Sinclair: What’s your three word bio?
Olive: Author. Speaker. Coach.
Sinclair: How did you get to where you are now in your career?
Olive: My writing career started with a hot dog. No joke. When I was in college, I wanted to change the world by becoming, you guessed it, a politician. Then I graduated college and realized how awful it would be to ACTUALLY become a politician. Hell naw. I joined a nonprofit that I loved and started doing important work in Cleveland, Ohio
Well, one day I went on a date at a fancy hot dog joint on the West Side. Long story short, I choked on the hot dog and nearly became chopped choking liver at the restaurant. I went to work the next day at the nonprofit and my coworker asked how the date went. I replied, “I choked on a hot dog, became asphyxiated, and had to Heimlich myself on the bar….so…I mean… ok!”
We had a good laugh about it after I showed her how I heimlich’d myself ( my date didn’t know what to do) and then she said, “You gotta start writing this shit down.
And that’s what I did.
I started writing my first comedic book, Unintentionally Celibate, shortly thereafter. I discovered that I had a talent and love for speaking, writing, and comedy. I realized there were many ways to change the world. Now I try to write things that help people feel less alone. Things that make them laugh. That make them say, “Yea, that’s how it is!” The ability to create art is one of the greatest gifts of my life.
“My biggest hope is that when is comes to sex and self-esteem, people will realize that we’re all muddling through this together.” – Olive Persimmon
Sinclair: In your 2016 article for She Knows titled, Porn has been warping my perspective on what satisfying sex looks like, you talk about your experience at Pornfest, Cindy Gallop of MakeLoveNotPorn, and your dry spell. How has this experience shaped how you see sex work and porn today?
Olive: I mean Cindy Gallop is a force in the industry. It’s incredible to see someone out there changing the industry.
Sinclair: Your latest book, The Coitus Chronicles: My Quest for Sex, Love, and Orgasms, talks about the end of said dry spell, an almost one night stand, orgasmic meditation, and so much more. What’s something you hope readers will feel and know as a result of reading this book?
Olive: My biggest hope is that when is comes to sex and self-esteem, people will realize that we’re all muddling through this together. When I write things, what I’m trying to say is, “I’m right there with you. That thing you’re going through, other people have been through it too, and it’s ok. You’re ok. We’ll both be ok.” We’re taught that it’s somehow shameful or embarrassing to talk about sex. As a result, I think a lot of us feel lonely and confused. I want people to feel less lonely and scared. And of course, I hope I do it with a bit of humor.
Sinclair: What was your writing process like for this book?
Olive: OMG. Basically just procrastinating a lot. There was one point in time where I was like, “NO, your ass is gonna stay in this chair until you finish this damn chapter.” I’m an extrovert, so writing solo is sometimes a struggle for me.
You did an awesome spoken word set at Sexting AF. What was a memorable part of that experience for you?
Oh thank you! Actually, there was a moment where I heard Cindy Gallop laugh and I was like, “Holy crap, Cindy Gallop thinks I’m funny!” It was so much fun to perform at the Sexting Art Festival, the audience was rowdy and had a great sense of humor.
Sinclair: What’s something we often get wrong when talking about sex?
Olive: I think in the sex positive scene, it often feels like there are two camps:
(1) Sex-positive people wearing see-through shirts, going to play parties, who feel comfortable talking about butt plugs at dinner.
(2) Everyone else. People who feel a little nervous, scared, and insecure about sex.
There’s a really nice middle ground. You can explore sex and be sex-positive without buying a butt plug (or buy one, I don’t care!). You know what I mean? I think we need to send the message that it’s wonderful if you’re coming to the metaphoric table a free goddess who loves and embraces their sexuality. And it’s also totally ok if you’re coming to the table a little scared and uncertain of what you even like or want to explore. It doesn’t have to be all or nothing.
Sinclair: What’s something we can do to end the stigma around sex work?
Olive: Talk to people actually doing it. Listen to their stories. I think that’s true for anything. It’s really easy to form an opinion about something from the sidelines. We’re so quick to form opinions about things with no actual knowledge about it. I do it all the time and I have to work hard to catch myself.
Sinclair: What’s something you wish you could say to your 16 year old self?
