“I don’t fully understand who Caroline Calloway is to be totally honest,” a friend revealed when I mentioned that I would be interviewing the Instagram socialite over the phone. “You know? I don’t either,” I responded, realizing that I couldn’t explain why the world was so captivated and simultaneously filled with a burning rage over a young woman that posted on Instagram during her every waking hour.
The social media starlet has been the subject of headlines for years now. In early 2019, when a Twitter user went viral after calling Calloway’s workshop event series a scam through a series of posts, Calloway did too. Calloway first rose to fame by Instagramming her career as a student at Cambridge University. The posts were romantic and innocent, shown through the lens of a young woman so obviously trying to be part of a world she had not grown up in. Photos of picturesque Cambridge University were accompanied by lengthy, fairytale captions written with a type of naiveté akin to looking at the world through rose colored glasses.
But behind the veil of a carefully curated Instagram grid stood a young woman in the throes of an addiction to prescription amphetamines. “After I quit Adderall and got clean I took about two years off from all forms of social media and I didn’t even return to Instagram posts until April ,” Calloway says. “When I came back I definitely improved in my ability to express myself authentically online. I definitely consider that December of 2018, right before I went viral as a scam, to be when I began posting with the intention not of selling myself as a product or even getting people to like me, but in making content that I felt was meaningful,” she says.
Today Caroline Calloway is much less synonymous with the dream-like Instagram posts that made her famous as she is with the unpredictable rawness that she operates under today. The one-dimensional character that once graced the feed of hundreds of thousands of Instagram users has now been replaced with a multi-dimensional character that values authenticity over likability. The performance of Caroline Calloway, today, is experimental and unpredictable, though grounded in a strategy that Calloway has long been perfecting from the back end of her public-facing persona.
Not long after initially going viral in early 2019, Calloway’s former best friend and co-writer, Natalie Beach, wrote a lengthy personal narrative for The Cut detailing her friendship and subsequent falling out with the influencer. The article, which recounted nearly every interaction that the two had shared throughout their multi-year friendship, revealed that Beach worked alongside Calloway on the Instagram captions and subsequent book deal that launched Calloway into internet stardom back in the mid-2010’s.
During the same week that the article was published, Calloway received word that her father died, a grim milestone that would later reveal itself to have been a suicide. “After [Natalie’s] article I didn’t get that many more followers—probably only twenty or thirty thousand—but I felt like that twenty or thirty thousand really, really hated me,” says Calloway of having to navigate a sudden onslaught of cyber-bullying while grieving her father’s suicide. “They just expected the worst from me,” she says.
Months later, Calloway’s cyberbullies are still as present as ever. Thousands of accounts dedicated to vilifying the Instagram blogger have taken to communities like Reddit, where each of Calloway’s posts on platforms like Instagram, Twitter, and now OnlyFans are picked apart with enhanced scrutiny. From how dirty her socks are to accusing her of pedophilia, Calloway’s trolls seem to be no less obsessed with her than her biggest fans. “I’m just really sad about it,” she says. “Last week they were picking apart my body and calling me a nazi and this week they’re calling me a pedophile. The body stuff really taps into the way they ridicule every inch of me and make me seem so repulsive. It just preys on the sort of internalized misogyny that we all have, as women,” says Calloway. Despite the enhanced lens that Calloway’s followers have put her under, she continues to share her every move on social media because, she says, it’s what makes her feel happy.
Of her father’s suicide and the damning essay published in The Cut, Calloway processed both experiences in great detail on her Instagram feed. Photos of her day to day antics, navigating a newfound fame and recognition in the real world, differed from her once fairytale life online. Unfiltered photos of Calloway in a bikini were coupled with introspective stories about what it’s like to be a young woman grieving, understanding, and thriving all at the same time. “Personally I really hate the word oversharing. I think it’s such a gendered verb. I mean when was the last time you ever heard of a man oversharing?,” Calloway says. “There’s lots of ways that English itself is very sexist. The language through which we understand the world has the patriarchy baked into it,” she says.
People hate Calloway the way they hate Kim Kardashian—because it’s the sophisticated thing to do and because, historically, vilifying women for taking unconventional, provocative routes to success is so nuanced in our culture that we seldom recognize when we’re doing it. “There’s no male equivalent for spinster,” Calloway says. “Bachelor doesn’t mean the same thing. There’s no word for a man that ends up alone in a sad and pathetic and sinister way, similar to [words] we have for women [who do the same]. Similarly, to that noun, oversharing is a really useful verb for devaluing female stories,” Calloway says of her latest strategy for Instagram: authenticity. “The language with which we describe female storytelling is really important. [Deeply rooted misogyny] is the poison that we all breathe in. Does anyone ever say men overshare? Don’t they just [get to] tell their stories and people just consume them at face value? But with women there’s this vulgarity to it,” Calloway says.
Her tendency to share the fine details of her personal life on social media are not unlike the reality TV stars of the early 2000’s that made careers out of performing provocatively in the public eye. Regardless of whether people appreciate figures like Kim Kardashian, Paris Hilton or Snooki, their success compounds each time someone mentions their name—both on and offline. That success, however, did not come by accident. “I really admire Paris Hilton and Kim Kardashian so much. No one wakes up with half a million followers by accident—unless you’re like me and you buy them. That was a joke. No one wakes up with sustained notoriety. No one keeps waking up day in day out with notoriety by accident. That takes intelligence. That takes ambition. That takes resilience,” Calloway says.
