A Decade in Coaching: The 5 Attributes of Successful Screenwriters

Lee Jessup6 CommentsGeneral Career Advice, Open Letters & Confessionals, Uncategorized

My friends and family know all too well: I love any opportunity to reflect and introspect. After all, many many moons ago, one of my friends came to see me in a whole new light once she declared that thinking was my vice. And what better opportunity is there for reflection than reaching a 10-year milestone for your coaching business? As I look back on a decade in coaching, I find myself thinking about what I learned in this time. What conclusions can I draw? What assessments can I make having worked with the hundreds and hundreds of writers I’ve had the privilege to get to know and work with over these years? 

This line of thought emerged during a conversation I had with a writer I just started working with a few weeks ago. A talented scribe building his body of work, the writer had his sights set on breaking in writing the one genre that most reps would tell you not to write as it’s near impossible to break in with it: Westerns. Now, before we go any further, let me just say that one of my longtime clients, the uber-talented Eileen Jones did sell a pitch for a Western feature (in which the word Western was never uttered) to New Line Cinema in 2020, so I know that everything in this industry is possible, but it did get me thinking: Over my decade coaching, what have been those writerly qualities that make a writer undeniable, whether or not they’re writing a Western? 

Talent 
To many, talent for scripted storytelling seems like a no-brainer. Surely, you’d have to have some level of talent to become a successful screenwriter. Over the years, I’ve found that different writers arrive at screenwriting with different levels of talent. Some begin their writing journey with a well-developed voice, but a lack of a comprehensive understanding of structure. Others arrive with an innate story sense, a feel for how screenplays, pilots and TV episodes work, without having taken classes or read books to understand it. 

However, there are also those writers who arrive at screenwriting, be it for TV, features, or both, not because their talent drove them to it, but rather because of a desire to tell stories visually. Those writer, in my experience, are going to usually find themselves learning the craft and developing their voice and talent over time and over many pages, often in writing classes where they will shore up their understanding of character, theme and story construction. There is absolutely nothing wrong with this – a good script is a good script, no matter how the writer arrived at it as long as he’s done the work to get it there. But I do find that the more innate talent a scribe has when starting off on this journey, the further they will get right out of the gate. 

And if you’re reading this and wondering what classes you should take, be they for solidifying structure or supporting your innate talent with craft, here are a few that I’m a big fan of: 


Passion
For me and when it comes to pursuing a screenwriting career, little is as important as passion on the page. Passion on the page can convert the biggest doubters into even bigger fans; it’s the thing that makes a Western pitch (which is not quite on the page but I’m sure you get what I’m saying) to sell. We’re talking about not just passion for writing as a whole, but passion for a specific project, a specific story that the writer has to get out of their system, needs to tell. 

Whenever I think about passion on the page, I think about my longtime client Michelle. Michelle and I started working together way back in 2013. Previously a development executive, Michelle was eager to get a new, solo-writte screenplay under her belt, and she knew what she wanted it to be: A Mad Hatter origin story. She’s been thinking about it and researching it for years. The only problem was… Tim Burton’s Alice in Wonderland came out just a couple of years before. Was there still an appetite for the Mad Hatter? Plus, it was a period piece, and both Michelle and I knew how the industry felt (and still feels) about those. Michelle and I debated whether to pursue this project or others. She brought more ideas to the table, but none of them quite stuck like the Mad Hatter origin piece she’s been wanting to write for years. It quickly became abundantly clear that Michelle needed to get this Mad Hatter script out of her system. Within a few months, she wrote the screenplay MAD, which, to this day, is one of my favorite feature scripts. Her affection for the original IP and the characters in hand is evident on every page. 

MAD went on to open so many doors for Michelle: She secured representation. Took a million meetings. Landed two writing assignments, which in turn got her into the WGA. It also got Michelle into WIF/The Black List lab. It has not been made (yet) but it’s done so much for Michelle’s career nonetheless. A reminder that passion on the page will convert even the biggest naysayers, and will get the script over some of the hurdles that are sure to come its way. So when writers come to me and ask what they should write next, I encourage them to ask themselves: What is the story that you are most passionate to tell? The answer to that will probably have a lot more promise than any script the writer could be writing with the sole purpose of an easy sale because… 10 years into my business, I can tell you that “an easy sell” just doesn’t exist the same way that it used to these days. Building a screenwriting career is never easy. Might as well fight the good fight for screenplays and pilots you genuinely believe and are invested in. 

