The Instagram influencer talks about the backlash to her ‘creativity workshops’, her reneged book deal, her addiction and the fallout from her relationship with her ghostwriter

It is hard to imagine Caroline Calloway being of any time before the internet – like picturing a present-day Joan of Arc. She laughs when I tell her so.

“Oh my God, are you kidding me? Caroline Calloway born in medieval Europe would be so fucking screwed. I’d be in the town square with a stack of pamphlets about what I ate for breakfast, being like ‘Hear ye, hear ye’. It would be a nightmare – mainly for the other villagers. I’d be living my truth.”

Calloway is arguably the world’s most infamous influencer. You may recognise her from her disastrous creativity workshops, for which she charged $165 a head and was branded a “scammer”; or from the tell-all essay her former friend Natalie wrote about their turbulent relationship – a she-said/she-said that is still ongoing.

Who is Caroline Calloway, and why can't the internet stop talking about her? Read more

When both went viral last year, Calloway was transformed from an aspiring memoirist who overshared on Instagram to a one-woman soap opera the entire internet loved to hate-watch. Who is Caroline Calloway, went several headlines, and why can’t the internet stop talking about her?

There are now 2,250,000 Google results for her name. Even seven months on from the publication of the Cut’s essay about her, the 28-year-old continues to captivate corners of social media.

Her critics loathe her for her self-absorption, her privilege, her perceived attention-seeking and questionable cash-grabs. Her fans love her for her willingness to draw them into her intimacy, her prettiness and pluckiness. Neither can look away.

If anything, Calloway’s “real life” is on the internet – especially now, a few weeks into isolating alone in her grandmother’s condo in Sarasota, Florida. Her social media output, always prolific, has reached new heights.

When I first reach Calloway by phone, I find her engrossed in making “internet art” from a snapshot of her and Natalie – scrambling their faces, she explains breathlessly, for her Instagram grid: “I’m very excited about it!”

I am reminded of how Calloway began her long-awaited “Natalie response”, her own take on the harms done during their friendship which also highlights Natalie’s part in building her public profile.

An online publication (she declines to say which) had offered her a “really big sum” for the essay: “It’s bankable clicks, whatever I wrote.” But in response to the worsening pandemic, she pulled out to self-publish the piece as a fundraiser for charity.

Facebook Twitter Pinterest Caroline Calloway: ‘People care about such bizarre and specific things about me.’ Photograph: Zack Wittman/The Guardian

My call finds Calloway ebullient after having raised $20,000 for the frontline medical organisation Direct Relief from the first installment. (Over a month, the total comes close to $50,000.) She tells me she celebrated by putting her phone down, pouring herself a glass of bubbly and eating two entire jars of caviar – “like a Russian oligarch”.

But as she goes on to speak about her experience of cancel culture – the pain of having her drug addiction turned into popcorn-fodder for the internet by her former friend, the vitriolic trolls she describes as “crusading for justice” against her – it becomes clear that her sense of achievement is tempered by frustration. No matter what she does, she can’t win.

Take her fundraiser: some on social media have speculated that it was a scam – and then, after Calloway posted evidence of the donations, a cynical tax break. It reflects the consensus of Calloway’s “snark community”, as she calls those online critics keeping tabs on her every move: she cannot be trusted, and she is only ever out to benefit herself.

“I wasn’t thinking about taxes,” she says. “I wasn’t even thinking about my own bills.” It was actually “sort of a sacrifice” to share the essay now, knowing that it would get less coverage. “I really believe in karma – I just hope this good will find its way back to me someday,” Calloway sighs.

But I wonder if, in focusing on her lost press, Calloway might be selling herself short. In publishing her counter-statement now, as the rest of us have been forced into quarantine – she has a captive audience.

•••

True to fragmented internet fame, Calloway still has little name recognition beyond her own following and the small subsection of society who consider themselves “extremely online”. Of them, however, many will know everything there is to know about her.

“People care about such bizarre and specific things about me,” she says, not without pride. Much of it is vigorously contested, from the mystery fate of the Yale plates given to her by Natalie, to Calloway’s claim to be the youngest-ever person to have their kneecaps removed (the latter was grounds for more than one online investigation, and Calloway’s mother has confirmed the surgery to a reporter).

