Sophie Kipner: On Creating Complex Characters, Adding Art to the Writing Process and Crowdfunding Her Debut Novel, "The Optimist"

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Sophie Kipner’s debut novel, The Optimist, is a whirlwind of a tale about a character whose hopeless optimism knows no bounds. In Tabitha Gray, we have a protagonist truly unafraid to follow her dreams, no matter how misguided they may be. Kipner’s effusive writing style paints a picture of a character determined to stop at nothing to achieve her greatest goal: true love. I interviewed Kipner via email about her creative processes, complex characters, and her own personal heroes.


To say that your protagonist Tabitha has an unconventional personality would be an understatement. In your acknowledgments, you mention that Tabitha first appeared in a short story from 2013. How did you come up with such a unique character?

Tabitha's character came from a really funny moment when I was nannying my childhood friend’s daughter. She was completely adorable and the smartest person in the room at all times... at five. I would take her to her gym class a couple times a week and would sit in the bleachers shoulder-to-shoulder with the other nannies and parents and grandparents. I was in a short story writing class at UCLA at the time and had been assigned to write another story after having completely bombed my last workshop for writing something that felt too forced and stiff. So there I was, watching this completely ridiculous, seemingly stoned and incredibly inflexible gym teacher try, unsuccessfully, to rally a group of wild children into a manageable circle. He had zero control of the room and was by most measures, unattractive, but when I looked around, all the women seemed to gush. Hands under chins, giggling. I wondered, what is it about a man with kids, this gym teacher who couldn’t even touch his toes, that gets everyone’s knees so weak? Something about him made his attention feel special, like he was looking at you, seeing you, despite it being so clearly misdirected and dazed. Were we all so attention-starved that even the smallest of droplets would taste holy? It fascinated me. When I went home, I sat down and started writing in the first person of what it would be like if you didn’t realize that was just old-fashioned mating psychology, even if a little off-kilter. What if you misunderstood his glassy, googly-eyed stare for mesmerizing, Jungle Book Kaa-in-love seduction? 

The short story, aptly called “The Gymnast,” received a much better reaction this time around the room. People were laughing and covering their mouths in embarrassment as I read aloud. I recall that moment as being when I found my voice, probably because I finally was writing from an authentic place. After the class, my teacher encouraged me to submit it to journals. So I did, and it was shortly after published in a great little literary journal for humor called Kugelmass. People then started to say, “This girl is nuts! I want to know more...” That interest in her character emboldened me to write another misadventure, and then another, and I started to figure out who she was doing this for and why. I took what I knew personally and what I saw to be true around me with regard to romantic desperation and I exaggerated it to the point of satire, and this completely unhinged protagonist started coming to life. 

The kids in Tabitha's life seemed to be the only ones who had any clue about what was really going on. So then I thought, what would happen if I made the only voices of reason these five-year-olds because all the adults were just too bogged down with years upon years of contradicting opinions? I think making it farcical was the only way to talk about how truly insane it feels to believe in the big kind of love, especially in a swipe left/right era of too many options. 

 

Tabitha’s narrative, at times, takes delightful cues from pop culture references, for example, the way her mother emulates Dorothy Parker. I particularly loved the scene where Tabitha meets Chrissie Hynde. Are there any heroes of yours, literary or otherwise, who inspire you or your writing?

I’m so glad you loved that moment in the book - thank you! I am so interested in the idea of meeting your hero, and how typically and totally crumbling that can be.  

I (clearly) have a particular affection for Parker. Every line of hers at once breaks my heart and fills it with joy. I fell in love with her when I worked at this small literary members’ club in London called The Society Club. It was a bookshop with a cocktail bar, essentially. What’s better than sipping on a Hemingway Daiquiri while reading one of his first editions from the shelves? It was heavenly. Being there in the room with others who also loved these books, these authors, who wanted to talk about the written and spoken word and everything in between, very much shaped my writing then and now. Dostoevsky, Twain, Nabokov, John Waters, Marquis de Sade (nothing like an 18th-century libertine!), Henry Miller. I love writers who just rip at your heart and get to the root of it all. The good, the bad, the nasty, the wonderful. Who take their skin off and expose the most raw part of themselves. I suppose, looking at this list, I love complicated, heady, hedonistic characters. 

