Writing Tips – Outlining for Success, Bottom Up and Back to Front

Author - Caitlin TurpinThey say we come in two types: outliner and discovery writer, and by way of disclaimer, I am an outliner to a fault. If you’re a discovery writer, I hope you still find this blog useful; if you’re an outliner like me, perhaps you’ll join me in the refining of the craft (or compulsion) of outlining, by which I mean, knowing when to stop. What’s necessary, and what’s just too much?

Here’s my writing tip. I’m going to go ahead and assert that, even for a discovery writer, there is a bare minimum of outlining that’s necessary. Whether you have it written down before you write any prose at all, or whether you discover it somewhere in the midst of writing, you need to know your ending if you know nothing else in advance.

A satisfying ending answers questions asked at the beginning, but in surprising ways. By this I mean that your ending, when reached, needs to turn out to have been there the whole time, if subtly. One way to do this is to (discovery) write all the way to the end, and then reconsider (and potentially re-write) the beginning with that ending in mind. The other (easier? outliner) way I’ve heard to do this (and my own experience has borne it out so far) is to decide on the ending first, even before you’ve decided on your beginning or any plot turns in between; in fact, especially before those. Write down your ending – it could be as simple and plot-level as, “Harry beats Voldemort,” or something a little more character-centered like “Steve Rogers regains his sense of self in connection to his redeemed past” – and you know what to aim for while you discover-write, if nothing else.

Your ending also gives you your beginning: just reverse the conditions of the ending, and that’s where you should start. Harry is a disadvantaged young orphan learning that Voldemort has killed his parents and is rising again to power: starting here, the readers both fear and expect the inevitable show-down, so they’ll root for Harry as he gains skill and confidence in the meantime. Steve Rogers struggles to engage with the modern world, given the loss of his friends and the modern world’s apparent loss of moral center: This makes us empathize with him when his trust is challenged, and really want to see his conviction, and those characters from his past, return.

Another way to go about choosing the ending is to find the one-sentence summary of your story. (For instance, “A set of characters come together from different backgrounds on an alien planet and end up preventing intergalactic war”.) That’s your ending. Expand it to two sentences; that’s your beginning and ending. (For instance again: “Racial tensions between natives and stranded colonizers heat up when a colonial probe crashes on an alien planet. Spurred by hope of rescue and fear of invasion, respectively, characters from both backgrounds eventually come together to prevent intergalactic war.”)

Imagine an outline as pins and yarn on a board. Two pins will give you one line of yarn, from beginning to end, and that’s all you really need. You’re free to discovery-write the twists and turns it’s going to take getting from pin A to pin B. Or, you can add more pins and maybe even more branching strands of yarn to your outline and really murder board it.

Push PinsWhat pins? They’re going to be different for every story. They will/should depend partly on character, partly on tone, partly on genre; so take time to get a handle on those things, (always remembering that you can change them anytime you think of something better), and they may give you some worthy plot points just as your ending gave you a decent beginning.

That said, make use of templates and archetypical story structures (where applicable) to suggest plot points. Some formulas are overused tropes, but many are archetypical for good reason, because they break down what sort of progressions and payoffs have historically Made Stories Work (example: Star Wars: A New Hope, basically just the Hero’s Journey in space). For your perusal, here are: an excellent analysis of the “monomyth” general story structure, a list of several other common story structures, and a video on story structure by Brandon Sanderson (skip to about the 26-minute mark to get into the details).

You don’t have to follow any template slavishly. Even if you reject the idea of using a template, knowing the “typical” story outline will give you a good idea of reader expectations, which means that when you want to subvert a trope or surprise your readers, you know how to set up expectations for thwarting.

Which pins is one question; how many pins is another. At what point is your outline so detailed that you might as well just be writing the prose? I think the answer comes down to character. Remember that your plot should be character driven. As any discovery writer would probably attest, the characters come to life in the prose, not in the outline. Don’t pin your yarn so tight that the characters’ life and agency is stifled. Leave them room to make decisions, react emotionally, act unpredictably as they find their arcs.

No matter how detailed your outline, ALWAYS REMEMBER (this is a reminder to myself, really) that you can change your outline! It’s only a guide. It gets you from beginning to end, and whatever happens in between is up to you and your characters. You can pull out an intervening pin if your characters are pulling a different direction; definitely, whatever you do, never scoop your characters toward the next plot point without their agency. (Of course things can happen to them, as long as they react meaningfully.)

Really, my writing tip to my fellow (obsessive) outliners is just to give yourself permission to leave out-of-focus areas in your outline where your characters can breathe. For the rest of you – I hope you found some of my linked resources useful, or at least interesting; happy discovery-writing.

~C.J. Turpin

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