It wasn’t easy to describe The Outline. That’s what made it great.

On April 3, the day The Outline was shut down and its editorial staff let go, my coworkers and I received hundreds of messages in public and private that went a long way toward making me feel better about suddenly losing my job during a pandemic. Weirdly, one of the sentiments that made me feel best was a critical paragraph written by Joshua Benton, director of NiemanLab, in a piece about our closure.

Benton started off kindly: “At its best, [The Outline] brought an intelligence and sophistication to the exigencies of contemporary digital life in a way that did feel unique, or at least legitimately distinctive.” (Thank you, we tried.) He continued: “It also did some work that felt thin and attitude-driven, like an angry tweet mistakenly blown up to 600 words.” (Actually, I got nearly 1,200 words out of “fuck Baby Yoda.”) Finally: “But it was never quite clear what an ‘Outline story’ was, the way it’s clear what a New Yorker story, a Wired story, or a Politico story is.”

He wasn’t wrong. I worked at The Outline for two-and-a-half years, and I never really figured out how to describe it to people who weren’t already familiar. When asked what it was by family members, strangers in bars, or august members of the journalism establishment at industry gatherings, I’d default to something like: “Our sales team pitches us as the New Yorker for millennials, which is not quite right, but it feels nice to say.” Joshua Topolsky, the site’s founder, didn’t know how to describe it either. Prodded in a pre-launch interview with Noah Kulwin (who would later work at The Outline as an editor), he chewed on the question before landing on, “What I’d say is that we’re a publication focused on telling a story of the way the world is now, and the way the world will be for a modern reader.” 

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The Outline launched at the end of 2016 with lofty mission statements about taking a new approach to media, an eye-catching website, and a talented staff who’d logged time at publications like Gawker, BuzzFeed, Bloomberg, Vice, The Verge, and The Fader. “It’s not for everyone,” the site’s tagline proudly touted. “It’s for you.” Before I worked there, I logged a few real differences between The Outline and its competitors: It only published a few times a day (opposed to the voluminous output typical of many websites); it looked beautiful, even if it was sometimes difficult to navigate (many websites are difficult to navigate and also look awful). It was experimenting with its identity in a way I found intriguing, and wanted to be a part of.

I joined The Outline in the fall of 2017 as its culture editor, and found that the site’s guiding principles were indeed a little unclear. In my mind, our freedom to experiment meant pursuing stories that resisted categorization, and the dominant formats of daily culture journalism—no listicles, no hot takes. When freelancers asked for direction on what topics to write about, I’d say, “Anything you really care about that you think might be too out there for another publication.” Despite their own struggles to summarize the site, the other editors shared this mindset, too. We were looking for stories that interested us in a visceral way—that made us laugh, or think about something new, or want to stop talking about it and just publish. That was it. Often from a left-leaning point of view, but not always; hopefully with a lot of voice, but not exclusively; preferably within the domain of “culture, power, and future” (our three verticals), but not necessarily. 

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At The Outline, you could read a lengthy reported piece about the cultural history of Sardinian stinky cheese, a beautiful essay about suicidal ideation, an incisive essay about the centrist children of leftists professors, an appreciation for Korean pomeranians, an investigation into the medspa industry, a reported reflection on a forgotten domestic siege, an experiential attempt at stealing Mark Zuckerberg’s trash, a photo essay about the children who grow up in Chinese restaurants, a long-running series about the failures of the MacBook keyboard, a gorgeously designed feature about group chats, the best personal advice column in the world, the best media newsletter in the world, and a lot more. Every publication prides itself on its versatility, but ours was driven by the freedom that comes with having no expectations besides “be different, and be interesting.” There was nothing we wouldn’t cover, if we thought we had a way in. And, blessedly, we had the money to assign at competitive rates.

The Outline empowered its editors to chase their interests, trusting that everyone’s sensibility was developed enough to let them roam for a while. As culture editor, I tried to decouple from the news cycle, which I saw as a strategic move: If there were already 1,000 articles out there about some viral bit of content, then it probably didn’t make sense to commission the 1,001th. (Not that we totally decoupled—sometimes, you just have to say “fuck Baby Yoda.”) This scattershot approach seemed to resonate. In 2018, our audience development manager broke down the topics covered by the culture section to see if there were any traffic trends. The good news: Everything seemed to be of some interest. (Except sports, but that didn’t stop me from assigning plenty of sports pieces that I liked.) The bad news: Everything seemed to be of some interest. That made it hard to decide what to cover. 

