Was Caroline Calloway the First Instagram Influencer?

Caroline Calloway talks to Man Repeller about becoming a personal brand.

Caroline Calloway is a 26-year-old from Falls Church, Virginia, with over 850,000 followers on Instagram. She is famous for something that didn’t really exist until a few years ago: a personal brand. However, she doesn’t like to think of herself as one — a confession she shared as we sat on the floor of her one-bedroom apartment in the West Village, surrounded by color-coordinated books, fresh flowers tucked into empty Martinelli’s Sparkling Apple Cider bottles and charred palo santo sticks.

An aspiring writer determined to score a book deal, Caroline saw something in an up-and-coming app called Instagram that many people at the time did not: opportunity. She started posting the first chapters of a would-be memoir in lengthy captions across a series of Instagram posts and quickly amassed a legion of readers who hung onto her every word. 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.

I spoke with her about all of this, including her coveted book deal — which she scored to the tune of half a million dollars, only to subsequently back out of the contract. Below, her as-told-to story.

On When She Started Taking Social Media Seriously

I joined Instagram in 2012, when it was just starting to become more mainstream, but the climate was totally different from what it is today. People forget how different it was. A typical photo and caption would be an aerial shot of your breakfast with the caption “#valencia” and that would be considered edgy. It was unheard of to share that you were having a bad day or were in a bad mood on Instagram, much less any extensive personal details about your life.

I was starting to learn about photography at the time, and I found it fascinating that the criticisms for why photography couldn’t be taken seriously in the late 1800s were identical to what we saw then with social media: the idea that it’s technology, that it’s science as opposed to art, that it’s too democratic to have artistic merit (i.e., anyone can buy a camera, anyone can make a Twitter account, etc.).

On Why She Decided to Write a Book on Instagram

I always knew I wanted to be a writer. I was constantly underlining things in books, trying to improve my craft, trying to get coffee with people who had interned with literary agents so I could get a literary agent. I had no idea Instagram would play a role in helping me achieve that. I just had the overwhelming determination to do whatever I could to make it happen. I’ve always been convinced that I have stories to tell and that I would be successful at telling them.

I started playing with the idea of writing a book on Instagram, and people thought I was nuts. Just imagine nowadays if someone told you they were going to build their writing career with a small, up-and-coming app that major news sources and brands don’t have a presence on. Everyone was like, “No, that will never work.”

I began by writing an autobiographical story that carried across multiple Instagram posts and introduced different people in my life as “characters.” I know that sounds strange, but think about what it’s like when you follow people on Instagram. You become invested in their lives and the people in them — their friends, their romantic partners, their coworkers. They’re like characters in one of your favorite books, except even better because they actually exist.

Once I thought about that, I realized one of the main assets of Instagram as a medium is that it’s a lot like reading a novel, but it’s also interactive. You can click on the handle of someone who is tagged in a photo, you can comment on a photo, etc. I thought about that great quote Holden Caulfield says in Catcher in the Rye — “What really knocks me out is a book that, when you’re all done reading it, you wish the author that wrote it was a terrific friend of yours and you could call him up on the phone whenever you felt like it. That doesn’t happen much, though.” With social media, it finally can. You can talk to the author. You can talk to the characters. You can see who they’re interacting with and what their worlds look like because they’re inviting you into them.

Another thing I did that was unthinkable back then was post about things that weren’t happening in real time. When I started sharing the story of my relationship with my ex-boyfriend Oscar, I told it slowly because I knew I wanted to sell a book about my life, and I understood that I couldn’t give away the whole plot. It took me two years to cover a period of ten days. With each installment, I let my readers get to know the characters. I would stretch out the narrative by saying things like, “Two years later, when things were so hard, we would look back on this moment with fondness.” A formula that worked really well for me was pairing beautiful photos with sort of sad or lonely captions.

My ultimate goal was to get a book deal. I didn’t know much about being a writer except that it involved book deals, and that they were important to get, and that everyone told me I wouldn’t be able to get one. Growing up as a creative kid, I received a lot of that kind of feedback. There were so many small moments with relatives or friends or teachers when I was like, “I’m going to do this,” and they were like, “you won’t make money” or “good luck with that” or “that will be hard.” I was determined to prove them wrong.

On Finally Getting a Book Deal

Flatiron Books offered me a book deal for half a million dollars in 2015. I promised a memoir where the only thing that happened to me were boyfriends and where the climax of my entire life experience to date was boy-related. The whole narrative arc was about my relationships with three different boys. For the record, no one forced me to write the proposal the way I did. I was simply caught up in my own ambition, and I lived in a world where I saw (correctly, in my opinion) that if I wanted to get the most money possible, this was the book I had to sell, so I sold it. I received around 30% of the money from the deal upfront.

It wasn’t long before I realized the boy-obsessed version of myself I planned to depict as my memoir’s protagonist was not one I could stand behind. I think there are a lot of people who would have written the book anyways and taken the money, but I couldn’t do it. So my choices were: write a book that wasn’t really about me — that was just about boys — and get lots of money, or back out of the contract and owe lots of money. I chose the latter, and I’m working on changing my business model so I have the income I need to repay them.

I had already spent my entire book advance at that point. I mainly spent it on rent for the apartment I shared with my boyfriend at the time in London, and on meals. At one point I just started giving it away to friends. The money meant nothing to me. I didn’t feel like I’d earned it and I loathed myself for how I’d gotten it. I had drifted so far from all the reasons that made me love writing and love art and made me want to be a writer in the first place, and it paralyzed me — artistically, emotionally and personally.

