How and why did you start working remotely?

Originally, I began working remotely as a way to facilitate my goals to become an actress in Los Angeles. I took an internship at a film company in college, and one of the producers there offered me remote work for his other company. I lept at the opportunity. I was graduating from university within a few months and I had plans to work as an actress in Los Angeles. The remote work gave me the funds and the location independence to pick up and move to LA, while also attending auditions once I was there. Within two years, however, I realized that my dreams of long-term travel were a larger priority. I made the decision to travel the world by booking a one-way ticket to Australia. Then I made a mad scramble to find additional clients and line up the roughly 25 hours of work that I would need to afford my yearlong trip around the world.

At the time, I didn’t see the remote work as a career move, but more as a chance to leverage online work to afford a lifestyle that I enjoyed. Over the years, my travel website has also become a part of my work and a portion of my income. My work and life melded as the years wore on. It’s an odd combination of work, travel, life, but I wouldn’t change it for all the world.

What are the biggest benefits to working remotely?

Freedom and flexibility are the two aspects of remote work that I would find hardest to leave behind. As a freelancer, I also enjoy the benefit of setting my own schedule. It’s these traits that have allowed me to build a life that includes so much travel. There’s a near absolute freedom to create your own priorities alongside your work and then see them through.

What are the greatest challenges to working remotely?

Over the years, I’ve seen discipline as the achilles heel of many friends. There’s this myth of the remote worker lounging in pajamas and living the high life once they’re not bound to an office. The reality is a far cry different. Although the pajamas are still often a part of the equation, it’s much harder to form the discipline of setting your own schedule and meeting deadlines. Without external forces (coworkers and bosses nearby), you have to show a great deal more discipline and organization of your time to make the lifestyle work effectively for you.

Do you keep a regular remote work schedule? What is it?

Working while traveling makes it impossible to keep a completely rigid work schedule. I am an early riser, however, and I use this to my advantage. I will spend the early morning hours working each day, and then by lunch I am ready to head out and explore whichever new town I find myself.

How do you avoid becoming distracted when working remotely?

I use a set playlist on Spotify, headphones, and a specific set of goals for that work session. So, before sitting down I identify my tasks on a set of Trello cards. Then I put on a playlist, close out of all browser tabs, and get down to work. I don’t often have issues focusing anymore, but at times I have used browser apps like Stay Focused to keep me from accessing Facebook, or casually turning to my reading list in Pocket. Using these apps occasionally has allowed me to teach myself laser-tight focus during my work sessions. Since I would often rather be out experiencing the world, I aim for hyper productive work sessions—no internet surfing allowed during a work session.`

What is a remote work pain point, and how do you address it?

In the early days when I was traveling back in 2008, internet was my biggest obstacle. Internet is ubiquitous now—I even found signal on the Maasai Mara in Kenya. The lack of consistent internet in my early days of working remotely while traveling is likely why I learned such discipline in my work sessions. When I found internet, I had to maximize my effectiveness to ensure my client work was finished on time!

Do you use coworking spaces? What are the best ones?

I rarely use these co-working spaces, they are new to the scene and by this point and I very accustomed to working amid the chatter of a coffee shop. That said, I have used Impact Hubs in various cities—Boulder, Seattle, and Oaxaca—and it was nice to have a spot with amenities like a printer and large work tables.

What gear can't you work remotely without?

• I have a Roost laptop stand that I love dearly
• A pair of noise-canceling ear buds.

What apps or websites can't you work remotely without?

• I use Trello to organize my life and could not live without it.
• I love Lightroom for editing photos.

How do you stay in touch with virtual teammates?

I use shared Google Calendar to track deadlines for clients and my freelance team. Then, we organize tasks and projects on dedicated boards in Trello. I switched to this system a few years ago, after trying to stay low-key using emails and such, and Trello revolutionized my ability to keep track of every aspect of current projects, both personal and professional.

Do you have tips for saving money while working remotely?

Splitting your time between costly cities and affordable locations is an effective method to combine remote work and travel. Many call this geoarbitrage, but it involves making money in a strong currency and spending it in places where your income travels further for every dollar spent. In this way, you can travel and work remotely for far less money than it costs to live in most U.S. cities.

What does your remote company do?

I am a travel writer and photography blog sharing stories of social enterprise and responsible travel.

Would you consider returning to a traditional office job, or are you remote for life?

Well, there’s nothing to return to for me. I started working remotely back in 2005, while I was still attending university. I waited tables as a student until I found remote-based work. From that point forward, I have never relied on any formal jobs for a living. I worked—briefly—in an office when I first moved to Los Angeles. I was new to the city and wanted to make new friends so I took a three-month part-time contract. I continued working remotely during this time, and that stint in an office was enough to show me how much I appreciate working for myself. I’ve been self-employed for more than a decade and I can’t imagine trading this lifestyle for office work.

How has working remotely impacted your career plans?

Working remotely is all I have ever known, and so the very fact that I worked online has shaped every aspect of my life. When I left to travel in 2008, I had no idea that travel writing and blogging would become the bulk of my career. But because I had freelance work in online marketing, I set out on the road and was able to build both aspects of my business. Everything has fed into each other aspect in my life to shape a lifestyle where I have a wide range of work, and more opportunities—personal and professional—than I could have ever imagined when I first started working remotely.

How do you stay connected with your local community?

