Outlining Like a Boss, Part I
Techniques and Strategies for Locking Down Your Plot
Welcome to late March. Welcome, that is, to the latter half of March. It’s early late March. It’s past the March midpoint. We’re in out-like-a-lamb territory now, boys.
Daylight saving time has begun, at least in the place where I live. If you’re reading from Arizona, first of all you need not read this part about daylight saving and also, I’m jealous that you did not lose a precious hour of sleep this weekend. Arizona and Hawaii readers—and readers from anywhere else that daylight saving is not observed—are exempt from this awful work-week-after-spring-forward malaise. Each working day of the week after the time changes in the spring, I hypothesize, is the most exemplary day of its type possible. Monday after daylight saving begins is the Mondayest Monday, Wednesday the Wednesdayest, and then even Friday will be the Fridayest Friday, in which we are all more relieved, even, than usual, to be heading into the weekend.
It remains the beginning half of the post-time change week, so that’s terrible. Everything is terrible. Listen, don’t mind me. Let’s move on.
Today’s Shelf Life is about outlining a longform written work—I’ll discuss fiction primarily but nonfiction as well. Not everybody likes to plan their writing out in advance, and I respect that. I don’t understand it, I don’t know how they do it, but I do respect it. Then there are those who would like to plan their writing ahead of time but they’re not sure what they need or how to start. If that’s you, this article has everything you need to get an entire novel outlined in no time. And then, I suspect there are also at least a few writers who do not like to plan their writing out in advance but find themselves stuck midstory, or lose the thread of the plot, and end up with a pile of unfinished manuscripts collecting dust. If that’s you then, even though you don’t want to plan you writing out in advance, you might consider trying it.
I know successful writers who do not spend any time laying this kind of writing foundation before they dive in, they just go straight to the draft and don’t run into trouble. But on the flip side, I have encountered so many writers who tell me: “Oh, yeah, I don’t do any planning, I just like to write by the seat of my pants”—and then I find out that they’ve never managed to complete a manuscript and they’re just not sure why.
It’s possible that the ability to write an entire book or novel without any advance planning, just sitting down and spitting out a story, is a gift that some people are simply born with. It could be, I suppose. Truthfully, there’s not many things that people are just born with and almost nothing at all that people are born knowing how to do. Almost everything that is admirable about a person is the result of work, practice, and the choices they make. You choose to think critically about things, or not. You choose to put thought and effort into appearance, or you don’t. Likewise, if you choose to ingest stories through reading and consuming other media, and you choose to write many stories—as many as you can—then you finely hone the craft of telling a story until you can do it off the cuff like that.
What I am trying to say is that a person might feel as though they’re a seat-of-the-pants writer, and also that they’re a writer who has trouble finishing a manuscript, and might not believe those two things are related. I think they are related. I don’t think you can do anything well until you have practiced it a lot. Myself, I am still in the practicing phase, for this at least. But in my editorial life, I don’t think I’ve ever encountered someone who was a successful, seat-of-the-pants writer without having built any writing experience.
Most writers, all types of writers, can benefit from an outline every now and then. Even writers who like to write more spontaneously might be in need of some administrative help when putting together an especially ambitious story with many interacting characters and interwoven plot threads. If you can’t think all the way through your story and plot to the end—if, when you start thinking about it, you find it gets murky and vague in the middle and then pops back to clarity toward the end—you could be in for a hard time actually writing it. Your mileage may vary. Maybe there’s people out there who get to an undefined middle and suddenly know how they’re getting to the end—but not most of us.
I got into outlining when I was in college and life was very different than it is now (my life, as well as life generally). At the time, I did a lot of fiction writing and I had the ability to open the floodgate in my brain and fiction would just pour out of it. Usually short fiction with the occasional longer piece thrown in. I can’t speak for the quality of the work or writing, but there was plenty of it. Expository writing, on the other hand, required more thought, research, and preparation. I applied the magic of outlining to all of my academic writing, however short or long.
I would begin my outline with two items: Opening introductory paragraph, and final closing paragraph. Any essay has those. That’s a no-brainer. Then I’d make a list between the two items of all the points I might want to make pursuant to the topic. Next, under each point, I drop all of my premises in support of or against the point. Finally, under each premise, all of my supporting evidence. Once I had this detailed, three-level outline in place, the paper would essentially write itself in no time flat.
Now, the tables have turned—at least shifted around a bit if not totally flipped. I can pour expository writing out of my brain in a great deluge, which is why you get so much of it. I attribute this to a formative writing experience that involved planning the writing carefully, again and again, until the planning aspect was so ingrained that I have become able to do it on the fly. On the other hand, as I have over the years wanted to tell more complex and longer stories, I’ve found I have not spent as much time building up that skill and so I need to do that work now.
Outlining for expository writing—nonfiction used to explain or teach—is a whole different animal than outlining for fiction. If you’re writing expository nonfiction (as opposed to, for instance, narrative nonfiction that is more along the lines of a novel), then your outlining process will be much as I described above, on whatever topic you are explaining. For fiction and narrative nonfic, I usually proceed as follows.
