Lee Jessup is a seasoned career coach for screenwriters, with an exclusive focus on guiding and supporting screenwriters as they parlay their screenwriting prowess into a focused and dynamic screenwriting career. Follow Lee on Twitter @leezjessup
In January 2016 I began work on my new book, BREAKING IN: TALES FROM THE SCREENWRITING TRENCHES, which was released just this past month. The book contained insights from industry professionals pertaining to all things breaking in, as well as sixteen interviews with newly minted working screenwriters making their way in film, television and new media, who broke in following the 2008 writer’s strike. But when I delivered the book to my publisher in July of 2016, I realized that I wasn’t anywhere near done talking to and learning from writers about their journeys to and experiences of breaking in. Which is when I decided to launch The Breaking In Initiative, an ongoing exploration of what it takes, in today’s unique industry climate, for new writers to break in and become bona fide professionals.
Recently, my good friend, Jeanne Veillette Bowerman, made me an offer I couldn’t refuse: Share these interviews through Script magazine, after which they will also appear on my site. How could I say no? Below is what I am hoping will be the first of many interviews exploring everything it takes (and then some) to become a working screenwriter in today’s competitive and ever-changing industry.
Deanna Shumaker was in no way born into this industry. Like many others who gravitate to it, she came from another state, drawn by everything she learned in her creative writing and television elective courses at the University of Florida. Since those days, Deanna worked as a showrunner’s assistant, was named to the coveted Warner Bros. Television Writers Workshop and a NYTVF Lifetime Writing Fellow, and staffed on NBC’S BLINDSPOT. Below is her story.
Lee: You originally hail from Florida. What inspired you to make the move to Los Angeles?
Deanna: I grew up in a really small town in central Florida, and I spent a lot of my childhood wanting to be a writer. At a very young age, I looked into what it would take to publish a novel, and it seemed super impossible. I was a practical kid, so by the time I was old enough to start thinking about colleges, I had given up any ideas of a creative career.
I started school as a radio television and political science double major, with plans to be a political news host, but a month into my freshman year 9/11 happened, and I just sorta lost all desire to pursue that anymore. I couldn’t figure out what I wanted to do and ended up changing my major a dozen times. But writing was always in the background. I took creative writing electives. I wrote film reviews for the school paper. And even when I finally settled on a career plan (and threw myself into it), it was public relations, which actually requires a lot of writing. However, fate intervened.
One week, instead of reviewing a new movie for the paper, I decided to review the Felicity Season 4 DVD boxset (it was my favorite show, the only show I’d ever seen in its entirety at that point in my life). I had to watch all the bonus features, which included a Paley Center interview with J.J. Abrams, Keri Russell, and Jennifer Garner where J.J. explained how he got the idea for Alias from the lack of stakes and excitement in Felicity’s life.
That interview did two things for me (besides change my life forever): 1) it made me interested in watching Alias, and 2) it gave a face to the television industry. It really had never occurred to me that all those names in the credits were real, nerdy people, like me, coming up with this stuff.
I had just signed up for Netflix, so I got the first disc of Alias, watched it, then immediately went out and purchased the first three seasons (the show was currently airing its fourth season at the time). I watched it all very quickly, and no realization in my life had ever (or has ever since) been so clear. I wanted to be the person that came up with shows like that.
I was six weeks away from graduating, but I canceled my plans to move to New York and find a job in financial PR. Instead I hopped on a plane to L.A. I mean, don’t be silly, I graduated first. But then I moved to L.A.
Lee: In your opinion, how important is it for writers to be in Los Angeles?
Deanna: So important! I kind of understand how feature writers can do it from somewhere else, but for TV, I just think you have to be here, learning how it works, meeting people, joining writers groups. Writers tend to be kinda solitary people, but I’ve found nothing more inspiring than surrounding myself with other people who want to achieve the same things.
Lee: A lot of writers who are not originally from Los Angeles are incredibly intimidated by the thought of making the move, and consequently finding a job in the industry. You, however, were able to do just that. How did that first job come about?
