Two years ago, Gail (names have been changed) felt like she was ready to step onto a bigger media stage. She had clips from a local alt-weekly and dreams of writing for a national audience, so she started hunting for opportunities at digital publications, eventually landing a job at Elite Daily.

It wasn’t exactly The Atlantic, but Gail thought a turn at a digital-native title with a national brand would give her more exposure, plus an opportunity to learn how modern media works. Before the learning came, she had an awakening.

“I really knew how to report; that’s what I wanted to do, and that’s what I was promised,” Gail says. “I ended up doing a bunch of aggregated stuff about the Kardashians.”

Gail says she was expected to file between three and five 600-word stories every day. She was also kept in isolation, unable to connect with her other remote coworkers, because Elite Daily did not offer its writers access to any kind of internal messaging system like Slack, which made it hard to build bonds with colleagues or forge relationships that might have helped her to grow within Elite Daily.

After eight months, Gail quit without so much as a clip to use in the search for future jobs, she says. What she left with, instead, was a more nuanced understanding of what terms like “high pressure” and “good with deadlines” mean.

“I’m better at recognizing things that are code for, ‘We’re going to work you to the bone,’” she says.

Gail, who’s been freelancing ever since, has a much stronger understanding of the media ecosystem, so when I ask her to describe it for this story, she uses the term with confidence.

“Digital media is a clusterfuck right now,” Gail says. “I knew the industry was in trouble, but I severely underestimated how deep the rot went.”

In the past several years, many different crises have erupted across media. But one of the least examined might be the dismal outlook and flagging resolve of the people that make it. A decade of constant upheaval — and uncertainty about what comes next — has created a lost generation of reporters, whose outlook will have just as much of an effect on media’s future as anything that Google or Facebook decides to do.

These writers esteem past greats and aspire to break stories and write things that leave a lasting impact. But they’ve also internalized the market logic that a viral collection of memes is, on some level, just as valuable.

A decade of enduring media’s unforgiving economics has convinced them that organized labor is important, not just for raising pay but for righting a long list of wrongs, including classism, racism and sexism.

And buried at the bottom of it all, there lurks a deep uncertainty that there is a future for what most of them do, either for a living or because they love it. And that uncertainty is suffused through everything they make.

“I think eventually everyone does the math,” says Kate Gardiner, who worked as a freelance reporter and led audience development and social strategy for media companies including Al-Jazeera and PBS before leaving journalism to found Grey Horse, a communications firm. “The fifth time you get laid off, the 10th time somebody skips out on paying your freelance check, the millionth time Vox changes your contract; every single one of us has had enough of those experiences.”

The No. 1 thing feeding this anxiety is layoffs. Most people in media are familiar with the numbers, or at least their dismal contours, but here they are again. Over the past 10 years, employment in newsrooms has dropped by nearly a quarter, according to Bureau of Labor Statistics data analyzed by the Pew Research Center. Strong job growth in the digital media sector has not done enough to offset the collapses in newspapers, which lost nearly 47% of its total workers from 2008 to 2018, Pew’s analysis found.

And even the top-line increase of people working in digital media jobs, which has risen to 82%, to 13,500 workers in 2018, obscures the tumultuous ride that industry has had. Between January 2017 and April 2018, a full quarter of all digital media outlets examined by the Pew Research Center reported layoffs.

But the second-biggest problem has been the industry’s seemingly constant pivots in strategies to find workable business models. As media companies lost control of their distribution and, by extension, their audiences, they have veered from one thing to the next in an attempt to grow their ad revenues: high-volume output in pursuit of scale; new content formats, from slideshows to videos to product guides, in a chase for advertiser dollars.

“To badly paraphrase W.B. Yeats, everything has changed utterly,” says John Crowley, who served as an editor at newspapers including The Telegraph and The Wall Street Journal and, more recently, at digital-native publications including The International Business Times and the Daily Mail. “At journalism school 20 years ago, we didn’t need to learn about page views.”

The skills that journalists were told they needed to learn often wound up on the scrap heap just a few years later. Writers that learned how to crank out stories in under an hour have watched publishers centralize news desks and pull back on commodity coverage; video teams that perfected the art of 90-second videos are being stretched to make things that are longer.

The whirlwind has led to a wave of organizing. For example, the Writers Guild of America, East, which seized on the opportunity to help organize digital-native titles including Vice and HuffPost, has seen its membership grow more than 40% over the past five years. Of WGA, East’s 5,000 union members, more than 1,200 of them work at digital media companies, according to a report the organization released this spring.

“There is something about the turmoil in the industry that inspires people to focus on their own workplaces,” says Lowell Peterson, the executive director of WGA, East. “It’s not like they’re living in a workers paradise. There are real issues that have come home, and we need to do something about it.”

What they want differs. Though some have fought for things like better pay — Peterson says that many of the shops WGA East helped organize were paying writers working 60-hour weeks just $30,000 a year — a growing priority in bargaining units is getting more information about where their companies are going, and how. Some have demanded seats on publishers’ boards, or insisted on quarterly strategy sessions where the newsroom is kept in the loop about what is going on.

Those gains have been harder to win, though Peterson said individual publications have found it productive to use the demand in their negotiations.

But even if the newsroom managed to grab hold of the steering wheel, it’s not clear that they’d know what direction to turn in. The cumulative effect of these disruptions is one of feeling like they don’t know what to do.

Even the much-discussed idea of the benevolent billionaire, a figure that has played a pivotal role in rallies among local and legacy news outlets, does not inspire much enthusiasm among some veterans of these.

“Billionaires are not going to save journalism. And relying on them is extremely dangerous,” says one former editor at The Village Voice.

This editor, who asked not to be identified, recalls a surge of enthusiasm that coursed through the building when Peter Barbey, the billionaire scion of the Barbey family, acquired the struggling alt-weekly in 2015, pledging to invest whatever was necessary to return the Voice to its glory days.

“At first, it was fucking incredible,” that editor says. As the money materialized to hire more staff, pay freelancers more and even overhaul the website, “we all felt like we had won the lottery.”

But ultimately, the good times didn’t last. After a few years of mounting losses, Barbey told staffers in the summer of 2018 that the Voice would no longer publish any material. (Barbey described the outcome as “sucky.”)

In the stories that have been written about management miscues that have set media companies back, there is the implied mirror image of someone lower on the food chain who would know better, or see a solution that would succeed where so many others have failed.

Yet perhaps the defining characteristic of so many members of this lost generation is that they don’t see one.

“If I knew the answer, I’d have made a lot of money and bought the Voice back,” the former Voice editor says.

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