Outline Troubleshooting (Outlining Series – Part 3)



As the final part of my outlining miniseries, I want to address a few pertinent outlining questions as sort of preventative troubleshooting. They are by no means comprehensive—much of what goes wrong in writing is individual to the story, and I couldn’t begin to help you troubleshoot unless I sat down with you and talked about your story at length. However, thanks to some fellow writers from Instagram, I have a short list of broader outlining questions that I can answer and that will hopefully help you as you outline.


Where do I start?

The beginning.

Joking aside, I use the same method for worldbuilding as I do for outlining: begin with what details you do know, then build the web from those points, filling in the holes as you find them. For outlining this would mean taking the plot points or character arc moments that you do know—the argument between the protagonist and his best friend, the first incident with the villain, the natural disaster that devastates the city, the protagonist’s realization they have anxiety—and putting them in the order you think (or know) they occur. Those scenes are the bare bones of your plot.

From there, connect the dots: figure out what occurs between those plot points that causes them to logically happen, and continuing filling it in until you have the entire plot/outline. The detail of how much you fill in will depend on the method you use, but this technique works no matter how big or small your story is.

In short, start with what you have and build your web from there.


How long does it usually take to outline?

It depends on a) the outline method you use, b) the length of your story, c) how much time you have to dedicate to writing, and d) your natural writing pace. I know, it’s a vague answer, but it’s true. If you pick a sparse outlining method, like a synopsis or brainstorming notes, you’ll be able to finish it more quickly than if you pick paragraph summaries. If you’re writing a novella without subplots, you’ll be able to finish it more quickly than if you’re writing a thousand-page epic or a trilogy. If you have an hour or two each day where you can sit down and work on your outline, you’ll definitely be able to finish it more quickly than if other life demands take up most of your time during the week. And, if you’re naturally a speedy writer, you’ll naturally finish your outline more quickly than someone who’s a slower writer.

I’m at a disadvantage as far as time goes: I use the bulkiest outlining method, write very long stories, naturally take longer to finish my stories, and my free time for writing varies depending on the rest of my responsibilities. However, it works better for me than if I tried another method—and, however you fall into the categories, you’ll find a method that will yield the most benefits and be quick (or slow) enough for you. Just don’t be surprised if your outlining takes longer than you think it will (which is why it’s probably best to start outlining ASAP, especially if you want to get a rough draft done by a certain date).


How in-depth should I go?

However deep you need to feel confident that you can sit down and hammer out your story. I know, from experience and intuition, that I need to complete a lot of pre-writing work (like outlining) before I can sit down and write—not only do I write more quickly, but my writing is better and I have more peace of mind. This means that I figure out nearly everything except actual descriptions of the landscape and lines of dialogue. But every writer is different in this area. You may feel more productive exploring as you write and thus following a looser outline, or you may find that you need a combination of outline levels. You’ll know when your outline is detailed enough for you to move on to actually writing. There’ll be a sense of confidence and peace that you didn’t have before that point. It’s a trial and error sort of process, but, that’s the only real way to figure out how much detail you need in your outlines.


What should I do when I get stuck with the plot?

The only way to get un-stuck is to figure out what tripped you up in the first place. This means analyzing the trouble spot or spots and figuring out why they’re causing you trouble. For example, I got stuck on my WIP’s outline pretty early in Part 2. I couldn’t figure out why, except that the vague ideas of what I knew needed to happen in that part were overwhelming me. So I sat down and began typing up notes of what I knew happened out of order and added in questions to answer about the gaps that emerged. In doing so, I recognized the gaps in the plot and what I needed to examine. Once I had specific questions to answer, I came up with specific answers and got “unstuck” (in this case, I didn’t have a clear idea of the investigation procedure of the crime, and once I sorted out those details I was able to continue outlining).

So, next time you get stuck on your outline, pinpoint exactly why you’re stuck—do you not understand how to get your character from one location to the other? Do the actions of certain characters suddenly seem illogical? Do you just have no idea where to go with the plot? Does the premise of the story seem off, like you may need to change it? Continuing looking and asking questions of yourself until you solve the problem. It may take a while, but with enough examining and questioning you can fix just about any problem.


For more tips and methods for outlining, check out the previous two parts of this series: Why Outline? and Outlining Methods for (Almost) Every Writer.

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