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Outlining: one writer’s approach

by Diane Duane

A note as we begin: Mostly this blog (per its name) is a place I talk about just about everything but writing. Over time, though, people have started asking me questions about the business and practice of novel- and screenwriting, and I’ve been thinking about where to put the answers. Finally I figured something out. So this post—along with various others on writing that have wound up here or on my Tumblr over time—will be colocated at the new FicFoundry.com site when it goes live in mid-2021. Eventually this post will be redirected from here to FF.com… just so people know.

First of all: The tweet from Rebecca F. Kuang that started off the thread is here.

Then adding:

…What followed was an off-the-cuff recreation of an ask-box answer on Tumblr that goes back a few years (so if you follow me over there and this seems familiar to you, you’ll know why).

…Let me say from the outset that from the beginning of my career as a professional writer I have always been a plotter. This started out, not as an instinctive preference or a random developmental thing, but as a mere fact of life—because after I sold my first book I went straight into screenwriting. And what’s important here is that, if you’re writing for series TV, there is no pantsing allowed. PERIOD. Your story editor (or producer, or showrunner, or head-of-story) needs to know immediately what the paying customers are going to be getting: needs to know exactly. Therefore the first thing you usually do (when not pitching verbally, or else having just done so) is submit a précis [very short description of characters and plot, 2-3 pp] or premise [same but longer: 8-10pp] for approval. Until this paperwork is turned in and approved, you’re not commissioned to do the work at all. So outlining—even if just a very simple sort—is at the very root of that entire creative process. Then you go on to a full outline (depending on the length of the script to come & how much money is riding on the work, this might be 20-30 pp…) before the screenplay stage. Every stage of the business of screenplay production has some kind of outline underpinning it.

So: multiply such a set of events by twenty or thirty scripts and you can see how with this kind of work history, if you’re not already an outliner, you’re likely to get hardwired that way in a big hurry. By the time I started my second and third novels in the mid-’80s, I was pretty much locked in as a plotter/outliner for life. And it’s worked quite well for me.

As regards the process of constructing an outline: C. J. Cherryh taught me a method which I now think of as “the Shopping List Technique” and which has served me well for the last three and a half decades or so.

Simply this: you sit down and make a list of the ten things that have to happen in your novel—the character actions or physical events without which your story simply cannot occur. Then, when you’re sure you’ve got pretty much the ten major “event beats” or character issues nailed down, you break each of those ten things into its own section and list the ten things that have to happen surrounding that event or supporting that character action. You take your time over this work, because this is the skeleton of the body of your work to come—the physical / emotional / action structure on which you’re going to build your novel.

And rather than being restrictive, being scene-by-scene detailed at this stage of the work is incredibly freeing. Having this solid scaffolding to build on lets you turn your full attention to character business and interaction… because you already know who’s got to go where and what they’ve got to do. You can now wallow in Drama and Spectacle and All The Feels, and not have to waste time sweating the workaday details of the who-goes-where-and-what-happens choreography.

You have, in essence, drawn your road map. Now you journey. If (along the way) you find that the road wiggles in ways that work better for your story than the original ones—then, fine, you redraw that part of the map. But the map preserves for you a sound basic representation of where you’re going; something you can fall back on in need, or if your focus shifts without warning.

Let me spend a little time here dealing with the actual process of outlining the way I do it. (And naturally I’m going to preface this with the caveat that just because this works for me is no reason for anyone to take this method as any kind of gospel. Finding your own way is a vital part of the Writer’s Journey. But if some part of this seems to work for you: steal, adapt, run off with the goodies! Others shared what worked for them with me: it’s a pleasure to pay that forward.)

Those lists of ten-things-broken-down-into-ten-more-things start out for me as incredibly messy scribblings on the fabled Magic Note Paper and then get typed into whatever outline processor I’m using at the moment. …Unfortunately I have none of those messy pages to show you, because as they’re transcribed, I destroy them to keep from confusing myself later as to whether that material’s been handled or not. …These days, anyway, the lists go into Scrivener …and the result is likely to look something like this.

