My Digital Nomad Origin Story

I was looking through my computer today for a file and stumbled on this reflection I’d written for myself two years ago while en route to Brazil.

Today, in Chiang Mai, Thailand, I had lunch with someone who was curious about my work, how I’ve done project management remotely, how I got started as a digital nomad… so I’d just been reminiscing on and telling my story, breaking down the steps that got me to where I am today.

So, an ever-so-slightly edited + abridged version of where I was 2 years ago — 6 months in as a “digital nomad”:

January 17, 2015

On the plane to Rio de Janeiro. It’s my first trip abroad since I moved back from Bulgaria in 2011. It’s a reminder that life gets away from you.

I remember when I surpassed my two year anniversary of living in the states — I was then more of an American than an expat.

Well, I don’t exactly remember it… it would have been July 2013. I was in New York City, where I’d been living for 9 months at the time, struggling and succeeding at my job, recently broken up with.

I felt something of a sense of dismay to realize I was just another 20-something living in New York. Of all the places to be just another 20-something, New York is definitely on the top.

And I know that if I’d instead stayed abroad for those four years, I’d be wondering what my life would have been like if I’d moved back and lived in New York, so it’s just as well.

But it was strange.

It made me sick every time someone told me that I’d had my adventure while I could — like living abroad was just a fun game I’d played for a couple years, another American studying abroad to get drunk and take pictures with landmarks instead of a real immersion into another place, another version of myself.

Maybe I have a heightened sense of the importance of my experiences abroad or that it was a unique or particularly special experience. But it was to me.

It changed everything about who I was and how I saw the world and what I valued.

And walking through the life of someone who had never experienced that and didn’t care and could compartmentalize the experience felt insane. I felt myself going crazy inside this life that was coming together into a recognizably successful path.

It’s ironic because I’d by no means “made it” — I was still living out in not-yet-gentrified Bed Stuy, spending my weekdays working on a salary that worked out to a single digit per hour on the bad weeks, chasing cultural experiences around the city on the weekends, counting every dollar and making every dollar count.

So I wasn’t the underdog on top yet, but I could feel that if I kept going, I’d be somewhere four or five years down the line, making good enough money to waste some of it on an overpriced apartment, drinking with coworkers and friends at every opportunity, buying increasingly expensive clothes, and bitching nonstop about the fantastic and self-imposed bullshit of my daily life.

In some ways, it was exactly the kind of life I’d come out there to pursue, but I also looked at my peers and superiors and didn’t want to end up where they were.

It didn’t matter that I could do it or I was doing it — except to prove to myself that I could. Once I knew that, once others knew that, I was ready to walk away from it.

I kept scrimping and saving, running numbers in my head and in spreadsheets on a daily basis. I reached out to friends and family. Built possible calendars and complex flight itineraries.

Do you have somewhere I can stay? How many days? I’m really coming, so tell me how many days. Don’t tell anyone yet, it’s not public knowledge. Are you really okay? I’m going to come. I’m doing this.

I decided upon a credit card to open, a new laptop to buy.

As the rough outlines of the plans started to coalesce, a friend reached out. Well, not even a good friend — a freelancer I had worked with on a few projects at my job, who I admired, who I talked to whenever I had a chance and she wasn’t slammed.

She’d encouraged me, found some things in me impressive, was friendly. She was older, seemed glamorous, was something of an idol in terms of an accomplished creative New Yorker.

She’d left the city and contacted me privately to ask if I wanted to help her, just a few hours a week, with her new company. I could do it remotely — she needed a producer’s mind who could help with budgets, contracts, whatever. Manage the beast that was slipping from her control.

I said of course. I didn’t have to negotiate — she offered me more than twice what I was making per hour at my job, a good rate for learning her business and helping it grow.

It started with a couple hours per week, us calling and learning what to even talk about, me finding tens of things to do but only having the time to manage a couple at a time. Slowly, we worked our way into rhythms in spite of the ever evolving nature of the company and our roles.

It was a contrast from my day job in every way — we were friends and partners, though it was her business and her work. But I was there to make it work and support her. It capitalized on my protective nature, my need to organize and formalize everything.

We worked together to make things happen for women, women who owned their own businesses and were real people. Our accomplishments didn’t ricochet through press headlines or social mentions, but it made a difference to them.

And it brought in more clients than we could take on. It didn’t feel totally pointless, and I didn’t have to deal with egotistical meltdowns on a daily basis or misogyny seeping into every interaction.

I had learned so much at my real job, been exposed to high level clients, grown in a plethora of ways through every thread of the experience. I loved the team, but it was all at arm’s length. I’d never truly be one of them.

So my night job was the perfect opportunity — I could be removed, I didn’t have to fit in or engage, I just had to do a good job and do it when I could.

After 19 months at my job, almost 3 years after being back in the states, I asked my favorite boss to go for a walk.

