No Wrong Turns: The Pros and Cons of Taking your Work Traveling

Three weeks before Tom and I left on this trip, a work opportunity came up allowing us to work remotely from Mexico. At first we weren’t too sure whether it was the best idea and initially we declined the offer, but after a little convincing and our joint realization that earning while traveling could keep us on the road longer we decided to go ahead and agreed to take the contract. It seemed too good to pass up.

Working while traveling is much more feasible now than it has ever been before. Laptops, teeny tiny portable hard-drives, the expansion of wireless internet, email, online storage facilities and companies like Skype have made connecting around the world easy. Some people (like Gadling blogger Tynan) have chosen to forgo the office and squeeze all they need, their life and office, into their backpacks. To most people this sounds like “living the dream” and although it is hard to complain when you live 10 minutes from the beach, working while traveling isn’t all it’s cracked up to be.

Here are some positives and negatives of traveling with your work:

  • Living Abroad: It’s amazing to be able to work in a foreign country. Days off are suddenly filled with amazing adventures, meeting new people and experiencing a new culture. You can set your own hours and determine when you take breaks and what you do on that break. (We surf on our time off.)
  • Live Where You Want: You get to choose what type of new environment to work and live in. Living in an area for an extended amount of time allows you to meet new people and build closer relationships whereas when you are just passing through you can easily miss out on these types of opportunities.
  • Cheaper Living: Some countries have lower living costs which means you can save money while continuing to earn. This way you get to pocket more of your earnings for more traveling.
  • Great After Work Adventures: When you are done work you can head straight to the beach or to whatever activity you feel like.
  • Taking Care of Yourself: A sore back caused by work means you should treat yourself to a massage and write it off as a business expense.
  • Technology Saves the Day: Portable technology is a good thing! There are amazing gizmos out there to help you save all your important info just in case your computer conks out. BUY A BACK UP HARD DRIVE and save all your important info…often.
  • Delays Aren’t an Issue: Being delayed can mean more time to explore the place you are working in. I try and look at it as more time for me to continue learning to surf. And when it all said and done you are getting paid to live, work and explore another country. Things could be much, much worse.

But there can be a negative side too:


  • No Face Time: Lack of face to face time with clients / employers can make it difficult to quickly solve work issues. Instead of being able to go in for a quick meeting you need to organize phone calls based on time differences while taking into account everyone’s already busy schedules.
  • Distractions: You will have to suffer through some unique distractions. Dogs barking, roosters crowing, goats baying and loud reggaeton music at all hours are some of the noises that we have experienced while living in the Baja. These disturbances can cause a bit of stress when deadlines are closing in and you can’t focus on the task at hand because the neighborhood dogs have chosen to perform a six part harmony of howls right beside your window.
  • You Really DO Have to Work: Set deadlines means that you have to stop and actually do the work. Some days it is the last thing you feel like doing especially when the sun is shining or when you are recovering from a party the night before.
  • Poor Office Set-up: Prepare for a sore back. Ergonomic chairs are nowhere to be seen unless you somehow find an actual office space to work in. Hunching over your computer in your palapa is going to do a number on your back. (The photo is where Tom and I are working, note the blanket on the chair in attempts to soften the rather hard seat)
  • Lack of Computer Help: Depending on where you choose to work finding a computer tech could be pretty difficult. Computer issues and malfunctions can happen anywhere and they can be a huge mission to deal with if you are far from the Apple genius bar.
  • Delays Can Make You Wait…Even When You are Ready to Go: Sometimes projects get delayed which can be a huge bummer when your planning your next move and all of a sudden you can’t leave. Try to have clear end dates to ensure that you stay on schedule, both work-wise and travel-wise.

Really we can’t complain — we are living in Mexico, surfing and earning while we are at it. We’ve already made some great friends and spent time exploring the interesting town we are staying in. If you are going to try to work while you are traveling it is important to be aware that although rewarding it can create some unusual challenges that you wouldn’t encounter at home. But with the right attitude and decent problem solving skills working while traveling can be a great way to see the world.

“No Wrong Turns”
chronicles Kelsey and her husband’s road trip — in real time — from Canada to the southern tip of South America in their trusty red VW Golf named Marlin.