2 Years on the Road, or How I Became a “Digital Nomad”
I’m currently living in Prague for month 6 of my Remote Year, the second ever group to partake in the company’s signature year-long digital nomad adventure.
Two years ago, I left New York expecting to spend the summer visiting friends and family before moving back to the city and finding a new job.
Instead, I find myself continuing to live out of a suitcase two years later, working remotely, with no set expectation of if, when, or where I’ll settle down again.
I’m often asked how it happened, and like all things, it wasn’t a single decision or moment when I went from a relatively standard 20-something working American life to being a “digital nomad.”
It was, of course, a series of small decisions, sacrifices, and opportunities, and it will continue to be.
- How It Started
- Money
- Work
- Planning
- Itinerary
- Remote Year
- Next Steps
The Impetus
Over the summer of 2013, my mom and stepdad bought The Akasha, a 48’ boat, and started making their plans to do The Great Loop starting in early 2014.
The Great Loop is a series of connected waterways around the US, and my parents were going to spent 11 months in 2014 following the seasonal route, chasing warm weather:
- up the east coast on the ICW from Florida to New York Harbor
- through the Hudson and canals and rivers and lakes around to Chicago
- down the Illinois, Mississippi, and Tombigbee rivers to Mobile, Alabama
- across the gulf to Florida, around the keys, and back to their starting point
I knew I couldn’t miss the once-in-a-lifetime opportunity to live on a boat with my parents and see the US from a perspective I’d never otherwise encounter. So I started brainstorming how I could spend 2–4 weeks on the boat.
That spring, my dad started organizing his 65th birthday celebration to be in Aspen, Colorado for July 4th week 2014. Then one of my best friends scheduled her wedding in Boston two weeks before his birthday and another had hers in California two weeks after. And so on with the summer scheduling.
After living in NYC on a very tight budget for two years, I hadn’t spent much time visiting friends and family.
I was getting promoted and doing well at my job, but I wasn’t sure it was ultimately the career or industry that I wanted to devote all my waking hours towards.
So I decided to take a summer vacation for the activities, weddings, and boat trip to make a great loop of my own around the country I hadn’t traveled since going on family road trips during grade school holidays.
What’s Your Cash Cow?
My dad’s a self-taught architectural designer and has run his own business for the past 30 years, so he always helped me with geometry and algebra homework and told me stories of teaching himself Lotus 123 and Autocad. I worked for my dad for two years in high school, helping do his personal and company bookkeeping.
Thanks to having this unpleasant (teen + parent + money = challenging) but informative experience, I learned how to use excel, make cash flows, and record expenses.
At 20, I started my own spreadsheets to record income + expenses to help me take advantage of experientially but not financially lucrative opportunities.
I created an estimate tab, a summary tab to see my annual, monthly, and daily progress, and a tab for cash & each of my bank accounts to enter line item expenses, categorizing each one with if-then equations that autofeed into the main summary tab.
Is it perfect? No, but it’s a great learning tool, and I always know what I can and can’t afford based on my current expenses and goal averages.
So I’ve always kept a spreadsheet recording my exact earnings and almost every dollar I’ve ever spent — in fact, I consulted in my google drive and found my old spreadsheets for all of these:
- Unpaid NYC internships:
For two summers, at the Museum of Arts & Design and Viacom/MTV, I negotiated part-time hours, worked side gigs as a waitress at restaurants, and found free housing one summer and got a scholarship stipend to pay for a dorm room the other. - Siena, Italy:
For my semester abroad, I made a proposal for my parents, calculated my financial aid coverage, estimated excursions, personal expenses, and then tracked it all in a cash flow to stay on budget. - Math intern teacher at the Casablanca American School in Morocco:
At my first job after college, I earned a total salary of $7500 for the year, plus $4500 in substitute teaching and $2000 in tutoring, though the job included housing and start/end airfare. - 8th grade English Teacher, American College of Sofia in Bulgaria:
I earned enough to save a few thousand dollars, which I then used to move to Austin, Texas without a job and attempt to settle into a normal American working adulthood. - Austin, Texas:
I struggled to find a full-time job (being an Art History major from Williams and teaching abroad didn’t count for much in the UT alumni stomping grounds), so I worked part-time at Kaplan teaching GRE classes along with waitressing at a local restaurant, until I found a contract position doing market research for a wind energy development company. - Brooklyn, New York:
When I started working at the design studio, I lived on a friend’s couch for 3 months (thank you, for the millionth time!) until I found an affordable sublet in Brooklyn for 3 months. Then I finally moved into an apartment with a friend, though it had a host of problems and took me 45 minutes to commute in from — off the same subway line in Brooklyn as my office.
People often think I’ve lived and traveled the world thanks to some glamorous job, comfortable income, or helpful external financial support. But the reality is that I’ve always lived on the razor’s edge to make this dream happen.