We sat out at the lunch tables in the DUMBO triangle on the most perfect, sunny May day, and I looked out at the Manhattan bridge and New York skyline across the water, finding the words, and told him I was leaving.

I said it wasn’t personal and that I’d loved my time with the company, but I had a lot of personal obligations and opportunities for the summer. I had to go, it would be too much travel, and I didn’t want to half ass my travels or my job — I was going to put my stuff in storage and go.

He told me there would be consequences professionally, and I agreed, and he wished me his best.

I didn’t have any plans for going abroad at the time, I only had plans for the next three months.

I had booked trips all around the country for various reasons, I had some money coming in to help assuage the impact, enough in savings to cover it, and a new credit card.

In my moments of panic and fear, I reminded myself that the worst case scenario was to move home to one of my parent’s houses and work as a tutor or waitress until I could afford the next thing — not an ideal scenario, but not scary or bad enough to warrant not taking the risk.

I loved New York. I love New York. It’s the only place I feel at home anymore. It wasn’t about leaving home or quitting the city — it was about stretching my legs because the world didn’t end at my doorstep.

So I leapt. 
And the nets I’d set caught me.

My night job turned into enough to cover everything financially (thanks in large part to the generosity of everyone’s couch, air mattress, guest room, or bed space), offers rolled in for hosts and future stops, and I felt secure exploring the world with a job title and productive outlet. While I still felt frustrated and confused on a regular basis, I also had moments of calm.

Every time I sat in an airplane or boat or car, I felt at peace. I was in motion, I was heading to a new destination, I was on an adventure.

As I neared six months on the road, it was clear I could keep going. As much as I wanted to get back to New York and figure out how to make life and work work, I couldn’t sacrifice the opportunity to travel for as long as I could.

I mentally committed myself to make it happen for another six months — I started calling it “The Year of the Nomad” as I waxed on internally, thinking about my experience.

I’d started by referring to it as “the 100 Day Adventure,” but it became clear early on that I was surpassing the 100 day mark, though I stopped back in New York to celebrate how much my life had changed in the course of a hundred days.

As I considered how the second half of my nomadic year should unfold, I knew I had to make it international.

I’d learned so much from my other experiences abroad that I had to continue getting abroad and spending meaningful time in other countries.

I had to continue making my life international so that people would stop calling it a phase, stop diminishing what it meant and that it was, and is, part of who I am and whoever I’ll become.

Brazil came together thanks to a family member with a ticking clock of residency in Rio de Janeiro. In September, I’d convinced a friend to take a job opportunity in Dubai, so my next objective was to make good on my promise to visit, linking in stops through Oslo to visit a friend and then Reykjyavik for my first solo trip.

Then I wanted a month to myself in DC to work and socialize before going to India for yoga teacher training with my mom, hopefully followed by explorations of the country and my first forays into Asia. I’d “only” been to Europe, Mexico, and Morocco.

I did essentially no research or any preparations for this trip. I learned a bit of the language, but I was so entangled in keeping up with work and preparing for my Juilliard audition that I couldn’t spare the time to consider Brazil.

So I have almost no expectations: there will be a beach, food, drinks, cultural institutions, sightseeing.

Whatever it is, I know I’ll love it — the challenge, the foreignness of it. The opportunity to let my brain struggle to understand everything around me, humming along in a heightened state of awareness in every moment out of the house.

I feel alive, pursuing the new, unlocking the puzzle of language and meaning around me, finding my way through even the simplest tasks: discovering a place, enjoying a meal, being awed by the sights and sounds.

My life pops off the page like a flat character finally given their reason for being written into the story.

All travel can do that, but something about truly being a foreigner gives me the ultimate permission to discover everything anew and feel wonder.

While I hate to look like an ignorant tourist, I’ve discovered that I also hate blending in completely because I find people expecting me to be like them, to know what to do, to follow the common expectations.

It’s a metaphor, maybe, for my entire life: I am at my best as an outsider.

I’m motivated to get in and figure out how it works, and in the moments when I don’t feel that pressing need, I can enjoy any emotion and any experience under the guise of an stranger in a strange land.

Once I’ve mastered a place, a job, a skill, I might return to relish in it, but I’m like a child who’s outgrown a toy. I’m so hungry for the new and different that I have and will sacrifice almost everything for it.

Whatever I might care for earthly possessions or human relationships fades in comparison to my desire to go, see, do, discover, explore.

I always come home, but I come home different. And once we’ve exchanged love and hugs, recalibrated ourselves to each other, I leave my family and friends behind again.

I love a constant puzzle, a constant challenge, a new world to discover, a new character to become.

I love experiences that end — I find my way inside a new life and persona, grow comfortable in its skin, and then shed it to move on to the next thing.

Katherine is a digital nomad, working remotely while she travels the world — on the road since June 2014. She was 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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