How did you become a writer?

I just started writing. That’s the beauty of it. You don’t need to ask anyone’s permission. You just sit down, start writing, start making mistakes, start learning from those mistakes. And hopefully, along the way, you get a little better at it.

The first time I ever got paid to write was as a copywriter in advertising. I had been working in the mail room and the Creative Directors took a liking to me and decided to give me a chance. So I’ve been paying the bills as a writer, of sorts, ever since.

As far as narrative writing goes, one day I just sat down and decided to try writing a novel. Then I adapted that into a screenplay. Then I wrote some more screenplays. I just keep writing. I find I learn a lot about myself and how I view the world when I force myself to really organize my thoughts around a specific story. So that keeps me coming back for more.

Name your writing influences (writers, books, teachers, etc.).

Richard Russo. Kurt Vonnegut. George Carlin. David Letterman. Leonard Cohen. Monty Python. Raymond Carver. Michael Arndt.

When and where do you write?

I don’t have any real routine. When I’m working on something, I try to stay on it. Try to write every day if I can. But I also try to pay attention to when I need to step away and solve some story problems in a way other than just bashing at a keyboard. 

I have an office in my house. So I pretty exclusively write there. Almost always at night. Or in the evening, at least. I find it easier to concentrate when the phone isn’t going to ring or an email isn’t going to demand immediate attention.

What are you working on now?

I have a feature screenplay that I’m working to shoot. It’s finished, but I’ll still be poking at it here and there right up until we shoot the scenes.

I’m also working on some new versions of my “At the Bar” series that are going to be on television. Kind of an interesting sponsorship opportunity. Those are fun to write. The tone is so specific that it’s a good repository for strange ideas that pass through my mind that wouldn’t really fit anywhere else.

Have you ever suffered from writer’s block?

Writer’s block, to me, is just a story problem. If I don’t know where my story is going, or why, then I find myself having trouble writing. So I try to recognize that and get down to the core problem. Do some more outlining. Try to figure out if I’ve painted myself into a corner somewhere along the way.

What’s your advice to new writers?

Write. And finish things. Don’t let yourself get bored by an idea after the initial thrill of it passes. Writing isn’t the act of turning words into sentences. It’s the act of turning ideas into stories. Stories have a beginning, middle, and end. So go all the way to the end. Then go back and fix things and make it better. Don’t stop in the middle because you think your story is no good. You might be right. But there’s a zero percent chance it will get better if you quit.

Jason Headley's short films have been featured on NBC's TODAY Show, the front page of Reddit, the front page of Funny or Die, chosen as a Finalist for the Comedy Central/NYTVF competition, a Vimeo Staff Pick, official selections of the Mill Valley Film Festival, St. Louis Film Festival, and the Best of Shorts programs at the Carmel Arts & Film Festival. His short "It's Not About the Nail" has over 10 million views and counting.

Coming from a long line of yarn-spinners and bullshitters, Jason began his storytelling career in earnest with the publication of his novel, Small Town Odds. His screenplays have made the Quarterfinals of the Nicholl Fellowship, the second round of consideration for the Sundance Screenwriters Lab, and the quarter- and semifinals of other national competitions. Fun fact: Jason is more handsome in real life than he is on camera, but he's still not actually handsome.