- Kathleen O’Neill
- The Instagram influencer Caroline Calloway, 27, has made headlines for holding “creativity workshops” for her followers that were criticized as poorly run and derided as “scams.”
- When Calloway relaunched her tour, I decided to attend her five-hour workshop, which was this past weekend in New York.
- Calloway rose to prominence in 2015 by posting personal stories about college life and heartbreak. Since then, she has amassed more than 800,000 Instagram followers.
- Many of Calloway’s fans say they admire her realness and authenticity and jumped at the chance to attend her $165 workshop.
While many of us were making New Year’s resolutions, the Instagram influencer Caroline Calloway was paving the way for her redemption tour.
Calloway, 27, made headlines as stories about her $165 “creativity workshop” gained traction in December. A viral Twitter thread accused Calloway of running a “scam,” and the Instagram star was forced to cancel her tour and refund attendees after receiving heavy criticism.
Details emerged that Calloway, who has more than 800,000 Instagram followers, was wholly unprepared for the tour and even considered asking attendees to bring their own food to events. Her supporters have said she was simply “in over her head,” but that hasn’t stopped her actions from drawing comparisons to the people behind the infamous Fyre Festival.
But last week, Calloway changed her mind: Along with the rest of the world – or at least Calloway’s followers – I found out she had decided to uncancel her creativity tour. The first rescheduled workshop was in New York this past Saturday, three days out from her announcement.
So I went.
Calloway’s ‘personal brand’
Calloway is considered by many to be one of the first iterations of what we refer to as “influencers,” the people behind those established social-media brands who are able to make ripples across the internet just by posting content for their thousands of devoted followers.
Calloway started to develop her following in 2013, when she began documenting her picturesque life as an American expat studying at the University of Cambridge – the “real-life Hogwarts.” Her posts were accompanied by long, flowery captions describing romantic relationships and emotional breakups with Josh, then Oscar, then Conrad.
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The first night Oscar and I slept together he didn’t kiss me. I had made it aggressively clear that kissing wouldn’t be allowed. However unlike the plot of Pretty Woman, I didn’t let Oscar touch me at all. Also I didn’t get paid. “I need you to stay with me tonight until I fall asleep,” I said abruptly. Oscar, who had been whistling as we navigated the maze of castles back to our dorm, went quiet. “But like seriously,” I said. “I’m going to need you to lie in my bed and maybe pat my hair, but only because I have anxiety problems.” I looked at him with an expression between ‘hopeful’ and ‘crazy eyes.’ “REAL ANXIETY PROBLEMS. If you try to make a move I will burst into tears and it will be super fucking unsexy.” I paused for breath. Oscar let out a strained sort of laugh. “Is this a question, Miss Calloway, or—” “Please.” I said more urgently, shutting my eyes. “Please.” I had felt fine until the sun went down. It’s always been like this for me. Not every day, or even every week, but once in a while I sink into a certain part of myself and get overwhelmed by loneliness. Fun fact! When I was little my father begged my mom to send me to therapy because I couldn’t fall asleep without audiobooks. I needed the stories, but also the illusion of human company. Nowadays someone will occasionally ask, “Isn’t it weird for you to have so many people following your life?” Obviously not! I’d feel even lonelier without them. As we sat on the banks of the River Cam, Oscar had watched the sun set while I watched groups of friends coming and going over the old stone bridges. Passing through the courtyard in this picture, I studied the red ivy on the roof—the same ivy that would be gone when we climbed up there in the spring. I wished that my own college wasn’t ugly and space-age. I wished that I lived in a castle with red ivy. I wished, for a moment, that I had never left New York. When Oscar climbed into my bed that night I said sternly, “If you try to pull what you pulled in the elevator tonight I will literally kill you.” But secretly I was glad to have him there. To Be Continued… #adventuregrams PS – Want even more adventures? Follow me on Facebook, friends!
By spring 2015, she had amassed 300,000 followers, the Daily Mail reported.