I have friends who save more in a year than I earn. I often have panicky anxiety attacks about not having achieved enough in my career compared to my classmates, or I feel insecure because I don’t have nice clothes or a home or any aspect of the image we categorize as a “successful” adult living the “American dream.”
But I love to travel, I love to live in new places, I love to pursue new adventures, even if that means tracking every dollar in a spreadsheet and narrowly (though successfully) avoiding debt instead of saving money. (I also have to remind myself of this choice constantly.)
In prioritizing travel and new experiences, I look for jobs that will take me to new places, and in 2014, I was lucky enough that an opportunity presented itself for me to work remotely.
How I Work, Work, Work, Work
In late May 2014, I gave my notice to my company — HUSH, a digital design studio in Brooklyn where I worked in production. I’d been there two years, helping produce projects for The New York Times, Under Armour, Nike, Estée Lauder, and other clients that needed innovative solutions to unique design problems.
Around the same time, Sarah Ancalmo, a freelance creative director I’d met through work and become friends with, told me she needed production help running her new branding + design studio, Public Persona, which catered to rebranding female online entrepreneurs. (Now we have a broader range of clients and projects.)
Sarah asked me to work a few hours a week supporting her, helping write proposals and contracts, and managing the projects. Because she had moved to DC, already worked with her clients remotely, we had experience working together, and I was already planning to travel, we decided to try it remotely.
My hours with Sarah increased over the months and added up to enough income for me to keep traveling past my initial July — September itinerary.
Constantly, but especially every few months, I’d assess my average hours and outstanding invoices to be paid, talk to friends & family, and then book out the next series of planes, trains, and automobiles.
(I spoke about how we work together remotely at our RY London professional networking event last month — post to come!)
Plotting My Course
I started a note for myself in my Evernote (which I live and die by for work and personal purposes) and titled it “My 100 Day Adventure”, expecting that I’d likely be back trying to find a job in NYC around October.
I later added a “+” to the 100 and calculated where 200, 300, and 365 day adventure would get me.
In my note, I listed the places and people to visit along with notes about my trips. The first year was all stateside, staying with friends and family and almost never paying for housing. I kept track of addresses so I could send postcards and snail mail back as I traveled.
I visited people for anywhere between 3 days and 3 weeks, staying longer with close friends and family. In spite of the “fish and friends” rule, I found that most people were delighted to have me around for a while — and not just because I’m a clean & charming guest.
Our society is not structured around consistent or easy socializing, especially outside work or for single 20-somethings. My friends enjoyed knowing they’d finish work and have a friend ready to meet for drinks or cook a simple meal at home together or order pizza and cuddle for a movie. No complicated coordination of calendars, just a week or two of companionship — almost like we regularly shared in college or as former roommates.
With all my parental units — my mom & stepdad and dad & stepmom — it was an opportunity to have more regular interactions and a casual family dynamic again instead of the high-stress visits at holidays that often overlap with many other activities and people.
Visiting this way, I got to know my parents, relatives, and friends as an adult, we learned more about each other’s work and skills and life experience, and the extended exposure allowed me to understand their lives better than a phone call or quick weekend trip could.
The Itinerary
On June 25, 2014, I moved out of my Bed Stuy apartment and into a Manhattan Mini Storage unit, and on June 29 (my dad’s 65th birthday), I flew out to Colorado to celebrate with my family and his friends. I had booked flights through September 8, when I would meet up with my mom and stepdad on their boat in Chicago.
From there, I continued to book travel out as far as I could expect to afford it, usually in 3–8 week chunks.
My former roommate from Morocco had recently moved to Dubai, so I booked a flight to visit her for two weeks in February 2015, swinging by Norway to visit a friend, and doing my first totally solo trip through Iceland on my way home.
I hadn’t been abroad since moving back to Texas from Bulgaria in the summer of 2011, so I was excited to start traveling internationally and visiting totally new places again.
I invited my mom to do a yoga teacher training with me in India, which turned into an 8-week trip together (just the two of us!) to Dubai, Delhi, Bangkok, Chiang Mai, and Phuket with our month-long course in Dharamkot.
She flew home to help my stepdad recover from shoulder surgery, and I went on to visit family friends in Hong Kong. While there, I planned an exciting and scary endeavor: 6 weeks of traveling alone through SE Asia. I felt like tackling the challenge of being a solo female traveler was a next step in my experience, and SE Asia seemed like an affordable and safe way to do it.
I flew back to the states on July 31 and met a group of my college teammates for our annual girls’ week. I went to NYC in November to move out of my storage unit, selling furniture and giving away four suitcases of clothes, and moved what was left into a friend’s basement.
From June 2014 to December 2015, I traveled to:
(not in this order)
United States: New York City, Boston, Washington DC, San Francisco; and Alaska, California, Colorado, Florida, Massachusetts, North Carolina, New Mexico, Pennsylvania, Texas, and Washington
Great Loop segments (on the boat): Chicago to St. Louis, Chattanooga to the gulf to northern Florida, and Key West.
