Survival strategies of an online freelancer

Photo credit: Micah Schmidt

Kyle Chayka comes off as more practical than driven—capable of knowing his goals, reading an environment, and deciding what his next steps should be without a lot of emotion.

A 26-year-old freelancer who makes his living writing online, Chayka’s preternatural calm sets him apart from a crowd balancing the competitive pressure of writing for some of the best-known publications on the internet with the financial uncertainty of piecing together a living in a medium where flat fees often replace word rates. In the chaotic ecosystem of digital journalism, reported material commonly fetches the same price as a lightly researched “take,” and even blue-chip publications pay embarrassingly little for a story. Yet Chayka will tell you that making a living this way is totally possible, that there is not only money but value in this line of work.

“People constantly express shock that I’m a full-time freelance journalist writing on the internet,” he told me when I approached him to ask about his career. “Someone’s got to do a story about how it’s not that bad.”

For Chayka and other winners in this economy, freelancing is both a career in its own right and a calculated risk, a bet wagered in the hopes of winning something better—whether that something is a staff job, a book deal, a larger professional network, a more prestigious beat, or some other means of advancement. The gamble is whether you can make enough money to survive in the near-term while producing work that’s strong enough to significantly improve your professional standing. The task of today’s digital freelancer is to build a business and grow as a writer in an environment where pay rates don’t seem to amount to a living wage.

Chayka has placed his bet. His end game is more about rising in the profession than it is about money. He is hardly the first young journalist to take the popular notion that writers should be a brand and a business seriously. It’s his degree of comfort with the equation that makes him notable.

‘People constantly express shock that I make a living as a freelance journalist writing on the internet. Someone’s got to do a story about how it’s not that bad.’

In a recent Twitter conversation between freelancers bemoaning low rates, Chayka sounded more like an encouraging journalism school professor than a young writer. After listing a few bits of practical advice (“If the hourly rate it’ll take to do a piece doesn’t work out for money or bylines, don’t do it”), he concluded: “Treat writing like a business, because that’s what it is until you have the luxury of pretending it’s not.”

But what kind of business? The internet, with its voracious hunger for content and dubious moneymaking potential, has led to a glut of copy that has kept pay rates low. The fact that there are multiple databases devoted to uncovering which online publications pay writers at all is a good indication of the financial uncertainty facing digital freelancers.

Yet for Chayka and others working primarily or entirely online, the internet has also created a niche that is profitable in more than monetary terms. An example of this complex calculus is Chayka’s work for the tech site Gizmodo. The site isn’t going to make a freelancer rich. Who Pays Writers says it pays $250 for a guest post, though Chayka wouldn’t share his rate. But it has the added appeal of being read widely by tech editors. Chayka wrote a story about online chat rooms for the site in December. Within a half hour, three editors had emailed to ask him for pitches.

The experience highlights the blurry line between exposure and connections. For freelancers, building an audience has fewer immediate benefits than exposure to editors, which is how visibility is truly monetized.

A lot of writers fail to make this calculation, Chayka says. “You can’t really talk about freelancing on the Web without addressing the fact that there’s such a disparity between the high end and the low end. It’s not just in terms of pay. It’s in terms of visibility and promotion and the value you’re getting from the publication itself.”

For Chayka, the payoff for visibility has been becoming a go-to freelancer for larger, better-paying sites such as The Daily Beast when those publications need a post on a trending topic. A freelancer who can give a site something it wants and doesn’t have the time to shop around for is in a good negotiating position. When you’re working at the lower end of the pay scale, a rate increase of $100 or $200 can make freelancing quickly more sustainable over the long haul.

