Caroline Calloway

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About

Caroline Calloway is an Instagram influencer and personality. She has been the subject of numerous controversies due to a failure to follow-through of various plans, including a book deal and a creativity seminar tour.

Online History

On June 5th, 2012, Caroline Calloway posted her first Instagram photograph.^[1] She captioned the photograph, "YOU GUYS. My first Instagram! Let's get this 5-follower-party started… In the beginning there was a gala at the Met. On the first day the party planner said, "Let there be a shit ton of votive candles," and it was so. I took my picture, discovered the Hudson filter, and I saw that it was good. #or #in #theimmortalwords #of #vanessahudgens: "#thiscouldbethestartofsomethingnew" Idk Instagram, but it feels so right to be here with you." Within eight years, the post received more than 2,700 likes (shown below).

Over the next seven years, Calloway's Instagram would become her main platform for interacting with fans, garnering more than 797,000 followers.

Book Deal

On February 6th, 2016, Publishers Weekly^[2] reported that Calloway had signed a book deal with Flat Iron books who would be publishing her memoir, And We Were Like. Calloway later reported that the deal was for $500,000.^[3]

Calloway later claimed that she willingly backed out of the deal after realizing that she "the boy-obsessed version of myself I planned to depict as my memoir’s protagonist was not one I could stand behind." The publisher later pulled out of the deal.

Creativity Seminars

In late 2018, Calloway began promoting a tour of creativity seminars in which she aimed to teach people to live a life like hers. On December 20th, 2018, Pajiba writer Kayleigh Donaldson began a Twitter ^[4] thread about Caroline Calloway, an Instagram influencer that she called "the worst." She wrote, "That Instagram influencer I occasionally check in on because she's The Worst is now charging $165 for a 4 hour 'seminar' on how to be yourself." Additionally, in this inaugural post, she added a GIF of Catherine O'Hara saying "It's a scam." The tweet received more than 1,800 retweets and 10,000 likes in less than one month (shown below, left).

Over the next month, she continued to update the thread on the seminars, writing that the seminars had "sold out," grossing "$15k." Eventually, she began referring to these posts as "scammer updates."

On January 13th, she posted a direct message from one of the workshops' attendees. They wrote, "I went to her workshop and was HIGHLY disappointed. No notes, no flower crowns, only about 1.5 hours (max) of actual 'teaching' if you can call it that. Icing on the cake? Her 'staff' are 20-year-old college girls with no event planning/logisitics experience that are just huge fans of hers." The tweet received more than 945 likes in two days (shown below, right).

On January 14th, Calloway published an apology on Twitter and Instagram. She wrote:

Yesterday I found out about a Twitter thread criticizing my tour. I think that criticism is really valid and I apologize to anyone who felt cheated by the price point of $165 […] I take full responsibility for letting my total inexperience with event planning and greed create a situation where the details of the tour were ever-changing

[…]

I'm cancelling the rest of the tour. Everyone will be refunded today.

The Scam

On July 21st, 2019, Caroline Calloway^[5] announced on Instagram: "Saturday, August 3rd near the West Village I am hosting my first event since I went viral. It is……………The exact same fucking event as before, but with a different name. The main thing that’s different is that this time I want you to bring a piece of writing to workshop and possibly share with the group" (shown below). The post gained over 2,500 likes in two days. Many commenters supported her decision to try out workshops again while many on Twitter called the tickets too expensive and Calloway too inexperienced to be teaching anyone.

Criticism

Following the fallout of her creativity seminars, many outside of Instagram influencer circles began regarding Calloway as a scammer and grifter, aiming to use her Instagram page to enrich herself by swindling followers out of money. In early 2019, Pajiba^[6] published "The Empty Mason Jar of the Influencer Economy: The Case of Caroline Calloway and her Creativity Workshop Tour." Author Kayleigh Donaldson writes:

Caroline Calloway is merely the sloppiest and most obviously incompetent version of the influencer economy run amok. She has had every opportunity handed to her, including a book deal that would be life-changing for most, but she had no intention of following through. The workshop tour merely exposes how unprepared and unwilling to learn she is for such experiences. Calloway’s main problem is that she doesn’t want to be an artist or a storyteller or a writer: she wants to have made art, to have told stories, to have been a writer, to have taught, and so on. But that requires work, research, planning, sacrifice, and an acute understanding that not everything you do will be successful or worthy of celebration. She has nothing to offer but is selling everything.

The Cut Exposé

On September 10th, 2019, The Cut^[7] published a first-person account of working with Calloway by her former ghostwriter Natalie Beach. The article depicts the two women in an entangled relationship that Beach was unable to separate herself from, drawn in by the lifestyle that Calloway had created for herself.

However, the report shows an opposing side of Calloway's struggles with her brand and her book deal. Beach details the drug use, all-night writing sessions and the price of the book deal, which Beach claims was for $375,000, not $500,000. The author continues to describe times when she felt used by Calloway. In one instance, she describes a time that Calloway had abandoned her. She writes:

I pushed past her, shedding my filthy clothes in the hallway. “You have no idea what I went through last night,” I remember shrieking. “Why didn’t you answer your phone?”

She told me she assumed I was home with the bartender.

“This is what I tried to tell you,” I said, and for the first time I broke down. I stood in front of her in just my leggings and a bra, sobbing stupidly. “Men treat me differently than they treat you. Everyone does.” I collapsed into the rented bed. Caroline hovered over me, weeping too. “And the really messed up thing is that whole night I thought something terrible had happened to you,” I said. “But you forgot I existed.”

On Instagram, Calloway seemed to both promote and dispute the piece, calling into question some of the reporting, particularly regarding Beach's claims that Calloway was suicidal (examples below).