How I Quit My Job to Become a Digital Nomad

It happened in Zion standing on the edge of the viewpoint at the end of Watchman’s Trail. It was the first hike we’d done when we arrived eight days earlier, and it was the last hike we were doing before we left. We’d planned to stay for three days but loved it so much that we refused to leave — we’d spent the last week doing every hike we could find in that magnificent National Park, but we were actually three weeks into our cross-country road trip. We’d already been to (and slept in) Yosemite, Red Rocks, and the Grand Canyon. I’d never felt more free in my life.

So while I stood at the viewpoint looking up the canyon, immersed in gratitude and awe, listening to Step Out by Jose Gonzales (yes, sometimes I like to pretend my life has soundtrack music), I felt something else — something…fiery. Something hungry. Something maybe even a little bit desperate. Something that felt like I was missing a place I hadn’t yet left, and I was determined to get back.

I stood there for a long time, alone, letting this feeling have me. I recognized it — inspiration, determination, and just a hint of fear. Fear that I’d never be back here. Fear that we’d return home to the east coast, I’d get a “real job,” and my two weeks of allotted vacation per year would never again allow me the freedom to visit places like Zion and spontaneously decide to stay an extra 4-5 days. Fear of the conventional and the stagnant (a fear I’ve always had).

But the inspiration and determination is where “it” happened. It’s where I decided that, for at least a portion of my life, I wanted to be nomadic. It’s where I decided that this “van life” that Nick always talked about was something I would be 100% on board with. So that’s when I decided that at some point, some way, somehow, I would need a job that could be done remotely.

That was almost two years ago. And just two weeks ago, I put in my notice at my full-time job, and opted to be 100% self-employed…remotely.

When I decided to put in my “two weeks” at my full-time job, there were fireworks — in my heart, in my brain, in my body. I was so excited and full of that same inspiration and determination that I felt up there on Watchman’s Trail, without any of the fear, which made the experience and the decision all the more bold and brave and powerful.

I’d been doing remote jobs on the side for a year. I built and managed websites, I wrote articles here and there, and then I began studying social media marketing, and I was hooked. I got a couple of gigs managing social media platforms for small businesses and events, and I loved it. I realized there was a need for it. And I knew — just knew — that I had the skills, drive, and perseverance to do these things, do them well, do them authentically, and do them from wherever I wanted.

So here I am. All the way from lightning bolts of inspiration in Zion, through two full-time jobs in my home city, to my kitchen where I’m sitting right now — Day One, completely self-employed.

It’s f**king terrifying.

The fear that was absent when I decided on this route returned in full force, and just in time to make me question anything and everything about almost every decision I’ve ever made (because if you’re going to panic and rethink your life choices, why settle for just one life choice? Bring them ALL back up, make it a party, play some music, serve hors d’oeuvres!). Here are the questions my fear asked me:

“Who do you think you are?”
”What do you think you’re doing?”
”What makes you think you’re good enough?”
”Who’s going to take you seriously?!”
”What makes you think you can succeed at this?”
”Do you really think you’re going to get enough business to support yourself?”
”Remember those time in college when you slacked off and read SparkNotes to compensate? What if you’re still a slacker, not a hustler?”
”No really, what do you think you’re doing?”

It’s a fun little parade, isn’t it? Nothing like crippling self-doubt to start off a brand new entrepreneurial career. And although these thoughts were running rampant in my head from the moment I opened my eyes, they weren’t alone. I also thought:

“What person has ever taken a risk in their career without being at least a little afraid?”
”What entrepreneur has ever ventured out on their own without having every single one of these thoughts?”
”If you never try, you’ll never know…and you’ll certainly never succeed, because you never had the courage to start.”
”Being afraid does not mean you made the wrong choice. You were never not going to be afraid.”
”Fear and excitement are not mutually exclusive. Neither are fear and determination, or fear and success, or fear and moving forward. Fear does not negate these things -- it coexists with them.”
”Wherever creativity and bravery go, fear will join them. This is not bad or wrong. This is life. This is taking chances. This is branching out. This is trying new things. This is normal.”

See, when I manage to breathe and be rational for longer than ten seconds, and I can look upon my fear with compassion, I know it’s really only trying to protect me (albeit in an odd sabotaging sort of way that I rarely appreciate). It wants to keep me safe. It’s my gatekeeper (a metaphor passed on to me by the fabulous Jessica Chilton), guarding the entrance to anything and everything unknown, warning me that if I proceed, there’s no telling what could happen. My fear is my bodyguard, and it takes its job very seriously. But it is only my bodyguard…not my boss. It is only the gatekeeper…not the gate. It cannot prevent me from doing things unless I allow it to.

And I’ll make space for it, certainly. It’s not going anywhere as I move forward in life, nor should it. It serves a purpose and wants to feel heard, so I hear it. But it IS constant work to make space for it and hear it without succumbing to it. Probably the hardest work I’ll do in my lifetime.

So I imagine that while my fears are running around in my head like dozens of Chicken Littles, panicking about the falling sky, my creativity and bravery are sitting quietly in the corner, looking on compassionately, waiting for them to calm down and realize that everything is okay…it’s just new; ready to tell them that even if they sky did fall, we’d just prop it back up and try again. As Elizabeth Gilbert says to her fear in Big Magic (aka the Bible…yes, the book is that good), “You’re allowed to have a seat, and you’re allowed to have a voice, but you are not allowed to have a vote…then we [can] head off together — me and creativity and fear — side by side by side forever, advancing once more into the terrifying but marvelous terrain of an unknown outcome.”

Because one day, perhaps, Future Me will be out there — enjoying my work, still trying new things, thinking about my travels, reflecting on my many journeys — and I’ll just be so, so pleased and proud that on a gray January day in 2019, I sat in my kitchen, acknowledged my fears, and proceeded anyway.

So for anyone doing something new this year — for anyone taking a chance or a risk or leap of faith, professionally or otherwise — I feel you. I’m with you. You are not alone. It’s f**king terrifying. And it’s pretty f **king cool, too.

“And you have treasures hidden within you — extraordinary treasures — and so do I, and so does everyone around us. And bringing those treasures to light takes work and faith and focus and courage and hours of devotion, and the clock is ticking, and the world is spinning, and we simply do not have time anymore to think so small.”

-Elizabeth Gilbert, Big Magic-