“You know what’s so, so rich about the kneecaps thing is that I was so fucking mocked for this in middle school,” she says merrily. “If I could travel back in time I’d tell my heartbroken little third-grader self, ‘OK, bad news. The teasing is going to get a lot worse.’

By her own admission, Calloway stokes those conversations, if only by providing continual fuel. Trying to keep up with her online is like trying to note the particulars of running water.

Whenever you look at Twitter, she’s just tweeted. Often it is a retweet of a quote-tweet of her own tweet – Caroline begetting Caroline like a little nest of Russian dolls, all bearing the beatific expression in her profile picture.

On Instagram, her life is serialised for an audience of 700,000 people, both in real time and in the long, stylised picture captions she claims to have pioneered.

She is often asked about how she can possibly cope with people knowing her private business. “The easiest way to explain it is that I just always wanted to write about my life, I wanted to be famous,” she says. “The idea that my life would be something I shared with the public wasn’t just something that I assumed – it was something that I actively wanted. I still want it.”

Born Caroline Calloway Gotschall in Falls Church, Virginia, an upper-middle-class suburb of Washington DC, at 17 she changed her name to one that would “look better on books”.

When she joined Instagram in 2012, Calloway began experimenting with growing her following with input (sometimes paid) from her friend Natalie Beach, another creative writing student at NYU. She honed her winning formula of “beautiful photos with sort of sad or lonely captions” while studying abroad at Cambridge University from 2013 to 2016.

Calloway had always aspired to being an Ivy League student, even keeping a “Yale box” stuffed with motivational memorabilia. But after she was rejected from Yale four times and then “for life”, Calloway was accepted into Cambridge on her third attempt. It is there that she first became known for her Instagram presence, depicting a fairytale life of “Harry Potter-like castles, Jane Austen-like balls” and punting on the River Cam.

Her breathless “#adventuregrams” inspired derision in her fellow students – “Cambridge fanfiction”, one called it – and distracted from her studies in art history. (She has said she graduated with “a second class”, widely interpreted to mean a 2.2 – the so-called “drinker’s degree”.)

Calloway did not mind. In two years, her following of 210,000 tripled in size, and she was trying to turn her Instafame into a publishing deal.

Had Calloway gone viral as a publishing success story, not a scammer, it is easy to imagine her being praised for her dogged pursuit of her dreams.

Back in New York the summer after her first year at Cambridge, her Instagram boosted by 250,000 new followers, Calloway engineered a meeting with star literary agent Byrd Leavell by pretending to his secretary to already be his client. (Leavell has since called her “deeply unwell” and dishonest.)

With his help, her memoir sold in 2016 for $375,000; foreign deals took the total above $500,000. But at the time 24-year-old Calloway was increasingly addicted to Adderall, an ADHD medication she had started taking recreationally in late 2011.

“They were delicious,” she says breezily now. “I mean, don’t get me wrong, they murdered my life and I’ll never touch it again – but drugs are fun.”

Calloway called on Beach to help co-write the book proposal, as she had her early Instagram posts. These collaborations formed the basis of Beach’s later claim to have been Calloway’s ghostwriter.

By spring 2017, Calloway says she was taking Adderall in such quantities as to be at risk of a fatal overdose: “I was really counting my sleeping pills to do the math right.” Later that year she publicly reneged on the deal with Flatiron Books, paid back most of the advance, and began her recovery from addiction.

Calloway says Flatiron still owns the rights to her story of her time at Cambridge and that, though that “dark, messy book” is not imminent, they are prepared to wait.

About 18 months later, shortly into 2019, she found herself going viral for her disastrous attempt at a global tour of “creativity workshops”. Venues weren’t booked, promised perks were downgraded or not delivered, and Calloway sought unpaid labour despite charging $165 a head. She became instantly infamous as a “one-woman Fyre festival” and a scammer akin to the socialite con artist Anna Delvey.

The backlash was the first time Calloway had lost control of the crowd she had courted. In response she cancelled all but two events and refunded all tickets, blaming her “total inexperience with event planning and GREED”. She reattempted the workshops in August, billing them as “The Scam” of which she had been accused.

