We had the good fortune of connecting with Paulina Pinsky and we’ve shared our conversation below.

Hi Paulina, how do you think about risk?
I teach Comedy Writing to high schoolers at Columbia University, and on the first day of class, the first three rules I tell them are:

1. Don’t be cool
2. Don’t be funny
3. Fail

Aside from getting a reaction out of them (usually/ hopefully laughter), these three rules have been honed and perfected over the last four years. And quite frankly? My entire lifetime. But more than anything, when it comes to my teaching philosophy, I want to create an environment in which risk is rewarded.

While telling each student to “play to the height of their intelligence”, I also tell them: Take a risk!

When I first started studying improv at the Second City Conservatory in Chicago in 2016, I couldn’t trust myself enough to take a risk– I didn’t think I would come out of it alive. It felt vulnerable to trust my whims. No room to edit in real time. But week after week, I would show up to class a nervous wreck, shaking with nerves, biting my tongue. Though I don’t improvise much on a stage anymore, I think that improv is instrumental to the way that I view life: there is always opportunity to take a risk, every single day, every single minute, every single second. But it’s the way that you take that risk that matters.

After graduating college, I felt insecurity about not pursuing a traditional job– my friends had 401ks and health insurance, and they judged me for not pursuing the same path. Thankfully, I now understand that the opportunity to pursue art was my only choice, albeit a privileged one. I did not have to take a corporate job; I did not have to work three jobs or pay for my schooling: I had the freedom to choose. And not everyone can say that. I was able to take a risk because it was a safe risk to take: I had parents who could bail me out.

Risk exists on a scale: from painful to benign. Pursuing Second City after graduating from college felt like a huge risk at the time. But in retrospect, I can see that it was the only choice. What was the worst that could happen? That I’d fail at being funny? Again, my safety net was cast pretty wide. But all in all, I think that part of risk is assessing your safety net– who do you have there to catch you if you fall? Your family? Your friends? Your scene partners?

I think that the best way to summarize how I view risk in both my life and career– As Julia Cameron once said: “Jump and the net will appear.” You can’t grow if you don’t push your comfort zone.

Can you open up a bit about your work and career? We’re big fans and we’d love for our community to learn more about your work.
I am the co-author of “It Doesn’t Have To Be Awkward: Dealing with Relationships, Consent, and Other Hard-to-Talk-About Stuff” forthcoming from Clarion Teen September 21, 2021.

And yet, even though I have a book coming out, it took me a long time to believe I am a writer.

When I was a junior in college, I wrote my first personal essay, “Get Your Teeth Checked” for the Columbia University Spectator. The essay was an exploration of my relationship with my mother, in addition to eating disorder recovery and feminized trauma. I was lucky: It was well-received within my college community. At the age of 21, I was recognized as a writer for the first time.

However, six months later: I was sensationalized. Pulling the hook out of the essay, The Today Show, Good Morning America, and other media outlets depicted me solely as Dr. Drew’s Bulimic and Anorexic daughter. To be frank: That experience kept me from writing for a long time. I learned that my proximity to my father’s platform is both a privilege and curse. I wanted to earn it; I wanted to be outstanding on my own. Everyone was waiting for a slip, but I refused to fall.

A year later, spring of my senior year at Barnard College, I took my first Nonfiction Creative Writing Class– it was the only A+ I have ever received. The course was taught by Elisabeth Sherman, then a Nonfiction MFA student. I saw an example of who I could become: A writer covered in tattoos. Someone unafraid of using their voice.

Growing up, I never had a vision for myself. A competitive figure skater from ages five to eighteen, the best I could come up with post-college was touring the world as a princess with Disney On Ice. Alas, I quit figure skating, and by the end of college, I was not ready to jump back on the ice. I had hung up my skates to play rugby and perform musical theater. I was no longer princess material. According to Google, I was Eating Disorder Daughter, so I decided to pursue comedy at Second City in Chicago. However, after nine months in the conservatory, I didn’t feel fulfilled, so I applied for Nonfiction MFA programs.

The first year of my MFA at Columbia, I felt like an imposter: everyone was humorless and the pieces I was writing were bad, like really bad. But in order to get better, you have to write (even if it comes out wrong, all wrong). And after the first year of my MFA (and a break up), I decided to not listen to the niggling voice in the back of my head that said I didn’t belong. I decided to dedicate myself to cultivating my voice on the page. I decided to cultivate myself.

I don’t believe that MFA’s make writers: Writing make writers. There are folks who skirt through an MFA for the prestige, for the name of the institution. However, I believe that an MFA is what you make of it. If you can focus on honing your craft, it will always improve. Additionally, I was able to pursue my MFA debt free due to the support of my grandmother. Not everyone has that privilege.

All of this is to say: A writer is someone who writes.

And now, day after day, I wake up and do three pages stream of consciousness a la Julia Cameron’s “The Artist’s Way”. Writing is both a goal oriented activity, but it also a way of life. I am dedicated to writing my way through life, because whether I recognized it or not, I am a writer.

Though I got my first book deal because of the family I was born into, I want folks to understand that I don’t take that privilege lightly. After my experience with media sensationalization back in 2013, I made it my focus to hone my skills and craft. I wanted to be able to back up whatever exposure I get with talent, perseverance, and hard work. Which is why I can say: I really believe in myself as a writer.

