Long-Term Digital Nomad Q&A
I often see requests for interviews and information about people who are digital nomads or remote workers.
Because I’ve been a digital nomad since June 2014, traveling full-time for 3.5 years while working remotely, I figure I’m close to being one of the longest running (and most frequent moving) out there.
Update — I was recently featured in TIME:
So scroll down to see my As to the most common Qs about my lifestyle, work, and how I got started:
- Who are you?
- What job did you quit to start traveling?
- What made you decide to make the jump?
- How did you get a remote job?
- What are you doing for work now?
- How have your professional skills and career developed as a digital nomad?
- Where are you living? What do you have next for travel destinations?
- What about traveling specifically inspires you?
- Do you think anyone can be a digital nomad?
- Where can I get more information?
Who are you?
Katherine Conaway — freelance writer, consultant & producer
- 2009: Graduated from Williams College (studied Art History, rowed crew)
- 2009–2011: Taught abroad at American schools in Casablanca, Morocco, and Sofia, Bulgaria
- 2011–2012: Austin, Texas
- 2012–2014: Brooklyn, New York
- June 29, 2014: left NYC to start traveling
- Feb 2016 — Jan 2017: Member of Remote Year’s second group
What job did you quit to start traveling?
I was an Associate Producer at HUSH Studios in DUMBO Brooklyn.
I have always enjoyed traveling, starting with family road trips. I studied abroad in Siena, Italy, and then taught abroad for two years at American schools in Morocco and Bulgaria. Then I moved to Austin before ending up in Brooklyn at HUSH.
What made you decide to make the jump?
I wasn’t sure I was on the right long-term career path. Although I liked production, my team, and the work that the design studio was doing, I wanted to be more directly involved in creative work.
I also really struggled with the culture of being at a desk for 50+ hours a week, regardless if there were big gaps of time where I wasn’t busy. I’d been a teacher before, so I was always either actively teaching students in the room or grading & planning lessons — no time was really wasted. I don’t like sitting around waiting.
Once I realized that I wanted a job and lifestyle that allowed me to be creative and actively engaged, I decided to take a few months away from working & the city to try and start figuring it out.
I had managed to save a bit of money, so I planned 3 months of travel to visit friends & family around the USA for the summer of 2014.
How did you get a remote job?
I don’t have a full-time remote job. I’ve been a freelancer the whole time, though I’ve had two long-term clients that are my primary “job”.
At first, I wasn’t even trying to work remotely, I just told my creative network that I’d probably need some freelance gigs when I returned to NYC.
Then one creative director I knew (Sarah Ancalmo) contacted me one day to ask if I would do a few hours of work managing her projects for her new studio. She was working with online entrepreneurs & knew I would be traveling, so my work with her was inevitably remote.
Once I had that income, I decided to keep traveling until I ran out of money or found something else I wanted to do more. And here I am, 3.5 years later, still going.
More details on how I got started in the post below, which I wrote in the summer of 2016:
I think a lot of people want to find the perfect full-time remote job with a nice salary and benefits, and that’s definitely competitive & hard to come by. But if you get creative & cobble together freelance gigs and budget your lifestyle around that income, you can start sooner and do more than you might initially imagine is possible (like I have).
I’ve gotten all my clients from just talking to people about what I do and what I want to do. I mean literally everyone I meet, I tell them that I am a freelancer & available for work — regardless of how busy I am at the moment. You never know what will work out (or fall apart) or when.
I am always interested in learning what people are doing, and that conversation can sometimes turn into me letting them know that I could help with a project or problem, or them asking me to work with them. (Or I recommend them to people I know, or it’s just an interesting conversation.)
What are you doing for work now?
That first gig lasted 2.5 years — I was the (remote) Head of Production for Public Persona, a small branding studio:
One of our clients in 2016 was Bluffworks, a men’s travel clothing company. Now they’re my main client, and I do strategy + PR + partnerships:
I also make / upkeep SquareSpace websites and media kits for a few other clients, and I do consulting, writing & editing work as well.
In 2018, I’ll be aiming to do more travel + culture writing, making use of the plethora of notes I take while traveling and my background as an art history major. I wrote an essay about a NYT job posting that has inspired me to move forward with my writing career:
How have your professional skills and career developed as a digital nomad?
My communication skills have gotten even better — everything I do is over email (or, at best, a conference call), and I’m even more hyper-organized than I was to start with.
Each client and project involves me learning how to do something new, so the past few years have been constant professional growth at a really intense pace, even though I’m “just” a freelancer.
Working with Sarah (Public Persona) gave me so many opportunities to be like a business partner, and I got to become more involved with the creative side of our client work — helping with design, copywriting, branding, strategy, etc. We developed & ran an online branding workshop last year, which was a great opportunity for me to use my experience as an educator in another context.
With Stefan (Bluffworks), I am learning about the brand side of working with media and bloggers, pitching, and marketing. It’s been really interesting to work with a very tangible product-based business (clothing). Plus, the company uses Kickstarter crowdfunding to launch new products, so I got to collaborate on the new dress shirt campaign this year as well.
Where are you living? What do you have next for travel destinations?
I am still traveling full-time, spending between 1 to 4 weeks in each place (my average for 5 months this fall was only 3.8 days, though).
So far in my life, I’ve been to 45 countries. This year alone, I’ve been in Vietnam, Thailand, Bali, Ireland, Wales, Scotland, England, Germany, South Africa, Zambia, Uganda, Kenya, and (briefly) in the USA.
In some of those places, I’ve met up with friends and other digital nomads, but most of the time, I’m on my own.
What about traveling specifically inspires you?
Traveling has definitely helped me be more creative.
Partially because of the inspiration and new references constantly coming in (especially because I’m a huge art nerd and always go to museums + galleries), but even more so because of the amount of alone time my lifestyle entails. In that space to think and process, I’ve had a lot more ideas and insights than I did when I was always busy and with people.
Having to constantly make my lifestyle happen (non-stop trip planning) has also helped me become good at executing things — I write and share essays often, I started recording and producing a podcast, etc.
Do you think anyone can be a digital nomad?
I wouldn’t say this lifestyle is for everybody — it’s definitely a challenge and does require a lot of constant planning and adjustment, especially if you’re moving frequently and not staying in one place for months at a time.
And if you’re on your own, it can be lonely. Whether it’s missing friends and family or a lack of romantic relationships, life on the road can be a super solo endeavor.
But it is an incredible opportunity to learn about the world & experience different things, and I love it. I really, really love it.
So if you’re interested in the benefits of the lifestyle and are up for its particular difficulties, then yes, it’s absolutely worth pursuing.
Where can I get more information?
I did Remote Year in 2016 (and yes, I finished the whole year). 6 months after it ended, I wrote a brief reflection on the overall investment and experience:
I also wrote a lot about Remote Year here on Medium during the year, so this publication has posts about specific cities we visited, experiences I had, tips, advice, etc:
This past spring, I published a book with a fellow Remote Year participant that’s intended to help people become digital nomads, and is generally helpful for travelers of all kinds: The Digital Nomad Survival Guide
I also host the Modern Work podcast. So far, all published interviews have been with digital nomads. We discuss their education, careers, working remotely, and passion projects.
And, of course, I post photos and stories regularly on Instagram:
Katherine works remotely while she travels the world — on the road since June 2014. Want more? Follow along on Medium and sign up for the mailing list.
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