Leaving Work Behind

4 Challenges of Working While Traveling (and How to Overcome Them)

Written by Ransom Patterson on July 5, 2016. 10 Comments

A assortment of travelling equipment.One of the best things about remote working is that you’re not confined to one place, or even one continent. You can work from just about anywhere in the world (with internet!), free to hop from place to place as the mood takes you.

At least, that’s the dream. In reality, we often shy away from travel because, well, working from the road can be tough.

From spotty internet, to delayed flights, to the fear that your client thinks you’re insane because you email them the final draft of a blog post at 4am their time (even though it’s 10am where you are), it’s not all sipping cocktails on the beach while an army of virtual assistants handles every detail of your business.

That said, working from the road doesn’t have to be difficult. With a few simple modifications to the way you work, working from the road is not just possible – it can even be enjoyable.

In today’s post, I’ll cover four problems I’ve encountered while working from the road, explain how I overcame them, and show you how to apply the lessons I learned to your own work.

Let’s get to it!

1. How to Turn Inconveniences Into Opportunities

“A pessimist sees the difficulty in every opportunity; an optimist sees the opportunity in every difficulty.”

~ Winston Churchill

Travel is disorienting. Disorientation is great for exposing you to new perspectives and cultures, but it can also be distracting when you’re trying to get work done. The local store doesn’t stock your favorite coffee, you’re still jet lagged, and there was no room in your carry-on for your favorite wall calendar. You’re out of your element, in other words, and this can make it hard to get into work mode.

But instead of worrying about these challenges, I say embrace them! Because just as traveling can open your mind to new perspectives on life, it can also open your eyes to new ways of working.

For instance, when I was in Barcelona on a recent trip, the place I stayed didn’t have a desk. Instead of letting that worry me, I took my laptop out onto the balcony and soaked in the sun and sounds of the street as I worked.

Street View in Barcelona

Wherever you travel, I encourage you to do the same – it can bring a new perspective and new inspiration to your work. Find a cool coffee shop to work in, set up for a couple hours in a gorgeous local library, or even take your laptop to the beach. For more inspiration, have a look at Sean Ogle’s search for the world’s most exotic office.

2. How to Deal With Limited Internet Access

In the introduction to this post, I mentioned that one of the perks of working for yourself is being able to operate from anywhere in the world…with internet. Those last two words are key, and as connected as the world is these days, there are still bound to be times where you find yourself without a network connection.

Now, there are two ways to handle this situation:

  1. Freak out and spend thirty minutes futilely waving your phone around in the hopes of getting a wifi signal.
  2. Prepare for a lack of internet in advance and use it as a chance to get other kinds of work done.

Personally, I recommend the latter (the former is bound to draw a few strange looks and tire your arm after a while). A short-term lack of internet is actually an opportunity to grow your business, if you use it correctly.

Constant connection, while enabling us to defy geographical boundaries to work, can also be the source of distraction and stress. I can’t count the number of times where I said I’d “take a quick look at email,” only to look up a couple hours later with the sun setting and several blog posts still unwritten.


When you’re without internet, you don’t have to worry about these distractions. Obvious work you can do offline includes things like writing blog posts or code snippets, but you can also use your offline time for higher level business tasks.

Bill Gates, for instance, takes a secluded “Think Week” each year to disconnect and, as the name implies, just think. He credits this practice with giving rise to some of Microsoft’s breakthrough innovations.

Even if you don’t have a whole week, being offline for even a few hours gives you a similar opportunity. Think about it: when was the last time you took thirty minutes just to think about ways you could optimize your workflow, increase your revenue, or even create a product?

It’s easy to get so caught up in the heat of day to day work that you forget to think about these things, but they’re essential for keeping your business out of stagnation.

And on the topic of business optimization, you should also make sure to structure your business in such a way that a few hours without internet isn’t a disaster. Agree to regular deadlines with clients in advance, communicate with clients on a set schedule, and warn clients if you know you’re going somewhere with limited connectivity.

This small amount of planning goes a long way toward making sure that being disconnected is not only stress-free, but also productive.

3. How to Manage Time Zone Differences With Clients

We all know that running your business online expands the pool of people you can work with, but often this also means working with people in different time zones. Even if most of the clients you work with are normally in the same time zone as you, traveling can suddenly place you on the opposite side of the world.

If you don’t manage these differences, it can cause a headache, but you can avoid problems by using the right tools and communicating with clients correctly.

I currently work with clients in four different time zones, and I manage the time differences with the following methods:

  1. Limiting real time communication. Occasionally, I might hop on the phone or Skype with a client for something important, but I do most of my client communication through email, Slack, and Asana. This means that I can deliver work or message clients whenever is convenient for me – and clients can respond on their own time as well.
  2. Setting clear yet flexible deadlines. Very little of the work I do is intensely time sensitive. In general, my clients and I agree on set days for work to be delivered, not set times. This means that so long as I deliver work reasonably early on the due date (or even better, the day before), the time zone differences are of little concern.
  3. Using the right tools and apps. I already mentioned the tools I use for communicating across time zones, but I also use a couple other apps to help me stay on top of the differences. First, I simply have the World Clock on my phone set to all the relevant time zones, in case I need a quick reference (see the above screenshot). Second, I use Calendly for scheduling any calls or Skype meetings with clients, since it enables me to input my availability in my current time zone while displaying it to the client in their time zone.