I also am so inspired by Denis Johnson and Oscar Wilde. I remember just drooling over every word in The Picture of Dorian Gray when I first read it many years ago, which might have subconsciously influenced me when I named my protagonist Tabitha Gray! I think I’m drawn to the cadence with which these types of writers write. It feels musical. Histrionic. I just want to sit with them, their characters, in their lives. I do come from a family of songwriters so that may be why I’m so captivated by the rhythm of the sentences and how they are strung together. 

One of the first books I remember being obsessed with though — and I mean truly, deeply, obsessed with — was Go Ask Alice. I read it when I was a teenager and couldn’t get enough. I think there’s something in particular about the first-person for me. It’s intimate. True or false, I feel it. I’m in it. 

 

Even when it gets her into trouble, Tabitha’s optimism is indefatigable. Her commitment to the hope that everything will turn out all right is admirable, though it does seem to be limited to her love life. What might her optimism look like in other areas?

I think Tabitha’s optimism, albeit focused on love in the book, is really indicative of her life view. I don’t think you can see one area of your life one way without it also bleeding into other areas of your life, like family and career. You can't be acutely optimistic… can you? 

Her motives are altruistic in that I think she really believes in the power of positivity, even if massively misdirected (because she’s never been taught better). She wants everyone to win even if her approach is accidentally coarse. She’s the self-appointed Braveheart no one knew they needed. But there is the downside of being too optimistic. At what point does a die-hard optimist start living outside of reality? It gets her fired. It gets her hurt. It gets her confused, but it also means she doesn’t put too much pressure on any one thing to work because you can’t mess up what is meant to be. 

I also wanted Tabitha to think she was learning lessons from each misadventure, but that the reader would realize that the lessons she thinks she’s learning are not at all the lessons she should be taking away. We see her wanting to learn, though. We see her trying, fumbling, and most often failing at everything — even sometimes at being an optimist. 

 

I’m very struck by the relationship between Tabitha and her mother. Did anyone inspire that character or that relationship?

Twilda, Tabitha’s mother, is an amalgamation of many wonderful, intricate, intoxicatingly complicated, and inspiring women I’ve met throughout my life. My mother is an actual angel and nothing like the mother in the book, but I wondered to myself, paired with the high-voltage optimism that my dad instilled in me as a kid, what would it be like to have a single mother like Twilda, with no one else around to model behavior after other than her? With no other adult to balance her extremism besides the ones deemed the abandoners, the traitors, the ones who settled? What if the optimism and the self-destruction were so intricately interwoven that you couldn’t figure out how to separate them without separating yourself entirely? If you love someone, you want them to be right. Especially if you are just like them. But what happens if they have it wrong, and what does that mean for you? 

Attachment styles are fascinating. If you have the same struggles as your parents, it’s like an insiders’ nod that you are with them. You’re part of the team. You’re in this storm together. But if you start to realize that, wait, this might not be what you want, this might not be the life that is healthy for you, mentally or physically, but if you pull back, how would that affect your relationship? How do you find your own path without abandoning the ones who want you on theirs? Making that decision can feel too painful, sometimes, so you do anything in your power to prove them right, so you don’t have to make that choice. That was the struggle I was interested in. 

 

Can you speak a bit about your creative process as both a visual artist and a writer? Also, how has your creative process changed in light of the global pandemic?

I think the art and the writing feed each other in a sort of symbiotic relationship. The art I’ve been doing for the past five years came organically out of me feeling frustrated in the final editing stages of writing the book. So my dad, a songwriter who knows well the perils of focusing too much on one thing for too long (without stepping back), told me to put it down and do something else creative for a while so it could breathe. If it had wings, he assured me, it would find its way later, but it certainly wouldn’t by strangling it and me hovering over it like an anxious, sleep-deprived new mother, checking for her baby's vitals constantly. 