Given that he’s running a business, Chayka won’t reveal his revenues. What he will say is that he makes a good enough living writing an average of 13 stories a month to put him in the salary range of a staff writer at many of the publications he writes for, which amounts to something between $35,000 and $65,000 a year. He pays $900 a month to share an apartment with three roommates in Bushwick, a rapidly gentrifying neighborhood in Brooklyn, where he also rents a co-working space for $175 a month; he has basic health insurance through the New York health exchange. About four of his 13 monthly stories are for Pacific Standard, where he’s on contract to post a weekly technology column throughout 2015. The remaining nine are either stories he’s pitched or one-off assignments brought to him by editors. He can’t predict how many stories will fall into either category in a given month, but he manages a consistent volume overall.

Part of the calculation made by any freelancer needing to earn a livable amount of money from a manageable amount of work is that heavy reporting, if respected, often doesn’t command higher rates—or even reimbursement for expenses. In a survey of freelance investigative reporters released in February by Project Word, an arm of Investigative Reporters and Editors, 38 percent of respondents said that outlets “often” or “regularly” commissioned pieces without covering the expenses of reporting them. Another 31 percent said this happens “occasionally.” Chayka finds feature writing for Web and print publications to be the most satisfying part of what he does, but he has to buy the time to do them by churning out a higher volume of “one-thought 800-word pieces.” His body of work includes, “Why every real man carries a tote bag,” which appeared in The Guardian last September, and “Is FOMO Driving the Bitcoin Boom?” for Pacific Standard in December 2013. The relative effort that goes into these pieces is small enough that he thinks they often pay better, in the end, than labor intensive feature writing at higher rates.

“It’s a funny calculation you have to make as a freelancer between who you’re reaching, how much you can get paid, what you can produce. All of those variables change for every piece you write,” he told me.

There’s no comprehensive data about Web pay rates for professional journalism, but the website Who Pays Writers gives a good sense of the low end of the spectrum. It focuses mostly on online publications that pay between $50 and $250 for a piece, and reveals vast differences between companies commingling at that end of the pay scale. VICE, valued at $2.5 billion, paid $500 for a 2,000- to 4,000-word “investigative” feature in 2014, according to Who Pays Writers. A tiny operation like The Awl typically pays $100 to $200 for a story, which is competitive with the rates offered freelancers by Web giants like The Atlantic. The New Yorker’s website pays most freelancers who cold pitch $250 for a reported piece; the Gawker network of sites pays about the same. The fees are always round numbers, and give you the sense that they were carved out from a budget by editors who didn’t want to bother with any complex accounting.

I spoke to a number of established freelancers for this story. Their answers to the question of whether freelancing for the Web was a viable way to make a living ranged from positive (“I make a pretty good living”) to tentative (“it’s pretty challenging, I must admit”) to despondent (“there is no way you can survive on just writing online”).

What’s clear is that even excellent writers with established reputations on the Web have to work very hard to make a living in this environment. The Gawker writer-turned-freelancer Michelle Dean wrote in 2013 that she worked 10 to 12 hours a day, seven days a week to earn her living writing for the Web. Jacob Silverman, who has written online for Politico Magazine and Slate, jokes with his wife that, “I don’t really make money. I just occasionally win money.” His three-day winning streak as a guest on Jeopardy! earned him most of his income in 2012. His latest win was a book deal, allowing him to escape the high volume demands of writing for the Web for a while.

Some feel that freelancing is a perpetual tryout for a staff job, and that it’s becoming the industry’s new version of the unpaid internship, throwing up a similar barrier to entry for those trying to get into the profession without a parental subsidy. “Someone who’s working two jobs isn’t necessarily going to have the time to pop out a really great piece for $150 to build their career,” Manjula Martin, founder of Who Pays Writers, points out. Chayka has managed to support himself through writing since college, but being his own boss doesn’t mean he can grant himself paid sick leave.

‘There is and probably always will be money in journalism. The question is, where is it?’