Deanna: I think it was a little easier for me to make the move, because I was at a naturally life-changing moment in my life. I knew I wasn’t going to stay in Plant City, Florida. It was definitely scary moving to L.A., a city I’d never even been to before. I cried the entire plane ride. I knew enough to know that it was very unlikely that I would make it, and I was terrified of coming home in a year or two having given up, and feeling ashamed about that. And that fear was made worse when I couldn’t find a job.
I had waited tables at Olive Garden all through college, so I transferred to the Burbank Olive Garden. I was trying to get a PA job, but no one wanted to take a chance on me because I had zero experience. A YEAR AND A HALF after I moved to L.A., I got a two-week gig on a Ryan Seacrest pilot, mostly because they needed someone with experience working big events, which I had from all the PR internships I’d done back in Florida. I had to quit OG which was scary, but I just made sure that I worked as hard as I could, and they ended up keeping me on to do post. So the two-week job turned into a two-month one, then they hired me as a PA on the pilot presentation of Keeping Up with the Kardashians. With those two new shows on my resume, I was able to get a job a few weeks later on CSI as a post PA.
My advice to people reluctant to move to L.A.: suck it up, but do everything you can to prepare before you move. I had done dozens of internships in college, but none of them were for anything TV-related. And once I got out here, I simply couldn’t afford to work for free. I don’t regret doing things the way that I did them, but I think I would have had an easier time with some experience under my belt.
Lee: While on CSI, you made the move from post production to the writer’s room, as writer’s assistant. Was that move deliberate?
Deanna: That move was very deliberate. I told the post producer in my job interview that I wanted to be a writer. At the time, I was excited to get in on the post side (early in my career) because I knew I wanted to be a showrunner one day, and knowing about all facets of the business would only work to my advantage later. However, I did not anticipate getting stuck there. I was a post PA for five seasons. I kept trying to move over to the writers, but they kept hiring their interns whenever they needed a new PA.
Finally I had a heart-to-heart with my boss, told her I didn’t think I could come back another year in post, and she pushed me to pitch myself to the writers one more time. There had been a bit of a regime change since my last attempt, and the new showrunner had no idea I was interested in writing. I interviewed for the job, an interview in which I wore my desperation on my sleeve! It worked. I became the writers’ PA and it suddenly felt like the entire world had changed. The people from post made fun of me a lot that first year — they said once I moved over to the writers, they never saw me without a smile on my face. By the end of that first year, they promoted me to writers’ assistant, and the next year they gave me a script.
Lee: What did you learn from being an assistant in a writer’s room?
Deanna: There is no better masters class in TV writing than being an assistant in a writers’ room. I can’t stress that enough. I’d read books and blogs on TV writing and taken a couple of courses at UCLA extension, but seeing what I’d read about actually being executed, and seeing all the tiny reasons why creative decisions are made at every stage of the story taught me so much more. I grew so much as a writer, just from watching other people write.
I’d written this pilot when I was in post that I loved conceptually, but it was… truly awful. After being in the room for a while, I dusted it off and read it and immediately knew everything that was wrong with it. I rebroke it and rewrote it in a week, and that’s the sample that’s really changed everything for me.
Not only did I learn a lot about the craft, but being a writers’ assistant is also a great lesson in office politics. The assistants always know who’s mad at whom and why, and how that situation could have been avoided. I’ve been very lucky so far to only work on shows where the people got along and treated each other with respect, and I think it definitely helped me to observe the proper ways to both pitch and reject pitches without being a bully.
Lee: While on CSI, you were awarded the coveted freelance script – two of them, in fact. What was it like working on your first freelance, and what were you able to learn going from your first freelance to your second freelance?
