On Monday, a Politico reporter named Mike Elk  — who was hired last fall to work on the Web site’s new labor and employment section — started making some labor news of his own.

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Bombast notwithstanding, Elk has done this before. He helped start a union at his previous employer, the lefty magazine In These Times, and a few months ago started talking with the Newspaper Guild — an affiliate of the national Communications Workers of America — about doing the same at Politico. Employees would benefit from some protection against Politico’s famously workaholic atmosphere, Elk says.

“The problem with the Internet is that people are on call all day long,” Elk says. “You’ve got to check your e-mail all the time, all the time. It becomes tough for workers to put boundaries on overtime…. I think people in the media take jobs way too seriously, and it leads to burnout.”

So far, it’s not clear that argument is resonating. No one else at Politico was willing to go on the record in support of the union drive, and Guild representatives have stayed silent, refusing to answer questions about organizing at Politico — or anywhere else. Politico declined to comment for this article.

If Elk managed to get an organizing campaign off the ground at Politico, it would be the first successful attempt at a major new media company. With no formal representation, online writers say they sweat away under traffic quotas, with little say in management decisions, sometimes subject to layoffs with scant notice.

Why have unions failed in new media? The reasons tell us a lot about the challenges unions face in staying relevant as all kinds of industries transform. There are two fundamental forces at work here: One is the loss of leverage, with more aspiring journalists than there are jobs and an environment in which content is becoming increasingly commoditized. The other is a shift in identity, with a generation of younger workers less familiar with unions who’ve built personal brands that they can transfer to other media companies.

All that adds up to a world in which unionization from scratch is incredibly difficult, even though unions might be useful in addressing some of the harsh conditions the new media age has created.

Let’s get one idea out of the way first: It’s not that the major union representing journalists just hates the Internet. The 34,000-strong Newspaper Guild — which recently changed its name to the NewsGuild, getting rid of the anachronistic “paper” — has lately been talking the talk about uniting all content producers under a single banner, and most of its members work both online and in print.

But the Internet did create a giant leverage problem.

First, the Web took a larger toll on its membership than most unions have had to deal with, even those in other fast-shrinking sectors, like manufacturing. Labor strength in media used to come from the unions that represented people who actually set the type, ran the presses and delivered the papers. Nearly all of those are gone.

Over the past few decades, Guild locals across the country have been busy trying to save the jobs that remain, dulling the pain of mass layoffs and fending off the attacks on pensions. (Sometimes, those two things get tied together in the public’s mind, as they do with the auto industry: “Inflexible unions killed their hosts,” the thinking goes, which tends to retard organizing unless the perception is debunked.)

That makes it pretty hard to stand up and ask for anything. For example, take this response from a 25-year-old employee of a print and online magazine in Washington. He has thought a union might be useful in reducing the anxiety of not knowing when his job might disappear, but he doesn’t know where to start.

“I suspect that the lack of knowledge, my own included, about labor laws probably contribute to that problem,” writes the young person, who requested anonymity to avoid retaliation from his employer. “The collective barriers to action with regard to starting a unionization drive — and the inevitable stress and problems it would create — seem more onerous than keeping one’s head down.”

The other phenomenon, of course, is that Web writing has become commoditized. Not only are there hordes of recent graduates who would gladly fill holes on a masthead, new media organizations don’t necessarily need large newsrooms of reporters; cheap freelancers and Web editors to repackage other articles are abundant. In part, that’s how places like Gawker and Forbes.com have thrived. When the Newspaper Guild tried to organize a boycott of the Huffington Post for refusing to pay its thousands of bloggers, even progressive contributors crossed the picket line. The Huffington Post didn’t respond to a request for comment.

“With an abundance of content, and content producers, many of whom are totally happy to give their stuff for free for the ephemeral compensation known as exposure, the whole marketplace has been upended,” says Alan Mutter, a veteran media consultant based in Silicon Valley. Accordingly, wages for reporters have grown at less than half the pace of pay in other fields.

At the same time, there’s a sense of self-imposed transience in the young media workforce. The job market is a merry-go-round: Web publications are seen as springboards to something better, so writers are willing to put in long hours for low pay until they’re poached by some other place, which is the only way to get a raise, anyway.

“With everyone always sorta half-looking to jump elsewhere, there’s not a lot of that sense of a workplace being this permanent institution, and I think you need that to make something a union shop,” writes one young employee of a large new media company in New York, who also requested anonymity because he’s not authorized to talk to the press.

Now let’s take the question of a shift in the sensibilities of the new media workforce — toward seeing management as an ally, or at least a client, rather than the enemy.

