Outlining—I Think I’ve Got It #amwriting

Occasionally I’ve blogged about @#$%@# outlining my novel. I’ve cursed. I’ve touted the latest book I’ve picked up telling me “how to outline your novel” or “how to write a good novel fast.” I haven’t spoken to the failures, the dead bodies, the frustration of being three-quarters of the way through 90k words and having NO idea how I’m going to END this sucker.

Outlining process… evolved to utility. At freaking last.

I talked a little about how Brandon Sanderson’s lectures helped out in The Short Story Rolls Forward! Now it’s time to reveal my… system. It worked for my short story; it’s working for my Novel In Progress. Let’s see if this process for directed seat-of-the-pants writing can stand the light of day.

The key idea that both Story Genius (Genius) and Save the Cat (STC) emphasised was that a story is about a lesson that is learned. A Deep Life Lesson. The protagonist is usually the one who learns it, but it can be another character. And the character in question can either a) learn it (drama or comedy) or b) not learn it and endure dreadful consequences (tragedy or tragicomedy.)

My story ideas almost always start with a character. This is where I can get stuck—I put my wonderful character through all sorts of situations but if I don’t have a lesson in mind, it means zilch. Hello, 70k words and no ending in sight.

I’ve learned that for me, that’s OK. Since I start with a character, as long as those cool scenes don’t run to more than about 20% of my eventual intended word count, I let ’em rip. It gives me a feel for my character, my situations, and my story world that I can’t get by top-down character construction and world building. It especially gives me a feel for what this character is good at—and where her weaknesses are. This stuff comes fast; it really doesn’t take that long to pound out about 10K words if I don’t have to direct it.1 This happens right in Scrivener, in my project.

Now come the hard part; taking a look at this hot mess and coming up with a lesson for my character to learn. This is the logline, theme and pitch building part of STC; the “What if?” portion of Genius. But for this, and much of the rest, I use STC, mostly because its practical language speaks to my engineer’s brain.

I’ve learned that I don’t have to “get this right.” Yes, my theme (the actual lesson) the logline, and the pitch (the blunt tool I’m going to use to bludgeon my lesson into my character’s head) can evolve. My first cut at this will be crude; I’ll know, for example, that the theme has something to do with the character’s relationship to her mom. I’ll take a good guess, but it doesn’t have to be right on. In practice, I evolve the theme more than I do the logline and pitch. I work these out on a whiteboard, scan them to Evernote, and transcribe them into a mind-map app. Alternatively, I can use a free-drawing note taking app (thence to Evernote and mind-map) instead of a whiteboard, but I strongly prefer a whiteboard.

Now, with the theme and logline in mind, I give my character(s) a past. What old ideas do my character(s) need to chuck? (Genius: Misbelief.) They must have them, or they wouldn’t need to learn anything, and I wouldn’t have a story. And how did they come by those ideas? (Genius: Worldview) Yeah, I go through the whole Genius “misbelief origin scene” and “reinforcing scenes” for my protagonist, and at least an origin scene for important sidekicks and villains. The only problem with this is keeping the theme in mind; but I find I can let these rip almost as fast as the original exploratory writing. This happens directly in Scrivener.

Finally, I fill out the fifteen “beats” from STC. I start with my bookends (my “Opening Image” and “Closing Image”) and fill in the rest of the pieces as they come to me. For this, I use a whiteboard, and I pace and talk to myself a lot. This is where I do classic brainstorming, which I can’t do while I’m sitting in a chair. This gets cleaned up, scanned into Evernote, and transcribed to that mind-map, which finally gets imported into Scrivener, both as documents and as a link to the original map.

It sounds a lot more structured than it is. Really.

What I don’t do is plan individual scenes / chapters. I know that STC and Genius both insist on planning scenes / chapters. All of them. In advance.

Other “how to outline” books and “how to write a novel fast” books do too; if not in advance, then just before writing the scene or chapter.

Sheesh. Every time I try this I get blocked for weeks.

Instead, I estimate the number of words between beats based on where I’d like the overall word count to be.2 I then draft a path of words from one “beat” to the next. If I get stuck I do a very loose mind map of a few things that have to happen between the beats. Once I make it to the next beat (I think of them as “islands”), I’ll do a preliminary trim to my beat’s target word count, as well as a quick “fit” to what’s gone before. If I need to adjust theme, logline or pitch, now’s the time. Then it’s typing a path of words to the next beat. Repeat until done.