Screenshot from the TALES OF THE FIVE #3: THE LIBRARIAN outline

…The formal breakdown-of-tens may or may not remain static or be visible in such a document at any given point due to sections or bits of business being combined or telescoped into one another, and the numbers of beats and sections may change without warning. This is perfectly normal for novel outlining. You discover as you start more closely investigating / filling in the Tree of Tens that some sections need different contents, lengths, or rhythms.

This is the “filling in empty spaces on your map” department, where (for me anyway) the real exploration and revelation of the story happens. In the outliner, scraps of scenes, dialogue, and descriptions of business can now get slotted in. (Scrivener makes it a lot easier to organize and rearrange them than it used to be in a Word document: but it doesn’t matter in the slightest in what kind of word processor you’re doing this. Just break the ten “big sections” into divisions big enough for you to comfortably work in.) In these separate sections, action can be amplified or refined: motives and character interactions can be expanded and explored.

In my case, the outline sections and subsections start to contain long text passages that arise to be written while considering the subsection titles. (Considering them as prompts may be helpful.) Or they may just contain very linear notes about what has to happen. Or both. And this part of the outlining can go on for a good while, as it becomes clearer what material is needed in the story and what’s surplus to requirements.

This business of describing what has to happen—in the strictly linear sense—will normally be pretty much complete before I’m ready to submit anything to an editor. It may be helpful to think of what we’ve been discussing so far as a much expanded or differently-structured version of what a scriptwriter might consider a beat sheet / beat outline. But also for consideration here should be what kind of outline you’re going to send to your commissioning editor when you’re querying and they ask you for a specific kind of “partial”, the traditional “three-chapters-and-an-outline”.

Around here, this sort of outline gets handled in different ways. The editor may have worked with me before and may already be familiar with how my outlines reflect the finished novel, even though they may not be broken out into chapters. Those editors will tend to get an outlined description of events that’ll be heavier on the emotional context. Example: the premise-cum-outline I sent Harcourt for The Wizard’s Dilemma. This is on the short side because I knew my editor was perfectly familiar with the first four books in the series.

On the other hand, one may be pitching to an editor one hasn’t worked with before, in which case breaking the outline clearly into chapters may be smarter. This version of a novel outline was what went to my editors on what became The Book of Night with Moon. Since in this case the editors already had chapters 1 through 3 as part of the pitch package, what they then got was the outline for the book onward from chapter 4. (You’ll have to just imagine the first three chapters. Essentially, a trio of cat wizards pick up an unexpectedly punk-ish apprentice.)

Now, the linear-looking stuff that you saw in the Scrivener screenshot above, and the outlines that went to the editors and sold the books, are obviously very different. The latter sort of outline is synthesized from the former. But it’s important to do so with the emotions, and the emotional content, fully in place.

And this is where the problem that @kuangrf was mentioning in that earlier tweet can easily be handled. While the List-of-Ten-Tens method is extremely effective for handling the mere business of physical action (“A goes to B, kills C, flees the country”), it’s just as effective for structuring the flow of emotional events and interactions among characters. I routinely include the two “streams” in the same section, particularly because for me they need to be driving each other; it seems inevitable to me that what you have to do will drive how you feel about doing it. So no need for an outline to be dry or abstract! In fact it works better (I think) if it’s not. The more emotional juice you can pump into it, the more will ooze out when the reader bites.

For example: the very first of the ten-of-ten for Tales of the Five #3: The Librarian (which we’ve been looking at in the screengrabs) said “[King] Freelorn has an unnerving dream that tells him he’s got to go on a journey…”. And the first of that chapter’s ten subsections simply said “He wakes up too early and spends a while looking at [his husband] Herewiss in ‘missing you already’ mode: then gets up, does his morning stuff, and goes to work.” And the first time I sat down to work on that chapter, I got this right back from that section’s prompt:

Text from TALES OF THE FIVE #3, THE LIBRARIAN
(A concept-art image of the moment is here.)

…So bake the emotion into the outline along with the physical action / broader thematic structure, and it will do it nothing but good. And make your job easier.

…There the thread pretty much ended. There’s just one background / thematic thought I want to add.

