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The Virtues of Outlining

by alexis
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Of all of the various and sundry side gigs that constitute my weird career, writing in various forms has always figured prominently. What with my technical writing, screenwriting, and the miscellaneous writing I do for proposals, planning, and of course this blog, it is known that I do a lot of writing. And as anyone who’s familiar with my output will attest, I’m unafraid of writing long things.

And so, folks who think they ought to do more writing frequently ask me for tips on how to be more productive. In particular, I’m often asked whether I use mind mapping software to help organize my thoughts.

I don’t.

I know myself, and I realize that if I allow myself access to a GUI for organizing the minutiae of organization itself, I will perish in an endlessly recursive loop of organizing the organization of my structure. I’ve done it before, every time I over-engineer a database or spreadsheet or scripting tool, and the result is usually that the thing I was building the tool to help make never gets finished.

So now I embrace simplicity by using Notes, on macOS, for pretty much all of my writing development (note-taking and outlining). Humble little Notes does absolutely everything I need. I used to use TextEdit, similarly for its utter simplicity and lack of features that might tempt me into wasting time on shit like style sheets and other nonsense. However, managing a folder full of individual document files, and putting time into different strategies for syncing them around my various devices, led me to try out creating the same kind of stuff in Notes, so that it would automatically be synced to all my devices without any farting around. And I liked it! Once Notes added folder organization, it reached a state of perfection for my workflow, as I could organize multiple notes into folders, one for each project. Bliss.

At this point I should probably explain myself. When I develop ideas for a writing project, I do two things.

First, I create vomitous piles of paragraphs elucidating every random idea I have for a project, in no particular order, sometimes separated by a bold-face title, usually not.

Second, when a certain critical mass is achieved, I find that I organically begin to crave some sort of order, and that’s when I begin development of an outline.

For both of these tasks, I require absolute simplicity and speed from my text editing environment. With the first task I’m primarily recording ideas I have in various states of being (taking a walk, in the shower, staring out the window, reading something, chatting), and then adding a bit of commentary or additional thought in the heat of the moment. With the second task, I’m looking to organize this information chronologically, to discover how all the bits and pieces I’ve cobbled together might fit into the context of a story that I can tell, or an explanation that makes sense, or a presentation of a topic, all of which require a beginning, a middle, and an end, preferably in a proportion that won’t bore an audience. In both instances, I simply require the ability to write and rearrange blocks of text in a vertical stack. Cut and paste, drag and drop, paragraphs with spaces in between, occasionally a bullet list. That’s it.

For every type of writing I do, I live and die by the outline. Now, I’m not saying that this is the only way. Some people like note cards, some people like mind maps, there are all kinds of ways of organizing the information you’re turning into a project. Me, I like outlines. I’ve tried these other methods, and they require too much preparation (writing notes on all those cards), or too much screwing around. When I’m in a position to write, I want to write. Simple text outlines with little to no formatting let me do that.

Both stages of my process are essentially the same task. I’m either wool-gathering concepts for my outline, organizing these concepts into an outline, or rearranging the outline. And I want to make it clear what the purpose of an outline is to me, because I’ve spoken with too many people who are afraid of outlining. And I believe they’re afraid of outlining because they’re looking at this task the wrong way.

I’ve been told “I don’t like outlining because I don’t have every step of the outline defined already, and I’m not ready to decide those things.” I certainly understand this hesitance, but here’s the thing:

Outlines are as much for identifying what you don’t know, as for organizing what you do know.

Every time I start putting together an outline, there’s all kinds of things I don’t know. The most pernicious are the things I don’t realize I don’t know. Once I start putting together an outline, usually with some sense of the general shape I want the project to take, I quickly discover “blank lines” in the outline structure where I know something should probably go, but I haven’t come up with anything yet. This is gold. Those blanks give me an opportunity to think about the project in a new way, to focus my time on considering the weaknesses and deficiencies of what I have so far conceived. In short, I welcome gaps in my outline, because they tell me what I should probably be researching or thinking about next.

The other thing I’m told, particularly by those writing fiction, is “I like the process of discovery, and if I outline the whole story then the process of writing it will bore me to tears.” I can understand this. At the end of the day, being a successful writer involves finding whatever combination of eldritch tricks and mind games will keep you writing. For some people, exploring the unknown is what keeps them typing in their chair. For others, attempting to write when everything’s unknown is a strong incentive to run away screaming.

I have no interest in making you do things the way I do them, because everyone’s different. However, if you’re outline-curious, here’s my perspective on outlines vs. the process of discovery:

Outlines are like planning a vacation; even though you’re choosing places to go, you still have to show up to see what’s there.

My outlines are usually a map of where the topic/story twists and turns. Ultimately, it isn’t until I get to each section or scene and start writing the actual text that I really start exploring that particular mental locale, and the result of that exploration may very well cause me to alter the structure of the overall outline in response.

And that’s why I like outlines. They’re easy to change, and I change them a lot. When it comes to filmmaking, I’d much rather delete a scene when it’s a couple of sentences in my outline, than take the trouble to write it out and get attached to it, to the point where I waste time and money shooting it, only to have the editor cut it out because they correctly identify it as extraneous (which I should have done in the first place).

So that’s pretty much my process. I take a shitload of notes. I cobble them into an outline. I use the outline to guide my ongoing research. And once the outline is complete enough for me to see where I’m going, I start writing. It’s a workflow that’s served me well, but of course your results will vary.

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2 comments

Jeremy W January 27, 2020 - 11:04 am

thanks for the prod, reminding me that I’m not doing much writing of things lately. have you ever tried using OmniOutliner to organize all your items? I used to LOVE the app (and it has cloud storage).

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alexis January 29, 2020 - 11:46 pm

I used to use the hell out of Omnioutliner, until I gave up on multiple levels of indentation. It’s a great program. The main thing I kept running into was that once I was done with my outline and ready to start working in another application (Final Draft, Pages, Word, Scrivener) converting my nicely formatted outline into a flat series of things that I could use as the structural basis for my work proved too much screwing around. So I embraced flatness. Maybe someday I’ll revisit, but for now I’m happy with my simple-minded workflow.

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