In Pursuit of Happiness: Why I Became a Digital Nomad

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If you long to escape your desk job for a business that allows you to travel the world, you’re not alone. There’s a new breed of professionals who’ve merged their bucket lists and careers into a mobile way of life: they are called Digital Nomads. In Pursuit of Happiness Why I Became a Digital Nomad

Last October, my husband Gregg and I joined this new generation of professionals. We skipped renewing our lease in oh-so-expensive San Francisco, sold most of our stuff and stored the remaining few items we own at my folks home to live a location independent lifestyle, along with our two dogs, Teddy a year-old Chihuahua and Zoe a 5-year-old terrier mix rescue. I know that this lifestyle is a special, happy, and fortunate one. One that I don’t take for granted.

Although, we are about four months into this whole new lifestyle, I’ve been getting a lot of questions from readers, family and friends on the topic of being a digital nomad couple. I thought I’d answer the top questions.

What does ‘Digital Nomad’ exactly mean? First, let’s define the meaning of a ‘Digital Nomad.’ According to Wikipedia, a digital nomad is “someone who leverages technology and the internet to work remotely and more generally conduct their lifestyle in a nomadic manner.” With that defined, my lifestyle is exactly that. I’m lucky enough to work for myself, and can virtually work anywhere in the world — as long as there is one thing: the internet.

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Why did you leave your 9-to-5? I understand that leaving a 9-to-5 job for the freedom to work anytime and anywhere may seem like living the dream — but it’s also an intimidating leap of faith. Even for us. My husband and I are in a unique situation, in which we’ve been working for ourselves for many years now. We have a routine already established which made picking up and travelling that much easier. The intimidating part came from second guessing ourselves if this was the best decision we were making. Thus far, it’s been one of the best decisions we’ve made. Whether we’re working in San Francisco or a cafe in Kennebunkport or on the beach in Tamarindo, we’re pretty much living the same life. We’re just in a new setting; that’s all.

When did you start your digital nomad journey and why? We officially started our digital nomad journey on October 1, 2014. Our journey truly began 6 months prior with the idea of travelling long term and living in a different country, state, city. Ideally, 2-3 months in each location.

This idea would always come up after returning, love-struck from another trip. We had dreamt of living in Italy and Spain, the “due date” kept getting pushed forward more and more, never really jumping on the idea. It seemed like a fantasy that would never come to fruition.  

In the Spring of 2014, during a hike, we came to the realization that we could virtually work anywhere in the world. We didn't have a job tying us down. No mortgage. No children. So, why were we living an unhappy life in the most expensive area in the United States? San Francisco was zapping our energy, diluting out pocketbooks, and making us some of the most unhappy people. This was hurting our relationship in the long term. Sure, San Francisco/Silicon Valley is "home." But, we didn’t have to live there, deal with awful commuter traffic of this increasingly more congested area, or pay sky-high prices for rent for a teeny-tiny space. ($3k for a one bedroom, no thanks.) After that hike, we decided with our lease coming up in October, that we wouldn’t renew it; instead, we would pursue our passion and travel the world. We would bring work with us on our travels. We had about six months to plan properly and to get our bearings straight.

How does my work sustain my life of travel? I earn my money as a virtual assistant, a business that I started back in 2009, which I’ve built a solid clientele base. In hand with my VA work, I business coach and mentor other aspiring women entrepreneurs. I’ve also been working hard to build my (healthy) food and travel blog, which I do get paid for via Google AdSense, affiliate links, brand endorsements, and sponsored posts. Some months I earn lots of money. Some months I don’t. Gregg earns money from his automotive focused websites that he’s been running for years. Similarly, he relies on Google, affiliate links and selling ads.