When it became clear to my publishers that I didn’t want to write this book, they withdrew from the contract. I more or less stopped posting on Instagram at that point. It was a really painful time for me. It was so hard to have come so close to something that I had dreamed of my entire life and trip over the finish line, but the idea of spending the rest of my life signing copies of a memoir that wasn’t about the real me broke my heart.

Backing out of the deal felt like losing a part of my identity. I started questioning everything. If I don’t have a book deal, am I still a writer? Am I still an artist? How do I define myself? Ultimately, one of the greatest gifts of getting out of it was having to find the personal strength to realize that getting paid a lot of money doesn’t make me a writer. Having a book deal doesn’t make me a writer. I am a writer simply because I have the desire to say, “This is what I am.”

On Having a Personal Brand and Being a Public Figure

I don’t like thinking of “Caroline Calloway” or “Caroline Calloway the Instagram Presence” as “brands.” However, as an artist and as a creative person, it’s both my responsibility and my right to support myself so that I can make the things I want to make. I acknowledge that in order to do that, it behooves me to understand and respond to the ways other people might see Caroline Calloway as a brand, and to act accordingly. Even though I don’t see it in my heart this way, I understand why I must in order to be the best businesswoman that I can be. I need to support myself.

Making a living this way isn’t always easy. People begin to feel like they are owed details of your life. They judge you when you share them, and they judge you when you don’t, and that is very difficult. Instagram is a medium that pairs seductively well with perfection, both in terms of what we like to consume on it and the standards we hold ourselves and others to on it. Maybe 200 or 300 years from now in the Shakespearean way that English evolves, there will be a word for the mixture of disingenuousness and sadness and loneliness you experience when you are portraying your life in a way that is not true to how you feel in the moment.

This past summer, my ex Oscar’s new girlfriend made a troll account about me. I wish I could say that when I saw the account, I had so much kindness and peace in my heart that it affected me not at all, that I anointed her on the forehead with oil and said, “Go in peace my child, I care not of this.” But that wasn’t the case. I was so angry and scared. She followed my dad’s private Instagram account, which I don’t even follow (he’s a really private guy; he shrivels like a slug under salt with public attention). He had 11 followers. One of them was her. She also followed all my other ex-boyfriends, all my family members, all of my friends.

I burst into tears. I was so upset. I called Oscar to ask him why she did this. If I’m being totally honest, I was calling him from a mean-spirited place. I would be lying to you if I said I wasn’t feeling vindictive, especially because she denied even creating the account, and Oscar believed her. She said it was a glitch in the system. That whole dramatic phone call — just having him believe her over me — was incredibly hurtful. So I posted on my Instagram Stories on what had happened. My followers were immediately up in arms. Their reaction was validating because I was so, so angry.

The next day, though, I woke up with a lot of regret. I wanted to take everything back. I started wondering how Oscar’s girlfriend must feel, and I felt so badly that hundreds of thousands of people knew what she had done — because of me. It really started to snowball into this thing where people were saying she was crazy and evil and bad. I decided it was important for them to know that I have flaws, too, so I decided to tell them that at the very end of my relationship with Oscar, I kissed someone else. I also told them I had been addicted to Adderall for about three years, and that I had only recently gotten off of it. I wanted to illustrate to them that people are human, and that there is more than one side to every story.

On Doing Sponsored Posts

I used to think I would never do sponsored posts because I wanted so badly to be taken seriously as a writer and as an artist and worried about what people might think if I monetized my Instagram. There is so much shame surrounding the idea of being an influencer and the idea of accepting money for being an influencer. People make a lot of judgments, but I’ve come to accept that. Like I said, I need to support myself.

I knew I wanted to be really transparent from the beginning about how I was approaching paid partnerships. When I decided to start doing sponsored posts, I posted about it publicly on my Instagram, and I shared my rates with my followers, which isn’t something I’ve seen anyone else do.

I immediately learned that I should be charging more, because I had a huge influx of asks for things I wasn’t interested in, even though they could technically pay my rates. Honestly, even when I raised them, I still got asked to do things I didn’t want to do. I don’t want to do, like, Fit Tea or hair gummies or those sort of things. It would be hypocritical of me to sit here and talk about how firmly I believed in getting out of a book deal with a sexist plot and then post an ad for appetite suppressant lollipops. It’s really hard being a girl in the world. I don’t want to contribute to that in any way.

On Meeting Fans

I get recognized in public about once a week. Maybe less, maybe more. It’s different with every person. Everyone reacts differently. One person burst into tears and that was the hardest for me to react to. I think I started crying, too. The thing is, all the fans I’ve actually met in person have been really normal people I genuinely want to hang out with. I’m probably happier to meet them than they are to meet me. A few weeks ago, I invited a fan to my apartment for dinner and cooked her dinner. I was like, “Come over.” And she did, and it was so great.

Her Advice For Young Girls Navigating Social Media

Try to shut out the noise of what other people think. Take serious stock of what parts of social media really excite you, whether it’s writing captions, or the experiences you end up having when you’re trying to take some photos, or being behind the camera, or drawing and taking a picture of that. Listen to yourself. Figure out exactly what aspects of the creative process lights you up inside and arrange what you make around those truths. After all, you never know what’s going to be hanging in a museum two centuries from now.

Photographed by Edith Young. 

Harling Ross

Harling is a writer and was most recently the Brand Director at Man Repeller.

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