks based on lessons learned and I though I’d share them with you.

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The challenges

So you’ve decided to travel and work at the same time. What could be so hard about that?

You need to actually work

Your boss agreed for you to go through with this because you were going to work 100%, right? And what’s so hard about working? I can tell you right now that it will be incredibly hard to work when you arrive in a new city where all you want to do is to go out and experience the culture; eat the food, drink the beer, go hiking, smell the smells or whatever. Staying inside in your Airbnb apartment or at your local café working 8 hours is more challenging than you’ll expect. Be prepared for the mental challenge. There’s a piece of cake right in front of you all day and you’re not allowed to eat it.

Time zones

Before traveling to your next destination, figure out what the time difference is between that spot and your office back home. Chances are it’s a pretty big difference and you want to be available to your employees when they are at work. They didn’t ask for you to travel and they shouldn’t have to wait for you to get up in the morning to be able to do their job. If you have employees back home whom rely on you, you will have to adjust to their schedule and not the other way around. I currently wake up at 05:45 to be available for my Norwegian colleague at 11:45. It’s not too bad once you remind yourself of all your benefits and what adventures are waiting for you the upcoming weekends.

Pro tip: If you want to go somewhere with a major time difference, try to schedule your trip to when there’s a summer/winter time schedule which can benefit you. I stayed in Brazil for three months and because of the winter time it was only a three hour difference rather than the regular five.

Getting in to the flow

Once you arrive in a new city it will take quite a bit of time and energy for you to settle down and be able to sit down and actually work. From my experience it takes around a week to have a 100% working flow going in a new place. I’m not saying you won’t be able to do your job the first week, it’s just that you’ll maybe spend a bit more time on certain tasks than you otherwise would. Why? Because everything will be new to you. Just setting up your workstation, finding a stable Wi-Fi connection, getting comfortable with working in a cafe. These things slow you down the first couple of days.

Pro tip: Before you decide what your new destination will be, do tons of research on your Airbnb apartment/hostel to find out if there’s a table, a chair and a good Wi-Fi connection. This is all you need for a kick start to get in to your regular working flow. If you end up going to a place where the time difference is big, you can’t rely on cafés since they have opening and closing hours which doesn’t necessarily fit with your working schedule. A good Wi-Fi at your Airbnb is crucial.

Why you should do it

Other than the obvious “you’ll get to travel” argument, I have a couple of other good ones I think will surprise you.

You’ll get under the skin of each place you visit

Since you’ll be working 100% you can’t travel to new destinations as often as you would be doing if you were on a normal vacation. You should aim at staying at a place at least three weeks at a time for you to have a good work flow. This is only a positive thing as you’ll be able to see much more of the city you’re visiting. You’ll see much more than an average tourist will when he/she is visiting the place you’re staying at for a weekend. You will even get to learn a new language depending on how long you stay.

You’ll grow as a person

Having to wake up super early or work in the evening will be a challenge. Over-documenting your work so that your colleagues back home won’t hate you will be a challenge. Getting your work done on a small laptop screen in a café with lots of crying babies will be hard. Juggling work and vacation will be super hard.

If you want to keep your job you’ll have no other choice than to be extremely disciplined. This will certainly make you a better person and benefit you when you get back home.

Downsides

Yes, there are some downsides to this. But they are minor if you learn how to tackle them.

It can get lonely

If you’re working 5 days a week 8 hours a day from your Airbnb apartment, chances are that you’ll feel isolated and alone. You don’t have your silly colleagues available whenever you want. The goofy guy in the office isn’t there to make you laugh. And if you are the goofy guy, you can’t be there to make everyone laugh. This is harder than you’ll expect. In the beginning of your stay in a new city you probably don’t know one single person and talking to a stranger in a super market isn’t giving you enough of what you need of daily human interaction. Even though I have my girlfriend as a travel partner I’ve had moments of feeling lonely and slightly depressed. So how can you avoid it?

Pro tips:

  1. If you have the money you could even rent a desk in a co-working space. There you’ll maybe even make some new friends and you won’t be alone during the day.
  2. Use a service like Meetup to find a community for the field you’re interested in. If you’re a web developer like I am you can be sure there’s some kind of web dev meetup or a WordPress meetup.
  3. Sign up for something that takes you out of your comfort zone for the sole purpose to meet people. Activities like yoga and cooking classes can sound awkward to some people, but it’s awesome for meeting new people and getting to know the people in the city you’re currently living in. (I did jiu jitsu in Brazil and it really helped me with integration and the language.)

Summary

If you’re as lucky as I am and have a job and an open minded boss which allows you to do such a wonderful thing as combining travel and work I say go for it. A wise man once gave me a piece of life advice I’ll never forget: YOLO.