Deanna: Haha. That’s actually a funny question. My first freelance script actually ended up being my second. My first season as a writers’ assistant, I knew there was an open slot in the schedule, but I felt like it was probably too early for me to go after it since I’d literally just been promoted. But the showrunner’s assistant encouraged me, so I wrote a CSI spec about a bunch of kids at a prep school who are basically playing the Hunger Games with each other with this high-tech equipment. Kinda like laser tag with bows and arrows. One of the kids ends up shot with a real arrow. It was actually super dark, but set in a fun/lighter world, which is sorta my MO.
I spent some time on the weekends with a Co-EP who helped me make sure the story had all the right moves, and then I had another Co-EP read it and give me notes before I showed the showrunner. It ended up going over really well, and my boss told me that we were gonna make that episode. Obviously, I was super excited… but then when it was actually time to start prepping that episode, we didn’t have the money to do it. The episode I’d written was pretty big with a lot of exteriors, and we were about to shoot the CSI: Cyber pilot as one of our episodes, which was also going to be very expensive. My boss told me that we’d have to write a bottle episode instead, and we’d have to do it very quickly.
A couple of us spent the first week of Christmas break at the showrunner’s house breaking an entirely new bottle episode, and then I spent the rest of the break writing, turning in an act at a time so my boss could get started on the rewrites. It was a super quick process, not ideal by any means, but exciting, and I learned a lot, and I truly feel like my positive attitude and immediate willingness to discard any plans for the holidays made my boss want to give me more opportunities in the future.
So the following season, he promised me we’d do the “hunger games” episode. He gave me notes, and I had just finished the rewrites when our episode order was cut. The slot that was supposed to be mine was the penultimate episode of what ended up being the final season, and it didn’t quite fit where we needed to take the series. I was paid for that script, and I got into the Guild after that, but alas, the “hunger games” episode of CSI wasn’t meant to be.
I think the most important thing I learned is that so much of the successes in this industry are built around attitude. Think about how stressed you get when you’re writing a script and then just imagine that you’re doing 15 other things equally as stressful at the same time, and that you have to repeat that process 22 times a year, back to back. That’s what your showrunner is going through. The best thing you can do is take one of those things off his/her plate. Or 1 1/2 of those things. Be a helper. Definitely do not add to the problem. And afterwards, share the credit, take the blame.
Lee: You were able to win a number of screenwriting competitions – what was that experience like?
Deanna: I like how you say “a number” of screenwriting competitions. Makes it seem like more than it was. The first thing I ever won (and the one that still makes me smile when I think about it) was the Nashville Film Festival Teleplay Competition. I’d entered LONG LOST, that reworked pilot that I mentioned before, at a bunch of places and then kinda moved on. CSI was cancelled and I was trying to figure out what was next when I found out I was a finalist in the NaFF. I decided to go to the festival and it was so much fun. I met some amazing people, and had a blast. And couldn’t fucking believe it when I actually won. I mean, I still can’t, to be completely honest. But it came at a really necessary time.
I was at a point where I was panicking about my next career move, wondering if I had what it takes, wondering if my boss had just given me those scripts because I was a good employee and worked hard, and not actually because I was a good writer. Then a few months later, I was one of five winners in the Lifetime Writers Project for the New York Television Festival which was great because I got to pitch my series idea and meet with a Lifetime exec. Those wins gave me some much needed assurance that I was on the right track.
I think entering these competitions in hopes of “making it” is a little naive, but they’re definitely a great barometer for where you’re at. If you’re winning or placing in contests, then you’re ready to be read by industry people.
Lee: In 2016, you got into the coveted WB Writer’s Workshop. What was the interview process like for you?
Deanna: Haha. I’m terrible at interviews. I had a phone interview for the NBC Writers on the Verge a few weeks before my WB interview. I called my manager after I hung up with NBC and said, “What are we going to do about WB? Because I think I just nailed this phone interview!” He very politely told me to chill out. After my WB interview, I was certain I’d bombed it, and my manager again, very politely told me to chill out. I didn’t advance in NBC WOTV, but I did get WB, so you just never know. My manager still has to remind me of that sometimes.
