I attended Instagram influencer Caroline Calloway's 5-hour, $165 creativity workshop that people have called a 'scam.' Here's what it was like inside

caroline calloway influencerKathleen O'NeillInstagram influencer Caroline Calloway hosts one of her "creative workshops" in New York.

  • Instagram influencer Caroline Calloway made headlines last year for holding "creativity workshops" for her followers that were poorly run and derided as "scams." 
  • When Calloway decided to relaunch her tour, I was able to attend her five-hour-long workshop this past weekend in New York.
  • Calloway first rose to prominence in 2015, when she started 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 the 27-year-old for her realness and authenticity, and jumped at the chance to attend her $165 workshop.

While many of us were making resolutions to bring in the New Year, Instagram influencer Caroline Calloway was paving the way for her redemption tour.

The 27-year-old Calloway has headlined the most recent news cycle after 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 she received heavy criticism.

Details emerged that Calloway, who has more than 800,000 Instagram followers, was wholly unprepared for the tour and even made people bring their own food to events. Supporters say Calloway 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 800,000 followers - I found out that she had decided to un-cancel her creativity tour. The first rescheduled workshop would take place in New York this past Saturday - three days out from her announcement.

So I went.

Calloway's 'personal brand'

By many, Calloway is considered 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 first started to develop a following back in 2013, when she began documenting her picturesque life as an American expat studying at the "real-life Hogwarts" - also known as the University of Cambridge. Her posts were unique for their accompanying long, flowery captions describing romantic relationships and emotional break ups with Josh, then Oscar, then Conrad.

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 wrote about Calloway in June 2018. "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 off the life she detailed on Instagram.

But that deal shuttered sometime later (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 backed out, and is 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 after she backed out of the book deal. But she leveled with her massive Instagram following in a post in November 2018, where she revealed she was feeling "broken and scared and still worthy of love," and archived two years worth of Instagram posts. She also shared on Facebook that she had struggled with an Adderall addiction during college.

The person that emerged, Calloway says, was her more authentic and true self. Instead of posts, Calloway informs followers about her day-to-day life through long Instagram Stories.

Her Stories contain lengthy blocks of text you might have to screenshot just to be able to read them 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 had secured myself an invitation to her un-canceled workshop. In a 1,500-word email I and other interested attendees received, Calloway shared the detailed itinerary for the five-hour workshop. She also shared 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."

caroline calloway warehousePaige LeskinThe warehouse where Calloway's creative workshop was held.

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 as I approached the building, 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 of them 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 followed her up four flights of dark stairs. (Later, I learned that Calloway's assistants are two sisters in college, overwhelmed and overworked by how much time they've had to devote to helping Calloway put her un-canceled workshop together at the last minute.)

We followed the assistant into a gorgeous loft apartment filled with knick-knacks and plants, tailor-made for an Instagram photoshoot.

caroline calloway influencerKathleen O'NeillCalloway, left, speaks to workshop attendees.

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 your notebook.

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 in the room, there was a woman in Yale University's nursing program who had traveled down from Connecticut for the day to attend. There was an aspiring actor studying psychology in the city, and two woman who had flown in from Seattle for the workshop and were making a weekend of it in New York. Another woman said she had just quit her job, and had bought a one-way ticket to Los Angeles for next week.

Four of the women there were given scholarships to cover the costs 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.

caroline callowayPaige LeskinAttendees were treated to coffee and oat milk from Rude Health, a London-based company. Rude Health said that although it doesn't have a "paid partnership" with Calloway, the company "sent Caroline off with lots of Rude Health stocks for her American adventure."

After an hour of mingling, Calloway arrived, albeit a little late. She showed off her white t-shirt that read "SCAMMER," and pointed out the Fyre Festival banner she proudly says 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 came in knowing 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 like they were her friends. She was bubbly and easy-to-like, if a bit calculated.

During the workshop, 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, which she hadn't revealed much about online. She said the book deal "suffocated" her. And she insisted she's not 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 says. "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 of the women in attendance told Calloway they had been following her since 2015. Several referenced a Total Sorority Move article from March 2015 that called Calloway's Instagram a fairy tale - "if a fairy tale 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" to the Internet.) Several of the woman said they were drawn in by Calloway's authenticity, and that 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" she and her fans had shared, that 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-----g s--t 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 stuck behind her loyally, even as stories have referred to her as the creator of "the next Fyre Festival," or have - as Calloway calls it - "hate-followed" her on Twitter. Multiple attendees told me they had enjoyed the workshop, and said 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 the blankets to be a tongue-in-cheek nod to Fyre Fest. 

caroline calloway influencerKathleen O'NeillThe "care package" that workshop attendees were given at the end of the day, which included a notebook, incense, and a mason jar.

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 workshop attendants sitting in front of her. "What do you guys think?" she asks them.

"10 out of 10!" someone shouts.

She then turns the camera back on herself and deadpans: "Total f-----g scam, right?"

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