Working Remotely

A Canadian freelance writer with a love of art, culture, literature and adventure, Kelly Dunning loves exploring foreign lands and expressing her experiences through the power of the written word.

She and her English boyfriend Lee run, a site packed full with travel guides, stories and inspiration for those who dream of travel.

Kelly has been an oDesk freelancer since 2010 and, for the past three years, has traveled with Lee around the world, Digital Nomad-style: no address, no car, and no fixed schedule.

How has this changed her life? We recently spoke to Kelly about her experience and the advice she has for others who want to do the same.

What does being a “Digital Nomad” mean to you?

Being a Digital Nomad means that Lee and I have the freedom to move anywhere in the world we want to, whenever we want to.

This week we are renting an apartment in La Paz, Bolivia. A couple of weeks ago we were in Peru. A month from now—who knows?

We have traveled through more than two dozen countries in the last three years, thanks to the freedom of our location-independent jobs. Lee designs websites, I am a freelance writer, and we run a successful travel blog.

When did you first become a Digital Nomad, and what did you change in order to become one? Did you quit a job? Start a new venture?

KellyDunning_Thai-tigerI first tried freelance writing online in early 2010, when I was backpacking around New Zealand on a working holiday visa; I had struggled to find a job in Christchurch and was running low on cash. I loved working and traveling, but it was a challenge to start from scratch and find a new job in each new destination.

My mom sent me a link to a job posting for online writers, and that got me thinking. I created a profile on a couple of freelancing sites — the very first writing job I ever got was actually on oDesk! I did a few writing jobs while I was in New Zealand and it was an interesting side earner, but nothing big at that time.

While I was traveling around New Zealand, I met my boyfriend, Lee, who is from the UK.  We were both working as tour guides in Napier at a creepy historic prison from the 1860s.

When he had to go back to England, I made the decision to cancel my flight back to Canada and follow him instead! I got a working holiday visa for the UK and landed a full-time job taking care of kids at a nursery, but I continued to do some writing jobs in the evenings and on weekends.

Lee and I started to realize that, if I could build up my writing career enough, we could have a source of revenue that was mobile; we could uproot ourselves and travel for as long as we wanted.

We also created a website where we could chronicle our adventures and provide tips and advice for other travelers:

It took about a year from the first few writing gigs to get to a point where I could quit my day job and see freelance writing as full-time income. Once we got to that point, we sold everything we couldn’t fit in our backpacks, hit the road, and never looked back.

If you’re talking to someone who wants to become a Digital Nomad, what are your top three tips help to make it happen?

  • Kelly Dunning's hammock office in ThailandDon’t quit your day job right away. A freelance career takes some time to build up, because you have to slowly grow your portfolio and find clients—you won’t be earning a lot at first. One of the best decisions I made was to build my freelance writing career on the side of a full-time job, in the evenings and weekends, until it was substantial enough to rely on.

  • Save up an emergency fund. Lee and I decided that we needed to at least have enough money saved up to buy plane tickets back to England if it all went wrong.

  • Work hard. Even though you are working from a beach bungalow in Thailand, you will still need to put a lot of time and effort into building your business. It might look like you are on holiday to your Facebook friends, but you’re running a business too. Digital Nomads still must take their freelance careers seriously, so they can consistently improve and bring in an income year over year.

Any cliches or misconceptions about being a Digital Nomad you want to dispel?

The typical clichéd image of a Digital Nomad is someone working on a laptop while lounging on a beautiful tropical beach. Well, I’ve tried this myself, and it’s actually not as nice as it looks. The sunshine makes it impossible to see your laptop screen, you get sand all over your keyboard and you start to resent your work because you wish you could just relax and enjoy the beach!

It is important for Digital Nomads to separate work and play, in order to enjoy both more fully. Instead of working on the beach, I prefer to get up early and concentrate on my work indoors. I will finish it much more quickly if I’m not half working/half lounging anyway. Then, once the work is done, I am free to fully enjoy the beach as much as possible.