I structure my Scrivener draft into folders based on beats (NOT acts) so that I can check the word counts on the fly.3 This keeps me from spinning off into the weeds writing forever on a cool side-plot. I write in documents inside the folder, breaking them into scenes as I go (based on change of location or time.)

This is working structure. When I’m ready to give output to someone else, I group the scenes into real chapters… about 3-5K words each that end on a natural cliffhanger. But I no longer work with chapters while I’m writing a draft. As far as I’m concerned, a chapter is a construct for readers, to give them a natural stopping point that nonetheless keeps them coming back to finish. I now first structure my draft so it’s easy for me to write, and add reader-friendly things like chapter breaks later.

So that’s it—my outlining “system”, such as it is. It’s designed evolved to give me maximum seat-of-the-pants room to wander around while herding me upstream towards my goal of a finished draft.


  1. A word about research: I research continuously. I write something that seems real-world based; I look it up, save the research to Evernote (no, I don’t use Scrivener for this) and modify the writing (or not.) I do the same thing for fantasy settings and science fiction settings, except using spreadsheets, typed documents, and drawn diagrams, scanned from whiteboards or created in a freeform note taking app. Certainly a lot of my research tends to happen towards the start of writing because that’s when things are still fluid, but I don’t research extensively in advance. It’s that seat-of-the-pants thing again. 
  2. I wrote a word count milestones estimator spreadsheet based on the pages in a script that STC suggests a certain beat be accomplished within. OK, I used to write apps for a living. Setting up an spreadsheet to do that is not hard for me. 
  3. A STC beat for a 90k-word novel runs anywhere from 3k to about 12k words. 

The Short Story Rolls Forward! #amwriting

The words are rolling.

I’d forgotten how good it feels to have the words flowing.

Oh, not fast enough to suit me. Never that! but a heck of a lot faster than they have been in the recent past. The short story I’ll be submitting for that anthology (positive! Think positive!) has a title now, “Fire Prevention” (which may change; who knows?) and the beginnings of a discernible structure—faint, but definite.

And I’d like to give some credit to Brandon Sanderson. Not that I’ve had the privilege of meeting the man, nor have I read his “How to Write a Good Book” tome—because he hasn’t written one. No, I’ve been slogging though the videos of his novel writing course at BYU.

Anyone who knows me face-to-face knows how much I loathe trying to learn from videos. It’s worse than having to sit through lectures. No lecture has ever gone fast enough for me, not even at MIT. No more does any video. My attitude is, “Just write it down, dude, and print your #$%^# lecture notes.” But I’ve gotten enough gems from the seven (of twelve) Sanderson lectures I’ve listened to so far that I (almost) don’t mind having to sit still for an hour and (try to) listen. At least I can rewind if (when) my ADHD kicks in. Problem is, it doesn’t go any faster on the second hearing…

But still. The most valuable stuff I’ve gotten from Sanderson’s lectures are a) what are the strong points v. the drawbacks of outlining, b) what are the strong points v. the drawbacks of “discovery writing” (AKA “pantsing”), and c) specific strategies to compensate for discovery writing weaknesses.

In case you hadn’t noticed, I am such a hard-core discovery writer that for formal technical writing I discovery-wrote and created the outline after. It’s part of the ADHD thing, I suspect, and attempts to force outlining upon my workflow have not worked to date. The dead bodies of numerous “How to Outline for Hard-Core Pantser” books litter my e-reader app, and various portions of outline anatomy likewise litter my Scrivener projects. (This is not to put down those outlining book authors. I’m sure it works for them, and seems to work for others.) Really, it doesn’t take much outline at all for my brain to start saying, “Wow, this is boring. I already wrote this story/technical paper/blog article; why do I have to write it again?”

But thanks to Sanderson’s lectures, I’m not saying that about “Fire Prevention.” I highly recommend them.

iThoughts and the Dreaded Outline

An Outline! For Real! Done with iThoughts by Toketaware
An Outline! For Real! Done with iThoughts by Toketaware
Well, there it is in all its multicolored glory. (The image is only two levels deep; the outline goes four levels deep but you’d never see any detail if I took a screenshot that way.)

It took me long enough.

iThoughts is a mindmapping app that runs on Mac and on iOS devices. The really nice thing about iThoughts is that, like Evernote, it’s everywhere. It uses Dropbox, or a WebDAV enabled server or cloud (according to Toketaware, Box and Google GDrive via PocketDAV will work). iCloud is not on the menu, but that’s okay for me. (I stopped using Apple’s service when it stopped being iDrive, and started being opaque.) I can configure as many linked folders as I want (one for each project suits me), and once I’ve set it up, it Just Works ™.