I think there’s too broadly spread-about (and often unquestioningly accepted) a narrative that says that outlines are somehow creativity-deadening or -defeating, or will suck the life or spontaneity or whatever out of your prose writing. Let me qualify this assertion immediately by saying that I understand perfectly well that there are writers for whom this mode of novel management doesn’t work; that they’ve attempted it, and feel that valuable creative energy is lost to them in the structuring process. That experience must be respected. Whatever you do that works for you is valid.

But I do feel that outlining isn’t given a fair shake, a lot of the time, by people who’ve never tried it and just don’t like the sound of it because it doesn’t sound fun enough. And what troubles me most about this is that too much unexamined advocacy for the Yay Let Us Be Utterly Free And Unfettered In Our Creativity school of thought* is depriving a lot of new writers of a really terrific tool that can keep you from doing something that over weeks and months and years is truly terrible: wasting creative time.

For my money, possibly the single most poignant line in Avengers: Endgame was Tony Stark saying to his dad (in both bittersweet and quite ironic mode, considering) that “no amount of money ever bought a second of time”. When you’re early on in your creative career, and possibly have your best energy levels at your command, it’s easy to feel as if all eternity is before you… as if blowing a week or a month (or six months or a year) on the free-and-unstructured development of a project is no big deal. But later on, in both the short and long terms, you may find yourself revisiting that attitude with considerable regret. And the paradox attached to the resistance of outlining among new / just-getting-started writers is that this is the stage at which it’s most likely to be useful to you. From that earlier post on Tumblr:

At the very beginning of this process, outlining is the easiest and most straightforward way to go, and eliminates the chance of you wasting time by running down a lot of blind alleys and getting caught up in choices that you don’t need to be trying to make at this stage of the operation. Later on, as you get better at this setup process and more confident about it, you can dump outlining if you find yourself disliking it and are able to produce reliable similar-quality results without it. For now, though? Help yourself out by making yourself a shopping list until you can be more certain you won’t forget the stuff you went to the store for.

So let an older writer just say here to the younger ones, the newer ones: We want more of your work, and of your best work: not less. Outlining might work for you—might indeed save you surprisingly large amounts of time, uncertainty and frustration that would otherwise be wasted in waiting for the stars to align or the Muse to arrive or whatever. Just give it a shot, okay? Please and thank you.

…So that’s that. Thanks for reading. And believe it or not, I actually do have to go work on the outline for something at the moment. So if you’ll excuse me? …And enjoy your day.

*Please don’t mistake me here. I’ve written in that mode often enough, and it’s utterly fabulous when it’s working correctly. But over the long run, over a career, with deadlines and other people’s jobs riding on your output turning up in a timely manner, depending on it always to work is dangerous. C.S. Lewis says somewhere that the greatest illusion in which creative people indulge themselves is that what they’ve done once, they can do always…

Also, for those who’ll inevitably ask: yes, I’ve tried pantsing! In fact I’m doing a pantsing project right now. And it is LIKE BREAKING ROCKS WITH MY HEAD. Excruciatingly difficult and painful! But I committed to [REDACTED FAMOUS WRITER] that I’d do this to give the concept a fair shake… so I will be following that project through to the end. (It’s this one. It is entirely possible that I’ll fail at this in ways that have never been seen before, but for fairness’s sake it has to be done. Because I can’t fairly ask people to do something, i.e. attempt the Completely Different Method, that I’m not willing to do myself…)

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Q&A: Getting into Star Trek, Managing IP work

by Diane Duane
From the ask box at my Tumblr:
How did you get into writing Star Trek novels? Are there any considerations you have to keep in mind when working with someone else’s IP?

— marypsue

Let’s break this in two.

First: How did I get started?

I am a first-generation Star Trek fan. I fell in love with ST:TOS* as soon as it premiered, and immediately started writing fanfic in that universe. (It should be mentioned here that – so long before the days of widespread internet-connectedness – not only did I have no idea that other people were doing something very similar, but I had no idea it even had a name. I was writing all alone, in a vacuum, with no support whatsoever… but however accidentally, I’d discovered something invaluable: it made me happy. We’ll come back to this later.)