This business really should just be that simple—pay people well to do great work—and yet, it rarely is. But we tried.

At some point it became obvious that scaling up without a narrower editorial vision wasn’t economically sustainable. There were a lot of conversations in which a boss gently suggested that we might try publishing more about X and less about Y, and we’d all nod and then proceed to not do that. 

It wasn’t entitlement—nobody thought we were too good or clever for anything, and we all understood the necessary calculus that goes into predicting whether a piece will “do well.” (One goal of our founders, after all, had been to eventually make money.) But we knew the pitfalls of chasing trends. If there was one unifying feeling among everyone who I worked with at The Outline, it was a fundamental cynicism about the media’s flawed algorithm- and advertiser-driven business model. We’d all worked for well-read and successful publications, and understood the uneasy relationship between site quality and financial reward. We’d sat on traffic-logging platforms like Parsely or Chartbeat, watching the numbers shoot up, and looking around to find budgets still tight and the future still uneasy. 

If we were all working hard, and all pursuing what we thought was interesting and worthwhile, and it was still maxing out at a certain point… well, then probably only a fundamental reshifting of the site’s purview would change that, and none of us had come to The Outline to give up the creative freedom it promised. 

Nonetheless, a lot of the site’s original investment was spent trying to figure it out, and we suffered multiple rounds of layoffs in 2018, after which a lot of people wrote us off as dead. (Including NiemanLab—nice try!) Despite our diminished staff, though, our editorial vision winnowed into its most essential self. The editors—who by the end comprised me, Leah Finnegan, Brandy Jensen, Drew Millard, and Noah Kulwin, along with contributing editor Shuja Haider and social media editor Rachel Millman—did away with the pretense we were ever going to be the world-beating empire envisioned from the start. We didn’t fully detach from the news cycle—especially with regards to electoral politics—but now there were really no expectations about what we needed to cover. 

We became more of a destination for weird, idiosyncratic stories, and we could still pay people nicely for it. We helped launch some careers, and published a lot of young writers, some of whom had never been edited closely or paid fairly for their work. I’m most proud of that. I can’t imagine what it’s like to enter journalism right now—the field is somehow worse than when I entered it a decade ago, on the tail end of the Great Recession. In a very touching post at Discourse Blog, Paul Blest, an Outline contributor, wrote about how the site had provided a financial and editorial lifeline when his former employer Splinter shut down. This business really should just be that simple—pay people well to do great work—and yet, it rarely is. But we tried. 

That’s what made me laugh about Benton’s characterization. We were never operating in the same realm as publications like the New Yorker and Wired, because we were never an institution. The rules were always changing for us, and we had to change with them. For example, there was our very public sale in April 2019 to Bustle Digital Group, a company that didn’t own any sites like The Outline, and rightfully inspired a lot of questions about our future. But we did some of our best and most read work in that year: In our last six months, I received more compliments about the site than ever, a lot of which came with some insinuated caveat like “I thought you guys were done for, but you’ve really found your lane.” 

Not that it bothered me. Tally up how many websites started in the past decade, and how many of them lasted three-and-a-half years. The media industry is built on quicksand, but The Outline managed to survive long enough to publish enough words for several handsome coffee table books. 

I don’t want to sound glib about the work we did, much of which was serious and occasionally even important. It was a great job, the best I ever had. But for a long time, I allowed myself to anticipate its eventual end. Digital media’s track record of viability, for as long as I’ve been a part of it, has not been great—and that was before COVID-19 completely upended the ad-driven model, confirming what we all knew already. Websites are good, and then they die: Gawker, Deadspin, The Awl, Grantland, Splinter, too many others to mention. That’s just how it goes. 

So it feels slightly alien to finally mourn my own website after an adulthood spent watching almost every site I loved disappear, or morph past the point of recognition. The world moves on very quickly, and while I’m not lighting a candle in memoriam every night, a “remember when…” text from a former coworker can still inspire a lot of soppy feelings. Yet The Outline was something, not nothing, so I’ll allow myself to be sentimental. If I had the chance to give Benton a snarky bon mot at an industry gathering, I’d say: “It wasn’t for you. It was for us.”

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Jeremy Gordon was the deputy editor at The Outline. His work is online at jeremygordon.xyz.

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