Her supporters have said she was simply “in over her head”, but that has not stopped her actions from drawing comparisons to the people behind the infamous Fyre Festival.

(The festival – a planned 2017 luxury music event over two weekends in the Bahamas, which had been promoted on Instagram by social media influencers, including models Kendall Jenner and Bella Hadid – was postponed indefinitely, sparking a series of lawsuits, after it suffered a series of problems.)

However, earlier this month 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 on January 19 – three days after 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 break-ups with Josh, then Oscar, then Conrad.

By spring 2015, she had amassed 300,000 followers, Britain’s Daily Mail reported.

“She is famous for something that didn’t really exist until a few years ago: a personal brand,” Man Repeller, the Instagram blog, said about Calloway in June.

“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.”

Calloway’s long captions read like excerpts from a young-adult novel and publishers agreed.

Calloway was offered a US$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.

However, she later backed out of the deal. (Her last post about the book is from April 2016.)

Calloway said during her workshop that she realised that the “the boy-obsessed version” of herself she painted on Instagram wasn’t the one she felt comfortable conveying.

She’s still responsible for paying back the US$165,000 advance she got for her book deal. (She joked during the workshop that she now takes UberPOOL – the cheapest ride-sharing service – instead of UberX because of “Hello, debt!”.)

Calloway’s personal posts didn’t end, but she levelled 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 wrote on Facebook that she had struggled with addiction to the prescription medication Adderall while at university.

The person who emerged, Calloway said, was her more authentic and true self. Instead of publishing posts, Calloway tells 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 that Saturday morning, I found myself approaching a nondescript warehouse in Brooklyn’s Bushwick neighbourhood in New York, double-checking Google Maps to ensure I had 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 uncancelled workshop.

In a 1,500-word email that 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 per cent chance you will, especially since you felt moved to buy this ticket in the first place.”

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.

Yet 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 at university, overworked and overwhelmed by how much time they’ve had to devote to helping Calloway put her uncancelled workshop together at the last minute.)

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

As we entered, we were told to explore the space and locate our “personalised 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 it.

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 three journalists, there was a woman from Yale University’s nursing programme who had travelled 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 US$165 workshop.

Some of these scholarships were able to be offered by charging reporters to “cover a sensationalised news-storm of their own making”, Calloway’s assistant told me in a text.

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 had 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 such as “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 there 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 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” 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 creater of “the next Fyre Festival” and as people have, as Calloway calls it, “hate-followed” her on Twitter.

Many attendees told me that they enjoyed the workshop and that it was worth the US$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.”

One of Calloway's assistants told me after the event: “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.

“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 colourful 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.

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?”

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