In sum, managing time differences is no different than any other aspect of freelance work – all it requires is clear communication with clients and the right set of tools.

4. How to Balance Travel and Work

I won’t lie: this is the hardest part of location independent work for me. When you’re traveling to cool new places, it’s hard to strike the balance between working and exploring.

I find myself either getting so distracted by the local beach that I forget to work, or so wrapped up in an impending deadline that I stay locked inside all day, the beautiful beach just a distant blue and gold strip.

Barcelona Beach

Luckily, I’ve found an easy solution: I just schedule set times every day for both work and exploring.

You’re probably used to the concept of scheduling time to work, but scheduling time to have fun is just as important – especially when traveling to new places.

The exact times vary depending on what I’m working on and how much energy I have, and no doubt they will vary for you as well. The most important thing is setting a hard deadline for when to finish your work. This makes sure that you start at a reasonable time and don’t end up working too late.

As a bonus, I’ve found that such hard deadlines, combined with the promise of exploration once I’m done, are a great motivator for completing more work in a given time than I thought possible.


And don’t forget that your schedule doesn’t have to be a standard 9–5. Want to go for a morning bike ride around the city? Want to hike the nearest mountain before it gets too hot? Want to go for an early dinner to beat the crowds? All of these activities are possible when you work for yourself, and you can easily accommodate them by breaking your work into several chunks throughout the day, instead of just one long block.

Balancing travel and work is always going to be a challenge, but introducing a set (yet flexible) schedule makes the balance much easier.


Working from the road may seem tough at first, but you shouldn’t let it stop you from enjoying the location independence that working for yourself allows you.

To recap, you can make working from the road easier by:

  1. Turning inconveniences into opportunities.
  2. Treating limited internet access as an opportunity to work without distractions.
  3. Managing time differences with clear client communication and the right tools.
  4. Scheduling time for both work and exploration.

What are your experiences of working while traveling? What obstacles have you encountered, and how did you overcome them? Share your story in the comments section below!

Image credit: Unsplash.

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10 Responses to “4 Challenges of Working While Traveling (and How to Overcome Them)”

  1. Gayla Groom
    July 5, 2016 at 3:54 pm

    Great aticle! I’ve lived in Mexico and Guatemala for several years now and have encountered pretty much every kind of internet situation. What doesn’t kill you makes you stronger! If the power’s out all day, then the power’s out all day. Your advice to not schedule things too tightly is very helpful — not only because the internet might be giving you trouble, but because being in and working from a foreign environment will bring lots of delays of types you could never have imagined. Still, sometimes things work like a dream.

  2. Joseph Skinkis
    July 20, 2016 at 5:39 am

    To me, my work as a teacher of English as a second language was more like traveling than working. I taught in Papua New Guinea for two years and in China for four years. I also taught for short periods of time in Europe, America, Noth Africa, and Asia.

    Today I work from home in Chiang Mai, Thailand as an editor and as a tour guide in Chiang Mai.

    • Tom Ewer
      July 20, 2016 at 8:48 am

      Wow! They say you should never combine business and pleasure, but how can you not when you’re seeing all those places?

      Thanks for your insight! 🙂

  3. DennyZhang
    October 16, 2016 at 4:59 am

    I like this quote: “Treating limited internet access as an opportunity to work without distractions.”

    As a DevOps professional, I’ve been working from home for over 3 years.

    Here is my biggest challenges, distraction from my wife and family. I admit. I should not ruin their amusements, while traveling. But … Sometime issues of prod env come at bad time. Also a bit hard to concentrate, when people keep talking and asking feedback.

    • Tom Ewer
      October 17, 2016 at 10:03 am

      A distraction-free environment enables you to work quicker, and get back to your family sooner. 🙂 It’s a win-win!

      Thanks for your insight. 🙂

  4. Rick Berger
    November 2, 2016 at 11:51 am

    I’m a software developer. My wife and I like to travel for 6-8 weeks at a time. We always rent an apartment wth internet, and I always travel with two computers and a monitor.

    On one trip to Paris, I ported a major 3d graphics package from Windows to Mac. It was one of the most productive and satisfying efforts in my career.

    I worked solid 8-10 hour days, I kept tight e-mail and sometimes Skype communications with the client, downloaded and uploaded progress, regularly.

    Basically, I worked very hard to insure I was as available as if I uere at the office (with a 9-hour shifted schedule. But, the evenings and weekends were mine to roam the streets of Paris.

    Without distractions during the workday (meetings and “cooler talk”, I was very effective. At the end, the client said, “Just stay in Paris. You’re getting more done.”

  5. Rick Berger
    November 2, 2016 at 12:03 pm

    Another way to deal with limited internt access is to set up a local environment. Do most of your work offline, and then go to an internet cafe to upload/download and e-mail.

    Not always practical – I worked with a client that required me to work on their system over VPN (if I could work remotel, at all). You can’t do much in that situation.

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