“She is famous for something that didn’t really exist until a few years ago: a personal brand,” Man Repeller said about Calloway in June.
The blog added: “Posting intimate personal details on social media is now commonplace, but when Caroline first started sharing stories about her life, her friends and her romantic relationships, it was different. Unique. A bit scandalous, even.”
Her long captions read like excerpts from a young-adult novel, and publishers agreed: Calloway nabbed a $500,000 deal with Flatiron Books in 2015 to write a memoir called “And We Were Like,” based on the life she detailed on Instagram.
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It’s been 84 years, and I can still smell the fresh paint. The bulletin boards had never been used. The wall-to-wall carpeting had never been cleaned. My freshman dorm was called the Ship of Dreams, and it was. It really—Wait. You know what? I’m sorry, guys. I’m doing that thing where I confuse my memories with Titanic. Happens to me all the time. But it's easy to get distracted with photos like this one lying around. Oscar’s is a face that was meant to front boy-bands, host Disney Channel shows, be used in the same sentence as the phrase ‘teen idol.' Clean cut, dirty blond, with an ‘aw shucks’ half-smile—basically everything a suburban teenage girl (like I once was) would want from a free poster. And I often wonder how if under even slightly different circumstances we would have started dating that fall. I can’t imagine how we would have met or spent so much of my first term at Cambridge together if Oscar hadn’t been randomly assigned to the same dorm, in the same college, in the same hallway, in the room that shared a wall and balcony with mine. And then, of course, there’s the exquisite fluke that Cambridge accepted me at all. And the fact that Oscar, quite frankly, would have been scouted, yanked from high school, and whisked away to LA for pilot season had he grown up literally anywhere in the world but the Swedish forest primeval. What I’m trying to say is that a lot of big variables had to line up exactly as they did to deposit Oscar on my bed in Cambridge as you see him in this photo. And while my dorm room no longer exists as it did my freshman year, I still hold on to certain details. Like how Oscar used to call me Miss Calloway because, at one point, we were strangers. Or early fall afternoons like this one when Oscar would stretch lazily across my bed after polo practice and crack the kind of smile that makes a belieber hurl herself against a police barricade. If there had been fresh paint, I would remember the smell of that, too. But instead I can still feel the adrenaline rush when Oscar patted the space beside him on my bed and said, “Come sit.” To Be Continued
But she later backed out of the deal. (Her last post about the book is from April 2016.) Calloway realized that the “the boy-obsessed version” of herself she painted on Instagram wasn’t the one she felt comfortable conveying, she said during her workshop.
She’s still responsible for paying back the $165,000 advance she got for her book deal. (She joked during the workshop that she now takes Uber Pool instead of UberX because “Hello, debt!”)
Calloway’s personal posts didn’t end, but she leveled with her massive Instagram following in a post in November where she said that she was feeling “broken and scared and still worthy of love” and that she had archived two years’ worth of Instagram posts. She also shared on Facebook that she had struggled with addiction to Adderall during college.
