How and why did you start working remotely?

After graduating college, I worked at a startup in Los Angeles for a year. It was a grueling yet rewarding experience, and towards the end of it I was convinced that I was not meant to be tied to a desk, an office, and a 9-5 job. I moved to Africa in 2010 to pursue a career as a photographer and journalist, and loved the freedom and mobility I had to create my own schedule and follow my curiosity. I’ve worked remotely or set my own schedule / hours / locations more or less since then.

What are the biggest benefits to working remotely?

The ability to work on my own time, and constantly gain new perspectives and meet new people by having the freedom to work from anywhere.

What are the greatest challenges to working remotely?

It’s often challenging to build a deep sense of community when working remotely or traveling. You have to be much more intentional about relationship building, and cultivating an intellectually inspiring community around you that doesn’t revolve around work.

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

I don’t have a fixed schedule, but I tend to gravitate towards certain routines or places depending on how productive I feel on any given day. For example, I might exercise in the morning and work later if I’m feeling restless, or I might work in a highly social space, like a coffee shop, if I feel like I need more creative inspiration.

How do you avoid becoming distracted when working remotely?

Set daily and weekly goals, and if you don’t hit them, try to understand what factors—internal or external—led to your distraction.

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

One of my favorites is iHub, in Nairobi, Kenya. The community there is incredible, and there’s always a fascinating mix of people working there or passing through for a few days. It also had an incredible view of Nairobi!

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

• Squarespace
• New York Times news app
• Slack

How do you stay in touch with virtual teammates?

We use Slack and Asana to manage our workflow, and often speak on Skype or phone at least 2-3 times per day.

Do you have tips for saving money while working remotely?

Traveling while working remotely can be cheaper in some places, although it’s easy to rack up expenses if you’re not careful. Some people think that you’re suddenly going to save on so many things, but throw in an average of one plane ticket every month, a few mid-priced hotels, and many of your fixed costs might remain the same (office space, health insurance, savings, retirement, etc.). You can stay, work, and eat cheaply, but you have to be resourceful. Find local friends, stay in local places (not just hotels or Airbnbs), and invest the time in finding ways to make your experience more enjoyable without breaking the bank and paying convenience premiums that regular short-term travelers may pay.

What does your remote company do?

Unsettled is the first global housing community for creatives, entrepreneurs, and independent workers. We provide everything needed to be connected, comfortable, and collaborative: a private apartment, coworking space, local hosts, and an immersive community experience.

We are a home for those who seek to take their work, life, and adventures beyond traditional borders.

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

The grass is always greener. Sometimes I’d love to be able to step into an office every day, see familiar faces, and have a standard routine. Other days I’d prefer to work from a coffee shop, or explore a new city and find a space there. It’s about balance—you don’t have to stick to one or the other, but you can work to balance it out by working from a few different places and rotating between them.

How do you stay connected to your professional community virtually?

I’m never afraid to reach out and meet new people in a similar space or industry. For example, the last time I traveled to Cairo, I reached out to a friend in the startup space there before I went. I was a journalist at the time, covering startups in emerging markets. He connected me to several incubators and accelerators, as well as a number of entrepreneurs who made my time there incredibly rewarding, both professionally and personally. I’m constantly having coffee, Skype calls, and meetings with people who are doing something I find interesting, and make it a habit to check in with people I haven’t seen in awhile to catch up.

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

It’s given me the flexibility and freedom to be curious, and experience life the way I want to. I can take opportunities to travel, see friends, go on new adventures, and not have to worry about clocking in, asking for permission, or disappointing others. It’s made my work-life balance much more fulfilling by allowing me to go where I need to while still feeling productive—whether it’s into the mountains to recharge or a new city to find inspiration.

How do you stay physically active while working remotely?

I’m an avid adventure junkie, and so I always look for ways to explore the outdoors and get some exercise wherever I am—kayaking, skiing, surfing, climbing, hiking, etc. My usual go-to in any city is biking and swimming. Many cities have a bike share program, and if not there’s usually a place you can rent bikes. And for a few bucks, you can usually find a public pool to swim laps in.

I find it also helps to set up daily routines that you can do anywhere. For example, I stretch every morning for at least an hour—a combination of yoga and sports stretching.

How do you cope with feeling lonely while working remotely?

It’s easy to feel lonely when working remotely. It just means you have to try a little bit harder to find community. I’m very intentional about making plans to meet friends, organizing dinners, and taking every opportunity to get out and meet new people. I’ve learned to make myself comfortable being uncomfortable by putting myself in all sorts of situations that cause me to grow, and build amazing relationships in the process.  

One thing I always do is let people know where I’m heading on Facebook. I’ll post something as simple as “I’m heading to Istanbul next week—anyone there or know folks I should meet up with?” I’ve reconnected with dozens of old friends this way, and also been introduced to a number of friends of friends who made my trip a memorable one and gave me a sense of community in a place I’d never been.

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

Working remotely from abroad certainly has its downsides. I spent the last decade of my life living outside of the same time zone as my family. Fortunately, they aren’t too demanding, and we talk or email every few days. With friends, since I’ve lived in about a dozen cities over the past 8 years, many are distributed around the world. While there’s a lot about Facebook I don’t like, it is a great way for friends to stay updated on what I’m up to and where I’ve been. I have regular Skype chats with a few friends, and the rest I catch up with whenever I’m back in their city.

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

Embrace the unknown. Say yes to new experiences and opportunities. Open yourself to the endless possibilities of the people you meet—because you have no idea where they might lead you.