Let's Get Drinks with: Caroline Calloway

In her first Substack interview, Caroline talks about sobriety, anger, and her debut memoir

Photo by Martin Schoeller

Caroline Calloway wears many hats: she’s an Internet celebrity, a writer (though for a long time she wasn’t actually writing – more on that below), an artist, and, now, a memoirist. 

But let’s backtrack. You may remember Caroline as the influencer who blew up on Instagram in 2014 as an American student studying at Cambridge University. Her social media posts depicted her life abroad like something out of a fairy tale: she attended literal galas, frolicked in castles, and had a string of handsome love interests. She wrote longform captions about her life and amassed an engaged audience of readers, eventually leveraging her Internet fame into a $500,000 book deal for School Girl, which she later renamed And We Were Like. 

But Caroline says she wasn’t entirely honest with her publisher or herself when she sold School Girl. Still in the throes of an Adderall addiction and struggling with her mental health, Caroline was ultimately unable to deliver the book that she promised. And although she eventually paid back the $100,000 she spent from her advance, she was publicly stamped with a scarlet S for Scammer.  

Other controversies followed. Her notorious creativity workshops (for which Caroline charged $165 a ticket and received major online backlash), a literary-themed stint on OnlyFans, and brief forays into selling re-creations of Matisse paintings as well as a skincare product called Snake Oil (which is still available for purchase on her website). 

In 2019, the biggest bombshell of all: “I Was Caroline Calloway,” a viral essay published by The Cut and written by Caroline’s former best friend, Natalie Beach, in which Natalie claimed to have written and edited the Instagram captions that first made Caroline famous. In the aftermath of her essay, Natalie scooped up a book deal and a cool $1 million deal with Ryan Murphy for the film rights to her story.  

Through it all, Caroline continued to promise that a book — her book — was coming. In January 2020 she opened up pre-orders for her memoir, Scammer. And while many lost faith that the book would ever surface, Caroline self-published Scammer last month, one week before Natalie’s essay collection, Adult Drama, was released. As Caroline told me, anger can be an excellent motivational tool. In her case, it was what she needed to finally tell her side of the story. 

Scammer (which Caroline is selling for $65 a pop) is a “luxury first edition;” each copy arrives signed and with a handwritten note. (Full disclosure: I read a digital copy, but the physical book looks beautiful.) Scammer cuts through the Internet noise surrounding Caroline’s persona with the precision of a blade, revealing a talented writer’s mastery of language and storytelling. I read it in a day which, Caroline says, was her intention: she calls Scammer a daybook for this exact reason. 

I first met Caroline back in 2019 when we were both living in New York City. Caroline in the West Village, where she frequently posted Instagram stories on her way to Pilates classes and parties; me in Williamsburg, two years sober and dipping my toe into writing personal essays of my own. We were casual acquaintances, but there is something inherently charming about Caroline. It’s hard not to root for her, even when you aren’t entirely sure what she’s about to do next. 

While she doesn’t call herself sober (she still drinks alcohol and uses other recreational drugs), Caroline is open about battling an Adderall addiction in her twenties. I have always identified with the chokehold that Caroline’s substance abuse had on her life when she was actively using. I, too, struggled to show up for commitments, write, and deliver on promises I made when I was drinking. And while I was never Instagram famous for it, I also spent years performing and depicting a distorted version of myself on social media, hungry for accolades. 

Caroline lives in Florida now and I’m in Los Angeles, but when we reconnected over the phone a couple of weeks ago, I was immediately transported back to the pre-pandemic New York we once called home. Maybe that’s also why I relate to Caroline; we both had to leave the city we loved in order to write about it. I talk about this in my memoir, Drinking Games, and, in Scammer, Caroline says she moved to Sarasota to begin writing and retire from the plot. New York, ripe with copy at every corner, is at the center of both of our stories; it’s where we partied, lost best friends, and destroyed parts of ourselves – both on and off the page. 

A condensed version of my conversation with Caroline is below. 

First off, how are you feeling? You self-published your memoir, Scammer, a few weeks ago after years of anticipation; what has the experience been like for you?

