The Squeaky Wheel Gets the Grease: How Persistence and Discipline is Paying Off for Screenwriter Kaylord Hill

I first took notice of Kaylord Hill on Twitter, where he was encouraging other screenwriters to apply for SoCreate’s “So, Write Your Bills Away” Sweepstakes. Encouraging is probably the wrong word. He was maniacally tweeting about SoCreate sometimes up to 30 times per day! And you know what, we took notice.

Kaylord gained bonus entries into our sweepstakes through his tweets and shares and eventually was drawn as one of our top 25 semi-finalists. I knew this man was determined to be a successful screenwriter, but I didn’t know just how determined he was until I learned more about him during a recent interview. I think we can all learn something from Kaylord’s story about persistence when it counts.

Kaylord took some calculated risks to get where he is today. He’s pursuing a Master of Fine Arts in screenwriting at the University of North Carolina School of the Arts, after leaving behind a great career.

“My conscience kept saying, “what about writing?” I was writing poetry, but it wasn’t fulfilling like it had been in my earlier years,” he told us. “One day in a hotel, I googled the word 'screenwriter.' Because I'm naturally curious and competitive, I started looking for the people that had accomplished the most in the field. I realized no African-American had ever won an Academy Award for Best Original Screenplay (gee thanks Jordan Peele) and that put me on my way.”

But can a person decide to be a screenwriter one day, and start working at it the next? Yes, and Kaylord is proof.

“I ordered Coffee Break Screenwriter. I was thinking, wow, I can write an Academy Award-winning script five minutes at a time,” he laughed. “That book is still on my shelf and a great resource. I went to script classes in Houston and Austin. Over the course of about five years, I developed enough confidence to finally apply to film school.”

But it wasn’t as simple to get in as it was to decide he wanted to attend.

“Persistence is key,” he explained. “I got waitlisted when I applied to UNCSA for the Screenwriting MFA. I probably called and emailed the folks at the school two to three times per week, until they told me after Mother's Day, okayyy … you can come,” he joked. “It was the most liberating feeling.”

Since then, Kaylord has learned to approach the craft of screenwriting with discipline and again, persistence.

“Once upon a time, I'd wake up and say I'm going to write until midnight. That ain't it. Now, I turn my phone off, and I block out a specific time to produce a certain amount of pages, “ Kaylord said. “I learned that from my mentor and Danny McBride (UNCSA alum 🙂). And I read. I read a ton of scripts. If I'm working on a feature, I'm reading feature scripts. If I'm working on a pilot, I'm reading pilot scripts.”
“Make a schedule. Turn your phone off. Go play. Your writing time is sacred time,” Kaylord explained. “The professionals you learn from or are influenced by treat their writing time like it's a precious gem. They're not attempting to be professionals or attempting to look the part; they're DOING. If you aspire to achieve audacious things in the industry, then you have to conduct yourself and train your writing to do just that.”

In speaking with Kaylord, it was clear to me that he treats his craft seriously and with respect. He thinks deeply about his tone, message, and who he wants to emulate. He’s patient with himself and with his work.

“I aspire to write as diverse as Billy Wilder, as culturally as August Wilson, and as visual as Barry Jenkins,” he told us.

Kaylord is currently adapting a book called “Solitaire” into a television series. In the 11th hour of Nazi Germany succumbing to its destruction, a woman deals the final cards of her life in an attempt to reconcile how she shed her humble Jewish upbringing to become Magda Göebbels, the “Unofficial 1st Lady of Nazi Germany.”

He’s turned off his social media until December 2, when he anticipates he’ll finish his project. Kaylord plans to launch his personal website summer 2020.

He graciously shared two shorts with us during the “So, Write Your Bills Away” Sweepstakes semi-finalist process, and you can read them here.

As my dad always likes to remind me, the squeaky wheel gets the grease,