Digital Nomad: A True Story
How we traveled and created our own businesses on the fly
When you stop for a moment and take a glance at where you were a year ago, what do you see? Are you in the same place? Have you moved geographically, but remain in the same situation? Or has your life changed so dramatically over the course of 12 months that you don’t recognize 1-year-ago you?
That last one is what I feel. (As I’m sure many of new workers feel.) July 2017 was a completely different place. A completely different person.
The same can be said for my fiancé — then girlfriend — Jess. We were both working for a tiny financial company in Hillsboro, Oregon. Fresh out of college, only one of us was in an applicable field based off our degrees (I have a BS in economics, Jess a BS in international communications).
I was on the low, slow track to becoming a financial advisor, while Jess was stuck. For the whole previous year, we had thrown everything to the side just to find breathing room. We started living together, we tried to start paying off student debt, we made sacrifices so we could fit the mold predestined for us.
It was awful.
The Script
It’s not like we’re special or anything. Everybody in middle-class America deals with the same shit. Your parents dealt with it, and their parents before.
Not to say that it’s anyone’s fault. Society is definitely to blame. Going to an unfulfilling day job five days out of the week just to get to a weekend filled with unfulfilling experiences is the social norm.
It’s all part of the script that goes like this:
- Be born.
- Go through childhood by going to public school, get decent grades, make friends, be social, do fun things while you can.
- Doing good in secondary education gets you to that overly-vaunted next level: Post-secondary education.
- Be adequate in college, graduate, celebrate, cry when there’s nothing for you at the end of the road. (Hint: They need experience, because college is definitely not that.)
- Find an administrative assistant job — or equivalent.
- Nab a suitable mate for (potentially) life, get hitched, pump out a couple small ones.
- Move to a house, buy a ton of crap, do that whole unfulfilling bit for the majority of your healthy existence.
- Retire from your work in an unsightly blob of disease, contempt, and lust for sitting in front of the TV for hours on end.
- Optional: Regret never doing that one thing because you never had time and now it’s “too late.”
- Die.
Sounds fun, no?
Well, hate to break it to ya, but you might just be a redneck who’s on this scripted path.
Jess and I sure as hell were. We were on step 5 — halfway through — and were being catapulted to step 6 and beyond.
What Changed?
Let’s go back to February of 2017. It was Jess’ birthday. She was 23, and I wasn’t far behind. The crux of our young lives, you might say.
She had something of an ultimatum breakdown, where she revealed that she was having an internal conflict: Me vs. South Africa.
Jess had gone to SA for an internship back in college, and to her it was home. Where she could be her genuine self. She would remember the beaches, the people, and the atmosphere, then cry because she wasn’t where she could be her best self.
And who could blame her? Have you ever felt that with a place or a person or a calling? I have the same affection to writing (and to Jess). A pull so strong you either bury it deep down below piles of unfulfilling garbage or you don’t ignore it and fly with reckless abandon into the eye of the storm.
To Jess, I was her little taste of that best self. I helped her shatter her previous thinking that she was inadequate, underwhelming, not enough. Together, we braved a long-distance relationship, got an apartment, and determined what our main goals in life were.
However, she couldn’t ask me to upheave my entire life and move to South Africa. The pull was strong, and she felt that if she didn’t go back soon, then she never would, and life might as well skip to step 10.
So, on her birthday, I gave her the greatest gift I could think of: I made the choice for her. I would go to South Africa with her, for three months starting in September.
Why did I decide to leap so unknowingly into the storm with her? I certainly couldn’t give you a concrete answer. The closest thing would be “I love her to a fault, so the trust was all I needed.” But love couldn’t possibly make a guy give up all that he had worked for just to galavant through the South African countryside…
…Unless There Was Another Love ❤️
And there was.
Up until her birthday, I had been a horrible employee in the sense that I was looking for other avenues of income while I should’ve been working.
I was looking for fulfillment.
I knew the script had a stranglehold on my future. Family, friends, and the common public were all silently cheering me on: Go you, you’re doing great! Don’t leave the beaten path, be in the same place we are — or better yet, a little worse off!
I tried my hand at everything under the sun:
- Options trading
- Affiliate marketing
- Copywriting
- Kindle publishing
- Poker
These had specific things in common. They were exciting, new, risky. Anything to satisfy the high that wasn’t being accomplished by my 9-to-5.
Writing. The one constant in my life. Everything always came back to the written word. No matter how much I — or the script — fought the urge, pen and paper prevailed.