Creating community is a struggle with this lifestyle I have chosen. In the early years of travel, I met new travelers every day, and they were often fast friends. In more recent years, however, I am looking for a way to continue traveling for part of the year, but I would like to pick a spot and have an apartment somewhere with a desk of my very own. It’s been nearly a decade since I had that luxury.

What's the best way to develop professional contacts while working remotely?

I would love to know the answer to this question! I am not great at networking or creating those high-level professional contacts that I know grease the wheels for so many. Instead, the vast majority of my clients and freelance work has come through friends and others I met on the road. We keep in contact as friends, we pass clients when needed, and we help each other find and maintain sustainable remote-based work. In this way, the majority of my professional contacts are also friends. I struggle to maintain those more distant (but likely beneficial) professional relationships.

How has your remote job impacted your life outside of work?

Working remotely has allowed me to travel the world these past eight years. Although I have no doubt that I would have traveled no matter my job, a traditional job would have changed the scope of my travels, and my ability to travel for years on end. Now, so many of my closest friends also work remotely and travel the world—it’s hard to imagine my life without this defining aspect.

How has working remotely impacted your family life?

Although I have mostly traveled solo over the years, because I work online I was able to take my niece on a long-term trip to Southeast Asia. She was 11 years old at the time and my family and I agreed that she would benefit from a year of homeschooling and travel. Because my schedule is flexible (and I already had the experience integrating work and travel), my niece traveled with me throughout Southeast Asia for nearly seven months. It was an incredible family adventure. Since then, I have traveled with her to Central America, and I also took my nephews on a monthlong road trip throughout Mexico’s Yucatan Peninsula. These experiences have positively impacted not only my life, but my family’s life as well. Without my remote-based work, many of these trips would have been more difficult to arrange and less affordable. During these travels with my family, I am always able to keep part-time income while we travel together (I work in the early mornings while the kiddos are still sleeping).

How do you stay physically active while working remotely?

This will sound very silly, but my best workout methods are my hourly “dance parties.” I have repetitive strain injuries in my hands, so it’s important that I take frequent breaks. I decided to combine these breaks with exercise by taking 10 minutes of every hour to dance like a fiend to a high-energy playlist I made on Spotify. This is tricky at coffee shops, but fairly easy in even the smallest hotel room (you can always dance on the bed!). I’ve tried traditional exercise too—I trained and ran a marathon a few years back—but I find that the dance parties provide the best consistency. Plus, I always finish in a good mood.

How does working remotely impact your diet?

Well, by working overseas and on the road these past years, I have discovered hundreds of new cuisines and tasty dishes. Southeast Asia is a hotspot for many digital nomads, and it’s easy to find affordable and tasty street food. In places with less ready street food, I often take advantage of local markets and will cook myself a feast.

How do you cope with feeling lonely while working remotely?

There are times when I feel lonely, but I’ve learned over the years to see loneliness as a spectrum of emotions, and not a static feeling. I’m introverted and tend to love my own company. Solitude is a precious gift when I find it on a mountaintop, in a park, or tucked into the corner of a coffee shop. This same feeling that I love, solitude, can creep into loneliness. But it’s always a temporary state and I’ve learned ways to counteract it when I see feelings of loneliness creeping into my days. At these times, I will often seek out a coworking space. Or I’ll go online and find other digital nomads in my area. I’ll also up my volunteer hours (or find a place to volunteer if I’ve let that fall to the wayside). These actions combined tend to right the scales and keep me balanced and enjoying working remotely.

How do you stay in touch with friends and family while traveling?

The range of apps for this is dizzying. I use WhatsApp and Facebook messenger with most friends. My teenage nice is exclusively on Snapchat, so if I want her attention I need to go there. I tend to call home using Google Voice at least once a week. And because I blog and share photos on Instagram, my parents and family usually check those mediums if they haven’t heard from me in a few days.

What are your tips for making friends while working as a digital nomad?

Find the courage to approach others. Learning to blend in new groups is a learned skill, like most anything. The more you engage in new conversations, the easier it is to approach others. When I backpacked during my first few years of travel, it was nearly impossible to not make friends at the hostels. Now, I use social media to connect and suss out bloggers and others nearby. When I was in Tbilisi, Georgia, I shared an Instagram photo of a gorgeous church there and a local woman commented to welcome me to her city. That was the opening and I asked her if she was keen to meet for wine. We talked for many hours and it was such a wonderful way for me to make a new friend and also learn more about her culture and country’s history.

Did you have to address concerns from family when starting out as a digital nomad?

My parents were worried when I first left to travel and work from the road. My trip lasted 11 months and they had their reservations, but they never asked me to change my plans. My dad’s only major request was that I keep my blog and social media two weeks behind my actual location. With the way that people update Snapchat and Instagram every moment now, it seems odd to consider he was so worried about that aspect of it. But back in 2008, blogging was new and I honored his wish. Every week I would email him a rough draft of my travel plans to keep him in the loop, and that made them feel secure in knowing that if anything went wrong, at least they had a starting point for figuring out the next steps.

What are your favorite cities in which to work remotely?

Although I have visited it in many years, I loved working from Chiang Mai, Thailand. The city is the ideal size—small enough that you can navigate it, but large enough to offer variety in the food, friends, and culture. Most recently, I worked from Bristol, England, while visiting friends—what a great city! They have a range of fantastic coffee shops, all hipstery with large wooden tables and good vibes. Like Chiang Mai, Bristol also hit that ideal size requirement that I have. I don’t love big cities, it’s all a tad overwhelming to live in cities like that, so I prefer the next step down from those.