Craft 
As noted above, talent and passion are so important when building and sustaining a screenwriting or television writing career. While it’s never going to be easy, all of my years in coaching have taught me that it’s very much possible, so passion and talent will be integral to power the writer through those more challenging career building moment. 

However, screenwriting is also a craft. Much as becoming an architect would require some learning of home building  fundamentals, screenwriting, too, demands that the writer learns the craft and use it to communicate their passion and display their talent. 

If a writer is writing on his own, without any desire to ever have a project financed, land a writing assignment, staff in a writers room, or develop a screenplay or pilot with counterparts in the professional space, then sure, craft may not play an important role for them. They may write as untraditionally as they’d like, rules and structure be damned. But for anyone who is looking to build and sustain a screenwriting career, understanding the inner workings of craft and the unique design that goes into every project will be integral. Writing is a developing craft. Therefore, the more the writer writes, gets notes, rewrites and adjusts, the stronger their craft will become. It’s the understanding of craft that will allow the writer to be successful not only when developing her own original projects, but also also when engaging with the industry on writing assignments, in writers rooms and on soon-to-be-produced projects.

360 view of any project 
Okay, this is going to be the part of the blogpost where I just have to vent: If I have one pet peeve when reading screenplays and pilots, it’s having questions about its characters and the choices that they make, things that don’t really track or add up, that the writer then does not have the answers for. It’s okay to have an answer that the reader may not see or agree with. It’s okay, especially with pilots, to make a choice to hold back on some explanations with the aim of revealing them later. But not having a full grasp of the material can be detrimental to its industry potential. 

By the time a screenplay or pilot goes to the industry, be it on spec or written on assignment, the writer must be the authority on everything it contains, be it character choices, thematic choices, world logic or mythology. In other words, the writer should own every word on the page. If the writer has developed a pilot, he needs to understand the multi-season trajectory of the show. In fact, some of my professional writer clients can’t begin to develop the pilot until they have an understanding of the full scope of at least the first season. TV projects tend to require more of a 360-understanding, but feature writers, too, should be able to answer any “Why?” driven question that is asked about their project. In other words, even if it’s not on the page, it better be something the writer thought about and is ready to share. That sort of authority over the material inspires executives and producers alike to want to work with the writer. 

Rebound 
If you’re thinking that being able to bounce back from disappointment and frustration has nothing to do with the actual writing, you’re not wrong. However, over the years I’ve found that those writers who are able to put their passion into a project only to then move on to their next project when the previous one didn’t receive the attention they had hoped for, are the ones who are able to keep pushing forward in their name of their career, whether they’re just starting out or already well on their way. 

Of course, it’s heartbreaking to put your heart and soul into a piece of work, to immerse yourself in it, to receive the feedback that confirms that it’s landing as you intended, only to come up short when the material makes the rounds in the industry itself. There’s no two ways about it: It’s hard to stomach, and difficult to recover from. But screenwriter will have a number of projects that she completes and gets out there throughout the life of her career, be they original pitches, pilots or screenplays. So while the disappointment is real and deserves to be given its moment, it’s also important to learn to move on from it, to get immersed in the next thing. 

And the truth is that nothing is dead in the industry, until it is. Last year, I had a writer client take an elaborate show pitch out to 20+ potential buyers. There was lots of interest but ultimately none of the  buyers came to the table. The writer went on to set up a different show over at Netflix and then land a page-one rewrite on a feature with another streamer. Over a year later, that project that was pitched to 20+ places without any takers suddenly came to life, and sold, over a year after it first went out, to a prestige network. 

If the writer wants a screenwriting career, the ability to recover from disappointments is going to be key. There will be heartache; that goes without saying, and it’s important that the writer has community in place to help see them through their career downturns, and onto what comes next. But it’s learning to recover, to move on to the next project, to remain creative and passionate and excited in the face of things not going the writers’ way, that is sure to compute into ongoing and sustainable screenwriting success.