How does my life of travel sustain my work? Family, friends and strangers alike have all said it’s nice that we can go on vacation for this long. Let’s get things straight. This is not a holiday. We work and travel at the same time. You cannot do one without the other; work is a constant in our life, as well as, travel. Sure, we may be in a new and exciting place, but we aren’t constantly “vacationing” and in the same right we aren’t working 8-hours straight. It all comes down to balance and structuring your priorities, and allocating the right amount of time for work and travel. If we have big projects or deadlines that need a lot of attention, we’ll find somewhere quiet to do this in whether it is in our rental, a cafe or the beach. If we have a bit more flexibility, we will pursue our travel goals like exploring a city, surfing, yoga or whatever it may be.

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How do we select our destinations? With so many places to visit, it makes the deciding part difficult. We always discuss where we will head to next, the pro’s and con’s of a place, and what we know about a place. Talking to other travellers helps as well. We picked Costa Rica because we had both been to Costa Rica and had enjoyed it. We wanted to be somewhere warm and where we could hike and experience fun outdoor activities, and that wasn’t nearly as expensive as back home. Costa Rica was the perfect spot.

What was the biggest challenge? Convenience is a black hole for anyone who’s ever wanted more out of life. It takes a very strong minded person or team to take the first plunge into the unknown. Traveling makes you confront your issues head on. No hiding or going around them. There aren’t distractions from being able to place them to the side. Going out of our comfort zones is a big challenge in and of itself. New cultures, languages and basically having no one else to rely on in everyday situations but ourselves. And, of course, a consistent high-speed Internet connection. Being in Costa Rica, we’ve come to terms that long are the days of reliable, fast internet. At least until April when we have to pick up and move on to our next destination, which will most likely be Portland, OR. We’re learning to accept this part of our daily life here.

Yep. This is me and my suitcase. I'm holding everything I'll be traveling with.

What do you want to achieve? We want to live life to the fullest. This is a sort of a world tour of potential places we’d like to settle. And if it ends up not being just one place, but a few that we want to route back to, that’s fine too. Being a digital nomad gives you a great opportunity to devote time to fulfilling personal goals, too, because you have the freedom to change your environment to suit that. New environments help you to be inspired. This year I want to work on developing more professionally, but personally as well. Work on better health, and being an overall happier person.

What are your next destinations? This year so far we’ve planned on staying in Costa Rica until April 8th, then returning back to the States. We’ll most likely stay in North Carolina for a week once we arrive back and head to San Francisco for the remainder of April. The plan is then to head to Portland, Oregon in May to explore the Pacific Northwest. Road Trip across the US over summer. We’ll be in Greece in August, Berlin, Germany in September and Barcelona, Spain in October. We'll conclude our year in Asheville, NC. Our original plan was to head to Barcelona after Costa Rica, but we would need to figure out getting a visa to stay longer than the allotted three months. But we’ll see…We’re still open to ideas for 2015.

Looking back a full year of travel, what has been the greatest challenge? It's challenging being away from home--family and friends. Seeing various events in their lives, and not being able to be there to share these moments is one of the hardest things. This year many of my closest friends got married or had their first child; family members welcomed new additions to the family; the passing of my grandfather and not being able to grieve with family... These are all things that make traveling a challenge. Keeping in touch in every form possible is important: Facebook, text messages, FaceTime and Skype, email, Postcards. Living out of a suitcase is also a challenge, especially when not being properly prepared with the right clothing. After a while, you get tired of wearing the same repeated outfits over and over and over.

Looking back a full year of travel, what have you gained? With travel, you've got nothing to lose and everything to gain. A new perspective on life itself. Looking back and reflecting on these last 15 months of non-stop travel has made me realize that time is the most valuable commodity. We've been lucky to have the "time" to pursue our happiness. We've gotten a chance to call many places "home" for a short time: Tamarindo, Costa Rica; Portland, Oregon; Berlin, Germany; Barcelona, Spain; Asheville, North Carolina. We've visited many places, have gotten the chance to experience some interesting things, and create memories around the world. We've gained a greater appreciation towards life, ourselves, our relationship and health.

Originally published on February 10, 2015.  Revised on January 1, 2015.