The interview process was intense, but I went in as prepared as possible. I had coffee with LaToya Morgan, a WB Workshop alum who I’d met through a mutual friends a few months earlier (and who coincidentally became my writing mentor in the program), and grilled her about her own interview experience. Later, I had a phone call with another WB workshop alum who I’d met at a WGA event, the incredible Rachel Caris Love, who gave me a lot of helpful advice (and who I ended up working on Blindspot with). [SIDENOTE: this is again why it’s super important to live in L.A. I had these connections just by going out and meeting people and doing things.]
It was by far the most intense meeting that I’ve been to in my very short career. It’s the three program execs/admins plus another WB exec, and they were all very friendly, but I was so in my head — I knew that if I got in, my entire career would be made. And if I didn’t, I might never make anything of myself. So yeah, the interview was me internally reminding myself of that over and over again.
One thing I keep coming across in a lot of these interviews, is that people want you to be ready to define yourself as a writer, which I hadn’t really thought about before. I mean, I write the kinds of things I’d like to watch, but I like to watch all sorts of different shows. I think part of it was that I’d written a JANE THE VIRGIN as my spec, but my pilot was more mysterious and darker. But I realized that both scripts, and everything I’d written so far, were stories about redemption or second chances. So it’s important to really be able to look at your body of work and figure out if there’s a common thread — both for when you’re selling yourself as a writer and for when you’re writing.
Lee: What were the biggest takeaways for you from this program?
Deanna: I don’t even know where to begin. Biggest takeaway for sure is the relationships. I became so close with the other eight writers in the program — some of them are like family now. We also got introduced to a lot of executives at WB, which is valuable for obvious reasons. Being an alumni of the program puts us into a little club of our own. I was at a WGA event last night and the guy sitting next to me was a WB workshop alum, which gave us a ton to talk about. Chris Mack and Rebecca Windsor who run the program really do a great job of cultivating an environment where we all feel a sense of loyalty to one another. We know how hard it is to get into the program, how rigorous the program itself is, so it’s easy to feel immediate respect for anyone else who’s been through it.
Another thing that really helped me about the program, and this requires a bit of insight into my psyche: I’m hyper-prepared for everything. I don’t go to a restaurant without deciding what I’m going to order from an online menu. I get to work at least an hour early every day to read through the notes from the day before and think about ideas to pitch. Spontaneity is not my strong suit. I don’t want to get into too many details about what they did in the workshop to beat this out of me, but there’s a sense of unsteadiness throughout the program. They’re sorta constantly looking for ways to pull the rug out from under you and see how you react. As paranoid as this made me, it really, truly helped me out in the real world. On BLINDSPOT, I had to pitch my not-quite-broken episode to the showrunner with zero notice, and I wanted to cry. It was my first big pitch, and not only had I had no time to prepare, but there were still holes in the story. And did it go perfect? Not even close. But I got through it. And I realized that there will probably be very few times that I will actually get to prepare as much as I’d like, and that’s okay too.
Lee: What surprised you most about the WB program?
Deanna: The talent and support. The first day of the program, I looked around at the room and wondered who would end up annoying the hell out of me. I was shocked when I actually ended up liking every single person there. Chris and Rebecca do a great job of selecting really genuine and kind (and not annoying) people. From the program itself — I was surprised at how willing everyone was to help each other. I expected it to be a little competitive, but we weren’t like that at all. If someone’s story got blown up, we’d spend several hours at the bar after class helping them fix it. And when it came to staffing at the end of the workshop, we were rooting for each other just as much as we were rooting for ourselves. That sounds so cheesy, but it’s one hundred percent true.
Lee: What should writers who are applying to programs such as WB’s TV Writer’s Workshop know about these programs?
Deanna: I mean, I can really only speak to the WB workshop. It’s so much work. And it’s intense. I spent the entire time thinking I was going to get kicked out of the program, that they’d figure out they’d made a huge mistake letting me in. But the truth is, they desperately want us to succeed. They’re putting a lot of time and money and energy into us, they want to have made the right decision.