So perhaps the love of writing, coupled with my love for Jess, was the perfect combo that catapulted me into this new adventure.
And in my humble experience, decisions built off love are usually the best.
So We Began
I calculated how much we each needed to save for three months of South Africa, from September to December of 2017. $3,000. A decent chunk of change for us.
In secret, we saved. We plotted. We dreamed and imagined what our lives would be like.
Jess started her own business, a digital communications/virtual assistant service she called Genuine Conversations Media. She took online courses, asked questions to others who were off on their own, and learned as much as she could. Amazingly, she got clients while we were still at the financial office. She pulled double duty for quite a while.
I, on the other hand, was stuck. I was still trying to get back to writing. I was on Medium for this entire time, but I kept waffling between being a fitness guru with zero education and a motivational speaker being drowned out by every other Tony Robbins wannabe.
But somehow, we got to the point where we told our employers it was Cape Town or bust. The chagrin of our parents and close friends was more fuel to the fire (because they didn’t seem satisfied either).
Enter Heaven On Earth
When that plane took off for Amsterdam — leg one of two nine-hour flights ✈️ — Jess and I felt nothing but calm. Peace. The start of something fresh we had rarely felt before.
Fulfillment.
Touch down. Uber drive. Our small apartment for the next 90 days. It was nighttime, so it wasn’t until the morning when we saw the massive amount of opportunity travel had blessed us with.
During our South African adventure, I rediscovered writing, became a freelance writer, built my own website (adorned with pictures from Lion’s Head), and gained clients of my own. I proposed to Jess (she said yes). I ran my first 5k, Jess ran her first half marathon. We tried biltong, did calisthenics and yoga by the beach, played ultimate frisbee in the sand, worked from Seattle Coffee Company, interacted with our apartment’s latchkey cat (we affectionately called him “Butthole”), conserved water during the drought, went vegan, and cooked new meals. We celebrated Halloween by making pumpkin cookies and watching The Nightmare Before Christmas. We put on an American Thanksgiving with all of our SA friends. We did CrossFit for the first time. We had dinner parties and walked everywhere. We went to markets and lived in the moment.
We did all of this, which might not seem super significant. What is significant is this: I can’t remember what I did last week. The memories Jess and I created in this foreign land will stay with us for the rest of our lives. Those three months gave us our best selves.
And that’s the whole point of life, in my opinion.
Digital Nomadism Gave Us Fulfillment
We ditched the script and broke free from the bonds of society telling us school and a good job and a white picket fence is the American dream.
To Jess and I, the American dream is to find your purpose and attack it with all you’ve got.
We came back after South Africa with this purpose, and we continued to work hard for our dream. We had another adventure in the chamber (which fell apart in dramatic fashion, but that’s another story for sure), and we have a great group of clients that pay us what we’re worth.
I’d like to think we are a digital nomad success story. And we want to help those who also feel that pull towards a purpose, towards fulfillment.
So that’s what I’m dedicating my space on Medium for: To aid anyone who wants assistance in finding their best selves. Because if you aren’t going for your best self, you might just be living the script.
The Year In Review
So, from July 2017 to now, Jess and I have experienced the full spectrum of human emotion. We’ve traveled to South Africa, Los Angeles, New York, Dahab, Egypt (that long story I mentioned earlier), New Orleans, Amsterdam, and all over Oregon.
This next year is bound to be even crazier: Getting married in a month, our California road trip honeymoon, making a pilgrimage to Bali — the mecca of digital nomads — in November, and going back to South Africa in February (for Jess’ birthday) are what we are definitely doing so far. No maybes. No only-ifs. These are absolutes.
Maybe we’ll head to Europe later. Or tour the east coast of the States. That’s the beauty of being in complete control: It’s up to us.
All I can do is picture a year in review if we didn’t travel and build our own businesses. It’s a horrible, complacent portrait, so I tend not to dwell on it too much.
I express gratitude every day (I write it in my journal), thanking the universe and my gut that we actually went through with risking everything. By doing so, we gained more than we could’ve hoped for. My wish is that others can gain the courage to do the same, through caution into the garbage heap with their unfulfilling 9-to-5, and join us on the road to unlimited potential and freedom.
Become your best self, no matter what that is.
Thanks for reading!
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(I’m a freelance writer and fiction author. I help Millennial solopreneurs and freelancers develop a well-rounded, fulfilling lifestyle.
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