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I Went to Influencer Caroline Calloway’s $165 Creativity Seminar So You Don’t Have To

Caroline Calloway teaches a lesson during a creativity workshop in Brooklyn. Photo: Madison Malone Kircher

“Fyre Festival! Wanna come?” reads my first Instagram DM from Caroline Calloway. She’s an influencer who rose to fame in 2015 for writing lengthy Instagram captions detailing her love life as a student at Cambridge University. (Calloway hails from Virginia.) Calloway’s earnest captions and, at the time, novel style — think of it as Instagram Stories before Instagram Stories — earned her a six-figure book deal. She’s now in the process of repaying more than $100,000 to her publisher after refusing to finish the book, citing creative differences. That was pretty much the last the world outside of Calloway’s fandom heard of her until January, when a Twitter thread documenting the implosion of her plans for a tour of so-called creativity workshops went viral.

It’s unclear if Calloway is calling me Fyre Festival or simply referencing the comparisons that so many, myself included, drew to her tour when writing about it. For the record, I said the saga of Calloway’s tour would “satisfy your Fyre Festival nostalgia.” I did not proclaim it the second coming of an event that left rich people stranded in the Bahamas for days without ample food or shelter and landed its creator a prison sentence. I told Calloway I’d be there and I’d even bring my own Mason jar. “As you well know Mason jars are included in the ticket price,” Calloway replied, emailing me a link to purchase a ticket. While planning for the tour the first time, Calloway — documenting the whole process on Instagram Stories — ordered 1,200 Mason jars and then realized she had nowhere to store them in her apartment.

This is how I wind up spending my Saturday at a loft in Brooklyn surrounded by plants and 17 other women who’ve come to drink oat milk and worship at the church of Calloway. When I roll up at 11:02 a.m., there is nothing and nobody to be found at the provided address. I wonder for a brief moment if I have been punked — a move so ballsy I almost respect it — and start to plan what I’m going to do with the six hours in my day that have suddenly freed up. I return after a lap around the block to find a man wearing a hat emblazoned with “SECURITY” at the door. He takes a look at his phone and checks off my name, then directs me to the proper floor. Calloway’s assistants Tara and Rachel, college-student fans she hired earlier this month via Instagram, welcome me into the loft and hand me a journal with my name spelled out on it in stickers. (All names in this piece have been changed, including the assistants’, whose identities Calloway insisted should remain a secret, despite repeatedly tagging them in her Instagram Stories, where she has 800,000 followers.)

The first hour of the event is a meet and greet, but for attendees to meet and greet each other sans Calloway. I chat with a 25-year-old from Florida who flew in for the weekend just for the event. (Calloway is 27.) She has been up since 5 a.m. because she and another attendee, whom she met via Instagram, decided to wait in line for SNL tickets before heading over. One woman drove in from Maryland that morning. There’s a set of cousins from Seattle, a mother of two, and a student who planned a trip to New York around Calloway. There’s also an Ivy League nursing student, an aspiring opera singer, and a number of women who have recently moved to the city and came hoping to meet new friends. “I actually listened to ‘Welcome to New York’ after getting off the plane,” one of the women says of her move, referencing a Taylor Swift song. “I did that too,” another adds. Several of them tell me Calloway is “relatable” and “authentic.” The room is overwhelmingly white.

Much of the kerfuffle around Calloway’s tour the first time was over the ticket price. The event cost $165, and promised lunch, teaching sessions with Calloway, customized care packages, personal letters, and fresh orchid crowns — most of which Calloway did not deliver. This time around, the ticket cost the same but she was more explicit. There would be singular orchids for wearing and picture taking — an orchid tucked behind the ear is a signature of Calloway’s — but attendees wouldn’t be able to keep them. The letters were nixed. Everyone got the same care package. Lunch would be catered, not cooked by Calloway. The workshop would be two and a half hours longer.