I’d say, if you get into the program and you have a little bit of financial freedom, quit your job and clear your schedule. It’ll make your life so much easier not to be working. Some of the other workshoppers had full-time jobs my year, but most of them had to take some sick days. The deadlines are impossibly hard, and you’ll be writing over Christmas for sure. But it’s only six months of your life and will all be worth it in the end.
Also — I think a lot of people torture themselves over what show to spec. There’s no perfect answer, but if you pick a show you know really well and love, and that fits your sensibilities, it’ll show in your script. And that’s what’s important. Good writing trumps an imperfect show choice. And this is so obvious, but be sure to format your script correctly to the show you’re speccing. So many people don’t make it past the first round because they have the wrong number of acts or they’ve misspelled a main character’s name.
Lee: You are currently on BLINDSPOT. How did you come to be staffed on this show?
Deanna: I got staffed on Blindspot right out of the program. I was very lucky because it happened very quickly. Blindspot had their season two order very early on, so Chris put a few of us up for it in March. We met with the showrunner and two Co-EPs and then waited to hear back. Typically, the idea is that we’d get staffed off the pilots we wrote in the program, but because the Blindspot meeting came when that pilot was still unfinished, Chris submitted my HOW TO GET AWAY WITH MURDER spec that I’d written in the workshop and LONG LOST, which was the pilot I used to get into the program (and was about a girl with amnesia who realizes she was maybe a bad person… so kinda perfect for Blindspot).
It took a couple weeks to hear back, which was very stressful, but ultimately I was grateful not to have to do the multiple meetings and waiting that is staffing season. And I got put on the show with another writer from my year, Hadi Deeb, who is so great. It was very scary being the new person on a show where everyone else knows each other, but it made it way better to have a close friend in the same boat. We’d just went through the trenches together, and here we got to do it again in a new environment. Plus there were two other WB workshop alums already on the show, and they were great about supporting us in the room.
Lee: Could you tell me a bit about what showrunner interviews are like?
Deanna: I’ve only had the one so far, so I can only speak to that, and I don’t think it was a typical example. Martin doesn’t read writers until after he’s met with them (which is basically the opposite of all other showrunners). So there was no talking about my scripts. We talked about Blindspot, and I think it helped that I was a legitimate fan of the show going in, so I knew it really well.
He asked what I didn’t like about the show, which is always a scary question. I was honest though — I think the thing they reminded us in the program — it’s no good to trick someone into hiring you. Those meetings only work if everyone does their best to be themselves. It does a writer no good to try to anticipate who it is the showrunner wants and then try to be that person because then they’re going to spend the entire season either out of their element, or disappointing the showrunner.
We actually spent a lot of time talking about my history in reality TV. Martin is a huge The Bachelor fan, and one of the Co-EP’s in the meeting was very curious about what the Kardashians were like in real life. What I do remember was that the meeting was very, very short. I thought it was a bad sign, but he’d schedule them that way.
Lee: You are represented by Verve. How did that relationship come to be?
Deanna: The Verve relationship is very new, and it came through my managers at Echo Lake. Around the time that CSI was ending, I formed a really great relationship with the CBS exec who covered the show. I’m actually gonna give a shoutout to her because I basically owe everything that’s happened to her kindness and generosity and expertise. Amanda Palley read my script and sent it around to managers. Then she read another script, gave me notes, and sent it out to more managers. She’s been a great advisor to me.
Just before NaFF, there were some bites, people were responding to LONG LOST. One of the people she’d sent the script to was Zadoc Angell at Echo Lake. He was someone whose name I kept hearing. He repped one of the women in my writers group, and she was very fond of him. A few of my friends knew him professionally and spoke very highly. I’d even read the interview you did with him, and I immediately liked him. You could tell from that interview that he was thoughtful and detail oriented. I’m a nerd, and I wanted someone like me, not some cool agent-type. He was the big get for me, so when he expressed interest, I was elated.