Redirecting my focus gave me a new outlet, which in turn relieved the pressure on the other. I think I need both. Blind contouring, which is the technique I use as my approach to painting (not looking at the canvas or lifting the pen when I draw the first line), not being able to self-judge, to analyze and criticize in the process of creating, was the perfect juxtaposition to the headspace I was in during that final editing stage of my book. I think the thing that connects them is that initial phase of almost free association. The making sense of it all afterwards is the hard part, for both, but that first approach to the page, to the canvas, is the same. I'm not much of a planner, in any aspect of my life, so I think the art and writing fit that bill, too. During the pandemic, my process has been much the same although time feels warped. 

 

I noticed that this book was crowdfunded! What was that process like for you as a writer? How does it differ from a more conventional publishing process?

Yes! Unbound is so wonderful and I think their publishing model is amazing. I met John Mitchinson, the co-founder of the publishing company, when I was bartending at The Society Club. He would come in, as many publishers, agents, writers and artists regularly did, for book launches and meetings. One of the co-owners of the club was a literary agent named Carrie Kania who would later become my agent, so she introduced me to John, and we became friends. He knew I was working on a novel and asked to see it when I was done. I loved Unbound’s philosophy and they also have a 50/50 split for authors, since they don’t do advances, but that way it can be even better for the author in the end. Their crowdfunding model allows their team of editors to decide to publish books that they believe in and love rather than solely based on if they think they will be bestsellers. If enough people pre-order the book, they make it, but only after their editorial board accepts the manuscript. The guaranteed pre-orders means they can take the risk in the first place and let the readers decide rather than the market trends.

By the time John said Unbound wanted to publish it, I’d already moved back to Los Angeles and was quite deep into the art series I’d started - because of that original writer’s block. So it was truly a beautiful full circle after having let it go to do the art, as my dad had encouraged, to then find out it would eventually be published with a company I loved so much from the start. I couldn’t have been happier because I knew it would be in the best hands. John’s wife, Rachael Kerr, was my editor on the book and was so incredible to work with. I feel so lucky that the book found its way to Unbound. We did the original launch of the UK hardcover edition at The Society Club where it all began, before the club closed in 2017. Maybe it’s the optimist in me, but it all worked out in the end, even if the path was circuitous. 

 

What have you been reading that you would recommend?

I’m loving Sally Rooney’s Conversations with Friends although I know I’m late to that party! I also read a poem out of Pablo Neruda’s Love Poems most days. Too much Dorothy Parker can get me down, even if I love it, so I have to sprinkle in some good old-fashioned love in there every so often, so it doesn’t make me too jaded.


Sophie Kipner is a visual artist, writer, and former Secret Society bartender who grew up in Topanga, CA, with an English ballerina mother and an Australian songwriting father. After graduating from The University of Southern California’s Annenberg School for Communication and Journalism, she hosted Channel 101’s long-running web show Everything, while writing and illustrating her own stories which have appeared in Kugelmass: A Journal of Literary HumorMetazen, Amy Ephron’s One for the TableFORTH Magazine, and The Big Jewel. Her series of abstract portraiture, DONTLIFTUPDONTLOOKDOWN, premiered during the Santa Barbara Art Walk at Ca’Dario Gallery in 2015, and has since been shown at KGB Studios in Downtown LA, WNDO Space in Venice, CA, and at Larrabee Studios in North Hollywood. Sophie lives in Los Angeles, and The Optimist is her first novel.


Kailey Brennan DelloRusso

Kailey Brennan DelloRusso is a writer from Plymouth, MA. She is the founder and editor-in-chief of Write or Die Magazine and is currently working on her first novel. Visit her newsletter, In the Weeds, or find her on Instagram and Twitter.

https://kaileydellorusso.substack.com/
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