The top level of my outline has four points on it: act one, act two, act three, and a denouement. If my project has a prologue (often just more fodder for the discard pile in the revision phase), then that will be a fifth point at the beginning of the outline. Although it’s got four or five top-level items, this is basically your three-act story structure. You don’t need to follow this structure, and I’ll share some alternatives in a moment.
For each of those top-level points, I set a start and stop point—which story event is the first one in this section, and which story event is the last. Act one is where you’ll need to assemble most of your main cast of characters, for instance, so act one will:
Begin with a scene introducing your main character;
Encompass all the actions that bring everyone together, including the inciting incident; and
End with an event or action that changes the direction of the story, inciting act two.
You can do anything you want in act one, I’m not the boss of you, but this is probably where you’re going to throw a monkey wrench into this character’s life that changes everything forever. And while you’re at it, throw in a dramatic question for them to answer by the end. Those are the critical dramatic actions that you need to include in act one. So when I’m setting up my outline, I consider at what point in the plot—during which scene—circumstance completely changes for the main character and alters their trajectory—that’s going to be the end of act one. So act one will be from introducing the main character to that scene.
Before moving on and setting up my next few top-level points, I’ll go ahead and add two sub-points under the “act one” heading: “main character introduced” and “that scene” that I mentioned above. All the other sub-points for act one are going to go between those.
Next I’ll do the same for act two and act three. Act two will pick up right where act one left off and continue till the main character is at their lowest, most challenging point and the antagonist is at their highest, most successful point in the plot. Act three will pick up where act two leaves off and follow the main character to the resolution of their conflict (answering the dramatic question in the process), and then the denouement will wrap up loose ends and tease whatever is coming next (if anything is coming next).
Under each of those four or five top-level headings, I now have two sub-points apiece—the first thing that’s going to happen in that section, and the last thing that’s going to happen in that section. Now I go back through and start populating sub-points between those with all of the other things that I know will need to happen between the two.
For instance, if I were outlining the first act of Pride and Prejudice, I would list “Introduce Elizabeth Bennet” as the first item that has to happen and “Lizzy meets Mr Wickham” would perhaps be the last major thing that must happen in act one before beginning act two with the ball at Netherfield. In between those two I would start listing all of the important events that need to take place to get from one to the other.
Once I have populated all five top-level points, I go back through each act adding all of the scenes—the units of action—that I know I need as the third level of the outline. Each second-level item will need at least one scene to accomplish whatever the action is that needs to happen to carry the plot forward—some items may need more than one scene to accomplish all of the necessary elements, if the item is complex. I just enter each scene as a very brief, one-line summary of what happens in the scene, for instance “a messenger arrives at the palace” or “the librarian is shopping for fenced machine parts on the black market.”
The first pass at this third level of populating the outline with individual scenes will go quickly. This is where you dump all the scenes you already have in your head into the outline format so that you can arrange them in a logical order. After you’ve transcribed all the scenes you know about, you’ll have to go back through and placing more scenes in the outline—scenes encompassing the things that need to happen to carry the plot forward but that you have not yet figured out how they will happen.
You will know you are finished with the third level of your outline when you can read through all the scenes in order and see a totally logical plot come together. However, you need not be completely finished with the third level before you begin populating the fourth.
The fourth (and perhaps final) level of your outline will detail all of the specific things that must happen in each scene. You don’t need to capture every little thing that happens in every scene, but if a scene must accomplish a specific thing other than its main action—if a character needs to learn something, if someone needs to see or recognize something or someone for the first time, if you have to introduce an item—these all go in here. You will also want to make sure that if anything novel pops up in late act two or in act three, it’s been foreshadowed earlier. Even if all you put is a note to yourself to “mention the necklace” two or three times throughout act one and two, that will go a long way toward the appearance of said necklace having the impact it is meant to have when it pops up in act three, instead of leaving your reader going, “Huh? What necklace?”
You can go on adding more depth to your outline for as long as you would like to. If you want your novel to essentially “write itself” from your outline, keep filling it in with more and more detail—for instance with bits of dialogue, details on what characters are wearing or eating, or notes about what secondary characters might be doing in the scene or “offscreen.”
Outlining the story you want to tell can be a terribly effective exercise for improving your storytelling expertise generally. I often find that my plot grows and changes in the outline phase, and character roles expand and dramatically change, as I pull the threads of the story tighter and tighter till it’s as neatly packaged as I can make it. Some writers have told me they find this restrictive—that they worry it will stifle their creativity. For me, having a structured plan to follow allows me to be more creative in my writing and focus more on telling each piece in the best way possible, with all the foreknowledge that I need to lay text down on the page with confidence.
Even if you don’t think of yourself as an outliner, I encourage you to give it a try. On Thursday, I’ll be back with a second part on this topic, which covers software and technology that can enhance your outlining and planning phases considerably. I mean, sure you could use a notebook—but where’s the fun in that? I hope you’ll stop by again later this week to check it out.
If you have questions that you'd like to see answered in Shelf Life, ideas for topics that you'd like to explore, or feedback on the newsletter, please feel free to contact me. I would love to hear from you.
For more information about who I am, what I do, and, most important, what my dog looks like, please visit my website.
After you have read a few posts, if you find that you're enjoying Shelf Life, please recommend it to your word-oriented friends.