I’ve honestly never been more happy and tired. My joints hurt. I am doing manual labor and making 80-100 books a day. But the whole experience has been so rewarding.

Although physically taxing, putting out a luxury first edition of this book myself has been creatively rewarding and financially rewarding as well. I’ve sold about 5,000 copies so far at $65 a piece. Yes, the materials cost a lot – I’ve spent about $30,000 on marbled paper from Italy alone – and printing costs a lot, too. But people pay for their own postage so it’s very lucrative.

I feel like I’ve accidentally stumbled upon a business plan that all authors who already have a social following should be using. Since I self-published it means I fully own the copyright to Scammer, and I intend to place it with a real publisher later this summer. I’ll basically get to sell my book twice; I get the sales from the first printing and then I’ll get to sell it again to a publisher. And because I’m making a $65 collector’s item, it makes the argument that my heirloom quality art piece is not in competition with a future $19.99 trade paperback. 

Wow – are you out here disrupting an industry? 

I’m just a girlboss and a disruptor! 

I want to talk about writing. For me, so much of writing is an act of confidence and believing you have something worth saying that other people want to hear. It can be intimidating, and I know you’ve struggled with feeling creatively blocked. How did you reclaim your confidence after Natalie’s essay in The Cut and start putting words on the page again? 

Name another living author who has famously not written a book for as long as I have. I really can’t think of a modern or historical comparison of someone who has had so much build-up to their first book. I often say that the best time to start marketing a book is 3-5 years before it comes out, but I also say 10 years is too long. Don’t do that! I marketed this book for 5 years too many, and it came back around and bit me in the ass. I felt so much pressure because there was a lot of pressure on me from the world by the time I actually sat down to write it. Honestly, the way I was able to push through my creative block is that I was really angry. 

Where did that anger come from?

Natalie has sold me out three times in my life, but the first two times really didn’t make me that mad. I grew up with a father with rage problems and anger has always been a very difficult emotion for me to access. When I get upset I don’t get mad; I get sad.

The first time Natalie sold me out was when I had my creativity workshops and she pitched her piece to The Cut. I didn’t find out about it until right before it came out. Two days after The Cut piece was published, my father’s body was found. He had killed himself. So I had bigger fish to fry and I didn’t have time to be angry about The Cut.

In a weird way — and I think a lot of former addicts can relate to this — I had so much guilt about how I had behaved during my addict years that a part of me felt like I deserved bad things to happen to me. So Natalie using me then felt like a punishment I deserved. 

The second time Natalie tried to use me was the day I found out about my father’s body and she tried to get me to sign a Netflix deal for $15,000. She didn’t tell me she got $1 million for her deal – a source found that out later. She really took advantage of my grief; she offered me 15K and her forgiveness for how I behaved during my addiction. And, honestly, in that state of having just lost my father, it seemed tempting.

The third time she used me was the first time I got angry. It was this past winter. A friend leaked a copy of the book proposal that Natalie used to sell her book and it was just so much about me. She was saying how, in her book, she would include more lurid details from my Adderall addiction, talk about her latent bisexuality, and expand The Cut essay and include more essays about me. She sold that book by using my name and my life story. And I was finally so sick to death of being used by her. 

So the way I honestly started writing was anger. I think anger can be a really destructive force, but anger with a purpose is incredibly constructive and helped me push through. That’s how I finally got the book done.

What was your writing process like?

I went into what I call gremlin mode. I would wake up around 11 AM, write until 6 PM, and only have water and caffeine all day. Since I wasn't exercising at all – which is a key part of gremlin mode, to just totally stop exercising – I wasn't that hungry because I was just sitting still for almost all of my day. Around 6 PM I would bring my laptop to dinner and give myself all the tasty treats. I would just let myself order whatever food I wanted after working myself to the bone writing. 

Did you give yourself a daily word count or structural goal?