Still, attendees tell me they thought it was worth it. Several had purchased tickets for Saturday’s event before Calloway announced she’d be canceling the tour. They were issued refunds but when Calloway announced the tour was back on — on Instagram she quoted “Franklin Delanor [sic] Roosevelt” and said the new events would have an added focus on “resiliency” — they sent the $165 right back. “I had the money, but even if I didn’t I was going to ask my mom if I could put it on her credit card,” one of the women says. Of the 18 women in the room, three are journalists. Three tell me they received scholarships. (Calloway later tells me she was able to offer scholarships because Rude Health sent her free oat milk for the event. Her assistants tell me in a different conversation that the event has no sponsors.) Another says Calloway told her to come, and offered her a comped ticket, after exchanging a few Instagram DMs. Three people don’t show up, I assume because their tickets were also free or because they did not care about losing $165.

After an hour, Calloway arrives. She’s wearing a T-shirt that reads “SCAMMER” under a navy blue cardigan she repeatedly refers to as her “Miss Honey sweater,” a reference to the kindly teacher in Matilda. She makes her way around the room introducing herself to the attendees, most of whose names she already knows. Throughout the day it becomes clear she researched everyone in the room in advance, name-dropping mutual friends. When we are talking, she lets the women around us know I am a reporter, something I’d already told them, and jokes that they should all be very mean to me. She then says she’s kidding and wants everyone to feel welcome and like they are getting the full value out of the day, even the reporters. It’s palpably awkward.

We settle onto a collection of chairs and couches and stools and Calloway takes her place at the front of the room. She’s seated under a banner reading “FYRE FESTIVAL” in shades of aqua construction paper which she proudly announces she cut out without stenciling. The letters do look good. Before she starts the workshop, Calloway once again lets the attendees know there are three reporters in the room. She points us out by name and by outlet and says she and I have a mutual friend who has vouched for my character. I quietly hope after this she’ll continue with the workshop as though we are not there; she does not. Calloway tells her fans that phones are encouraged. “People judge me [when they see me on my phone] but they don’t know I’m building an empire with this selfie.” She says at the first workshop she told attendees it was like Fight Club and the only rule was that there are no rules. Calloway jokes that she has also never seen Fight Club.

Calloway asks each woman to introduce herself and tell a little about when they started following her on Instagram. “I was actually in the bathroom at the Met,” one says. Another mentions a picture of Calloway kissing a boyfriend in an airport with a caption about their breakup. “People ask me this all the time … I had a stranger take that picture,” Calloway says. Most of the women have been following her for years. “Since Oscar,” the man Calloway dated during her Cambridge days, is a common response. Other women cite different men’s names as markers of follow time. Calloway responds to each anecdote and it’s easy to see how she’s built the cult of personality that surrounds her. She easily recalls details about her attendees, like mentioning a specific hometown, in a way that makes it seem like she’s not an internet personality, but a pal. For many of these women, who brought her letters and mixtapes and gifts, that is exactly what she feels like. “Caroline speaks to her audience as though we’re her closest friends,” one attendee says. “This sometimes comes off as disingenuous, but I do believe that she’s genuine.” Calloway spends a little bit of time talking about her Instagram brand, which she later describes as “fucking bizarre and very excited to meet you.” We break for lunch, which is, as promised, catered and vegan. It is also delicious and the healthiest thing I have eaten in 2019.

During lunch, Calloway speaks with me and the two other reporters. We ask her how this iteration of the workshop is different from the earlier versions. Calloway says, due to media scrutiny and presence, she can no longer “offer sanctuary” to her followers at these events. This seems off, given that she actively invited press to attend. By 2:45 p.m., she has brought up the reporters in the room so many times I start to keep count. She’d mention us eight more times before the event was over. As we resume following lunch, I tell Calloway I want to change seats because I’m worried being so close to her is taking away from the experience for the other attendees. She tells me not to move. After the workshop, one attendee tells me she wishes Calloway had “laid off the reporters.” A different attendee describes Calloway as “very defensive and on guard throughout the whole day.”

More than two hours after we’ve arrived, the teaching begins. Calloway says she’ll be covering resilience, heartbreak, making art, and how to find our voices. She talks a lot about the importance of professional mental health care and reminds the women “the world is not owed details of your life.” At this point, she stops her train of thought and calls out Nora, a British attendee who is taking notes — like everyone else — in her sticker-covered journal, and accuses her of only being there to write a story about her. She talks about how the reporters in the room are not here because we’re hoping Calloway’s workshop will “mean something,” but instead “we’re waiting to do whatever we want with it.” It feels like a maneuver meant to cast us as villains, as outsiders. Calloway proceeds to tell her life story since 2015 in excruciating detail, bopping from topic to topic with very little connectivity.

