Nomading Unravelled: How A Digital Nomad Trip Changed My Career Trajectory
Remote worker on sailboat in Lesbos, Greece on a windy day

Nomading Unravelled: How A Digital Nomad Trip Changed My Career Trajectory

I stepped onto the Lesvos tarmac in mid-May 2018 as a fully employed Quality Assurance Coordinator who, five months prior, had just scored her first location independent job. With the aim of absorbing my job’s learning curve with minimal impact, I had delayed balancing work and travel as a digital nomad by staying in my routine, native California life for those first sweet months of location independence.

This attempt at approaching my new job in a professional manner worked, but it was ultimately in vain: four weeks after I arrived in Lesvos for my Hacker Paradise trip, I quit my job and left Greece as a fledgeling freelance writer.

How did it happen? What led me to throw away a job I dreamed of in pursuit of something much less secure? First, let’s rewind to the yellow brick road that led me to Hacker Paradise.


Finding an Online Job

A year ago, I had no idea how readily available remote jobs are. I was not yet a part of online social networks that post freelance job opportunities several times a day. My friendships with digital nomads were yet unformed. Unaware of the entirely virtual teaching, marketing, designing, writing and entrepreneurial positions available, I thought that having a web-based job meant being a techie, something that seemed unattainable to me.

I dreamed of finding what seemed, at the time, that one elusive, remote opportunity and grasping it before time slipped it from my hands.

In November, I applied for the job, and in December, I got the job. The job was as a Quality Assurance specialist with an online medical cannabis education company. I had already known about Hacker Paradise for several years, and finally, my opportunity to go on a trip had come! I went into planning mode, spreadsheet style.


Although the virtual position was not ultimately right for me, the milestone that getting my first online gig signified is not slight. Landing this job reinforced the notion that the concept of ‘unattainable’ is often a mental construction created when we are afraid to risk. When I first chanced upon a Hacker Paradise Facebook ad in 2015, I felt stuck in a city with a job that never challenged me, and the idea of living this life I’m now living seemed destined to never happen.

Starting my first remote job demonstrated that this lifestyle is attainable, as is creating any kind of intentional life, location independent or not.

But it does involve something that many are averse to: a shift in mindset, a mission to destroy the shrine we have mentally built and dedicated to ‘The Impossible.’ The Impossible has god-like status in the lives of most humans, and although fear has its place, we have a say in how much it controls the tiny choices that culminate into the monolith of each life.

My Hacker Paradise Experience

A few months after landing my job, I chose to go on the four week trip to Lesvos, a smaller Greek island near the Turkish coast. Along with my digital nomad peers, I did all the things: I explored an ancient Roman aqueduct, bathed in the healing hot springs of Eftalou, learned the basics of sailing, and wandered the streets of ancient towns. I met souls who prioritize growth – some of whom I wish to call friends for my entire life.

I learnt traditional pottery methods, and crafted two bowls from start to finish with my friend Tam. In encountering an incredible trainer with an unfamiliar teaching style, I improved my horseback riding in subtle, but deeply significant, ways. My joy peaked when seven other participants rode horses for the first time.

More than anything, the little moments of connection with both fellow participants and locals created tiny sparks that, in sum, illuminated the entire trip.


But something else happened, something I didn’t realize the importance of until months later. I met people who loved their online jobs. At that point, I had already realized I had a micromanager for a boss. Even though the job was advertised as suitable for any time zone, I was on meetings with her at 3 a.m. in Greece. When she accused a contractor of abusing her in a past life, I knew it was time to go.

My peers were hard workers, but I noticed they were happy in their professional lives in a way that I was not. They, to varying degrees, lived out healthy work and travel balances. They were empowered. I will always consider Lesvos a home, but the greatest gift this trip gave me was the power of association with individuals who were, and are, intentional in creating their lives and their workflows.

Life as a Freelancer

I quit my job a few days after the trip ended. Still plugged into the Hacker Paradise network, I picked the minds of other freelance writers. I applied for every writer-esque freelance job I could, and my friends tagged me in job opportunities they came across. I use my own unmonetised blog as a showpiece, and even as I still get used to having a fluctuating ‘beginning freelancer’ income, the writerly wildfires raging online have been helpful in spreading my work and increasing my rates.

Writing is an eternal home base for me, but the writing pushed me past writing. With so many remote opportunities out there, why not explore? Why pigeon-hole my career?

Now, I’m a part-time freelance writer, part-time professional matchmaker (yes, really), and I’m about to embark on a scholarship-sponsored coding boot camp in Minneapolis…because other Hacker Paradise participants convinced me that coding is, like writing, all about creative problem-solving. Remember how I thought being a techie was unattainable?


Tailoring my own career has forced me to be clear with boundaries, both with others and within myself. It has demanded that I familiarize myself with my own worth. It has asked that I not let another person determine it. It has disciplined me to create my own opportunities. It has insisted that I tap into the power of no, leaving my people-pleasing former self in the dust of time. It has crystallized the concept of hard work.

I still have no idea what I want to do in the long-term. That’s part of my point, though. To all who dream of life as a digital nomad, or to all who have an undesirable remote job, to you I say: don’t make it your initial objective to find the dream job as a digital nomad.


If you land it on your first try, great. If you don’t, use a job, any job you can stand, as a digital nomad to travel, meet other remote workers – through meetups, at coworking spaces, or on organized work trips for digital nomads  – and be inspired by them. Opportunities will unlock opportunities. The open roads this journey can take you on are limitless.

You will find more than what you sought.

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