International: Rio de Janeiro, Brazil; Dubai; Oslo, Norway; Reykjavik, Iceland; Delhi & Dharamkot, India; Thailand; Hong Kong; Tokyo, Japan.
6 week solo trip: Hanoi, Vietnam; Luang Prabang, Laos; Siem Reap & Phnom Penh, Cambodia; and Kuala Lumpur, Malaysia.
The Big Commitment
While in Hong Kong in May 2015, a friend sent me an email about a company called Remote Year that recently launched and would facilitate a group of 75 people working + traveling the world together for a year.
For 20 months, I spent 10–20 hours a week planning every detail of my life out to work + travel as a digital nomad. A year in, I was starting to get lonely, wishing for people to explore the world with and who could understand what the experience realistically entailed (it’s not a vacation). So I was intrigued by what RY had to offer.
I poked through the Remote Year site, found a contact email for Greg (the founder) on the footer, and sent him an email saying that I was envious of his group. He wrote me back and asked if I’d be interested in joining a future group. I said yes.
He interviewed me via Skype while I was in my hotel room in Hanoi at the start of my 6 week solo trip. I paid my $3000 RY deposit via credit card a few weeks later, asked for money as my birthday gifts, and allocated the funds towards chipping away at my balance.
I spent the 6 months before RY getting my life ready for such an extended experience and said my goodbyes to family and friends for (at least) a year.
On January 30, 2016, I boarded a flight from Dallas to Miami to Montevideo, Uruguay to meet up with my group and start our Remote Year.
Five months later, I’m writing this from our (beautiful) coworking space in Prague, approaching our year’s halfway mark.
Remote Year is a much different style and structure than being a digital nomad on my own. It’s much more expensive and I don’t control the itinerary. But I have a community, and the structure provides me other freedoms. It takes a certain mindset to stay on and enjoy Remote Year.
I still work for Sarah, and it’s still part-time freelance, which means that while I have 2+ years of experience working together and building her company, I don’t have job or income security. I take on additional freelance jobs (typically copywriting) as they come up, and I’m constantly strategizing ways to make enough money to support myself and this experience.
I write about my experience here on Medium because a big part of why I wanted to join RY was to use it as a platform for future opportunities with writing. I also visit galleries and museums everywhere I visit because I hope to work with arts organizations in the future as well (I’m an ArtH major and big art nerd).
Looking In The Crystal Ball
What does the future hold? I’m not sure.
Sarah and I are launching new workshops around branding, which allows me to participate more with content development and design as well as indulge in teaching again. She’s asked whether I might land in DC, which would allow me to work in-person with her and our clients more often.
When I imagine living somewhere again, it’s hard not to feel drawn back to NYC. But as I get older (turning 30 this year), it becomes harder to reintegrate with my friends who are living lives far different from mine.
When I finish my Remote Year on January 31, 2017, many friends will be married and have children. Our careers are already on very different tracks. And I don’t long (much) for that life. It’s hard (for me) to imagine sacrificing this freedom of constant movement and learning for security or a resume builder or a bigger bank account.
While I sometimes fantasize about having my own kitchen to bake in again, buying the perfect cozy chair for reading, sleeping in my own bed with just-right pillows, or simply not having to pack and unpack multiple times a month… ultimately, I still prefer to live on the road.
Update — my post-Remote Year reflection:
My dad loves to tell stories of me on road trips, wistfully staring out the window as the Dixie Chicks sang “Wide Open Spaces” through the speakers.
I’ll (barely) refrain from cheesily quoting the song, but I suppose that’s what it comes down to. This is something I’ve always felt drawn to — just like others aspire to being a parent or doctor or being promoted or owning a home or making a million dollars.
I won’t say, like most overly optimistic digital nomads, unilaterally, that “everyone can do it!”
For those that could make it work, they often dream about it but don’t really want to give up the security and comforts of a routine, of having a home, of going in to a job at 9 am and be told what to do.
Beyond that, it’s just not a realistic option for many people. Not every job can be done remotely — many things require a person to be physically present to do the work. Not everyone has the opportunity to leave their family, friends, and lives behind.
Yes, I’m hard-working, smart, and intentional in my choices, but I am, above all, lucky to be able to have the education, travel + work experience, and familial support to take advantage of the opportunities I’ve found to pursue the life I want.
Becoming a digital nomad probably won’t present itself to you, and it won’t be an easy choice to make or an easy lifestyle to maintain.
Is it worth it? To me, yes.
Cheers — to two years living on the road.
Katherine is working remotely while she travels the world — on the road since June 2014. She’s a member of Remote Year 2 Battuta, living around the world with 75 other digital nomads from February 2016 to January 2017.
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