To Dig Myself out of a Writing and Outlining Hole

24 January 2023, 12 March 2023

My current approach to writing has gone through a handful of changes. Actually, really more like frustrating starts and stops. Right now, things are going alright, but early in the new year they were really going really not alright. Here are some of my own reflections during that time, as I tried to dig myself out of a writing and outlining hole.

Right now I have an issue where the outline feels so out of date that I don’t even want to touch it. I am working with two different outlining techniques. A “storyline,” which is something of a condensed, prose-style, active summary of the story. Like a mini novel which still reads like a story, but is much easier to manage (to edit and fix) before it’s rewritten into the final full novel.

I tried making my plans more approachable by taking the storyline and putting it into the list. That was alright, but the outline now just feels huge and unapproachable. This is very frustrating. After journaling earlier about getting into the minds of characters, along with allowing for the mystery of inspiration, I wanted to just sit down and start writing.

But the list, while easier to navigate, is far more difficult to output inspiration with. Or is it even easier to navigate? (I just paused to read over it for 5 minutes, trying to navigate and see how I might fix things up. Five whole minutes. It is not that much easier to navigate.) Working with this list is possible, but so far it has been a fight. The fun of writing doesn’t really manifest with the list.

Writing the condensed storyline was much more fun, and the only downside was that I sometimes ended up accidentally writing full scenes rather than just condensed outline. (Which can be a nightmare, because it makes to document even more difficult to navigate. It also undermines the point of a storyline in the first place; that it’s easier to edit than just writing out a full first draft.) This could easily be addressed by removing the full prose scene and copying it into another document for later, and writing a condensed version in its place.

I had an idea for a solution to the navigation issue. It was doing the storyline in a document that was one giant two celled table. I could write the narrative outline on the left column, and then list the key parts of the scene on the right. This would give me a hybrid; having both in one place. The only thing is that it would feel a little clunky, and the list on the right would likely be a very thin column, so maybe difficult to read.

Okay, what about if I did a storyline, but before each paragraph or scene wrote a one or two sentence summary of the text? That way I could have the benefits of the storylining method, the ease of natural writing, letting ideas flow onto the page, and still have what I needed from the list–which is easy navigability.

(March 12 th Edit / Update: Over a month later, and this technique is going swimmingly, with a few adjustments. But that will be its own blog post.)

Looking at future issues that will likely come up.

One of the benefits I hoped for with the list idea was the easier re-arrangability. That is, if I got a new idea for an earlier scene, I could just insert it in. Or, if I needed to move some things around, such as an event needing to be moved to later (which has happened already), it would be easy to fix up the list. Copy a bullet point from one part of the list to the new location. But it is apparently not so easy to do. As I mentioned earlier, the list isn’t as easy to navigate as I thought, despite the fact that I have multiple levels or tiers.

How would re-arrangability work with this new way of doing things? This “Storyline with Headers” idea? Well, it might require a little more hunting, but the headers will help. (And they do, a lot.) They ought to be more easy to understand and navigate than the highest tier of the list because they will be more intentionally written. Rather than just being the beginning of a scene, or break point, a header could be a proper summary of what’s below in just a sentence or two.

The next issue is that I could forget to write the headers. The solution would be to develop a habit of going back after each paragraph / scene / chunk of text, and summarizing what I just wrote. Another issue? This breaks the flow of writing substantially! Should I really lose the flow state? What about doing it later? At the beginning of the next session? It isn’t a bad idea; it would give me an opportunity to get back into the story as well. But the downside is that my memory of the content (and more ephemeral, the intent) of what I wrote previously will have faded from my mind.

(March 12th Update: I have largely not executed on this idea of summarizing a paragraph or scene after writing it. Instead, I write the header before based on what I’m pretty sure will happen and usually just leave it as is at the end. Sometimes I do go back and add to / change the header to match though. Gotta keep it navigable right?)

I think in the grand scheme of things, as long as I make sure to actually write the headers in, I’ll be okay. Be that at the start of a new day, after each scene, or perhaps even at the end of a session, (or what I actually ended up doing; see the previous paragraph). In fact, the end of the session idea seems to have many advantages, since it doesn’t break up the flow of writing, but the content/intent is still fresh in my mind.

And what if this also ends up failing?

I will do another written brainstorm like this one.

March 12th Conclusion

My current method of outlining, which is more or less what is explained above but with a couple more moving parts to solve problems and prevent getting stuck, is working out great. Look forward to an update where I explain that method and those improvements soon! (And by soon, I mean maybe in a month or two haha.)

Thanks for reading,

Daniel Triumph.

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