The Challenge of Defining Success as a Freelancer

What does it mean to do well in your career when you can’t be promoted?

To find a better way to measure success, I spoke to several freelancers about how they track their accomplishments. I assumed the results would be evenly split among industries, with those in more creative fields citing self-expression as their goal, while those in fields like consulting or brand development would have more quantifiable, money-oriented targets.

As it turned out, most of them were blindsided; they had simply never been asked this question. But across the board, most conceded they divided their day-to-day tasks into two buckets: the actual gigs, and the effort required to get them.

“I’d really love to be in a place where I don’t feel so busy that I can’t look out for my own business,” says Geoff Yost, a freelance branding and strategy consultant based in Charleston, South Carolina. “I always say whenever I can, I’m going to hire an assistant,” he added. “That’s the success I’m looking for.”

It was a sentiment echoed by several other freelancers I spoke to: that they’re either too busy working to find new work, or too busy finding new work to do what’s already on their plates, and that a primary career goal was being able to balance the two. “I want doing the work, day in and day out, to be what success looks like for me,” says New York-based illustrator Kath Nash, who recently left her job as a graphic designer for the website Apartment Therapyto freelance full-time. (She was able to keep her former employer as an anchor client, which, as any freelancer knows, is a crucial first step toward income stability.)

To Jacki Huntington, a Los Angeles-based filmmaker, freelancing, at its best, offers a chance to break free of routine in the pursuit of a more self-directed sort of career satisfaction. “It’s a sort of a meditation, where you let go of any expectation and embrace what makes you feel fulfilled every day,” she says. Many freelancers would probably agree, citing an appetite for variety and the opportunity to apply a wide range of skills as two of their primary motivators. But, Huntington added, remembering the recent grant applications she had to fill out for a new podcast she’s developing, “You’re spending a lot of time writing about what you’re doing, instead of doingthe thing you say you’re doing.”

I, too, measure my success by how little work I have to do to find new work. To me, it feels like trying to establish the ideal balance I can imagine in an office job, where the tasks are already laid out every morning. For better or worse, offices are a controlled environment: Since you collect a paycheck and (sometimes) benefits, you know you can measure input and output with some regularity — this much effort for that much money. Freelancers who struggle to focus at home may shell out a few hundred dollars a month for a co-working space, simply to simulate that feeling of comfortable, measured productivity. “To be able to physically afford a space to be a studio for my work,” says Yost, “that in and of itself is a certain amount of success.”

So, too, is the ability to ensure that you’ll be treated well. Whereas full-time workers usually sign a single contract detailing the terms of their employment at the outset, freelancers are renegotiating those terms on a weekly or even daily basis, so being able to advocate for ourselves becomes even more crucial — especially when no one else will do it for us. “Our labor and skills are unprotected and undervalued,” says Caitlin Kelly, a freelance journalist who coaches other journalists (full disclosure: including me). Huntington, the freelancer from LA, added: “All these people in the digital media space don’t quite understand how they can build coalitions together.”

The kind of long-term, committed activism that has given traditional workers the power to fight for fair wages, overtime, workplace regulation, and unions has yet to take shape in any meaningful way for freelancers, though the Freelancer’s Union and Freelance Isn’t Free Act are good first steps. Freelancer networking groups have also shown a willingness to band together for short-term gains. Most recently, when the website Contently rolled out a new “cash out” fee, charging freelancers to access their earnings generated on the site, many rose up in protest, writing letters to the CEO, tweeting their dismay, and switching off their work availability while imploring others to do the same. Of course, it was their status as freelancers, juggling many sources of income, that allowed them to put pressure on just one of those sources.

In years past, I’ve often found myself overwhelmed by the work I accepted, taking on both jobs that excited me and jobs that didn’t quite fit in an effort to keep that stream of incoming flowing. All too often, it became a torrent. So when I imagine some future, more successful version of myself, while I can appreciate the utility of having an office to go to or the luxury of having the work come to me, what I want most of all is to be in a position where I can comfortably walk away.