Zen and The Art of Outline Maintenance

Recently, talking with some writers, the question was put out about outlines. Specifically: Do you outline, or just dive in and see where it takes you? I was genuinely shocked at how many of them (it was a sizable majority) said they never outline. It actually annoyed me. Not in a ‘ooh, your free spirit makes me jealous’ way… in a way that was waaaay more cantankerous than that. 

‘Going out of turn at a 4-way stop’ annoyed.

‘Putting the milk back with only a quarter-cup in it’ annoyed.

‘Drinking expensive whisky with ice in it’ annoyed.

But why? Why did it bother me? Sure, I always outline. (okay, generally not blog posts and, yes, I recognize the irony). My approach in writing is always I want to know exactly where I’m going, and I want to be wrong.

In other words, map the arc and ending, but hope to have moments of inspiration that surprise and grow the narrative as it develops. But it can’t just be that people do it differently than I. 

Acknowledging that my way isn’t the only way (maybe), and that there are better writers than I who don’t outline (I suppose…), here’s what I could concoct as to why I was annoyed:

1. Teaching academic and creative writing, I’ve had hundreds – if not in the thousands – of conversations about loose, boring pieces that still somehow manage to fizzle away at the end. Invariably, they are not outlined. If it’s a non-fiction story about getting lost in Paris, 40% of it is about driving to the airport and going through security. If it’s an academic analysis of the use of setting in Charles Yu’s Interior Chinatown, by the end they’re just rambling about how without a setting there’d be nowhere for the characters to go!

2. Those times I’ve been writing something, thinking about it, obsessing over it, grudgingly working or eating or bathing. Just living the piece as it consumes me. Then it comes up in conversation and the other person says, “Oh! I write, too!” Then tells me about the 5 books they’re “writing,” but bailed out after about 5 pages of all of them because it wasn’t going how they’d hoped, but someday they’ll go back to them.   

3. Stories where it feels like it just meanders and gets lost in the weeds and the ending is enigmatic, at best, and you’re trying to make order out of it and make it all make sense. And to discover it just… doesn’t…?  

I don’t think my annoyance is justified on this. But, in the things I dug from it, the thread seems to be respecting the story, the process, the audience. Maybe that’s what I reacted to?

Or maybe it’s that the last project I worked on had fourteen distinct, interwoven outlines and it drove me a touch mad.

That’s not… out of the question…