Many attendees said they were satisfied, even for $165; “I would have paid MORE!” wrote one. But journalists questioned charging such a sum for a meet-and-greet. The same criticism is made of her charging $140 for her art, a pastiche of Matisse’s Blue Nude II.

There are two persistent complaints, says Calloway, with weary authority. “One is that I take people’s money, which I don’t – I’m really on top of making sure everyone’s a satisfied customer. Then there’s the idea that I charge too much, and like I’m somehow tricking people into buying stuff from me.

“Those people fundamentally do not understand the business model of an online creator.”

•••

At the heart of what seems to rile many about Calloway is her apparent privilege. Her great-grandfather, a real estate mogul, once owned most of Sarasota; she has described herself as being “born into material wealth”, but denies being rich herself.

Last year a Vice reporter was moved to investigate how Calloway paid rent and found court evidence that she had often struggled. Between paying for a Greenwich Village apartment, thrice-weekly therapy, and a web developer to manage donations, Calloway says now: “I am so fucked in terms of income flow.”

She adds that she eschews sponsored content, many influencers’ bread-and-butter: “Selling my audience’s attention … it just doesn’t sit right with me.” Yet her critics keep score of her purchases (pedigree kittens, a trip to Berlin, an expensive ring) and confront her with them whenever she attempts to monetise her following.

Facebook Twitter Pinterest ‘I don’t really mind if people think I’m a bad writer, if they don’t understand my weird Instagram performance art or they find my long captions annoying.’ Photograph: Zack Wittman/The Guardian

To the world at large, the “Scammergate” debacle remains proof of Calloway’s shameless profiteering. Just this morning, she says, she blocked an anonymous Twitter troll for “tweeting at me over and over for not providing food” at the workshops. (She did.)

But it was over a year ago, I say, confused – and unless they attended, why do they care?

Calloway explodes. “I KNOW,” she nearly screams, her voice distorting on the line. “Oh my God, I am going to go Incredible Hulk on my grandmother’s condo if we keep talking about this. Like, flip the dinner table over.”

She takes a deep breath. “I love fame. I love being written about. I don’t really mind if people think I’m a bad writer, if they don’t understand my weird Instagram performance art or they find my long captions annoying. That’s part of the package of being in the public eye, and honestly I find it exhilarating.”

What is hard, Calloway says, her voice quavering, is delineating where the standard scrutiny of celebrity should end.

“A lot of people tell me to shut up, ‘don’t play the victim’ – but when you Google my name, the related searches are criminals,” she says, with mounting incredulity. “It’s not normal to be famous and to be associated with criminals who are literally in jail, when I myself am a law-abiding memoirist!”

•••

It is true that, if the conventional wisdom is “don’t feed the trolls”, Calloway’s never go wanting. She continues to engage with her critics lustily, and at length.

Her tendency to single out individual journalists has led to accusations of bullying; a T-shirt she made targeting one by name (“Stop hate-following me”) was pulled from sale for harassment.

Even her supporters can find their goodwill tested – such as when Calloway likened the backlash against her workshops to being diagnosed with cancer. When a fan said it was insensitive, Calloway defended it as “good art”: “If you don’t like my free content, you can unfollow me.”

Instead many opt to steep themselves in their hatred of her – and find company in doing so. There are now two groups dedicated to “Caroline snark” in Reddit, each with 5,000 active members, whose conspiracy theories and vitriolic pursuit seem to suggest obsession.

They will even rally en masse against journalists they see as being sympathetic to her. The New York Times’ Taylor Lorenz was inundated with abuse for her assumed association with Calloway, despite having never reported on her.

Calloway likens her “snark community” to rightwing trolls “who feel so passionately, and so righteously, that they’re crusading for justice”. It is hard not to get the sense that not only do they want her to go away – they want her to suffer.

“Of all the hands for a suicidal depressive to have been dealt, having so many people want them to not exist – the irony almost seems cruel,” says Calloway grimly. “A lot of people do want me to just stop being, period.”

•••

Calloway has been diagnosed with general anxiety disorder and depression. She says she inherited mental illness from her father, William Gotschall, who she describes as a bipolar, paranoid agoraphobe. Weathering his bouts of “black rage” when she was a child led Calloway to believe that “we should take people seriously when they are host to a brain that wants to kill them”.