“There’s a difference between doing what people think is right for you and doing what you think is right for you,” Calloway says at one point. Amid the rambling anecdotes — which actually don’t drag as much as one might think; Calloway’s charm is unquestionable — she offers up lines like this: “Don’t spend time waiting for other people to like you.” “Forgive yourself for the things you don’t like about yourself.” Not outright clichés, but things you’d not be surprised to find scrawled on the cover of a diary in gold foil.

Many of Calloway’s stories center around her abuse of Adderall during and after college. She has been sober since getting out of her book deal. She begins telling these stories with the preface that she is frightened of what people will think of her, saying the reporters will have to choose what to do with this information — which I, wrongly, assume is new to everyone in the room. She describes withdrawal as difficult and “beautiful.” Later, when I ask another attendee, Tess, about it, she says Calloway has spoken publicly about substance abuse before. “I have to open these stories up to the world,” Calloway says. “Stories I was not ready to share and don’t feel fully healed from.” At no point during the day does she take questions from the group; all her stories appear to be shared voluntarily.

Other lessons include a suggestion that we do “exit interviews” after our breakups where we ask our former boyfriends (Calloway offers no consideration that the women in the group might not only date men) “what did you learn from me” and vice versa. It’s good for closure, she says, assuming your partner is willing. If not … “sometimes closure is picking up a pretty, red leaf and leaving it on a park bench and walking away.” During the “making art” lesson, Calloway recommends a technique from Julia Cameron’s The Artist’s Way called morning pages, which involves journaling after waking up. “I got to week four and I dipped,” Calloway said of reading the self-help classic. The curriculum doesn’t seem all that different from accounts of the first two workshops Calloway hosted earlier in January.

With about an hour left, Calloway ends her lessons and breaks off to do one-on-one photo sessions with each attendee. We were asked to answer several questions — “What’s in your heart? What’s causing you the most anxiety these days?” — before the workshop. I imagine that’s what Calloway and the other attendees talk about as she clips an orchid, the same orchid, to each of their heads. I don’t know for certain, though, because Calloway has made it clear that since I am not a true fan, I don’t get to take orchid pictures. Instead, she busts out an orange, emergency heat-trapping blanket for me. The Fyre Festival jokes continue. Because I am truly no fun, I thank her but decline to take a photo wearing it. In lieu of the custom care packages, we’re each given a blue tote bag full of goodies. A scented candle. A crystal. A Mason jar with a packet of seeds. A journal for morning pages. Calloway-branded matches. A bit of wood I have since learned is a Palo Santo incense stick. It looks like a two-inch piece of scrap from Home Depot.

After spending the day with them, I can say with absolute certainty that Calloway’s fans, at least the ones in that room with me, do not feel they are being scammed. Three of them, having met six hours earlier, say good-bye and then leave to attend a party together. They love Calloway. They love her stories and her candor and they love whatever the hell she whispered in their ears during photos and those things, to them, were worth the much-mocked $165. Calloway tells me she has one more event planned in New York and then she’ll focus on rescheduling in other cities where she canceled.

“I think of it less as a workshop and more as a group hangout and sharing session. A little like group therapy. And to be honest, that’s kind of what I expected,” Tess tells me via DM after the event, saying the friends she made were the most valuable part of the experience. “I didn’t expect to learn anything I didn’t already know — except maybe to gain a little more insight and detail from Caroline’s personal experiences, which really aren’t that relatable … Caroline may not be a teacher, but she’s definitely not a scammer.” Was it Fyre Festival 2.0? No, of course not. Nobody was marooned on an island. Calloway isn’t headed to jail. Everyone was well fed. If it weren’t for the banner, we might have forgotten about the comparison entirely. Well, the banner and the part where we ran out of toilet paper well before the event was over.

An earlier version of this story said two women left the seminar together to go to a party. It was actually three women. Intelligencer regrets the error.

I Went to Caroline Calloway’s Seminar So You Don’t Have To