Do you feel that the Digital Nomad lifestyle is growing in popularity? If so, why do you think there are more now?

I have only met a few Digital Nomads in real life, but I have read many blogs online about those following this lifestyle. If there are more Digital Nomads now, perhaps it’s because of the abundance of online jobs allowing people to work remotely, and how easy and affordable it is to work from the road.

Where have you been? How many places total?

Kelly Dunning in Penang, MalaysiaWe have been to more than 30 countries in Europe, North America, South America, and Southeast Asia.

We took a road trip across Canada, visiting every province, and spent three months in the Eastern and Southern USA — New Orleans and New York being wonderful highlights for us.

Our trip to Southeast Asia was 10 months in total, and we backpacked around Eastern Europe for two months. We are currently in Bolivia, slowly making our way around South America. Some of my favorite countries so far have been Malaysia, Sri Lanka, Peru, Vietnam, Cambodia, Laos, Slovakia and Portugal.

Do you think you’ll be a Digital Nomad for life?

We really don’t know! Lee and I don’t like to make plans “for life” because we know that things change and you can never really tell what the future will bring. Perhaps someday we will semi-settle somewhere and have a family, but still take our little ones on long-term travel adventures. However, at the moment, being Digital Nomads is the most amazing thing in the world, and there are still plenty of countries to see. We don’t plan on stopping any time soon!

Where to next?

We are in La Paz, Bolivia, at the moment, and it’s a pretty cool place, so we will stay here for at least a week, maybe two. Next, I think we might head to the Salar de Uyuni, which is the world’s largest salt flat. It’s a beautiful and surreal landscape, and I really look forward to seeing it.

What’s been unique about your journey?

The journey itself is unique. A Canadian girl meeting a British guy in New Zealand, then starting a business together and traveling the world—it isn’t your typical story!

Travel gives new perspective on life. What lessons have you learned along the way?

We have learned a lot during our travels. Seeing Third World poverty in countries such as Bolivia, Cambodia and the Philippines gives us a perspective on just how lucky we are and how we should never take our lifestyle for granted.

We have also learned that with our freelancing Digital Nomad lifestyle there is no pre-determined formula for success: we are designing it as we go along, and we get what we put into it.

A conventional lifestyle is somewhat like driving a car down a road; you have a path laid out in front of you and a few options to choose your direction, but you can’t really go “off road.” Following the road will get you to the pre-determined destination.

Our lifestyle is more like having a boat: We are free to sail wherever the wind takes us, and there is no limit to where we can go. Sometimes it’s a little more challenging to sail through the storms, but the freedom of the open sea and the ability to chart our own course is worth it.

Another thing that we have learned on our travels is that there are wonderful, generous, kind and friendly people all over the world. In every country we have been to, people have helped us out, hosted us, cooked for us, bought us drinks, showed us the way when we were lost, shared warm conversation and companionship with us, and offered us friendly smiles and waves.

Seeing the beautiful scenery and eating the delicious food are some great aspects of traveling, but it is also the people who you meet that make the trip truly memorable.

If you are considering making your own dreams of a location location-independent career come true, my advice is: “Go for it!” Put the hard work into building your career and take it seriously.

It will take a while to establish yourself and to make enough income to support yourself while traveling, but one day when you are working from a café in Prague or an apartment overlooking the beach in Malaysia, you will be glad you did.


images contributed by Kelly Dunning

Shoshana Deutschkron

Senior Director of Communications

As senior director of communications, Shoshana Deutschkron brings to Upwork extensive experience in strategic communications for the technology industry. Her unique data-driven background helps uncover insights from Upwork's online workplace data. Prior to Upwork, Shoshana was a vice president at market research firm Penn Schoen Berland, where she provided research-based communications counsel for companies including Ernst & Young, HP, EA and eBay. Throughout her career,… read more