Screenwriting Career Coach & Big Break Mentor Lee Jessup on Connecting the Storyteller to the Story

In today’s evolving film and television landscape, having a fresh, compelling screenplay or TV pilot is a must for emerging writers. It’s what gets you into a meeting. But Lee Jessup, a longtime advocate for screenwriters and a key figure in the Final Draft Big Break winners’ mentorship process, says agents, managers and producers are looking for something more. 

“Today we’re in an age in the industry where it is about connecting the story and the storyteller,” Jessup says. “Not just about who has the most interesting story, but rather what is your personal connection to it.” 

Beyond the Script: The Missing Piece

For many emerging writers, this can be a blind spot. They spend years studying structure, dialogue, and genre, yet when they finally get in the room, they struggle to answer a deceptively simple question: Why this story? Why you?

Jessup’s work with Big Break winners often begins there. Before the meetings, before the pitches, before the networking strategy, she helps writers identify the personal throughline that ties them to their work, whether that connection is thematic, a lived experience, or an uncommon point of view.

That preparation becomes critical during the whirlwind of industry meetings that follow a major win. Writers aren’t just presenting ideas, they’re presenting themselves as artists, collaborators, and long-term creative partners.

“It’s really accessing that personal story, connecting the personal story to the work,” Jessup says. When you connect your screenplay to your own lived experience or point of view, the story will unfold more organically and become more emotionally accessible. 

So it’s not just about writing a powerful story, it’s about how you embody it and how you invite others into it with you. For writers, that means understanding that every room is different. The way you frame your story should shift depending on who you’re speaking to, what they respond to, and where common ground exists. It’s less about delivering a rehearsed pitch and more about creating a dynamic.

Being Your Own Champion

Sometimes, writers can be a bit shy and prefer to stay behind the scenes. But Jessup urges all writers to put themselves out there by applying for competitions, labs and workshops, and also exhibiting a strong brand – both in-person and online.

Writers, she says, need to think of themselves as their own representatives long before anyone else steps in. “You are your own champion, and as your own champion, you have to look at the avenues that can open doors for you.”

In other words, no one is going to build your career for you. The work isn’t just writing the script, it’s actively finding the places where that script can be seen and having that script fit into your brand as a whole.

Beyond script submissions and developing your brand, be thoughtful about relationships. Whether you’re in Los Angeles or not, Jessup stresses the importance of finding ways to connect with other writers, with industry professionals, and with anyone moving through the same ecosystem. “You never know where your break is going to come from,” she says. Instead of focusing solely on reaching the top of the ladder, she encourages writers to build connections with peers, assistants, and collaborators who are all on their way up. Those relationships are often the ones that matter most.

To capture that mindset, Jessup offers a metaphor that feels both daunting and liberating: “Your job, as a writer, is to put boats in the river.” Every screenplay submission, every opportunity and every relationship is another boat set afloat. When you’re consistently creating, submitting, and showing up, you begin to multiply your chances.

“Every single one of those represents a boat on the water,” she says.

Of course, volume alone isn’t enough. “Those boats need to be well-built and well-maintained,” she says, meaning your scripts need to be strong. The effort needs to be intentional. The more thoughtfully you put your work into the world, the more opportunities you create for something to come back.

The Takeaway: You Are Part of the Pitch

Jessup’s guidance ultimately frames how writers should think about their careers.

The script gets you in the room. But what happens next depends on your ability to connect your work to your lived experience, your perspective, and your voice. That’s what transforms a strong sample into a memorable introduction.

And it’s not a one-time exercise. Jessup works with writers not only on how to tell their story, but on how to adapt it in real time, like reading the room, finding points of connection, and building relationships that extend beyond a single meeting.

Because in an industry built on collaboration, the goal isn’t just to sell one project, it’s to establish yourself as a storyteller worth investing in long-term. It’s also a good reminder not to underestimate the value of your own perspective.

Enter the Final Draft Big Break Screenwriting Competition for your chance to be mentored by Lee Jessup or learn more about her work at leejessup.com.