Online freelancing has the feel of a young person’s game. But Steve Friess, a 42-year-old freelancer based in Ann Arbor, makes a six-figure income writing reported stories for the Web—often for newer entrants like Al Jazeera America and Take Part, a site recently launched by the film production company Participant Media. “There is and probably always will be money in journalism,” Friess says. “The question is, where is it? And that moves. You sniff out where the money is at the moment, and you go there, and you accept the notion that a year from now they’ll probably run out of money, and you’ll have to find other places. And this process of moving from one grazing field to another has certainly always been my experience as a freelancer.”

He says his own key to financial success as a freelancer comes from his newspaper days. He can write quickly and well on many topics. Although he says he’s generally well above the $250-an-article range, volume is still the key to making an income writing on the Web. He wrote anywhere from 10 to 20 stories a month in 2014, including multiple features.

Chayka became a full-time freelancer in 2012, after leaving his job as associate editor at ARTINFO. It took him about six months to “stop freaking out” about whether he was going to make any money. But it took a full year and a half to gain confidence that he could produce ambitious work while paying the bills. That’s arguably his greatest strength as a freelancer—a talent for indulging his interests while still earning enough to support his larger ambitions.

It certainly helps that his interests often center on the Web itself. In December 2013, he produced a massive viral hit for The Verge by tracking down the owners of the Shiba Inu dogs currently starring in Doge, that season’s hottest internet meme. (People found pictures of Shiba Inus and added captions expressing the dogs’ internal monologues in Comic Sans type.)

Chayka’s skill at covering some of the lighter aspects of technology and culture has bought him time to pursue more ambitious journalism. In April of 2014, he wrote a Newsweek cover story on biometric surveillance.

The benefit of treating writing as a business is that the days you’d rather forget helped finance your proudest achievements. The tradeoff is that efficiency often wins out over craft. When I called Chayka’s longtime editor at Pacific Standard, Nicholas Jackson, to talk about his work, one of the highest compliments Jackson could manage centered on Chayka’s lack of perfectionism. Jackson explained that, on the occasion when a draft Chayka files needs more work than Jackson has time for, he’s able to say, “We’re only going to be able to get it to a place where we both think it’s good enough but maybe not as great as you originally imagined, but I’ve got to move on to the next thing. Hope you’re okay with that.” He is. It’s one of the things “that make you want to just keep working with somebody,” said Jackson, who had 18 drafts waiting in his inbox as we spoke.

As successful as Chayka has been at finding his way in the wilds of freelance digital journalism, his ultimate goal lies elsewhere. He’s better than any writer I’ve spoken to at battling down the anxieties that come with balancing craft and commerce, but that doesn’t mean he’s content to stay in his current niche forever.

“No one wants to be forced to churn out stuff for money,” he says. “I think everyone would be better off if time and space and money allowed more online writers to put more thought into their work.”

The Web has given him a solid niche for his business. But, as in any business, the key metric of success is growth. And Web freelance rates only afford so much opportunity for growth. Long online features are becoming more common and starting to pay better, with outlets like Matter paying rates competitive with high-end magazines. But print remains the place to go if you want to hone your skills as a writer and get paid for it, Chayka believes.

“It definitely feels a little weird to be aspiring towards something that’s arguably less stable than internet media,” he says. “But as a writer and as someone who wants to be a more literary writer, print magazines are still the place that you go to kind of stretch out. I think that transition to Web features being just as respected as print features is happening, but we’re definitely not there yet.”

Talking with Chayka, I was struck by how hard it is, in an industry undergoing constant change, to know how much of our comfort with present circumstances is based solely on our optimism about the future. Nowhere is this truer than among freelancers, who consider their prospects not only in terms of years but also in terms of the assignment that must appear tomorrow. Chayka is an optimist. He believes he’s going to be working tomorrow for better rates than he worked for today. He believes his native medium will continue to grow to meet his ambitions. He believes it’s a good time to do business.

Michael Meyer is a CJR staff writer. Follow him on Twitter at @mcm_nm. This story was published in the March/April 2015 issue of CJR with the headline, "Making it."