INTERVIEW: JESSIE ROSEN

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From top blog to book deal, writer, storyteller, and producer Jessie Rosen has taken Hollywood by storm with her bold and charismatic stories. Jessie’s blog, 20-Nothings.com, was named a Top 25 Blog by TIME magazine and among the Top 100 Websites for Women as well as Top 10 Websites for Millennials by Forbes in 2013 and selected by Jane Pratt’s xojane.com as one of SAY MEDIA’s supported portals. Since launching her award-winning blog, Jessie has conquered just about every genre in the biz. She has published essays and articles in E! Online, Marie Claire, AOL and The Daily Beast. She recently sold a YA novel to James Frey’s publishing company, Full Fathom Five. Additionally, her “no-boys allowed” Sunday Night Sex Talks storytelling series has become a nationwide guilty pleasure.
 

We were thrilled when Jessie took a break from blogging to share how she survived “the most significant, least important decade of her life” and how she plans to use these experiences to teach her upcoming classes: So You Want To Be A Writer, (4 Wk) starting March 7th and So You Want To Be A Blogger, on March 14th.

 

1) How and when did you make your debut into writing?

 

I technically made my debut into writing as a senior at Boston College. I had an incredibly supportive journalism professor who encouraged me to submit assignments to a few local publications where he had contacts. But the real start of finding my voice and developing my own style was my blog, 20-Nothings.com, that I launched in 2007. That’s when I started writing every single day. From the blog I was approached by places like Aol, Marie Claire and The Daily Beast to contribute pieces. Today, I maintain the blog but have made another debut into writing for film and television. That began after a friend in New York recommended I submit a one-act play to a festival in Manhattan. From there my love of writing in that format was born, and TV/film followed shortly.

 

2) You’ve written across several mediums. Do you find it challenging to switch hats? Have you found a common thread between styles?

 

My love is writing for stage/screen, so I do find it hard to slip into straight prose only because I miss the dialogue heavy format. As a result I was told to write very dialogue-heavy prose! But the real challenge for me is slipping between drama and comedy. I’ve been doing more and more of that now that I’m working on a dramatic novel. I find it takes me a beat to lighten my tone and mood or weigh is down if I’m starting from comedy and slipping back into drama. It just takes practice.

 

3) How did the Sunday Night Sex Talks storytelling series evolve?

 

The storytelling show started because I was looking for a way to become more part of the community here in L.A. I moved here in 2010 and realized quickly that so much of career development is about the development of friendships and contacts, so I wanted to find a way to cultivate that in a fun, dynamic environment where I could also challenge myself. I have always been a huge fan of storytelling, so the idea for Sunday Night Sex Talks developed out of a combination of that AND a really funny, real-life sex talks night that my girlfriends and I would organize in college. Luckily Bar Lubitsch was willing to try it out, and now three years later we’re sold out every month!

 

4) Last week you held the first co-ed Sunday Night Sex Talks, how did that go? Will you ever do it again?

 

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We are already scheduled for another co-ed sex talks at UCB on March 31st! I’m staying loyal to the girl’s only events in addition to this co-ed shows, but it is really interesting to see how the show shifts from a no-boys crowd to a co-ed group. I love the opportunity to have both.

 
 

5) You recently sold the YA novel, “Full Fathom Five,” to James Frey’s publishing company. Tell us how you did that and what your book is about.

 

The book is a twisty revenge tale about a mysterious death at a high school. I like to think of it like GONE GIRL meets PRETTY LITTLE LIARS. I sold the book off a proposal and outline that I worked on with my manager and book agent. The whole process began because my manager felt I could expand my writing into books and challenged me to try out a new genre and new voice. Apparently she was right!

 

6) You’ve been blogging since 2007. Has anything changed since then that has made blogging more difficult? Easier?

 

I think blogging is more difficult now because the landscape is busier. People spend less time really reading long articles online and are more interested in the Tumblr or, even shorter, Instagram-style content. For me that means diversifying what I write in terms of length and format so I can meet the reader with the amount of time they have to spend reading.

 

7) You blog at least twice a week. What makes a compelling post and how do you keep your page fresh for readers?

 

For me, compelling is always about personal content. I write a lot about what it’s like to be a newly married person struggling to build a career in a difficult industry, and I try to be as honest as possible about that experience. I also think compelling posts have easy-to-digest topics like “Why I Didn’t Change My Name” or “5 Ways to Give Yourself Fake Confidence.”

 

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8) You’re making a transition into television and film writing. What’s next for you in that world? What television shows and films do you look to for inspiration?

 

I’m working on a number of pitches now that are both based on content that I’ve developed personally and content out there in the world such as other book properties available for development. I watch a LOT of television, so I’m always looking to see how stories are being told in different ways – for example Black Mirror which is a sort of updated Twilight Zone style – or stories being told in traditional ways but with great, great twists – for example The Good Wife which is a traditional procedural show done incredibly well.

 

9) Do you have any advice for aspiring writers?

 

WRITE. Write as often as you can and for as long as you can tolerate. Do not focus on making it perfect or making it marketable at first. I think so much of writing is about finding voice, and you cannot find your voice unless you’re committing a lot of time to getting words on the page (or screen) and figuring out how you sound best.

 

10) What can students expect to learn in your creative writing class at Writing Pad?

 

At the beginning of my class I explain to my students that we’re going to cover how to write AND how to be a writer. Those are two different things, but they’re equally important. The first is about getting comfortable with writing dialogue, developing a strong ability to show vs. tell, finding ways to create interesting plots and characters, etc. But becoming a writer is a different game all-together. It’s about confidence, persistence, desire, and overcoming fear, frustration and negativity. That’s my favorite thing to teach.

 

You too can be a successful writer like Jessie too! Check out Jessie’s workshops: So You Want To Be A Writer, (4 Wk) starting March 7th and So You Want To Be A Blogger, on March 14th.