After her workshops went viral, Calloway started taking antidepressants. Nonetheless, for seven months she was a “wreck”: “Nothing had ever hurt that bad.” She read Jon Ronson’s So You’ve Been Publicly Shamed, “one page at a time, having to take breaks to wipe my tears. I didn’t know how I’d get through it.”

Calloway continues to take an SSRI daily; “A silver lining to that cancellation: it made me reconsider my approach to pills.” Her experience of addiction had left her leery of prescription drugs. Over about a year from May 2017, she had “all but disappeared from Instagram”, working through recovery steps with a therapist.

The following March, Calloway sent Beach a heartfelt apology for being a “trainwreck” during their friendship, and expressed hope that they could begin anew and “make something beautiful out of the mess”.

A month later Beach replied, accepting Calloway’s apology, and kindly but firmly refusing to resurrect their friendship. Calloway remembers sobbing as she read Beach’s email – but, she says, “I respected that boundary.”

When Beach’s essay I Was Caroline Calloway was published 18 months later, it made no mention of Calloway’s apology or their empathetic email exchange. Instead it dwelled on Calloway’s offhand slights, erratic behaviour and broken promises – culminating in Beach being abandoned by Calloway at a bar in Amsterdam and spending the night on the street.

Many readers praised the essay as a relatable account of a lopsided friendship not uncommon in one’s 20s. “If you can’t identify the Caroline Calloway in all of your female friendships, then you are the Caroline Calloway” was one assessment.

Only a minority voiced discomfort at the gleeful reception of what seemed to be a voyeuristic account of an unwell young woman. Roxane Gay – not one to shy from drama – damned Beach’s essay as “quite a white girl journey. And rather depressing.”

Calloway says Beach reduced her to the stereotypical self-obsessed influencer, the sum of “the dumbest shit” she had said in sophomore year. “She really flattens me into a one-dimensional villain. It’s not confusing about who’s the plucky underdog and who’s the maniacal, vapid bitch.

“Most of all, when I talk about being stripped of humanity …” Calloway grows somber. “Her essay is over 6,000 words long – yet she doesn’t use the words ‘mental illness’ or ‘addiction’ once.”

The only mention of her addiction was forced by Calloway to a factchecker; she also clarified Beach’s passing mention of her threatening suicide.

“I don’t think that my depression or my addiction excuses or undoes or makes up for any of the ways that I hurt Natalie – her hurt is very real, and my bad decisions were very real. Five years later I am still knitting together the broken pieces of my life,” says Calloway, her voice wobbling.

But, she says, she was “floored with pain” to see her suicidal ideation “scrubbed from the record”: “I was shocked.”

(When reached for comment, Natalie Beach said she “chose to tell the story solely through my perspective, feeling that it would be presumptuous and irresponsible to otherwise diagnose or label a person I hadn’t spoken to in two years. She mentioned the suicide threat “because it was directed at me personally, and marked the moment I stopped writing her book and the end of our working relationship”.)

I don’t think that my depression or my addiction excuses any of the ways that I hurt Natalie – her hurt is very real

The week the essay was published, Calloway’s father died by deliberate overdose of painkillers at their family home. She says he was close to bankruptcy, and had recently been discharged from a psychiatric hospital after having his petition to stay hospitalised denied.

In a later installment of her Natalie response, Calloway confronts her father’s suicide in moving but graphic detail, with pictures of the autopsy report and the scene. Though it is affecting writing, one imagines that a compassionate editor would have urged Calloway to reconsider for her own good.

“If I’m not ready to open something up to the scrutiny of the internet, I don’t write about it,” says Calloway. “Natalie made public, for the first time, the fact that I’d struggled with suicide. I really wasn’t ready to talk about that publicly.”

•••

Facebook Twitter Pinterest ‘I know all the hours of work that it took to get here. And I don’t mean just writing posts – I also means the hours I cried myself to sleep, because the literal news was saying what a bad person I am.’ Photograph: Zack Wittman/The Guardian

It speaks to the bottomless appetite for “Calloway content” online that, even at 6,000 words, Beach’s essay proved the Cut’s best-read piece of 2019 – above E Jean Carroll’s accusing Donald Trump of rape.

