How I Left My Full-Time Job to Become a Freelancer

Confronting the Social Stigmas & Pains of Being a Freelancer

This article was written by featured guest writer Zach Schepis

Embarking on the road to freelancing is a bit like that old adage about “leaving the nest.” There’s uncertainty, sure, along with a certain surrendering of comfort and the real potential to fall. There are days of resounding self-doubt and seemingly insurmountable hurdles. But without the risk of failure, no reward or learning would ever be possible.

Without the desire to fly, we would all build our nests and then we’d never leave them.

I know the feeling too well. For four years, my proverbial nest was a windowless office in the heart of Chelsea, Manhattan. You’d never even know you were tucked away into the epicenter of life itself; the steady thrum of car horns and scuffled footfalls of thousands of zig-zagging pedestrians were a distant murmur, swallowed up by concrete walls and the heavy silence of darkened conference rooms.

I started as an intern at the media company fresh out of college, eagerly pushing past morning commuters like a circus performer vaulting carefully balanced trays of coffee. In the years that followed, I would become a part time contributor to the company, then later a full-time staff writer, creative producer, and eventually, the editor in chief.

Yet I wasn’t happy. I finally had the job security and impassioned team that I’d always dreamed of, but felt somehow like I was stuck. Every day, Monday through Friday, there was the same routine, the same rituals. Wake up, commute on the train, get to the office, drink coffee, read the news, meet with writers, edit their articles, turn out the lights, catch the train home. Rinse and repeat. It was like clockwork.

Then one morning, everything changed. I was meeting with John Knefel, a freelance writer and warrior for social justice whose works have been published everywhere from Rolling Stone to The Nation. Knefel is the kind of freelance reporter who puts himself into the line of fire to shine a spotlight on the voices that need to be heard most. At the time, he’d just been released from police custody after being arrested and booked for nothing more attending a social equality demonstration in the financial district.

He was still visibly shaken from what had happened, but was already sitting down at the keys to pen his experience. I stopped by his desk, inspired by his tenacity and desire to help make a difference, no matter how slight.

“How do you do it?” I heard myself ask. “You risk everything, and you never know how it will turn out. How do you do that every day? I wish that I could.”

Knefel looked at me with more than a degree of understanding. “I used to have the same kind of job as you,” he said.

“But I realized I’d be doing the same thing for the rest of my life, without trying to make some difference, without meaning. Life is too short for that; let your work be meaningful. If you can find a way to help someone else through your words or actions, let that be your calling.”

His words sparked a fire in me. I quit the next week and never returned.

The following six months were equal parts exhilarating and terrifying. Suddenly, there was no safety net anymore. I took solace in the knowledge that I wasn’t alone, in the calculated comforts of statistics and figures of assurance. There’s more of a demand for freelancers than ever before, I’d repeat to myself. There are 53 million other Americans just like me who are freelancing, and by 2020, almost half of the workforce will be.

Still, I couldn’t help but feel the social stigmas all too-often unfairly associated with the word “freelance.” Telling someone at a social gathering that I was a freelance journalist focused on social justice and nonprofits would draw furrowed brows and hushed scrutiny. Unspoken words like directionless, unprofessional, and under-employed would hang suspended in the air between us.

Other challenges would soon present themselves. I was beginning to feel isolated and missed the joy of having a team to collaborate with. The variable workloads and variable income made it difficult to find footing on solid ground, and maintaining discipline with securing clients and managing distractions were weathering my ability to sustain real motivation.

No matter how pervasive the shadow of doubt cast, everywhere I turned there were reasons to push forward and helping voices to assuage me.

“You have to ask yourself if the juice is worth the squeeze,” Molly Rose Levine’s voice crackled over the phone. She’d left her full-time job to study violence against marginalized peoples, and ultimately became the executive director of the United States chapter of Clowns Without Borders — an organization devoted to offering humor as a means of psychological support to communities suffering from trauma in war-torn countries around the world.

“I think you’ll find that it is. It’s no easy road, but no road worth taking ever is. If you want to do something meaningful with your work, if you want to bring light into the lives of others, you have to make sacrifices. But the joy you can ultimately bring will enrich your life in ways you wouldn’t have thought possible.”

We’re all looking for purpose in what we do. Studies have even shown that meaningful work is critical to worker happiness. Choosing to make the leap to freelance work requires considerable courage and determination, but for those who have braved the leap from their nests of comfort, there’s no need to look back.

My former assistant editor stopped by the other day to catch-up over coffee. She now organizes women’s empowerment workshops with TEDxBushwick and fights for the rights of disenfranchised women in South America with the nonprofit Pro Mujer. She made the leap, and couldn’t be more grateful about doing it.

With a characteristic light in her eye, she offered words of assurance.

“Don’t worry about what everyone else thinks, or what they’re doing,” she said. “If you want to make a difference and find meaning, you have to start yourself. It’s living a few years of your life like most people won’t, so that you can spend the rest of your life like most people can’t.”

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