Kelly's Workationing Story: How I Became a Digital Nomad

As I think most digital nomads will tell you, the decision to untether your life to travel on a long-term basis begins with a single thought.

It’s the seed of a bigger idea, one that was sown in you almost by accident and settles without notice. It’s a hearty and resilient thing. It doesn’t need much light or tending to begin to grow — you might not even know that it’s there for years. In the back corner of your mind it unfurls deep roots, weaving quietly through your dreams until one day you wake up and realize that it’s something that you can no longer shake. That little seed of an idea has become a part of you, and at that point acting on it is as inevitable as breathing.

For me that idea came on February 27, 2006.

I’d been staying with my family as my father battled a rare form of thyroid cancer. It had been months of surgeries, radioactive iodine and radiation, but we’d finally been granted a reprieve. My dad was strong, his treatments were aggressive and he’d caught it early. We had nothing but reasons to believe that the worst was over.

When the phone rang, my dad was in the basement on the treadmill. A week after ending radiation he was already back to running five miles. He looked almost like himself again as he climbed the stairs two at a time, running a towel over his forehead to grab the phone from me. His eyes twinkled at me as he put it to his ear. It was the doctor, and this was the call that we’d been waiting for — the one where they would tell us that his scans were clear.

Kelly's workationing story
My favorite picture of my dad.

Except that it wasn’t. My dad’s face remained impassive as he listened, but I could see something inside of him crumple. I sat down in the rocking chair and began to cry.

When he hung up the phone we just looked at each other. I don’t remember much else from that day or the following 18 days until my dad passed quietly at home, but I do remember this:

Filled with grief and searching for anything that might help I asked my dad, “Is there anything I can do? Is there anywhere that you want to go?”

My dad, who had stayed so strong through his sickness, suddenly let out a sob and said, “Everywhere I’ve never been.”

My dad was a pretty incredible guy. He grew up in poverty, the son of an abusive, alcoholic father whose greatest paternal act was disappearing when my dad was seven, never to return. My dad’s life after that went about as you’d expect for a kid with little support and no resources, and by the time he was a teenager he was a high school dropout who was well-known to the local police.

However, that’s where my dad’s story stopped being predictable. He joined the army. He got a degree and became a nurse. He got married and had kids and got another degree. At the age of 35 he was accepted to medical school, and by his early 40s he was a well-respected psychiatrist.

The person that my dad was when he was younger is a stranger to me. Every memory that I have of my father is steeped in his hard work and discipline. He spent all of my childhood going to school and working multiple jobs. He focused all of his Herculean efforts on climbing the ladder out of the life that he came from and into a life that probably didn’t even seem real or possible to him when he began — but still he climbed.

Kelly's workationing story
My brother and me with my dad on a rare family vacation.

My dad didn’t take vacations. My dad didn’t take days off. But I knew that he dreamed of travel. He was a scholar of eastern history and mysticism who devoured all that he could on the subject. He talked about going to Asia, to Europe — everywhere. And once he’d become a doctor and his kids had grown up, he would.

Except that it didn’t work that way — and so the seed was planted.

My dad’s death sent me into a bit of a tailspin. It changed everything about who I was and how I saw the world. To people who knew me, it probably looked like I was spiraling — and I suppose that wasn’t entirely inaccurate. But looking back I can see that the ensuing chaos was the inevitable result of a seismic shift in my personal values.

I began to value things like freedom and autonomy over everything else. I found myself leaving good jobs and solid relationships for reasons that I couldn’t quite name. I was restless and unhappy, but without any real idea of how to remedy the situation. I was searching for a life that would somehow resonate with that seed of an idea that had suddenly become the core of my being.

It was in the middle of all this that I met Kari. I’d followed that restless feeling (and, admittedly, a man) to a new city and gotten involved with the startup scene in Pittsburgh. In startups I finally found a working environment that made sense to me. It satisfied both my need for freedom and flexibility and my desire to always be driving forward toward a goal that felt just a little farfetched.

