Based on the media’s coverage of her, 27-year-old “influencer” Caroline Calloway would appear to be a third rate villain. If you’re on Twitter, you’ve likely seen stories about her myriad of grifts: $165 workshops, $500,000 for a book she never wrote, selling paintings that seem like they never arrive in the hands of the people who purchased them. We've all watched as Calloway’s ploys to make money and get attention succeed. The metric for success here is obviously not a positive one. It doesn’t seem ideal, after all, to be known as the girl — and then the woman — whose greatest gift is ripping off the people who, for some reason, are most devoted to you. And soon, a former friend of Calloway's will publish an essay for The Cut, detailing the inner workings of their own failed relationship — including that she ghost-wrote many of Calloway's now-infamous Instagram captions.
Calloway is, more than nefarious, pitiful. She’s the byproduct of young women’s avid and ceaseless desire to carve out space for themselves in a world that has set a high price on self-empowerment. Constructing an identity is often conflated with constructing an online brand, a marketable edition of who you are. Calloway admittedly excelled at this. She has 782,000 followers on Instagram, many of whom have been fans since she first started writing narrative captions that gave nearly all of herself over to the whims of the internet. Her fans are young girls and women; her style vaguely reads like the first person young adult novels of Sarah Dessen and John Green.
From everything I can gather, the circumstances she’s found herself in — even her inability to pay rent at one point — don’t come from any sort of systemic lack of resources. She’s a Cambridge-educated white woman living in a West Village apartment that was aptly described by VICE’s Anna Iovine as one with “decor to rival the inside of an Anthropologie.”
Iovine went undercover to a Calloway event called “The Scam” in August — the espionage was required because Calloway had banned all press from the event. In a caption leading up to the event, Calloway promised fans something of a workshop on creativity. "I can’t wait to make memories and inside jokes together tomorrow and tell you about the things I know about writing, heartbreak, and being judged," she wrote. Iovine was able to conclude that the $170+ in ticket costs were for nothing more than a glorified meet and greet. The misrepresentation wasn’t new. Calloway faced similar allegations over an ultimately-canceled tour in January, and spoke to BuzzFeed about the controversy. “If I had known how hard it was, I never would've tried,” she said at the time.
The grift of Calloway is that you can achieve self-fulfillment through constant self-indulgence and "radical" vulnerability. She’s not alone in selling the idea — the difference is we also have to watch her buy it. Calloway might genuinely believe that she’s on the way to becoming a better self, that obstacles she contends with are merely the marker of growth and not signs to change her behavior. And her close to one million Instagram followers imply that plenty of other people believe this too.
But we’ve sustained her through our hate. For the New Yorker, Jia Tolentino wrote that “we like scammers most when they fail,” and that’s true of Calloway. I am sure that if she organized another of these doomed events, a similar cycle of outrage coverage would ensue. And it’s understandable. Here is a woman who, apparently unable to stop herself, indulges in the chaos she creates. In an essay that Calloway wrote for Refinery29 — seemingly in response to Iovine’s article, but also the countless others — she blamed the disorganization of her massive creativity workshop tour on the fact that she herself is disorganized, and that she has since learned to pride herself on her apparent faults.
To constantly preach about introspection but then lean into being a “self-obsessed mess” so much so that you put it on a hat not only says that you might not have enough respect for yourself to put distance between you and the descriptor, but also that you know that you’re allowed to be that way. Most of us aren’t. Being unthinking and unaccountable is only a quirky trait for the white and the wealthy.
It's why watching the Calloway coverage has made my brain rattle. For the sake of self-preservation, I decided long ago not to follow lifestyle bloggers like her; I don’t care about the inner thoughts and daily musings of people who engage with their realities as something consumable. I grew up poor, lucked my way into hundreds of thousands of dollars of debt for the privilege of attending NYU, struggle every day with the decision to pursue a passion over a field that would better support my economically insecure family. In these ways, Calloway and I live in different worlds. But there remain demographic similarities: We’re both white women in our 20s who live in New York City, who ponder over the authenticity of their experiences and their ambitions, who like to write.
Unlike Calloway, I don’t get to make a mess to the extent that she has. If I squandered a six-figure book deal, that’d be it for me. That’s the case with many young people who feel the weight, rather than the benefits, of the systems we all inhabit. I’m fairly certain that most other people who have committed the amount of hedonistic foolishness that Calloway has would be given a worse fate than public vilification; they’d face obscurity.
But on the internet, we’ve immortalized someone we could have simply avoided. We’ve taken on the girls getting scammed out of a couple of hundred dollars as our causes, and added this 27-year-old who seems to exist in the headspace of a teenager to the vast canon of deceivers and thieves taking our money and wasting our time. In a better world, Caroline Calloway would be too boring to observe. Unfortunately, she’s a sensation.