He and Amotz Zakai rep me at Echo Lake, and after I got into WB, we sorta decided to hold off on getting an agent. The great thing about the program is they work as your agent at the end of it, so there’s no rush or need for one right away. After I was comfortably settled at Blindspot, Amotz and Zadoc came up with a short list of people who they thought would be good for me and they sent me out. It goes to show how good of a job Zadoc and Amotz did — I really liked everyone I met with, but when I met Felicia Prinz and Zach Carlisle from Verve, it felt like a very easy and obvious decision.
(Shameless Plug: Zadoc Angell is also one the managers I interviewed for my new book, BREAKING IN: TALES FROM THE SCREENWRITING TRENCHES)
Lee: What do you expect of your reps, and what do they expect of you?
Deanna: I expect them to keep me employed, and I imagine they expect me to keep myself employable. I’m still so new to this, so I’m not sure what to expect honestly. Definitely regular communication. And I know one thing that was important for me when I was looking for managers was that I wanted someone who had a good eye for story, who could give me critical and constructive notes on my work, and my managers are great at that. I know a lot of people are on the fence about whether or not they need both agents and managers. For me, I knew I needed both, because I rely on that extra development help.
A lot of people get into this mindset that’s like, “Oh, they’re my reps; I’m their boss,” which is kinda an unhealthy attitude. It’s a relationship that paychecks depend on, so it’s a delicate thing. I think when it’s working right, it should feel like a team. I’m so grateful to have them though — I spent ten years in L.A. feeling like just one person, afraid I wasn’t going to make it. Now, I have this team of people around me whose job it is to make sure that I do. That’s a pretty exciting thing.
Lee: What is next for you?
Deanna: I don’t know! It’s exciting and scary. We don’t know if Blindspot is coming back for a third season yet, so I’m just reading pilots and getting ready for staffing season. We’ll see!
Lee: Finally, do you have any advice for other writers who are trying to break into television writing?
Deanna: So much advice. Always be writing. I think getting a job as an assistant in a writers’ office is the way to go, but don’t limit yourself to just that. Apply to the fellowships, go to networking mixers, do everything you can to put yourself in a position to break in. There’s no one way.
Some people might think that I wasted eight years as an assistant on a job that ultimately didn’t lead anywhere. That I should have just applied to the WB workshop eight years ago. But honestly, I don’t think I would have gotten in back then. I became a better writer after being in the room at CSI. Plus every one of my big accomplishments can somehow be attributed to my time at CSI. I met Amanda Palley who introduced me to my managers. Don McGill, my old showrunner at CSI, called and made a hard sell for me at Blindspot. Besides, the more writing staffs you work on, the more writers you will know, and those are the people who will be hiring you at your future jobs.
Lastly, surround yourselves with people who share your ambitions and who will support you in your own. This industry is so much easier to navigate when you have people in the trenches with you.
Deanna grew up in The Winter Strawberry Capital of the World (Plant City, FL). As a child, she spent her free time writing stories on her dad’s computer and avoiding normal human interaction with other children. Always a writer at heart, Deanna attended the University of Florida, where she majored in Public Relations and was taught how to write press releases and bios like these. However, it was her creative writing and television elective courses that really excited her and eventually pointed her in the direction of Hollywood. After a brief stint on the pilot of Keeping Up With the Kardashians, Deanna got a job on CSI, where she held positions in both post production and the writers’ department. She ended the show’s run as writers’ assistant, with two freelance scripts under her belt. In addition to getting into the Warner Bros. Writers’ Workshop, she was an NYTVF Lifetime Writing Fellow, and her pilot Long Lost won first place in the 2015 Nashville Film Festival Drama Teleplay Competition. She now works as a Staff Writer on NBC’s Blindspot. Follow Deanna on Twitter: @deannashumaster
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Breaking In: Tales from the Screenwriting Trenches