Beach had pitched her side of the story in the wake of Calloway’s first “cancellation”, and was paid at least $5,000 (says Calloway). “Sometimes I feel like the best thing I can do for Natalie is to just let her capitalise on me, you know?” says Calloway – a putdown so masterful, I am momentarily left breathless.

What often goes unacknowledged is that, by online metrics of success, Calloway is a rising tide that lifts all boats. Tweets about her go viral. Stories about her get read. After Beach’s essay was published, Calloway was briefly a bigger search term on Google than the British prime minister, Boris Johnson.

This seems to have led to a perception of Calloway as an online commodity, or as fair game. Even Jameela Jamil – an outspoken campaigner for kindness, and no stranger to online pile-ons – unthinkingly joined in on the Calloway-bashing on a recent podcast. Calloway’s own theory on why she is so polarising is that she is too open about her flaws: “When I pretended my life was perfect at Cambridge, I never got any hate. I do think the more vulnerable you are online, the more vulnerable you make yourself to criticism.” It is true that, more than many in the influencer economy, she is less concerned with presenting an aspirational image than the work of maintaining it.

Sometimes I feel like the best thing I can do for Natalie is to just let her capitalise on me, you know?

“I made such smart early investments in Instagram,” she says, describing how she bought fake followers (before it was stigmatised) to boost her profile and advertised on Harry Potter fan communities to attract readers already “predisposed to become obsessed with what they read”.

If she overweights these achievements, it may be because people are so disinclined to give her any credit. Today Instagram is arguably the most influential social media platform in the world; Calloway used it for storytelling when it was dismissed as “Twitter for people who can’t read”, and understood the value of commodifying herself long before respected writers followed suit.

Calloway says she feels justified in monetising her audience, not least because of all that she gives away for free. “I know all the hours of work that it took to get here. And I don’t mean just writing posts – I also means the hours I cried myself to sleep, because the literal news was saying what a bad person I am.”

Surviving cancellation, Calloway says, “is much like getting caught in a riptide. If you fight against it, you will expend all your energy, and you will drown … I think it’s so unfair that people look at the ways that I let myself be carried by the current – the only other choice being to let it break me.” (I later find that her analogy borrows generously from her idol, Taylor Swift.)

She appeals to me directly: “How would you feel about yourself if we woke up in a world where your name was replaced with my name?”

I would get off the internet, I say, truthfully, and she laughs.

•••

In fact, the tide seems to be turning in Calloway’s favour, just as she learned to swim. She tells me excitedly she was texting an ex the other day (“I’m horny as fuck in quarantine, I’m ‘reaching out’ to everyone”) who told her that it has “never been more popular” to like her.

It is possible that the virulence of her trolls has turned public sentiment towards her – or, as Calloway suggests, that her return to Twitter has shown people that she is self-aware and funny: “No one can roast me better than I roast myself.”

But it could be that the rest of the world has finally met her on her chaotic terms. From social media it seems that, during lockdown, there is greater appreciation for Calloway’s constant spectacle. The internet has always been her world; now, increasingly, we are living in it.

“During this quarantine, I feel almost a burden to be entertaining more than ever,” says Calloway. “Chaos is a weakness of mine – but it can also be a strength.”

The next day, not 12 hours after our interview, I check Twitter and find it in meltdown: Calloway has posted an uncensored, full-frontal nude of herself and made it her pinned tweet – equivalent to hanging a framed print on your front door.

It was, she wrote, a “humble apology” for those who had paid for her essay expecting it to be 15,000 words and only got 6,000. That was a “really funny joke”, Calloway patiently explains when I call her a few days later. “The apology part was like when the pizza delivery boy shows up in the first minute of porn – it had nothing to do with what’s about to happen.”

In reality, the nude was her small way of compensating for the loss of a Playboy shoot that she says was slated for this spring: “I’d really adjusted to the idea of the internet seeing my nipples.” (Playboy says no shoot was discussed, or promises made.)

So, I persevere – was the nude to build hype for her essay?

I can almost hear Calloway shrug. Then she says something so spectacularly Caroline Calloway, I think maybe she could be a genius. “You could just as easily say the essay was hype for the nude.”