How and why did you start working remotely?

By accident. I quit my job as a corporate lawyer to travel for a year, having long wanted to visit Siberia and Mongolia and explore the trans-Siberian trains. That year turned into more when I realized that I had over-budgeted for the trip. At the same time, I had started a website to keep my family and friends updated with my travels, less intrusive than a bulk email. The site grew with my extended travels, and suddenly I found myself receiving pitches for freelance writing work and grappling with the idea that I might not be going back to being a lawyer after all.

What advice would you give someone considering a remote job?

I think it’s important to be realistic about the limitations on resources and/or access to technology in some far flung places. While it might sound romantic to work from the desert, it doesn’t often translate to a productive day. The more a business grows, the more solid the infrastructure needs to be, which is why researching destinations fully and testing them out matters.

I also think it’s important to leave space for the psychological changes that come with remote work without a fixed residence. It might seem easy, and it is great, but the opportunity costs of stability and certainty are ones that people underplay. Both are important to discuss with fellow remote workers, and to acknowledge as valid. Doing so will only make your business stronger.

How did you convince your company to let you work remotely?

I quit and became my own boss.

What are the biggest benefits to working remotely?

The flexibility to both spend extra time in places I love, and to be able to spend time with people I love. This means going home to family if they need me, and being able to work from there. The thing about being flexible is it also allows you to stay still when you have to, something many jobs don’t build room to do. I’m grateful both for the extraordinary experiences I’ve had around the globe, and also for the time I could never have spent with family were I still a lawyer.

What are the greatest challenges to working remotely?

The uncertainty is a tough one, but that applies whether you’re a remote or local entrepreneur. Those ups and downs!

The understanding that if you get sick, it’s not necessarily an easy fix. I got respiratory infections and dengue fever in Vietnam, and they wreaked havoc on my body. And those times that you get sick are also the times you feel the lack of consistent community and/or care.

Thankfully it’s easy to reach out to fellow, likeminded remote workers thanks to technology, but that doesn’t supplement the more consistent friendships when you move around less.

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

I tend to treat weekends as weekdays and do my bigger days off during the week, for less crowded spaces and a quieter inbox.

My morning routine involves waking up, doing stretches and meditating, and then making a cup of coffee and working until I’m hungry. The rest of my day depends on whether I need to head out and take photos, or interview someone, or just need to write.

How do you avoid becoming distracted when working remotely?

I don’t use apps to do so, as they don’t address the underlying problem of discipline. They just hold your hands for a bit.

I try to divide up my time and tasks in ways that keep my brain feeling the varied nature of the different work. If I tired of writing, I move to editing photos.

I do wall stretches on breaks, and try to move around when I remember to.

I close my tabs for Facebook or the web, and sometimes even turn off WiFi when I’m writing and want to get into a phase of deep work.

We are all in a constant battle with our minds in that sense, given how accessible distractions are. But I think the meditation helps my focus, and I basically just sit with the discomfort of wanting to do something else when I am working, if it arises. It’s not easy for any of us! But I think it’s still more effective than using an app that shuts off my browser.

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

I don’t, no. I can’t write well with any noise so I prefer to write at home.

Occasionally I’ll go to events at a coworking space to see what’s going on in the area, but not to actually get work done. 🙂

What gear can't you work remotely without?

• External keyboard
• Roost stand

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

• Trello
• Canva
• Dropbox
• Smugmug

Do you work from a home office? How is it organized?

No, I don’t have a home base so I don’t have a home office. No matter where I am, though, I use my Roost stand—it’s changed my ability to work without pain.

How do you stay in touch with virtual teammates?

Using a combination of Trello comments, Dropbox notes, and bi-weekly calls.

Do you have tips for saving money while working remotely?

There are plenty of articles out there about geoarbitrage and choosing places that are cheap to work from. There are always places you can live in that aren’t expensive, but it’s also important to figure out if they meet your needs in other ways, such as community, food (for me this is really important), safety, and internet.

I think as not working remotely tips are the same: don’t spend beyond your means, think about the ways that you can budget more effectively, and consider owning less stuff.

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

I would consider it later in life but for the moment I’m enjoying the flexibility of what I’ve built.

How has working remotely impacted your career plans?

My career plans involved lawyering, so I would say so! Inadvertently, though, as they put me on a whole new path.

For what I’ve built, I think it’s important to be accessible for part of the year—for speaking opportunities, meetings, time with team members. But this does not need to be for the full year. These are also scattered around the globe, so my current career and remote work are jiving nicely!

How do you stay connected to your professional community virtually?

Typically on membership groups for other remote workers or digital nomads, as well as Facebook groups for people in food and travel writing.

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

Attending conferences within the ambit of your career but not necessarily completely on point; good way to meet adjacent people who may become partners or colleagues in the future.

Meetups at coworking spaces are a fun way to meet others in the same space, or working on interesting, compelling projects.

Joining a mastermind group where you can bounce ideas off likeminded people and work through problems in your business.

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

I’ve made great new friends and communities, and we have planned our time so that we coincide when we can. There is a lovely consistency with the friendships I’ve made that I can pick them up in a new place wherever we left off.

How has working remotely impacted your family life?

I am able to spend more quality time with my family than when I was working as a lawyer.

How do you manage work life integration?

I definitely struggle with what to do to rejuvenate me, given that what I do for a living is also what most people do for fun (travel/food). I have had to work on creating routines that I can overlay on my life, regardless of where I am to try and delineate between work and play, else it all bleeds into one. I think this is a common problem for all entrepreneurs, not just remote workers.

How does working remotely impact your diet?

It allows me to eat on my own schedule, which I find is far healthier for me. I get hungry every few hours but eat small portions, grazing throughout the day. This is easily handled when not in an office environment, and decreases the friction I felt when trying to fit my hunger into society’s ideas of meal times.

I tend to get hungry at 5 p.m. no matter what, so living in Saigon or Mexico means there are also always street foods to eat then—soups or memelas, as the case may be!

How do you cope with feeling lonely while working remotely?

No, though I am asked this question a lot!

I’ve both been able to find meaningful friendships that technology bridges when we are apart, and have made friends with others who find it a great plan to change their schedules to fit with spending time with likeminded people. So I end up in cities or towns with at least a few others who are remote workers, and it feels a bit as though I have an instant community each time.

These are people who are now good friends after years of crossing paths, but do I think it’s possible to find people who jive with your mentality now far more easily than when I started out in 2008. Lots of forums and meetups out there. The danger is simply not to spend time with people just because they may get what you do; we are all still the sum of who we spend time with, in some ways. So if they aren’t people you see yourself connecting with over and above the commonalities in work, I think it’s important to keep looking.

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

Skype, FaceTime, What’s App

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

Be yourself, smile often, ask sincere questions that reflect a curiosity you can’t fake.

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

They were and are concerned about my safety, which I understand. They were concerned about this not being a business initially, but have seen my work take off and are on board with my choices—so long as I keep coming back in the summers to get in family time.