“This past year, especially coming off of a two year period where I just focused on getting securely sober, I really just wanted to shed those followers that I gained [after Natalie’s essay was published],” says Calloway. “I used to be really concerned with being liked and getting big numbers and getting a book deal that would make more people like me and that would pull big numbers from a publisher. I’m very lucky that all of the attention—positive and negative—has kept my publishers interested in me, but what’s the point of being liked if you don’t like yourself? What’s the point of making content that other people like if you, yourself don’t enjoy it? I’m trying to get rid of those followers. I want to have an audience that enjoys what I make,” she says.
These days, Calloway posts on Instagram as often and as excitedly as someone would text their best friend something exciting that happened to them throughout their day. Just like any other social environment, Instagram has a set of unspoken rules that dictate how often someone should post, and what kind of content is ‘instagram-friendly.’ For Calloway, pushing the boundaries of what it means to create good content is precisely part of her latest schtick. “I plan degrees with my social media strategy in advance,” she says. “I’m going to do some more multi-grid things with the last part of my Natalie essay. Then I’m going to do this big content push over the summer to get down into the 690,000’s, and then next fall I’ll probably return to something a little bit more normal to how other influencers use it,” Calloway says.
Unsurprisingly, the bizarre nature of Calloway’s posts are, likely, precisely how the Influencer has canonized herself as Instagram’s favorite ‘spiral.’ “I try not to hold onto any social media rules. [There is] this idea that you can’t post too many selfies or that something has to be this certain aesthetic to be gridworthy, or that you can’t post two times in two minutes, or you can’t, you can’t, you can’t, you can’t. Because Instagram has become such a vulnerable, nuanced place I think people forget that, although they’re posting more freely than they ever have, they’re still following so many rules. I try not to listen to any of those rules and I try to post what I feel like posting. I don’t think about likes at all,” she says. “I don’t even know if i’ll always post this way but I think i’ll continue it until [my followers] get down to the 600,000’s. Then I’ll maybe start posting in a way geared toward growth,” Calloway says.
Today social media followers are treated as capital. The more followers someone has on social media, the more valuable they are to brands. With a little under a million followers on Instagram, Calloway’s presence on the platform translates into a cash flow comparable to some of the world’s most successful celebrities, but not in the way of the traditional influencer business model. “The normal business model of an influencer has never sat right with me [for my brand],” Calloway says of how she’s monetized her social media following. “Both because—as you know—I paid for fifty thousand of my followers in the beginning of my career and I don’t know how much Instagram has culled those bots over the years, [so] I have no way of knowing what my actual follower count is. I would feel so—so scammy—selling an advertiser a sponsored post on my page. Combined with that, it’s so weird to me that, of all the influencers, I’m the one associated with scamming people when everyone else in my industry feels so okay with selling their audiences’ attention span,” she says.
“It’s so tough because we all need to pay our bills. I don’t want to vilify anyone, especially women—get your coin ladies,” Calloway says. “My feelings of support for those women exist side by side with my feelings of betrayal when I see an influencer post something that might not be totally in line with their values, but also my uneasiness at the thought of maybe falling into that trap myself,” says Calloway. “I just didn’t want to do that. But I need to be my own patron and I need to make my own art. And I need to keep the lights on and pay the bills like everyone else so it just seemed obvious to make whatever I do sort of an optional, ‘if you want it, buy it’ business model—you know? I feel like I’m mansplaining capitalism to you now. If you want it, you buy it,” she says.
Calloway describes the sort of renaissance we live in today, where everyone is creating, in the real world, content for the virtual world. We live in an era of artists, musicians, photographers, painters and story tellers that depend on the capitalization of their audience in order to continue making. The symbiotic relationship between capitalism and this renaissance both allows artists to create and trains them to hate their own trade—a relationship that also hinders the trust that their audiences have toward them in the first place.
We are not so much in an era of dismantling capitalism, but dismantling the relationship we have with capitalism and what it means to live in a world where capitalism is both a hindrance to society in so many ways and a path to artistic freedom in others. While many scoff at the idea of their favorite artist “selling out,” shaking their heads in disappointment that a creator sold stake in their audience to a brand, the reality is that capitalism is the inevitable, necessary evil that allows creators to grow at all. Without capitalism, there would not be room for everyone.
“When the camera was first invented all of the criticism on it was that it was science and technology and too democratizing. [The argument was] that anyone can buy a camera but to be a real artist you have to go to school and learn how to paint,” she says. “I think the criticism of social media is identical. This is technology. This is science. This is too democratizing! Anyone can have a Twitter account. I’m not saying that all Tweets are the next great american novel. But I’m not saying that all novels are the next great American novel either. I just think that social media—as much as dance or sculpture or pastels or oil paints—has the potential for human creative expression. In addition to creating my own content and working in more traditional mediums like painting or making collages, or even just digital graphic design and social media, I would love to get the necessary certifications to become a leading voice in art criticism that brings social media into the fold of what is considered canonical fine art,” Calloway says.
Capitalism, the very thing that allows for Calloway to monetize her social media presence by selling access to her Close Friends content, posting to OnlyFans, and selling watercolor paintings of boobs, is also why people associate Calloway with being a scammer in the first place. Americans are hyper-productive, by nature, thanks to the decades of capitalism that told us that our value is based on our output.
Many of Calloway’s trolls and critics latch onto the idea that because the book deal she got years ago has yet to come into fruition, or because the other self-published book (the one literally titled “Scammer”) has yet to see the light of day, that they are correct in thinking that Calloway is scamming her followers out of their hard-earned money. Perhaps, in that regard, Calloway is her own worst enemy to promise deadlines that are almost never met on time.