The New Freelancer: What It Means to Work in the Gig Economy in 2018

By Emily Gaudette August 17th, 2018

Hustle. Side gig. Moonlighting. We’ve invented many words for freelancing, and until recently, they all denoted something peripheral to “real” work. For a long time, quitting your job to freelance full-time was right up there with backpacking through Europe or hiking the Appalachian Trail—a pipe dream.

While the names persist, freelance work has really started to push in from the periphery, replacing day jobs. More freelancers are thinking in terms of careers. That means adopting a long-term perspective and embracing strategy. We spoke to a handful of full-time freelancers in different stages of their career journeys about how they identify in an economy that’s still referred to as “gig.”

The Newcomer: Redefining Work

For years, freelancers like William Seaton lived on the edges of America’s working culture, exchanging the stability and social perks of office life for flexibility and agency. But Seaton and other twenty-somethings may soon be in a position to reshape ideas about how we all work.

Seaton, 27, has been a full-time freelance writer for two years since leaving a digital agency. In that time, he’s amassed a roster of over a dozen steady clients, predominantly in the healthcare industry, and works in “perfect, hermetically sealed bliss.”

“Flexibility is a huge tradeoff between full-time work and freelance, and it’s been important for me to grow a body of work in a way that I, myself, can choose,” Seaton said.

Each year, more millennials express a desire to operate as he does: from home, on their own terms, and for clients who value their unique skills. And as they comprise more of the workforce, the entire landscape is changing. Recent projections say a majority of the American workforce will freelance full-time by 2028.

And while it’s tempting to attribute the desire for freedom with a certain, ahem, lackadaisical work ethic, the image of the freelancer rolling out of bed at noon to jot down a few lines is far from the truth. Seaton actually begins his workday early and keeps a strict schedule to stay productive.

“Two things are critical,” he said, “to set myself up for the next day by outlining, editing, or taking notes during the late afternoon … and to take time away from the screen when I’m really and truly braindead.”

As for ever returning to the full-time office job life, Seaton hasn’t ruled it out—as long as he has the room to experiment.

The Professional: Finding Stability

Caroline Ryder, 36, a freelance music journalist and screenwriter, laughed as she recalled moving to Los Angeles for her writing career in 2004. “I really hammed up my Britishness in order to market myself early on,” she joked, “But it worked!”

After four years of freelancing, the Great Recession forced Ryder into full-time work again, writing web and marketing copy. But soon, she felt restless and went freelance a second time, landing cover story after cover story profiling figures from James Franco to Snoop Dogg. “I knew from the beginning that I wanted to move in an arts and culture direction and interview artists, but I had to build to that,” Ryder explained.

Unlike freelancers in their twenties, Ryder remembered what happened to media jobs in 2008. Like the rest of the American workforce, experienced writers were left piecing together work opportunities in a faltering economy. And unlike (some) twenty-somethings, Ryder put in enough time to understand that freelancing in the 21st century is less hustle and more career-planning. She developed resilience and grit by switching back and forth between full-time gigs and freelancing when the right opportunities arose.

By putting the work in early on and being goal-oriented, she achieved the kind of stability enjoyed by traditional employees. A regular writing schedule and a well-kept work calendar helped as well.

“There have been up and downs, of course,” Ryder said, “but I’ll always been able to pay my bills. I’m neither a blogger earning two hundred thousand dollars a year nor a beat journalist getting up at six a.m. to churn out content all day and night. I feel very lucky.”

The Veteran: Owning a Business

Dahna Chandler, 54, knows rebranding. It’s evident when she describes the trajectory of her career as a freelance copywriter, media consultant, and journalist. “I think of myself as a business owner or a consultant,” she said, “because people tend to discount freelancers. It’s just a word that still connotes things about your work ethic. You know, ‘Oh, she’s just a freelancer—she doesn’t need stability.'”

Since the late ’90s, Chandler has crafted her own version of stability, working from home on freelance projects years before work-life balance was even a concept we complained about. “Back then, no one understood why I wanted to be on the internet. Journalist friends of mine thought it was a fad, that no one would ever give up print publications, and I remember saying, ‘Well, let’s see where we’re at in ten years. Let’s compare notes.'”

After a short break in the mid-aughts, Chandler returned to her freelance career, this time thinking with the mindset of a business owner. Like any owner, she looked for needs in the market to find better opportunities. While she does different types of writing, she’s found a particularly lucrative niche in corporate. “Most executives can’t write at the level you’d expect them to, so I learned that someone with messaging skills and writing skills was going to be in high demand.”

A career-minded approach to freelancing allowed Chandler to raise her son and attend graduate school, all while maintaining her income and expanding her professional network. Now, after amasseing a wealth of knowledge about the business, she’s thinking about training new writers and small business owners. Whatever she prefers to call it, it’s working.

Image by Dillon Shook for Unsplash
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