When The Chips Are Down

How a leap of faith can break a streak of idle discontent and, with time, bring fulfillment.

By Alana Cloud-Robinson

Photos by Alexandra Isabella


In collaboration with Urban Outfitters and Dickies, we comissioned a series of stories that feature creative leaders who offer their insight on the “new” work world.

Seven months ago, I quit the best-paid job I’ve ever had with nothing waiting in the wings. From the outside looking in, it may seem that this was a thoroughly well-calculated plan of action—after all, since entering the workforce at eighteen, I had always been exceptionally responsible regarding my livelihood.

I made it out of high school by the skin of my teeth. I remember visiting the college counselor's office and telling one of the surly, wizened old creatures there that I planned to submit applications to all the top colleges in the country despite my poor grades and abysmal test scores. Spurred by teenage hubris, I would submit a short yet compelling piece to each school in which I would explain that while I didn’t have a report card to write home about, I did have good old-fashioned, home-grown intelligence. I would demonstrate that I was an exception to the rule, a free-spirited genius they’d never seen. Given the chance, I would excel within their fine establishment and go on to become a literary giant, blackening pages with the kind of work that would secure my place on the shelves of future classrooms alongside the greatest writers of all time.

In a cinematic turn of events, the person reviewing my application would be so impressed with my courage to fly in the face of decency that they would accept me on the spot, thinking to themselves, “Well, on paper, she’s not much to look at, but by god, this one’s got moxie.”

“Seven months ago, I quit the best-paid job I’ve ever had with nothing waiting in the wings.”

I outlined my plan for the college counselor, even pantomiming a “ta-da” motion with my hands like a circus performer at its conclusion. With a mixture of irritation and amusement, she informed me that with a transcript like mine, this fantasy was unlikely to pan out. Somewhere underneath all this class clown bravado was the truth: I was incredibly intellectually insecure. The way I saw it, if I never tried with any genuine sincerity, I could never fail, and I was comfortable forfeiting any possibility of success in exchange.

Through a series of lucky breaks and divine interventions in my early twenties, I worked my way up from nannying and retail to a salaried position as a copywriter. Over time, I grew into the role and found my stride, but even still, I couldn’t shake the imposter syndrome. Having risen through the ranks with nothing beyond a high school education, I often felt like a con artist, plagued with the anxiety of being found out.

Worse still, after five years of the 9-5 cycle and the daily ritual of rising, driving, arriving, working, leaving, eating, and numbing myself by the blue light of three different electronic devices at once, I was starting to unravel. Anxiety bred insomnia—I averaged three to four hours a night, which only lowered my dull, depressive baseline. I had no room for my writing—my creative well was bone-dry, and the notion that I was wasting precious time circled my brain like a vulture, causing an ever-present pall to settle over my life.

“I had no room for my writing—my creative well was bone-dry, and the notion that I was wasting precious time circled my brain like a vulture, causing an ever-present pall to settle over my life.”

I was exhausted and unfulfilled—but I hadn’t allowed myself to dream of anything beyond the endless hamster wheel. I couldn’t fathom having the audacity to want more than what the universe had so graciously given—in my mind, I had reached the zenith of what was available to someone like me. I tried to weed out the creeping dissatisfaction for many months—I exercised, ate well, and went to therapy. I pruned and pruned at every dead leaf and stalk within my life until nothing was left but the truth: I had to take a chance on myself.

With no plan besides the vague objective of “finding myself,” I finally mustered the courage to quit. Leaving was scary enough, but the real fear came with the realization that I was emerging from the tepid bath of corporate servitude and identifying myself to others as an artist. To avoid scrutiny, I hid behind humor—telling people I was moving on to become a full-time unemployed “it girl” intent on devoting myself to traveling, partying, and general vibing.

Once again, I created a mythology around my life, a protective mechanism to keep myself from the risk of failure. In the following months, I struggled through financial and personal insecurity, wrestled with finding the middle ground between discipline and over-permissiveness, and finally began to address those self-beliefs etched into the stonework of my being.

Now, all these months after that leap of faith, I wish I could share clear evidence of my achievements, but it’s complicated. I have yet to establish myself as the brilliant author I dreamed of becoming as a teenager. Still, I have been able to keep myself afloat through creative endeavors and work at my craft with clear, continuous focus. While I miss the security of a steady paycheck, I’ve found that urgency can alchemize to steam-power a sense of hustle. I’ve been overwhelmed with a new sense of gratitude for the small things—the simple joys penned in the margins of each day that are most often taken for granted.

It’s easy to find yourself in idle discontentment, waiting for someone to pick you out of the crowd and make you a star, but truthfully, only movement begets movement. Yes, there will be days when dinner consists of tinned fish and saltines, when you can’t bear to look at your bank account, and when hocking your most prized possessions, seems inevitable. But when the chips are down, and you’ve called out loud to bet it all on yourself, life becomes a game of endless possibility. Trials become teachers, contentment becomes fulfillment, and even small victories bring all the riches in the world. In the end, at the very least, it’s never boring.

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