Recently, as I’ve attempted to mature as a writer, I’ve been working on becoming a better outliner. Until recently, I never even attempted an outline. Even when working as a writer for a Government contractor I hated outlining. It’s really not how my brain works and from what I’ve read in interviews with established writers it seems I’m not alone.

Let’s look at what I think of as some of the pros and cons of outlining (this is nowhere near an exhaustive list):

Pros:

  • Gives you a clear sense of where your story is going
  • Improves continuity
  • Limits tendency to ramble
Cons:
  • Destroys spontaneity
  • Delays the writing process, extending time to finished product
  • Drains enthusiasm
Obviously, there are far more pros and cons to outlining than the three examples I listed for each, but these do an admirable job of getting to the meat of the debate on outlining: Preparation or spontaneity?
When I wrote Granted, it was almost completely spontaneous. I had Evan’s initial short script, but the only things I kept from that were the basic idea and certain characters. Where I think I was most successful with Granted, and something that I would contribute to not outlining, is the characters. Because I had no real plan for the story (outside of certain plot points) I was able to let the characters dictate what happened based on their personalities. Granted was a character-driven story, and for better or worse I allowed the characters to take me where they wanted to go.
Now, Granted is a bit of a special case because of the collaborative aspect of it, but its problems are indicative of problems with my other scripts – ideas that aren’t fully developed and excessive fat to the story/individual scenes. These could have been avoided with an outline, so I knew exactly where the story was going at all times, or even a stronger focus on revisions (not that I didn’t revise the shit out of it, but that’s a completely different story about the aggravations inherent in working with other people).
For my last script, The Time Bubble, I tried outlining the story beforehand. I had certain troubles with it because I don’t typically see my work in the broad strokes that outlining requires. Sure, you can get down into tiny details with outlines but to me that begs the question of, “Why aren’t I just writing it?” 
The most recent script I’ve started I’m finding that my characters are being forced into pushing the plot instead of the plot being pushed by the characters. I didn’t have this problem with The Time Bubble. The reason, I think, might be because of the allowances I gave myself with outlining. Basically I followed this workflow:
  1. Outline major plot points to first act.
  2. Write first act.
  3. Outline major plot points to first half of second act.
  4. Write first half of second half.
  5. Outline major plot points for second half of second act.
  6. Write second half of second act.
  7. Outline major plot points of third act.
  8. Write third act.
  9. Read.
  10. Revise.
  11. Read.
  12. Revise.
  13. –  45. Repeat read/revise adnauseum. 
I found that this strategy allowed me to see part of the larger picture while allowing for the characters to surprise me a bit. Typically, as I was writing an act, bits and pieces of the following acts would reveal themselves.

However, it wasn’t perfect. I stumbled a bit in the third act. While writing Act IIb (or, the second half of the second act) I came up with the climax, but was missing how to get there. That led to a bit of a block, but ultimately resolved itself in a way I think works.

There are other ways to outline than just hammering out plot points. For my next script I may try to write a story summary beforehand. This will give me the benefit of having written it stream-of-consciousness before putting anything down on paper, but give me the structure needed to keep the story moving and avoid writing blocks.

I’ll let you know how that goes.