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Living the Dream…or a Nightmare? Working Online While Traveling Isn’t a Paradise

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“You have to work today?” my dad asks me as he drives the RV through a deserted stretch of highway in New Mexico.

Yes,” I shoot back. “I have to work.”

I just landed in Albuquerque yesterday to begin a camping trip with my parents, but while my dad points out the mountains lining the landscape, I shrug off his comments and continue typing on my laptop.

The disadvantages of working online while traveling don’t get as much attention as the benefits, but I think it’s important to talk about both. This isn’t the first time I’ve encountered people not understanding that when I’m on the road I’m also “at the office.”

Last year in Toronto my Airbnb host knocked on my bedroom door to check on me. “Are you hungry?” she asked. “You’ve been working all day. I thought you were starving in there!”

Spend eight hours sitting in an office building and no one bats an eye. Spend eight hours working on your laptop in your Airbnb, and people start to worry. 

When I was in Peru, most people saw photos of me smiling with my mom at Machu Picchu. What they didn’t see was me sitting in the dark lobby outside our hotel room in Aguas Calientes, pounding away at my laptop while my mom slept because we had to get up at five the next morning to begin our ascent.

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    “Your life is a vacation!” a friend told me in 2015 before she left on her vacation to Ireland. The irony of this was I actually hadn’t taken a vacation in two years. 

    Why Working Online While Traveling Isn’t the Paradise You Think It Is

    This year, I’m fed up. I’ve just returned from my first real vacation since 2015: five weeks traveling by train in Italy and Eastern Europe—without doing work! I say “real vacation” because, though I travel often, I am almost always working online while traveling. I loved being able to be fully present to my friends and not have to sneak away to find Wi-Fi.

    disadvantages of working online while traveling - austrian countryside from my train window
    The Austrian countryside from my train window

    Being a digital nomad is often touted as a dream—and don’t get me wrong, it is my dream.  I love working remotely. It’s why I quit my desk job in 2013, and it’s why I write about travel and remote work on The Wherever Writer. But I don’t think people have a strong enough grasp of just what it entails.

    Here are the disadvantages of working online while traveling:

    Traveling Is Exhausting. Working While Traveling Is Doubly Exhausting.

    Anyone who has traveled knows this simple truth: Travel is actually exhausting. Being outside of your normal environment requires extra mental energy. When you’re navigating a city in a foreign country, in a language you don’t speak, your brain is overloaded with new words, sensations, sights, and smells. When you’re constantly moving from place to place, your entire routine is disrupted.

    Now, add to that the stress of work. You still have to make your clients happy, meet deadlines, and perform at your best.

    At the end of the day, you’ll be exhausted from juggling travel and work.

    Not Every Destination Is Conducive to Work.

    “Working from anywhere” almost always means “working from anywhere there’s reliable Wi-Fi,” which limits you to select cities and countries. Usually a solo trip to a major city will work out just fine for working online. But if you plan to go camping in the desert or backpacking through Peru, forget it.

    My four-and-a-half month stay in Cusco, Peru, was a constant search for Wi-Fi. If internet was offered at hostels or hotels, it was often spotty and barely usable. I was able to get a sweet setup when I got my own apartment and installed my own Wi-Fi, but when I went on day trips outside the city, I had to go from hotel to hotel asking about their internet connection. Peru is still a developing country, so Wi-Fi was not standard. If I was able to find it, sometimes it was so slow I could hardly even load a webpage. This often disrupted my work.

    Additionally, if you plan to travel with family or friends, or if you plan on staying with a host, you can expect to spend much of your time entertaining them or feeling terrible for having to shut yourself into your room to work on your laptop. I’ll explain the issue this creates in my last point below.

    When Your Work and Personal Life Become Inseparable, Both Will Suffer.

    If you work remotely, your personal life and work life become intertwined to the point there seems to be no separation at all. Your airplane seat, restaurant table, and even your own bed become makeshift workstations. Friends will want to chat when you’re writing a work email; family will want to go out when you have to stay in and take a client call. Eventually, both sides of your life will suffer.

    I have come to appreciate having a separation between work and personal life. Being able to go on a rail trip through Europe and know from the start that I would not have the pressure of work was a relief.

    It’s Not Really a Vacation if You’re Working.

    The Oxford Dictionary defines a vacation as “an extended period of recreation.” It defines recreation as “activity done for enjoyment when one is not working.” So, strictly speaking, you can’t call it a vacation if you’re doing work.

    Sure, you can go on a trip to Buenos Aires and do some work one day and then go exploring the next, but as I stated in my previous point, constantly mixing work and play on one trip becomes stressful. It feels like you’re never really “off.”

    You Constantly Feel Like a Bad Person for Not Spending Time With Your Travel Partners.

    Of all the disadvantages of working online while traveling, this one upsets me the most. I’ve been working remotely and traveling for three years now, and I have gotten to the point where I am sick of doing this to my friends and family.

    You’re not able to be “all there,” and even if your loved ones say they understand, it still hurts to have to deny them. Your friends may want to get up at 4 a.m. to catch the sunrise at St. Mark’s Square in Venice, but if you’re staying up late to finish work assignments while they sleep, you’re not going to be as enthusiastic about the idea.

    I got to the point where I couldn’t bear the guilt anymore. I didn’t want to have to send my friends away on their own in a foreign city while I went to a cafe to write articles. I didn’t want to have to constantly check my emails while trying to enjoy a dinner with my mom in Argentina.

    I may still allow people to join me if I’m working while traveling, but only if we have a certain amount of expectations set beforehand. And even then, I’ll probably still feel bad for working on my laptop while they enjoy the city.

    Working Online While Traveling: A Trade-Off That May Be Worth It

    I am not saying that working online while traveling should be avoided; I just wanted to offer a different perspective on this digital nomad dream. The truth is working online while traveling is exactly what gives me the opportunity to experience so many countries and cultures. While many choose the route of spending months or years saving up before they can travel, I am able to do it right now. Of course, as with anything, there is a trade-off, but I wouldn’t do it if I didn’t think it was worth it.

    “Don’t kill the golden goose,” a friend and fellow remote entrepreneur once told me. I was complaining to him that I wanted to cancel my client contracts before going to Paris so that I wouldn’t have to work while traveling. He made an excellent point: I wouldn’t even be able to go to Paris for five weeks if it weren’t for my ability to work remotely.

    In the end, it is up to you to decide if the sacrifices of working online while traveling are worth the rewards. For me, it is. But I have a new appreciation for stopping to take a real vacation—one where I don’t do any work!


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