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

Hi Jessie, any advice for those thinking about whether to keep going or to give up?
I picked this question because it literally made my stomach clench. In my experience as a writer, that means it’s worth pursuing.

I think the decision to keep going when you’re the CEO of your own company – in my case a company of one television/film writer – is hard to explain but easy to know in your heart.

Since leaving my 9-5 in marketing eight years ago I’ve worried about my ability to support myself financially. I’ve feared that I won’t “succeed” in the traditional, name-on-a-marquee sense. I’ve even wondered if I need to pivot my focus from TV/film to maybe novels? But I have never lost my passion for this work. And despite many huge professional disappointments, I’m still able to focus more on the wins. They motivate me to keep pushing and remind me that I have the ability to make and sell my work.

Let me be clear, though. There is nothing wrong with “giving up” – especially in a punishing industry. There is no shame in realizing a certain path is not healthy or productive or nourishing for you and your life.

But it’s always been important for me to not let the common rejection of the entertainment industry get more of a seat at my personal life table than hope and, more importantly, reality. Frustration is different than total exhaustion. And the fear of failure is always louder than the actual setbacks themselves. So part of why I keep going is because I’m able to look at my feelings and realize they will pass – I will be able to move on; I still have ideas that I dream of getting down on the page. And they are still louder than anything else.

But I think there’s another really important factor at place – the support of people that encourage me to keep going.

I have been represented for the past eight years by managers (Rachel Miller and Jesse Hara at Haven Entertainment) that remain focused on the long game of my career. They are not deterred by all the stopping and going along the way. And, more importantly, they help me see how my work is evolving and skills growing, whether or not that’s matched by a long list of credits. In addition to that team, I am married to an incredibly supportive man willing to modify our lives to support the nature of my career, specifically the fact that money is not always regular. And finally, I have a group of friends that live in my same career world. We are a constant resources for each others’ experiences climbing up the many ladders of this industry, and we quite literally tell each other to keep going – in Gif form, of course.

But, to attempt to answer the question in one sentence I’m going to rip off my favorite Anais Nin quote: “And the day came when the risk to remain tight in a bud was more painful than the risk it took to blossom.” My version: you give up when the risk to keep going is more painful than the risk to walk away. And even then you know that you can always change your mind.

Alright, so let’s move onto what keeps you busy professionally?
I am a writer/producer/storyteller that started as a very lowly blogger at my site 20-Nothings.com. I didn’t even believe I could pursue the dream of television and film writing until this little online passion project caught the eye of an LA-based manager. She encouraged me to try my hand at writing for theater (I was living in NY at the time) then pushed me to write a television pilot. That was twelve years ago. I’ve since moved to Los Angeles, been through that manager and two others (before landing with my dream team), and had countless successes and failures in my journey toward the big goal of creating my own work for film and TV. My heroes are the Nora Ephrons and Jenji Kohans and now Michaela Coles of the world. And I like to think that what makes my work unique is the ability to express complicated, modern, female experiences through relatable, accessible stories. It all harkens back to the way my career began – blogging. I was lucky to develop an early comfort mining my own life for subject matter that I’m comfortable sharing. That’s taken many shapes, so far. I’ve sold comedies to Netflix and Warner Brothers TV based on my own family experiences, I launched a live storytelling series called SUNDAY NIGHT SEX TALKS because I noticed how my own friend group was struggling to communicate around our sexuality, and I even wrote a dark, YA thriller called DEAD RINGER because I was eager to explore the ways young women are affected by bullying. None of this has been easy, and I still have so many dreams unrealized. But I still pinch myself that I’ve come this far. And I’m still building toward the full picture of what I want to offer people as a writer and creator.

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
LA is one of those cities that people have trouble really understanding in a quick visit. Most people stick to the hits – Santa Monica and Venice, Hollywood for a little “walk of fame” history, and Silver Lake/Los Feliz because they’re the hip places to shop. I think the most exciting thing about Los Angeles is the insanely varied topography (you can go from the beach to the mountains in minutes) and the culturally diverse food. When people come visit me I pack our days (people have literally complained…) with a variety of walking and eating. We hike Griffith Park (my favorite trail is Fern Dell to the Observatory) then drive immediately down to Koreatown for eats at the famous Dan Sung Sa then a soak in the Korean Spa (which there are more of in LA than any city in the country). The next day we might walk to see all the incredible street murals of Downtown LA Arts District, then head to Boyle Heights for out-of-this-world shrimp tacos from the Mariscos Jalisco truth. And if I can convince them, we head outside of LA for a drive up to my favorite place in the “area” – Ojai. A charming town filled with vistas and shops and wine tasting and its own set of gorgeous walks (specifically the Signal Road path). I try to show people what it’s like to actually live in LA, not what it looks like on Real Housewives of Beverly Hills. Though, I get as much of a thrill out of seeing certain celebs as anyone. Who else deserves some credit and recognition?
My shout out is for HAVEN ENTERTAINMENT, the management and production company that has represented me for eight plus years and specifically my managers Rachel Miller and Jesse Hara. They named the company HAVEN because it was their goal to create a safe haven for writers/directors/producers/talent to build their careers. They’ve done that and more. The company truly feels like a family, each members supporting each part of your journey in the ways you need to succeed. I feel so lucky to have them by my side. And their hard work inspires me to commit just as fully to my own projects.

Website: jessierosen.com

Instagram: jessierosen

Linkedin: jessierosen

Image Credits
Avia Rosen, Jenny Anderson

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