Olive: “Girl, that tuxedo shirt is super dope.”
Sinclair: What’s something you’re working to unlearn?
Olive: Oh boy. I was overweight for most of my life and I believed for a long time, that I wasn’t the type of girl people wanted to date. That I wasn’t pretty enough. Or thin enough. Or just enough in general. I’d go on dates with men and assume they wished they were on a date with someone different. Someone told me I was the “Ugly Friend” once and I subconsciously believed them.
There’s two chapters about this in my new book because I had to spend some SERIOUS time and energy on this one. It still creeps up sometimes when I’m talking to a boy in a group of people. I’m still workin’ on it.
“We’re taught that it’s somehow shameful or embarrassing to talk about sex. As a result, I think a lot of us feel lonely and confused. I want people to feel less lonely and scared. And of course, I hope I do it with a bit of humor.” – Olive Persimmon
Sinclair: Who do you go to when you’re needing support and guidance?
Olive: My best friends. My parents.
Sinclair: What’s one challenge you face in your work that you’re still working on navigating?
Olive: Getting paid for art.
Sinclair: When was the last time you practiced self-care? What did you do
Olive: I’m taking surfing lessons. It’s so much fun and I’m not doing it for any other reason than it’s fun. I don’t always let myself do stuff just because it’s fun
Sinclair: What’s something that’s been bringing you joy lately?
Olive: My friend, Giancarlo, told me how he wakes up every morning to his “Good vibes” playlist and I wanted to try it. I made a playlist of upbeat songs and I play it every morning while I’m in the shower. The minute “Jump” by Van Halen comes on, I immediately feel happy and energized.
“I discovered that I had a talent and love for speaking, writing, and comedy. I realized there were many ways to change the world.” – Olive Persimmon
Sinclair: What’s something that’s been pissing you off lately?
Olive: Politics. The subway system in NYC. How everyone keeps posting these sexy pictures on them eating ice cream out of a giant cone on Instagram.
Sinclair: When was a time that self-doubt was at its worst for you while on your career and life journey?
Olive: Between my first book and my second, I got rejected by 145 agents before I found mine. We were subsequently rejected by dozens of publishers before the book finally sold. That’s a lot of freaking rejection. You gotta have thick skin in this business.
Sinclair: What are your unshakable values and when did you become clear on them?
Olive: Compassion is my religion. I’m very superstitious about words. I rarely say anything truly unkind about anyone, it hurts my heart. I mean I’ll complain about people but it’s never vindictive or mean. I try to live gently and kindly as often as I can.
People are afraid to date me because they are afraid I’ll write nasty things about them, and I’m just like, You must have never read my work. I’ll tell the story how it happened but I’ll rarely attack the person.
Sinclair: Who are a few amazing people that we should follow and why?
Olive: Greg Mania is the funniest up-and-coming comedian I know. And he’s kind. He never gets a laugh at someone else’s expense.
Becky Berardi is pretty cool, she’s doing a lot of cool work to destigmatize the foot fetish.
Sinclair: What is one piece of advice you’d give to a writer or speaker struggling with self-doubt and feeling like giving up on their dreams?
Olive: Hang in there kid. Making art in NYC ( or anything) a lot of times has less to do with talent and more to do with unfailing persistence. I like to think of it like a hamster wheel that someone keeps turning aggressively and it’s all about who can cling on the longest without giving up.
Sinclair: It’s years in the future. You’re on stage to accept an award for your life’s work. What’s your five word acceptance speech?
Olive: I’m grateful to God for the ability to create art (ok, ok a little long)
Sinclair: Imagine that all your life’s work disappeared and you only had 1 minute to tell the world what you truly believe to be true. What would you say?
Olive: Be kind. Make art.
Olive Persimmon is an author, speaker, writer and everyone’s favorite celibate. Mostly, because there’s a very small number of publicly-outed accidental celibates (for a reason). Her first book is called Unintentionally Celibate and She’s currently working on the sequel, The Coitus Chronicles. On her journey she sucks some toes, tries out the tickle fetish, and finally (maybe) has THE sex. When she’s not writing or speaking, she teaches public speaking. In her free time, she enjoys writing letters to friends and coming up with new speeches.
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