It was less about a word count and more about a page and vignette count. Scammer is 67 vignettes. I was shooting for 142 pages, which I know is really specific, but I just like the number 42. Pure “Taylor Swift and the number 13” numerology energy and vibes. So I would try to keep my vignettes as short as possible in order to force myself to make every single word “zing.” I tried to really tell the story in as few sentences and pages as possible. 

Every night at dinner – while eating like a Roman emperor who hadn’t exercised in weeks and possibly was developing gout – I would decide on the places I would go in my writing the next day. I would be like, “Okay, tomorrow we’re doing the Harvard Lampoon vignette, the grief vignette, and the LA vignette.” 

You’ve been very open about your Adderall addiction and sobriety from pills. I know you don’t identify as being completely sober, but how did you first get clean? I’ve shared about getting sober through a 12 step program  – I honestly don’t think I could have done it on my own – and I’m always curious to hear about other paths to recovery. 

I consider myself amphetamine sober. That’s the term I use for it. I would never touch a Vyvanse or a Ritalin or, obviously, meth. Actually, I shouldn’t say “obviously.” If someone offered me meth, I’d have to physically leave. I would have to go to another location because I would just be so tempted.

How I got amphetamine sober was through therapy. I sought out a therapist who specializes in AA addiction treatment and I still work with him. While I didn’t do all 12 steps, I made amends and offered apologies to all the people I had wronged. I respect AA so much and I am so pro-AA. I don’t even think I know the full extent of how AA has helped me.

I’ve always toyed with going to AA, but I’m wary of sharing my deepest, darkest secrets with a roomful of people. I’m always afraid someone is going to sell them. To The Cut. For $5,000. And I think that’s just a really specific and real trauma I have. Also, maybe being an only child, I really thrive with 1:1 attention. 

Can you share some of the tools you’ve relied on to stay amphetamine sober? 

A lot of my good friends have ADHD and take pills for it. I don’t like Type A bitches and Type A bitches don’t like me. I like the feral girls, the messy girls, the girls who are having a rat girl summer. Those are my girls, and a lot of those girls have ADHD. So something I ask my close friends — the ones I spend a lot of time with and can be vulnerable with — is to not to carry their pills around with them. I would just hear them rattling around in their bags and would want one. I know my friends probably wouldn’t give me a pill if I asked for one, but worst case scenario, what if I stole pills from them when they went to the bathroom? I don’t even want to put myself in a situation where I would be tempted to relapse. So one of the tools that helps me is asking my friends not to carry large quantities of their pills around with them. 

Being a memoirist has been your dream for so long. Now that the book is here and you’ve added your narrative to the Natalie/Caroline record, what are you most excited to write about next? Do you feel like you need to start mining for new material?

Luckily, I don’t think I don’t need to mine for new material. I hope something interesting happens to me again someday and that I go to a fun party before I die at least once more. 

But if that didn’t happen, I’d be fine. I want to expand Scammer into And We Were Like. It’s funny you say “now that you’ve added your narrative to the record,” because I actually want to put out two more things that I think will really settle the record on Natalie and then I think I’ll be done with this era.

I want to put out The Cambridge Captions – the Instagram captions that made me famous –  because I wrote them all by myself and I alone own the copyright to every single word. If Natalie thinks she wrote them, she can come sue me for the copyright. She didn’t write them; she just made it seem that way in her essay. So I’m going to release The Cambridge Captions and I think that will sell really well and be easy to promote. 

A book I think will not sell as well and will be more difficult to promote is based on my “I Am Caroline Calloway” essay. It came out during the pandemic and raised $50,000 for doctors who needed face masks (Note: she has the receipts!). It’s a tailored response to Natalie’s piece that follows her plot from my perspective.

I want to put that out because, honestly, I am better at PR than Natalie. My skills are writing and marketing. I know that I will dig myself into a little bit of a hole by going further down this Natalie/Caroline path and putting more of myself in this brand. But I’m putting us both in this hole and it’s one that only I have the marketing skills to climb out of. I just want to dig her down so deep that she will never be able to escape my first and last name. Since she’s made the choice to sell me out not once, not twice, but three times, I’m going to make that choice of hers into a curse that she will never be able to escape.