Does a working writer keep improving?

questionmarkI am a reasonably successful screenwriter. A working writer. I’ve sold two pilots, gotten a freelance episode of a high-quality one-hour drama, done some comic book gigs, and just sold a feature with myself attached to direct at a production budget of $3M.

Not A-list, or B-list, but maybe C-minus working my way up. I’m in my early thirties and have been at this a couple years.

My problem/question is: I feel like I have hit a wall with respect to my sense of story. I feel like most of my success has been gotten on a combination of ability-to-pitch, charisma and the ability to turn a phrase inside a scene. But I have this real weakness when it comes to knowing what the right scenes are in the right order. Story. Plot. I can put two people in a room and have them riff in a pleasing and entertaining way and to the extent that my story supports this kind of loose, Kevin Smith-esque writing, I do well.

But I know that if I want my career to go to the next level, I need to improve my understanding of story and plot.

So I guess I have two questions…

1) Any ideas on how to do this on an intermediate/advanced-level? How can I go from a “B” understanding of story/plot to an “A” understanding of story/plot?


2) What are your thoughts on how to keep making breakthroughs in the quality of your work when you are at an intermediate/advanced level? Do you feel like you are constantly improving? How do you keep improving?

– Scott
Los Angeles

You’re already the envy of most of the readers of this site: you’re a working Hollywood writer. So congratulations, and don’t dismiss what you’ve accomplished. I’m happy to hear you attribute it your skills (pitching, wit) and not pure dumb luck.1

So let me offer some good news. The stuff you’re not especially good at — story, structure, plot — can actually be learned. If you were writing in for advice about how to be funnier or more charismatic, I would have probably let your email sit in the growing folder of unanswerable questions, because those are pretty much inherent qualities.

My advice for you is to dedicate one day a week to disassembling good movies. Take existing films (and one-hour dramas) and break them down to cards. Think of yourself as an ordinary mechanic given the task of reverse-engineering a spaceship. Figure out what the pieces do, and why they were put together in that way.

Here are the questions you need to ask about each scene or sequence:

  • As the audience, what am I expecting will happen next?
  • What does the character want to do next?
  • Is this a good moment to let the character achieve something, or knock him back?
  • How long has it been since we checked in with other character and subplots?
  • What would have happened if this scene had been cut? Or moved?

By asking these questions about other people’s movies, you can take some of the pressure off.

When it comes to your scripts, it might be worth writing something that’s deliberately outside of your comfort zone, a script that doesn’t let you rest on your scenework. Because to answer your second question, yes, I think you can keep making breakthroughs in your writing, but only by challenging your preconceived limitations.

I’m currently writing my first period movie, my first stage play, and my first stage musical. Part of the reason I’m enjoying them is because they scare the be-Zeus out of me. I’ve passed on some more obvious projects that I’m sure I could have written competently simply to stretch a little more.

Yes, I’m deeper in my career than you are. And my flitting from genre to genre has probably hurt me in some respects.2 But a career isn’t one script, or ten, it’s the years of your life. You’re working. Your ability to turn clever phrases won’t go away. So you’re right to focus on the areas you think you can improve, if only to increase your confidence and enjoyment of the career you’ve chosen.

  1. Luck accounts for a small but not unimportant part of success in screenwriting, or any career. Being ready to be lucky, and what you do with that good fortune, is a big part of how a career goes. I was lucky to get into my film school — I honestly didn’t know how competitive it was. I was lucky that Tim Burton happened to be looking for a project when Spielberg dropped off of Big Fish. And, of course, I was lucky to be born in an upper-middle class family in Colorado.
  2. Despite Big Fish, I rarely get sent the “big books” that sell out of New York. And it’s hard for me to set up a pricey original, because I don’t have a long track record in a specific genre.

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