It was around this time last year that things were starting to look a little dicey for the media industry’s once breathlessly-hyped digital unicorns. Both BuzzFeed and Vice made news for substantially missing their revenue targets. Mashable was sold at a dramatic price reduction. Vox Media was forced to terminate 5 percent of its workforce.

These companies, which once heralded the dawn of a new media age—replete with massive valuations, large fund-raising hauls, and millennial sex appeal—now appeared to exhibit some traits of the brands that they once attempted to disrupt. They were large, less nimble, and increasingly vulnerable to Facebook and Google. They seemed virtually encircled by competitors familiar and new. On one side was a new generation of smaller yet influential companies focused on monetizing their direct relationships with consumers, like Axios, TheSkimm, Crooked Media, and the Athletic, to name a few. On the other were a tandem of revitalized shit-kicking legacy players, such as The New York Times and The Washington Post, who were converting subscribers at unforeseen levels in the Trump era.

A year later, the challenges have hardly abated. Mic canned the majority of its staff last week as part of a last-resort sale to Bustle for about $5 million—$95 million less than its previous valuation. Vice, under turnaround C.E.O. Nancy Dubuc, is in the process of trimming its 3,000-person global headcount by 15 percent, according to The Wall Street Journal, which reported Vice’s losses at more than $50 million in 2018. At Refinery29, 10 percent of the workforce received pink slips this fall. BuzzFeed’s Jonah Peretti recently floated in the pages of The New York Times the quixotic notion of a multi-company merger between BuzzFeed, Vice, Vox Media, Group Nine Media, and Refinery29, as a means to rival the Facebook-Google ad duopoly.

Boutique players have not been spared either. Lena Dunham and Jenni Konner’s Lenny Letter shut down in October, and last week brought the end of Rookie magazine, the 21st-century answer to Sassy, created by precocious tastemaker Tavi Gevinson. "Digital media has become an increasingly difficult business, and Rookie in its current form is no longer financially sustainable,” Gevinson wrote in a farewell note to readers. Traditional magazine companies, meanwhile, are trying to adapt to the digital world. Hearst, whose holdings include Cosmopolitan and Esquire, has endured layoffs, restructuring, and a leadership shake-up. Condé Nast, which owns Vanity Fair, is looking for a new C.E.O. who can streamline and maximize its global clout.

The chilly environment has created an opening for bargain shoppers and turnaround artists. Bustle founder Bryan Goldberg has been a regular at the fire sales; Jon Miller, a former AOL and News Corp executive, is shopping for Web sites with funding from the private-equity titan TPG.

But everyone else seems to operate on a relentless pivot schedule. “It’s a moment of real pressure,” one digital media executive told me. “My sense is, it’s tougher times for everybody.” Summing up the latest portents, a veteran digital-media strategist warned, “I think this is the tip of the iceberg. I think it’s gonna get worse, not better.” Tony Haile, founding C.E.O. of the Web-analytics provider Chartbeat, echoed that sentiment. “No one’s looking forward to this Q1,” said Haile, whose latest project is a publisher-friendly subscription ad-blocking service called Scroll. “You’ve got that kind of thing going on where everyone’s for sale.”