It’s humiliating to consider the things we know instead of the things we should know. I can’t tell you exactly how the Michigan Republicans are trying to illegally gerrymander their state, but I know why Lana Del Rey is angry on Twitter. So it goes: We want to be educated, conscientious, intellectually activated citizens, but occasionally (if not often) settle for the most fun thing in front of us, in order to avoid losing our minds under the burden of all there is to consider. You can call this self-care, but it’s better if you don’t.
So it’s with some knowledge of my own behavior that I understand why, of all current stories, the saga of Caroline Calloway has so fervently gripped people across the internet, or at least across a significant swath of East Coast-media (many of whom are my treasured peers), which tends to be parasitic towards stories about the internet on the internet because it means they never have to leave their seats. The abbreviated version: Calloway is a popular Instagram user who amassed a massive following around 2014, when she began posting rapturous, romantic dispatches about her art history studies at Cambridge and the attendant social experiences that were swiftly promoted by the platform’s algorithm. She signed a book deal for a proposed memoir, which mysteriously fell through shortly thereafter; she continued posting on Instagram to her still-present following, but came to more mainstream attention at the beginning of 2019, when she staged a series of “creativity workshops” that also fell through, outing her as a potential scammer in an era obsessed with them.
On her Instagram, she became increasingly obsessed with the negative media attention, frequently tagging journalists and Twitter users who’d written about her, funneling more attention to her because her behavior seemed so flagrantly gauche, and also because journalists and Twitter users simply love to be tagged. Finally, on Tuesday night, The Cut published a massive essay by Natalie Beach, a former friend of Calloway who says she was responsible for ghostwriting some of her material, that detailed their friendship and gave us the most behind-the-scenes look into the psyche of this seemingly unremarkable white woman who has nonetheless managed to capture the attention of at least hundreds.
If you Twitter search for the essay or Calloway’s name, you can plainly see the interest from professional writers and editors reacting to the story even though they don’t particularly have anything to add, simply because it’s the dominant topic of the moment. This is a recurrent phenomena on the internet: the perpetually generative interest in a subject most compelling because it’s being talked about a lot, prompting users to say something just so they don’t feel like they’re being left out. (This is why I know why Lana Del Rey is angry on Twitter, and why I also posted about it.) But also (and pardon the awkward transition): Why Calloway? Why now?
The details of Calloway and Beach’s relationship are familiar in our modern era, but traces back to time immemorial. An unconfident beta is mesmerized by the apparent intelligence and glamour of a confident alpha and is sucked into their orbit, ignoring their own feelings in service of enabling the other’s behavior. They have some good times, and some extraordinarily bad ones, before going their separate ways. Calloway is known as an Instagram influencer, and her existence has been most obsessively tracked on the internet, but all of this behavior happened offline. “It’s about being in your 20s,” a co-worker said. And most of our alpha friends, if we’ve had them, were never so excessively online as Calloway, who’s teased the existence of The Cut piece — again, an essay that “exposes” her — for weeks and even linked to it in her Instagram account.
What’s interesting about Beach’s essay is how she resists the idea Calloway has been “scamming” anyone with her presence, even given the aborted creativity workshops and myriad get-rich-quick schemes like selling her (heavily derivative, overpriced) art. “People ask me if she’s a female Billy McFarland, both characters from Ingrid Goes West, Anna Delvey with an art-history degree, but I push back. If it was just money and fame she was after, all she had to do was be quiet and let me do the work. ... But she had to be the one to tell her own life story, even if she couldn’t. Caroline was caught between who she was and who she believed herself to be, which in the end may have been the most relatable thing about her. This is why, when people ask me if Caroline is a scammer, I try to explain that if she is, her first mark is always herself.” There is no large-scale scamming, beyond a few people who haven’t gotten their paintings in the mail, her publisher (who got some of their advance back), and maybe her landlord.
But Calloway is guilty of a more existential scam. She pretended to be someone she’s not, and maintained the facade even as it became increasingly unsustainable. She built herself into such a glamorous ideal that was all held together with tape and string. This wasn’t entirely her idea: As Beach narrates, she was able to convince both of them that they were doing something new and vital. “Instagram is memoir in real time. It’s memoir without the act of remembering. It’s collapsing the distance between writer and reader and critic, which is why it’s true feminist storytelling, I’d argue to Caroline, trying to convince her that a white girl learning to believe in herself could be the height of radicalism (convenient, as I too was a white girl learning to believe in herself).”