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I’ve fallen in love for the first time since Oscar and I broke up. His name is Conrad. But for a long time I lost my love of writing. I had a whole plan to do non-stop sponsored posts going forward, but it turns out you don’t reconnect to the work that gives you purpose and joy by monetizing it. Shocking, I KNOW. What I love is pairing beautiful photos with sad stories and flowers. And so that’s why I’ve archived all of my posts from the past two years. ARCHIVED—NOT DELETED. Maybe I’ll bring them back some day, in some form. But my favorite kind of writing is when you say inventively and with grace and without trying to look cool at all: This is how I am. Broken and scared and still worthy of love. And those old posts were incohesive and just not vulnerable enough. So I trimmed my account down to my last “To Be Continued.” The last time I told our story—the one that takes place at Cambridge, in my freshman year dorm room. The story I want to pick up and intertwine with all my new memories and all I’ve learned about activism and all the parts of old memories I never told until now. I ended the post prior to this one with these words: “and that was how I began to fall in love.” I was talking about Oscar then. “When you fall in love the things you lost come back to you.” That quote is from @lianafinck’s beautiful memoir and it sunk its fangs into my heart. I’m talking about Conrad now. But to her quote I would also add: When you fall in love the things you lost come back to you—just not all of the things and you don’t choose which ones. I don’t know if you’ve ever gone through a tough chapter with your creativity. Maybe you had it once and drifted away from it. Maybe you’re still trying to find it. Well. Creative engagement is not a guarantee just because you have a loving partner in your life. Creative engagement is something you have to find. Like love, it meets you when you’re ready. But also like love, you really have to look. Things that have come back to me since I’ve fallen in love: breathlessness, a sense of comfort, cuddles. And the memory of what it was like to sit at my desk in my freshman year dorm room as Oscar sat on my bed. To Be Continued…
The person who emerged, Calloway said, was her more authentic and true self. Instead of publishing posts, Calloway informs followers about her daily life through long Instagram Stories.
Her Stories contain lengthy blocks of text you might have to screenshot just to be able to read in their entirety. She’s used the Snapchat-like feature since it debuted in 2016 in a way much like she used her image captions: as a personal journal to share with the masses.
‘Are you here for Caroline Calloway?’
So on Saturday morning, I found myself approaching a nondescript warehouse in Brooklyn’s Bushwick neighborhood, double-checking Google Maps to ensure I had plugged in the correct address. There were no markings and no numbers on the building’s exterior.
After messaging Calloway, I secured myself an invitation to her uncanceled workshop. In a 1,500-word email I and other attendees received, Calloway shared the detailed itinerary for the five-hour workshop, as well as what would change this time around: There would be no flower crowns, but there would be catered food.
“So can I guarantee you’ll like this workshop? No,” Calloway wrote in the email. “But I think there is a 95% chance you will, especially since you felt moved to buy this ticket in the first place.”
- Paige Leskin
When I arrived at the warehouse, I had a fleeting thought that this was the scam itself – that all these people would show up to a building that didn’t exist to attend a workshop that wasn’t actually happening.
But walking toward me with the same confused look were two 20-something women with blown-out hair, expensive-looking boots, and long designer coats.
“Are you here for Caroline Calloway?” one asked me. The two women were lost and had banded together to find the workshop.
I was definitely in the right place.
We were ushered into the warehouse by one of Calloway’s assistants, and we followed her up four flights of dark stairs. (Later, I learned that Calloway’s assistants are two sisters in college, overworked and overwhelmed by how much time they’ve had to devote to helping Calloway put her uncanceled workshop together at the last minute.)
We followed the assistant into a gorgeous loft apartment filled with knickknacks and plants, tailor-made for an Instagram photo shoot.
- Kathleen O’Neill
As we entered, we were told to explore the space and locate our “personalized notebooks” before sitting down to talk with other attendees and grab coffee. The cover of my notebook was adorned with cheap, sticky letters spelling out my name, and an envelope inside contained scrapbook-ready stickers you could use to decorate.
The first hour of the five-hour workshop was devoted to “new-student orientation,” which Calloway said she wouldn’t attend because she didn’t want to “steal focus.”
During the orientation, I chatted with some of the women seated around the room. Besides the three journalists, there was a woman in Yale University’s nursing program who had traveled from Connecticut for the day to attend. There was an aspiring actor studying psychology in the city, and two women who had flown in from Seattle for the workshop were making a weekend of it in New York. Another woman said she had just quit her job and bought a one-way ticket to Los Angeles for next week.
Four women were given scholarships to cover the cost of the $165 workshop. Some of these scholarships were able to be offered by charging reporters to “cover a sensationalized news-storm of their own making,” Calloway’s assistant told me in a text.