All in all, writing is a way of life. And I am lucky that I get to put pen to page every single day.

Any places to eat or things to do that you can share with our readers? If they have a friend visiting town, what are some spots they could take them to?
I hate driving and most likely we are staying at my childhood home in Pasadena, so unless you ask for it: we won’t be going to the Westside.

First things first: I would take you to Lucky Boy to get a bacon breakfast burrito (add avocado). The size of a newborn, their burritos are what I crave most when I’ve been away.

If you are of legal age, I would take you to Cornerstone Wellness. Once you load up on gummies and tinctures and pre-rolls, I would take you to Cacao Mexicatessen because, let’s be real, it will be time to eat again. I’d suggest the carnitas de pato because it will rock your world and your mouth.

We need to shop: I would take you to Big Bud Press and The Plus Bus in Highland Park. Both stores cater to plus-sizes, but more than anything: their flagship stores rule.

Next, I’d take us to Silverlake Meadow, where I’d make my LA friends Lori and Jourdan come hang out with us because they are beautiful and talented, and I want you to believe that I am the company I keep. We will giggle and laugh and bask in the sun, until we get hungry again. Next stop: Melody Wine Bar in Silverlake.

Over a bottle of white and oysters, we would discuss the day we had. A little tipsy, we’d both decide we want tattoos. And so, I would get on my phone and see if we can get book at Supersweet Tattoo. Last time I was in LA, my fiancé and I had pieces done by Amy (@mclametattoos)– got a deer in honor of my great-grandmother who won archery competitions and hunt deer. You’d tell me you don’t need a tattoo with that much meaning, and I’d say “Okay, not all tattoos have to have meaning.” We will soon discover that Walk-ins are a thing of the past, so I’d suggest manicures or tooth gems. If you choose manicures, we’d head back to Pasadena to Belle Nails. But if you choose tooth gems, we would go to GBY in Silverlake.

If you want out of LA? We’d head to my favorite place in the world: my grandparent’s beach house in Laguna. You’d say, “Yes, please take me to the ocean” so we’d leave around 9 PM to beat the traffic. And most likely, I speed. But this is preferable to seeing my in stop-and-start rush hour traffic: I am a very angry driver. But zooming through empty lanes, that I can do. We’d most likely spend the next few days at the beach. But when you feel ready, I’d be ready to take you back to LA to eat some more.

All of this is to say: I will to feed you and pamper you. And if you really, really want me to: I guess I’ll drive.

Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?
I have had the distinct privilege of having amazing teachers throughout my life.

I would like to give a shoutout to: Norm Holly, formerly at Second City, who taught me how to take risks and to believe in myself; Lis Harris at Columbia University, my graduate school mentor who taught me to write fearlessly, but not as an act of revenge; Jennie Kassanoff at Barnard College, whose brilliant guidance was the sole reason I finished my undergraduate thesis on Joan Rivers (without her, I would not have graduated college on time); my ice skating mothers, Erika Schorr and Barbara Susman, who always made me feel cherished; and Catherine Baker-Pitts, who ushered me through eating disorder recovery.

Additionally, I want to thank MacDowell for introducing me to amazing artists (Matthew Lansburgh, Heather Sellers, Caleb Curtis), in addition to believing in my craft. In addition, Kira Kamamalu’s Holualoa Artist Residency in 2019 changed my life– thank you for believing in me and for allowing me the time and space to live and breath and experiment on the Big Island.

I want to thank my first Writing the Body cohort, which became Pseudonym Collective– ya’ll taught me how to take myself seriously as a writer. And to my current Book Writing Support Group, I am indebted to your unwavering support and critical eye.
I would also like to take the time to say that every single student I have ever had inspires me. Once you’re a student of mine, you always have a place in my heart. Whether it’s taking risks on the page or on the stage, know that I believe in each and every one of you.

And to my amazing friends, who inspire me in more ways than they could know: Jenna Lomeli, Chelsea Conley, Kaylin Mahoney, Lori Dorfman, Mingus Daniels-Taylor, Jourdan Jerome, Alley Horn, Peter Hoffman, Jack Lowery, Marina White, and Alex Dabertin.

My story would be incomplete without my parents, Drew and Susan Pinsky, who have always supported my vision, no matter what that vision entailed. Even if it meant leaving 3,000 miles away and writing about sex. And I would like to thank my brothers for tolerating the fact that I write about our family. And to my fiancé (I hate that word) Zach: Thank you for loving me.

Last but not least, I wouldn’t be the writer I am today with these literary influences: Mary Karr (Cherry), Lucy Grealey (Autobiography of a Face), bell hooks (Teaching to Transgress), Miriam Toews (All My Puny Sorrows), Audre Lorde (Uses of Erotic: The Erotic as Power), Jeanette Winterson (Written on the Body), and A.M. Homes (Safety of Objects).

Website: www.paulinapinsky.com

Instagram: @mizpiggy111

Linkedin: www.linkedin.com/in/paulina-pinsky-210

Twitter: @mizpiggy111

Facebook: https://www.facebook.com/paulina.p.33

Image Credits
Paul Gerben, Haley Jakobson

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