Workationing story
Pittsburgh’s North Side, where I met Kari.

And in Kari I found something really special, too. I found the kind of friend that lights you up and makes you feel like anything is possible. We had an instant connection founded on a love of fancy cocktails and an eerily similar (albeit slightly twisted) worldview. It turned out to be a fated meeting.

Fast forward six years and Kari is now my boss at The Content Factory. We have an awesome working relationship and an even more awesome friendship, which we manage to balance in a way that feels pretty effortless. The company that she started allows us to work remotely, and we’ve taken advantage of that by workationing together in places like Mexico, the Dominican Republic, and even beautiful New Hampshire (trust me, it’s way wilder there than you think).

Through those trips and through the traveling that I was suddenly able to do on my own, that idea that had been planted in me a decade before suddenly came to the forefront. Kari and I talked about it over fish tacos during a lunch break on the beach in Mexico.

Why don’t we just live this way?

I saw the vision come into focus while drinking mamajuana on a boat in the crystal clear waters off the coast of Punta Cana.

This is what life should be.

I started to hear the words every time the wheels went up on a plane, every time I sat laughing over drinks with strangers who had become new friends and with each new stamp on my passport.

Everywhere I’ve never been…

Workationing story
Taken during that fateful lunch on the beach while workationing in Mexico.

Sometime in late spring of this year it stopped being just an idea, and I started thinking seriously about logistics. Where would I go? How much would it cost? Who could I get to go with me? Could I do it alone? Did I even want to?

Then on July 31st, everything fell into place with one phone call. It was a Sunday afternoon and Kari called me on Skype. We talked about the usual work related things, but the conversation began to drift. I could tell that there was something that she was trying to get at, but I couldn’t quite figure out what it was.

Then she asked me if I wanted to try a long-term workation — like, a whole year long. I couldn’t say YAS GIRL YASSSS fast enough. Having a traveling partner like Kari to do this with would solve most of the problems that I was facing, and based on our working relationship I knew that if we just set an aggressive deadline and ran at it full force that we’d figure out the rest.

We quickly started sketching out our plan. We’d do a different country every month. We’d stick to a budget. We’d set solid goals for things that we wanted to accomplish on each stop. During that call, was officially born.

It was another 30 days of phone calls and texts to check in with each other to see if we were both still on board. We were excited and we were terrified, but neither of us seemed to be budging on our conviction that this was what we wanted to do. So on September 1st I put in my 30 days notice at my apartment and began the process of untethering my life.

As I type this it’s October 23rd, and although my my plane ticket for our first destination is booked for January 1st I feel like in a lot of ways this journey has already been underway for a while now. We haven’t even left yet and this has proven to be one of the most meaningful, challenging and revelatory experiences of my life.

Let me tell you, if you want to do some serious soul-searching, ditching your permanent address and putting all of your worldly possessions into a 10 x 10 storage unit is a pretty fabulously traumatizing place to start. But honestly, that’s the whole point of doing this.

I want to live my life intentionally. I don’t want my fears to dictate my horizons. I don’t want to let momentum and a desire for security to create a sense of inevitability in my life that carries me from one major life event to another without stopping to reassess if this is really even the direction that I want to be going. I don’t want to take for granted the time that I have left (however long that may be). I don’t want to wait to have adventures.

You only get one life and I intend to live the hell out of it. Through the Workationing blog, we’ll tell that story. Thanks for following along.



P.S. – If you’re interested in our story and what happens on our journey, check out The Workationing Podcast (subscribe and rate, and we’ll be your besties forever). If you don’t have iTunes, you can find us over at SoundCloud.

You may also like

12 Things To Look For In An Airbnb

12 Things To Look For In An Airbnb

Ashley’s Workationing Story

Ashley’s Workationing Story
  1. I just read your peice and become inspired. It is great to to live instead of exist in the world. I’m finding the motivation day by day to get up and travel more of the world. Thank you you for your story.

Comments are closed.

{"email":"Email address invalid","url":"Website address invalid","required":"Required field missing"}