The transition from print to digital hasn’t just cut down on the number of jobs (about 30 percent of newsroom jobs were lost between 2009 and 2012, according to the American Society of News Editors). It’s also changed the composition of the workforce: Recent entrants to the journalism profession tend to be more educated and come from comfortable backgrounds, says Freddy Kunkle, the co-chair of The Washington Post’s Guild unit. All Washington Post reporters are covered by the Guild contract, but Kunkle has been frustrated by the low number of new recruits from the paper’s year-long hiring spree who have joined the union as dues-paying members. He thinks part of the reason has to do with a weakened connection to the middle class.

“They tend to think that because of their education and their talent, they don’t need [a union],” Kunkle says. “What they’re doing is not coal mining: It’s not dangerous; it’s not dirty. What are they going to get out of it?” One data point: When The Washington Post Co. acquired Slate, which was founded and largely staffed by techno-savvy Ivy Leaguers, there was no discussion of its employees joining the Guild.

Slate, of course, is also one of the Internet’s first major Web magazines. And the class transition is perhaps especially true of Internet-only media, says Choire Sicha, who was an editor at Gawker and co-founded The Awl.

“If you look at the big ones, like BuzzFeed or Vox, the young workers are in general SO homogenous, and SO unprepared for anything like union organizing,” Sicha says in an e-mail. “They all went to good schools, and very few of them seem to have any experience with labor in the real workforce. And they’re all young and haven’t started worrying about their future yet. (Surprise: they don’t really have one!)”

In some of those places with the potential to go public or get bought — like Buzzfeed and Vox — employees are paid partly with equity shares, like any tech company. When workers are also owners of capital, their interests are aligned with management’s, and solidarity is hard to gin up.

And in fact, as many of these new media institutions mature, workers are generally getting better treatment. Salaries have risen at places like Gawker, which this year is moving from a walk-up in Manhattan’s Nolita neighborhood to chic new space on Fifth Avenue (“We have higher expectations of ourselves now,” said CEO Nick Denton). Editors are frequently not much older than writers, and executives sit in the middle of open-plan offices, breaking down the separation between management and the proles.

“You don’t really feel like rabble-rousing when they cater you lunch on Tuesdays,” writes Sicha. “And part of that is the weird in loco parentis thing that many new media employers do. I’ve met a lot of young employees who ‘feel bad’ about causing problems at work (including, like, taking comp time!) because, you know, their employers ‘take such good care of them’ and ‘everyone’s so nice,’ etc. etc. Boy are those kids gonna get a rude awakening!!! Poor millennials, they don’t know what they’re in for.”

The vast separation between unions and new media workplaces doesn’t mean that unions couldn’t be useful in that environment. Just ask the Daily Beast, which is the only young, Web-only publication of any size to be represented by a union.

The Daily Beast wasn’t organized by traditional means. Rather, it inherited its Guild membership through its merger with the unionized Newsweek in 2011. After IAC sold Newsweek, though, it negotiated a standalone contract for Daily Beast employees. During bargaining, the very issue of what it means to be a “reporter” in the Internet age was a key sticking point: The Guild argued that all journalists should be hourly employees eligible for overtime, as most reporters are at publications like Reuters and The Washington Post.

Management, on the other hand, argued that several of the reporters should be exempted under the Fair Labor Standards Act as “creative professionals,” with greater latitude over their assignments. The union lost that fight, and that handful of Daily Beast writers currently aren’t eligible for overtime. But those who were reclassified at least got a raise out of it, and a management structure that fits with the realities of the Internet age.

“We recognized the need of the company to have a workforce that was flexible,” says Susan DeCarava, the New York Newspaper Guild’s rep for the company. “It wasn’t practical to have them watching the clock at any moment.” Meanwhile, the contract protects severance pay and minimum salaries for new hires, and created a new labor-management committee where issues can be worked out.

Mike Elk, whose mother belonged to the United Auto Workers and whose father is a negotiator with the United Electrical, Radio and Machine Workers, identifies with the working class very strongly. He’s still trying to introduce his Politico colleagues to the idea of a union, and he thinks that’s a balance that could be struck even at the most hyperactive of workplaces. For it to have a chance, Politico would have to at least remain neutral during a union drive, rather than retaliating against employees who try to organize.

“If Politico was really true about this commitment not to fire workers, what does that mean for Buzzfeed, what does that mean for the Huffington Post, what does that mean for all the digital media companies that are non-union?” Elk asks. Besides, he points out, Politico boasts a lot about its profitability — putting it in a better position than many legacy media organizations to grant requests at the bargaining table.

“I think it would further the type of innovation that [Politico editor] Susan Glasser and the Albritton family has been doing there,” Elk says. “I think it would be a real step forwards.”