- Paige Leskin
After an hour of mingling, Calloway arrived, albeit a little late. She showed off her white T-shirt that said “SCAMMER” and pointed out the Fyre Festival banner she proudly said she made herself, without using stencils.
“It was not a part of my dream to be compared to a literal Caribbean island where people almost died,” Calloway said.
Calloway made her way around the room, stopping for long introductions and intimate conversations with some of the groups. Her prep for the event was evident: She knew each person’s last name and was ready with remarks about any mutual friends or interests. She smiled widely and cracked cheeky jokes, letting attendees in on secrets as if they were her friends. She was bubbly and easy to like, if a bit calculated.
Calloway said her class would cover topics like resiliency, creativity, heartbreak, and authenticity. In reality, this translated to long narratives about her life – many of which her fans already knew, since she had told them in past Instagram captions.
She also shared philosophical one-liners like “You cannot read that doubt like tea leaves” and “Sometimes closure is picking up a pretty red leaf and putting it on a bench and walking away.” At one point, she compared sex to Thai food: “If you go to a restaurant and order Thai food and don’t like it, you shouldn’t keep eating Thai food.”
Calloway also talked about her past. She talked about her addiction to Adderall in school, something she hadn’t revealed much about online. She said the book deal “suffocated” her. And she insisted she wasn’t trying to scam anyone despite what the media says about her.
“People make a lot of assumptions of young, fit, white girls on Instagram,” Calloway said. “You know what? I don’t even read the news. I haven’t read about what people think I am.”
‘I just totally connected with you on another level’
Many women in attendance told Calloway they had been following her since 2015. Several referred to a Total Sorority Move article from March of that year that called Calloway’s Instagram a fairy tale, “if a fairytale consisted of drinking wine, flirting with boys, and studying in Europe.”
These women said they felt a connection with the raw emotion she described in her captions. (Calloway maintains she was one of the first people to post a “crying selfie” on the internet.) Several women said they were drawn in by Calloway’s authenticity – she seemed to just “get it.”
“I just totally connected with you on another level,” one attendee told Calloway.
That connection does not seem lost on Calloway. She described her life as a “journey” that she and her fans had shared, saying her highs and lows were something everyone in the room experienced. She painted a picture of “us versus the world” – Calloway and her followers on one side, the “haters” on the other.
“We’ve been through some crazy f—ing s— together,” she said at one point during the workshop. “You guys are in your own category of people I’ll never forget.”
Her fans have loyally stuck behind her even as stories have described her as the creator of “the next Fyre Festival” and as people have, as Calloway calls it, “hate-followed” her on Twitter. Multiple attendees told me that they enjoyed the workshop and that it was worth the $165 fee.
“I think she is someone who is learning and growing like the rest of us,” one attendee told me in an Instagram message after the workshop. “I didn’t expect too much from it after the rescheduling, but she is very relatable and kind. She went out of her way to remember everyone’s first and last names as well as their letters they’ve written.”
“Caroline did a brave thing. She wanted to offer her time, her heart, and her experiences to a community that she has quite literally grown up with,” one of Calloway’s assistants told me after the event. “Even though there were details of the tour and workshop that weren’t perfect, I think she did a good job of making something beautiful for the people that came.”
Later, after attendees took their solo portraits with Calloway, each person was given a “care package” to remember the workshop by: another notebook, a mason jar, and small colorful drawstring pouches holding a small candle, a “crystal” rock Calloway swears by, a bunch of flower seeds, a matchbook with a “Calloway House” crest, a face mask, and a stick of incense. Journalists attending the event were also given an emergency thermal blanket – Calloway said she wanted it to be a tongue-in-cheek nod to the Fyre Festival.
- Kathleen O’Neill
At one point during the workshop, Calloway interrupted her lesson to take a video for her Instagram Story.
In the video, she pans around the room of eager attendees sitting in front of her. “What do you guys think?” she asks them.
“Ten out of 10!” someone shouts.
She turns the camera back on herself and deadpans: “Total f—ing scam, right?”