So. Time went by and I slid from that genre of fanfic-writing into writing fic that was much more Tolkienian in genre, and from there, into writing original fiction that Tolkien would have found, well, rather different. Cutting another longish story short, in 1978/9 I sold and had published my first novel, this one – the initial volume in the LGBTQ-and-poly-ish Tale of the Five / Middle Kingdoms series that would later get me nominated two years running for the Astounding Award for best new writer in the SF/fantasy field.

Now when something like this happens to you, it gets a lot easier to pitch new novels to people. I’m not just talking about the increased attention that awards nominations bring you. But just having a traditionally-published book out tells other potential publishers that you’ve mastered at least some important aspects of the novelist business: (a) being able to conceive of a plot that will sustain a novel-length work, (b) being able to go from concept to starting in on a novel, © being able to finish a novel, and (d) being able to cope with the editorial process – handling suggested edits, dealing with a copyedited manuscript, dealing with proofs, etc etc.

As it happens, while I was dealing with the sequelae to publishing The Door Into Fire – meaning the inevitable question “And what are you going to do next?” – I had also been doing some typing for an acquaintance who was typewriter-challenged. They were writing a Star Trek novel. And I have to say that what I was typing up for them was giving me hives. It was…not anything like what I thought a Star Trek novel should look like. I remember saying to a friend or two, on the quiet, “I could eat a ream of typing paper and barf a better Star Trek novel than this.” And finally one of them – I can’t remember who at the moment, but the odds are it was David Gerrold, who (God love him) has a history of daring me into doing things I want to do anyway – turned around and called my bluff and said, “All right, go on then, quit your kvetching and just go do it.”

Which left me staring at the problem with a lot more intent. Fine, you’re going to pitch a novel to Trek: what story are you going to tell? It’s not like you’re constrained by a TV budget here. Stretch out and tell the biggest Star Trek story you can find: one that can only be told, or best told, in this universe. (This being my working “prime criterion” for stories told in other people’s universes: for best effect the story should only be capable of being told within that set of characters and circumstances. The jewel must be cut to suit the setting, not – however counterintuitive it might seem – not the other way around.)

So I sat with that concept for a while, and eventually the right idea, or set of ideas, presented itself. I can vividly remember the moment. I was sitting on a bus bench near Victory and White Oak in the San Fernando Valley when the idea hit. It was a long time before cellphones, so I had to wait an hour or so to get home so I could call my agent and say “Don, guess what? I’m going to write a Star Trek novel!”

There was the briefest pause, after which he said, only half joking: “Do you have to?” Because both of us knew perfectly well that from Paramount’s point of view, Star Trek novels were merely another kind of merchandising, like plastic phasers and James T. Kirk action figures. (And strictly speaking, regardless of how we love them, they still are.) …But then Don said, “Okay, do an outline and we’ll see what they think.”

And so I wrote the outline, and my agent sent it along to the editor of the Trek books at Pocket – who was then Dave Hartwell (God rest him, a fabulous editor of any and all kinds of SF) – and Dave read it and liked it, and he sent it to Paramount for approval, and they read it and liked it, and gave Dave the go-ahead to buy it. And that turned into The Wounded Sky. (A nice overview is here. But I am also charmed to tell you that this book has its own entry at TV Tropes.) As a tied-for-second novel went – So You Want To Be A Wizard was written at very close to the same time – it doesn’t seem to have done too badly.

Anyway, after that got written and turned in and published, the people at Pocket said to me, “Okay, what have you got for us next?” …It was that simple… and I was that lucky. I liked working with them: they liked working with me: and they liked what I’d done enough to ask for more. So I was in for eight novels more, spread over a fair bit of time. (And I have one more plot lying around that I should really get in touch with present editorial about and see if there’s any interest. You never can tell…)

So that’s how I did it. Everybody else’s mileage will inevitably vary. But I don’t think there’s going to be much argument with the idea that before working with other IP-holders in their worlds, you might usefully do as much work as possible in your own. That way potential publishing partners will have something to look at to help them get a sense of what your voice sounds like outside someone else’s world.

…Now as for working with someone else’s IP – anyone’s – this is how I manage it.