There is some psychology here that’s familiar to me. This level of galaxy-brain confidence — we’re doing something radical, even if it’s just posting — is found across the millennial media, as my peers have found themselves having to build careers in an industry that’s steadily collapsing. For many, this takes the shape of brand-building through social media — they are not simply their work, but the persona that accompanies it. This has been immensely lucrative for some, even if their work is sort of shitty, which lends itself to a wild amount of backchannel gossip about who deserves their success, and who’s really a hack. Pursuant to this is the paranoia for any brand-building writer that they, too, may be a hack — if it’s true of other people who post too much and buy into their own bullshit, then it could be true of them.
Other feted scammers like Billy McFarland and Anna Delvey operated in circles alien to the common writer, but Calloway is much closer to the people who think they are tasked with analyzing her for an audience mesmerized by whatever “content” they produce.
Some people deal with this by publicly quitting Twitter — of course, you can’t just Irish-goodbye it, you have to tell people you’re leaving, luxuriate in their pleading replies of “don’t leave!” and then probably come back a week later because you can’t function without the dopamine. Others double down, convincing themselves they’re doing bold, original work posting unfunny jokes and dispatches from their therapy sessions in order to defeat the nagging anxiety that they’re spinning their wheels, and should actually maybe go to law school. That’s what Calloway did: She, along with Beach, sold herself (and thousands of others) the myth that she was doing bold, original work, when it was just the garden variety Adderall-fueled gallivanting familiar to any young urban shithead with money and some social access. And, like many other hacks, she became momentarily successful because of this — as well as excruciatingly transparent, without exactly being self-aware, about her failures as her miniature influencer empire came slowly crashing down.
Other feted scammers like Billy McFarland and Anna Delvey operated in circles alien to the common writer, but Calloway is much closer to the people who think they are tasked with analyzing her for an audience mesmerized by whatever “content” they produce. We (and by we, I specifically mean the peers who can’t stop talking about it) can recognize exactly what she’s doing, and for some, it’s exceptionally infuriating because it’s the success that we should have. For this, she’s earned the focused schadenfreude of a media class empowered to dump all over her because she’s an outsider — given the stark social divide between Twitter and Instagram — engaging in many familiar behaviors. I mean, I can think of at least a dozen other socially manipulative, intellectually bankrupt writers who’ve perpetuated far worse personal and professional scams, but who my peers will never air out loud because they don’t want to shake the tree and bring down a world of bird shit. But Calloway, a white woman with unfettered internet access and a pathological commitment to never logging off, is an easy pressure valve for the anxieties and obligations felt by a generation of writers and editors attempting to authentically build themselves up even as it’s obvious that cheaters do prosper.
It’s not exactly envy fueling the commentary — not everybody wants to be a professional Instagrammer, and certainly nobody wants to weather such a public airing of grievances. I’d qualify it as a fascinated disbelief: This is what wins a six-figure book deal and legion of devoted fans? This is the lack of shame required to “make it,” in some writing circles? Could I rise to that level of shamelessness? Have I already? How fascinating, even if one feels, as I did reading the Beach essay, that that it is so personal and banal that it should’ve been litigated offline, rather than in public for everyone to chime in. Familiar psychology aside, it’s not like any of us know Calloway, or what ails her. But that doesn’t matter, when the discourse keeps churning.
There’s many other facets to this story that I can’t write about: I’m a man, so I’m not attuned to the gendered specificities of Calloway and Beach’s behavior and relationship; I only use Instagram to look at Korean dogs, so I don’t know how that community is taking it; I’ve only been familiar with her since the beginning of this year, and thus have surely missed many of the breathtaking incidents and small betrayals that have occurred over the years.
But I do know a little bit about why writers and editors on Twitter decide to obsess about something, even when it seems inconsequential to the great world. In this case, it’s because Calloway hit a level of success to which many of us aspire, under increasingly limiting circumstances. It’s a hackneyed scam, but it’s more than a lot of people have done. I’d almost be impressed, if it weren’t so upsetting.