I can designate as many sync formats as I like, on a per-linked-folder basis. My iThoughts documentation folder only uses the iThoughts native format (.itmz), but my outline folder . . .

I have iThoughts iOS automatically sync .itmz, .opml (many outline processors), .xmind (the open source XMind mindmapping program that runs on Mac, Windows and Linux), .docx, .markdown, and .png. This is less than a third of all the formats that iThoughts can sync. Several Windows formats besides XMind are on that long list. If I change any of the outline or mindmap formats on another device, my iOS iThoughts will update its native outline accordingly, then update all those other formats sitting out on Dropbox. Net result: my research, outline, and background information is always available. I can link to Evernote notes. I can clip internet research at least as well as I can in Scrivener.

One thing to note is that iOS iThoughts came first, and the iOS (rather than the desktop Mac) version drives all this synchronization. I can recommend iThoughts for anyone running Windows or Linux on their desktop or laptop computer – choose your weapon (mindmapping or outlining app) and iThoughts will work with it. But if you run Android phones and/or tablets, you’re out of luck.

It works better for me than Scapple, from the people who make Scrivener. I can do just as much free-form brainstorming in iThoughts, and use my synced .opml for import into Scrivener. So, my first-cut chapter headings and synopses (the result of all that outlining) went from iThoughts into Scrivener just as easily as with Literature and Latte’s proprietary index-card brainstorming software. In addition, I can easily have separate titles and synopses for each card, rather than the first sentence of the card being echoed as a title. And I have a beautiful, automatically color-coded two-dimensional map of everything that supports my document. Sorry, Keith.

IMG_2666Finally, iThoughts works as a project management tool. I’ve set up a branch of my structure to track the hours worked on outline (well, once I started using it) and on my new draft, as well as percentage complete. I could get this with other mind-mapping tools, but at a breathtaking cost (more than $200). iThoughts for all my devices, Mac and iPad and iPhone, cost less than $70. I could have gotten by with XMind for Mac (free version, total cash outlay less than $10) but it lacks the time-tracking feature and is harder to use.

So now that I’ve started my draft, I can set up my iPhone on a stand with iThoughts open, and type away in either Index Card or Editorial on my iPad. I can check any of my research and background material on the phone. When I finish a scene, I can update the project management info on my phone and have everything summed up for me. If I use Index Card, I can update my scene’s title, document notes and synopsis. I can update stuff like character or setting information on the iPhone as I go along. I can work anywhere, and have it all show up in Scrivener when I’m back at my Mac.

Yeah, it’s cool.

For the record, I am NOT an affiliate of any software or hardware vendor. I make no money from any of my reviews.

How NOT to Write a NaNoWriMo Novel…

…if you ever want to do anything with it.

Don’t get me wrong. I am grateful for the 50,300 words I produced in November. But next time (and there will be a next time) I will work somewhat differently.

I probably won’t have more than a scrawled paper semi-outline in advance, no more than I had this time. (I am what NaNoWriMo veterans call a “pantser”, i.e. someone who only has the vaguest idea of what they want to write before they start.) BUT —

I will create an outline as I go along. Let me explain.

In order to make keeping track of my word count easy, I broke my novel into thirty 1,667 word chunks. Each chunk represented a nominal day’s output. Even when I was behind, I would break my novel at the arbitrary 1,667 word boundary, thus when I had thirty chunks, I was done. Each chunk had a name that more-or-less represented what was happening in the narrative when I started that chunk, but which had pretty much no relationship to what was happening in the narrative at its end. These were each part of a Scrivener project, so that my output looks like it’s a thirty chapter novel, in which each chapter has one scene. In fact, each “chapter” has between two and five scenes. (A scene change being defined as a change in time, place or both.) Some scenes are split across a chunk boundary. And I have to open them up and read them to figure out what is going on in them.

What a mess.

Next time I will break my narrative after each scene. So if my setting changes, I will begin a new section. If there is a gap in time, I will begin a new section. I will give each section a descriptive name, and a brief synopsis. I will not break a section in the middle of a scene. Then, when it comes time to revise, I will have scenes of my novel separate and identifiable, ready to move around into a real outline. I take a solemn oath that I will never again spend two weeks reading chunks, splitting out scenes, naming them, and writing synopses for them, when it would have taken me two minutes tops for each scene to have done it while I was writing.

The good news is that I am about 30% done with this process, and as I get more practice with it, it’s going faster. I may have my scene breakdown in a week or so. sighs

I suppose this is learning by experience. While a useful process, it never fails to suck.