(a) Remember it’s theirs. They were there before you arrived and will doubtless be there long after you’re gone. They own that property, are likely enough to have worked hard on it in their time, and – whether they originated it or are just its buyers – are almost certainly powerfully protective of it. You can press against the edges of their envelope – quite hard, if you’re careful and have permission – but break through the fabric of their corporate reality without warning and you are going to be in deep trouble.

Do your homework. Know your licensor: know their history with other creators. Find out where there have been problems in the past and keep your eyes open for warning signs that you may be discovering some new one. If you were lucky enough to be invited in, act like a considerate houseguest (creatively speaking); while working in that universe, don’t (for example) sneakily attempt to jettison parts of the property that annoy you or covertly subvert bits that seem to call for subversion. (Overt subversion is a different story. Be in communication with your IP owner about this, and you may be able to win them over.  [Though you should be prepared for them to take credit for this after the fact.]) If there’s a work-with-us guide or in-house bible, sleep with it under your pillow.

(b) Know your subject / universe. KNOW it. It is an absolute certainty that no matter how well you think you know it, there are fans out there who know it better than you do – massively, obsessively, eat-drink-and-sleep-ively better – and if you put a foot wrong, they will come for you. Leaving aside the issue of not wanting to be left looking like an idiot on the Internet, you ought in any case to be deeply cognizant of your host-world’s internal verities before you can expect to write it flexibly and well.

– And add (b1) to this: Know your characters’ voices. Not just the way they phrase things, but the way they think about things and (possibly more importantly) feel about things. It’s not you the readers will have come for. It’s them. You must channel the core characters at the very least authentically, and (ideally) affectionately, or it’ll all end in tears.

For the duration of this work, you are in service to them. Treat them courteously and give them your best words to speak; but always in their own voices. Don’t be afraid to let them be more real than you are. For a lot of people, unquestionably, they are. If that’s a problem for you, you shouldn’t be doing this kind of work. (At least not more than once.)

© Don’t do it for money. Don’t do it for fame. Do it for love or not at all. Let’s be realistic: any licensing IP is likely to (in the great scheme of things) be far better and more widely known than you are. You may acquire some positive press for your work with it, but in many people’s minds the positivity will have to do far more with the property than with you, regardless of your gifts or how much you love that universe, or whether or not you “came up through the fandom.” As regards money, some licensed work will pay competitively with original work done in the same genre, but most will not. Not even being a Hot Name with a given IP will necessarily guarantee you any kind of serious money. (In particular, IP licensors have a historical tendency to pay lower-than-normally-accepted royalty rates, and in the past it has taken very energetic and insistent agents to break this habit.) It therefore stands to reason that, for the sake of your own best functioning as a writer, you need to be doing work of this kind because you really need to do it (or have done it) to make yourself happy: to scratch a creative itch, or to give something back to a property/universe that you love.

Now, “do it for love” can cover a lot of ground. You don’t have to be head over heels in luuuuuuuurrrrve with a property to write for it well. (In fact I suspect this state could conceivably hinder a writer’s ability to do their best work for a property: you need at least a little separation from it so that you can realistically evaluate how what you’re producing is stacking up.) You can just be in really strong like with a given property. But you ought to be in at least some kind of like. A personal commitment to the stylistic, rational or emotional core of a given property will get you through the times of challenge that will inevitably surround your involvement with it far better than any unrealized hope of a big payday or of more widespread recognition of your own talents.

This may sound heretical, but I don’t believe that licensed work is necessarily most fruitfully viewed as a natural stepping-stone to doing original work. (Or even to becoming a licensor yourself, though that does happen.) I think that, well and thoughtfully handled at both ends of things – the auctorial as well as the editorial – not-your-own-IP-work can be entirely worth doing wholly for its own sake. To write for the enjoyment of readers who’re using licensed work to scratch the same itch or feed the same passion that fanfic readers/writers know – of just wanting more good story in that universe? That’s entirely honorable employment, in my book. You’re an entertainer! Entertain, and fear nothing.

(And read your contracts closely.) 🙂

*A minor edit. These days you have to tell people which Star Trek series you fell in love with as soon as it premiered. What a time to be alive…

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