The Emotional Toll of Freelancing



YES! Illustration by Jennifer Luxton.

How to cope with anxiety, self-doubt, and “the check’s in the mail.”


By Brandon Ambrosino / 09.11.2016


I’m currently waiting for around $10,000 worth of paychecks to reach me for freelance writing projects I’ve done. Most of these projects were completed months ago. Some editors have since gone silent, leaving me to wonder if I’ll ever see my money. My partner is a dentist, so I am not going to starve, but it’s still frustrating to be unable to plan my finances like a traditional worker.

Not getting paid impacts my sense of identity too. When I don’t get paid—or paid on time—or I have an assignment killed or don’t hear from an editor, I second-guess myself and the work I’m doing. I wonder whether I’m being honest when I tell people I’m a writer. I wonder if it’s accurate to say I have a job.

And because the second question we often ask a new acquaintance is what they do for work, these self-doubting questions lead to an enormous amount of stress and anxiety for me.

According to a recent study from Roosevelt University, I’m not alone. Many freelancers regularly experience anxiety, frustration, anger, and depression.

Gianpiero Petriglieri, a psychiatrist and associate professor at the graduate business school INSEAD, studies the psychology of gig workers.

“We join organizations for a defense against anxiety,” says Petriglieri. “They give life a sense of security.” Gig workers, on the other hand, can struggle to find security, a sense of purpose, and fulfillment. While the traditional office offers a stable paycheck and shared responsibilities, freelancers are responsible for all aspects of their business, including marketing.

A 2004 study found that the cyclical nature and 24/7 brand management required by independent work creates “more rather than fewer constraints on workers’ time.” Freelancers are never not on the clock—that’s physically and emotionally fatiguing. Gig workers also feel anxiety over what Irvin Schonfeld, a psychology professor at City College of New York, calls “reputational threat”—the concern that one client’s bad review is all it takes to make them unemployable.

Despite the challenges of gig work, many freelancers are able to “transform their anxiety from something debilitating to a source of learning and growth,” says Petriglieri.

So how do they do it?

The following suggestions come from the research of Petriglieri and others, as well as from freelance workers who have found ways to navigate the psychological obstacles they encounter in their work.

1. Plan ahead

Seven in 10 freelance workers have trouble getting paid on time, according to Sara Horowitz, founder and director of Freelancers Union. To chase down their paychecks, many freelancers have to take time away from other activities, which means non-payment and late payment are doubly taxing. “Savvy freelancers will build in padding in their rates to compensate for potential client nonpayment,” says Horowitz. They’ll also learn to live on a budget and save up big paychecks for rainy days.

2. Foster connections

“You’re so lucky to get to work from home!” If I had a nickel …

In fact, working in isolation is the source of a lot of freelancers’ anxieties. In a traditional company, failures are shared. When a freelancer learns his pitch was rejected, his gig was killed, or his paycheck is MIA, he has to shoulder that burden alone.

To address this issue, Sara Frandina, a content strategist in Rochester, New York, co-created One Woman Shop, an online community and resource to help female solo business owners connect. Frandina thinks connecting with other freelancers is paramount for their success.

“Finding a community of like-minded individuals has been key to getting out of my own head, building in accountability, having productive conversations, and feeling like I’m not alone in this business journey,” she says.

3. Catch as catch can

“My strategy is to not turn down any work that’s offered to me that pays well,” says Matt Brennan, a freelance reporter and film/TV critic based in New Orleans. Successful freelancing, he says, is basically “catch as catch can,” meaning gig workers should take advantage of opportunities that come their way—even if it’s not a dream job. As long as corporate gigs don’t require a freelancer to compromise her integrity, what’s the harm in writing a travel blurb for an airline magazine or creating a photo spread for a restaurant?

Schonfeld says this mentality is critical to success as a freelancer. “Every job has [a] certain amount of conformity and autonomy. Even when you’re self-employed, you do have to conform to customers’ expectations—otherwise you won’t get by.”

4. Know your value

Magdalyn Duffie, a 32-year-old freelance graphic designer who specializes in social media, websites, and art installations, says she sometimes has to deal with impostor syndrome, the feeling that she doesn’t deserve her success. Duffie, based in Raleigh, North Carolina, says she feels this the moment she sends off an invoice, when she puts “a number to the skill.”

Although it can be tough, self-employed workers need to learn to stand up for themselves financially, says Duffie. More often than not, she says, the companies you’re working for can afford it.

So, she says, roll up your sleeves and tell yourself, “I am good. I can do something that is worth hard cash.”

5. Ditch the word “should”

“It’s easy to [think] we ‘should’ be doing specific things [when] we see other people we deem successful doing those things,” says Frandina. That musician landed a gig with the symphony. That dancer booked a Broadway show. That writer had a cover story in The Wall Street Journal.

We rarely know the stories behind other people’s successes. “It’s all too easy to compare our beginning to someone else’s middle,” says Frandina. “Success is a relative term.”

Perhaps a little grass-is-always-greener wisdom might help here. I’m regularly surprised to hear that freelance writers I’m jealous of are actually jealous of my accomplishments.

6. Have a sense of purpose

Of the freelancers Petriglieri interviewed, those with a clear sense of purpose were better able to manage their anxiety. For example, if they were writers, he said, they wouldn’t say they “just write.” They’d say something like, “I try to change people’s perception of this issue.” Same thing with musicians: They don’t “just make music”—they enrich others’ lives through art.

Keeping my sense of purpose in mind motivates me on those days when inspiration doesn’t strike. Then, I file invoices, update my calendar, send pitches, and clean my workspace—all the things I have to do if I want to call myself a writer.

Gig work isn’t new, but the sheer size of the industry is. If projections are to be believed, 40 percent of U.S. workers could be freelancers by 2020. That means conversations about self-employment and mental health are becoming increasingly important.

In the meantime, I’ll update my editorial spreadsheet to show I completed another article. And I’ll look forward to receiving my paycheck in two to three months.