Traveling and Working-It’s not always a fairytale

Jocelyn Hellested
Nomad Things
Published in
5 min readJan 16, 2020
Photo by JESHOOTS.COM on Unsplash

Mixing business with pleasure is generally frowned upon, and yet it is also something we crave. Who doesn’t want to wake up every day and eagerly anticipate “going to work.”. But what if going to work was waking up and walking to the desk in your living room, the comfy chair on your porch, or the coworking station filled with other passionate individuals? What if it meant working in a new city or country every couple of months? Upon consideration, combining a life of travel and work is an attempt to mix business and pleasure. Mixing a passion for travel while also trying to earn a sustainable income. Doable, but by no means easy. It has been four months since I started this journey, and I feel ready to share some insights.

Find Your Reasons

Why do you want to travel and work? When considering this lifestyle, you should start the journey by contemplating why you want to pursue it in the first place. Is it so you can experience new cultures, create a better work/life balance, or give yourself space from a hectic and busy life? Honing in on why you want to pursue this lifestyle will help ground you as you move across the globe. Your reasons may change as you learn more about yourself but hold onto these reasons when things get tough. Working and traveling is not always glamorously sitting at the beach with a cocktail reading emails on the computer (let’s be honest, it is tough to see anything on a computer when you are in direct sunlight!). Do not be fooled! At some point, the wifi will go out while you are trying to work, or you’ll miss your bus, which may also mean missing work, and you may begin to yearn for the comforts of home. When this happens, remind yourself what attracted you to lead this life.

When you travel and work you have to do just that….work

Traveling and working means you have to do just that. It is not a vacation, as some of your friends and family may insist. Yes, you have time for fun and thrilling adventures, but you also need to work. Hopefully, you are like me and have come to love what you do; however even if you love what you do you cannot spend all of your money on excursions, eating out, and souvenirs. You are not on vacation but are trying to create a sustainable life for yourself that organically integrates the things you love in life, like travel.

You may not be able to spend all of your time and money on travel, but at the same time, you didn’t come all this way to spend your days sitting inside and working 24/7. To help put things in perspective, I usually ask myself, “10 years from now will I regret spending the money to do this particular thing, or will I regret not doing it in the first place?”. Work and travel is a balancing act, the longer you do it, the better you’ll get.

Be Patient, Be Kind, Good Things Take Time!

Finding a routine when you are always on the move can be difficult. In the time since we started to travel, we have spent anywhere from 1 week to 1 month in a new place. Each time we settle somewhere new, we need time to adjust. We need to make sure the wifi works, locate the grocery store and set up our working stations. If we wanted a mundane routine, we wouldn’t have pursued this lifestyle. Still, the constant change does make it difficult to establish a routine, and it takes time to become comfortable with the unpredictability of it all. As you work and travel be kind to yourself. As my dear mum encourages me, so I will encourage you to “listen to your inner mother voice.” the helpful and loving voice that understands that change is uncomfortable, and it takes time to adjust. Life may not turn out exactly how you planned, but it has a funny way of working out in the end.

Working and Traveling can be Overwhelming

There are days when I wake up and become overwhelmed by the countless things I could be doing. When you are in a new city or country every couple of weeks, you are never at a loss of new things to do and experience. New coffee shops and restaurants, hiking trails, and excursions! I could go on a tour, visit a museum, sit by the ocean OR write a blog, create products for my store, and prepare for my English classes. With so many options, it can be overwhelming and easy to get bogged down and feel guilty about not ‘doing enough’. Before jetting off, I imagined myself throwing on cargo pants each day and enjoying elaborate adventures daily. The reality? I wake up in the morning, just like everyone else and go to work. The difference is my office is just a few steps from my bed and confession time; I wake up 10 minutes before my first online English class. I teach for three hours, make myself breakfast, and a cup of coffee before I ponder how I’d like to spend the rest of my day. This isn’t to say that each new day doesn’t offer something new and exciting, but I would quickly grow tired if I had Indiana Jones level adventures every day.

It can be unsettling when your reality does not match up with what you envisioned, but this is not necessarily a bad thing. Some days all you’ll want to do is sit, relax, and be lazy. And you have to realize that it is ok! Just because you are in a new place does not mean every second needs to include something you’ve never done before. That would be exhausting! Take advantage of your surroundings, but do not overextend yourself to the point where you become tired and cannot fully appreciate the glorious things around you or effectively do your work. You are moving away from a typical 9–5 pm workday and ‘living for the weekend’ attitude to days that are slow with a flexible schedule. Maybe you are a contractor and can set your own hours, perhaps you operate your own business or are working less than the typical eight-hour workday. Each situation is unique, and it will take time to adjust. Taking time to recharge and relax is just as important as planning the next adventure.

Yes, working and traveling may not be a fairytale, but is anything in life? This lifestyle has given me a lot of time to think about what I want to pursue and what is important to me. It has given me perspective and taught me to problem solve, be empathetic, and innovative. These are skills and tools I can carry with me wherever I go in the world and in my career. Better yet, the journey has only just started and I cannot wait to see what other things I learn along the way. I am just as excited about the things I am creating as the people I meet and the places I explore. In life, you need a balance, sometimes it is hard to manage, but when you find it, hang on and don’t let go.

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Jocelyn Hellested
Nomad Things

Currently in South America improving my Spanish, teaching English and finding the hidden joys of everyday life.