How to outline your way to a better, stronger book

by Geoff Hart

Previously published as: Hart, G. 2017. How to outline your way to a better, stronger book. http://thewritersally.com/articles/how-to-outline-your-way-to-a-better-stronger-book/

This month we’re pleased to welcome editor and author Geoff Hart as a guest blogger to The Writer’s Ally blog, sharing some wisdom on how to outline your fiction or nonfiction book before you begin writing (or after) to create a better reading experience for your audience, and a better writing experience for you!

Pay attention to the best stories, and you’ll notice how (unlike life) they flow smoothly from start to finish, with the only interruptions provided (intentionally) to challenge the characters. Pay attention to the best nonfiction, and you’ll notice something similar: it starts by explaining the context to orient you, musters the knowledge you’ll need to understand the author’s argument, and then guides you smoothly through a logical sequence that lets you grasp the author’s argument and decide whether it persuades. In both cases, the author clearly knew where they were going, and wrote in a way that would get you to that destination efficiently.

They did that by creating a kickass outline.

In this article, I’ll teach you how to create an outline that supports your unique story and helps you communicate that uniqueness to your readers. (I’ll use the term “story” for both fiction and non-fiction; in both cases, you’re leading your readers on a journey, and you want to be the best tour guide you can be.)

Start with a Summary

Before you begin, create a summary statement that clarifies where you want to go that nobody has gone before; that is, explain what distinguishes your story from every other story with a similar plot. You’ve probably heard the phrase “elevator pitch”. The basic notion is that during an elevator ride, you’ve got at most a couple minutes to tell someone your story. Years ago, I turned this into a party game I called “the 50-word challenge,” in which the goal is to explain any concept, no matter how complex, in 50 words or less. If that seems intimidating, check out the “Explain a Film Plot Badly” Twitter feed, in which the best efforts skewer films in fewer than 140 characters.

Consider the seemingly daunting task of describing Shakespeare’s Romeo and Juliet. If I were asked to summarize this in 50 words or less, I’d try the following:

A boy and girl from two feuding families meet and fall in love. Rather than using this opportunity to unite their families and end the feud, the families pursue their feud. Many people die, including the young lovers, but perhaps some lessons are learned.

Such a summary sacrifices considerable nuance, not to mention some of Shakespeare’s most elegant writing, but it does convey the gist of the story. Each sentence of such a summary leads readers to a major waypoint on the story’s journey.

Identify the Key Waypoints

Sometimes, like crossing a river, the journey’s start and end are clear: you start on one side and cross to the other. If you’re lucky, stepping stones lead you across in short steps that get you there safe and dry. If not, they may take you across a ford that leaves you muddy and wet, but exhilarated by the rushing water. Other times, neither the start nor the end are clear, and you must grope your way along. In my novel Chords, the journey began with a compelling image that lingered for years before I found the story it belonged to and determined where the image fit within that story. Whether your waypoints are crystal clear, or as yet unknown, you’ll find it easier to plan the journey you want readers to take if you’re dealing with less information—that is, with an outline that boils your story down to its essential elements.

Waypoints are based on dependencies. In Romeo and Juliet, the lovers must meet before they can fall in love, and they must die before their families can understand the cost of their feud. In technical nonfiction, dependencies are things you must learn before you can learn other things; for example, in a diet book, you might need to understand the relationships between food consumption, exercise, and metabolism to understand how to use the diet to lose weight. In nonfiction such as memoirs and other forms of history, those dependencies may take a different form; for example, they may be crucial events that led to major changes in the rest of the author’s life, such as the loss of a parent or of an election. In some types of nonfiction (e.g., political advocacy, self-help books), you may need to adopt an approach from persuasive rhetoric: start with a compelling example that motivates the reader to keep reading, provide reasons for them to believe that you’re a credible guide (e.g., present your credentials, support your recommendations), and end with a call to action. These dependencies define the sequence your story must follow, and they’re easier to see in an outline because it eliminates the obscuring details.

Fiction writers tend to have looser dependencies. Events (effects) must still follow from causes, but once you’ve figured out those dependencies, you can sometimes shuffle the order in which you present these events. For example, it’s fun to strategically omit crucial information and only hint at its existence, thereby raising questions the reader will be eager for you to answer later, perhaps via flashbacks. Chronologically, these events occurred earlier in the story, but structurally, placing them later in the narrative emulates how human-centered stories tend to work: in real life, we often recall an earlier event that suddenly took on great importance in the present.

This kind of approach is less useful in nonfiction because it disrupts a carefully planned sequence designed to present information in the most logical order. However—somewhat surprisingly—it can be used effectively in technical writing, in which you’re often creating books readers won’t want to read from cover to cover. This is true of cookbooks and reference books, for example. As another example, readers of software manuals usually only want to solve a specific problem with the software, and want to read as little as possible to do so. In that case, understanding cause and effect and other dependencies lets you ensure that each topic contains all the necessary information: here’s where you’re coming from when you reach this topic, here’s what you need to know to understand the topic (including cross-references to longer explanations and related topics), here’s what you need to do, and here’s where you’re going when you finish reading this topic. In fact, you can use this kind of approach to create a standard outline that all topics must follow, thereby helping to impose consistency on a long manual full of complex information and helping to ensure that you don’t omit any essential information.

Organizing these waypoints into a logical and effective sequence creates the first draft of your outline.

Review and Revise the Outline

At this point, you’ve listed a series of waypoints in a logical order: in short, you’ve created the reader’s itinerary. The overwhelming advantage of such an outline is that it’s short: you can see and grasp the overall structure of your story more easily than if you had to sort through dozens of details for each waypoint. (Providing those details comes later.) The ability to clearly see your story’s structure lets you review that structure in search of omissions, redundancies, and speed bumps that will disrupt the reader’s journey. You can perform this analysis at a high level, as in the case of reviewing the order of chapters in a book, or at a low level, as in the case of reviewing each chapter’s structure. In practice, you’ll probably start at a high level, then work your way down to progressively lower levels as the structure begins to gel.

Since the outline is your plan of action for the story, whatever its length, you’ll need to revise your initial effort. The carpenter’s adage (“measure twice, cut once”) is worth keeping in mind: the more effort you spend polishing the outline until it shines, the less hard work you’ll have to do later to fix structural problems. Outlining is no different from other forms of writing: it’s wise to set aside your efforts and return to revise them only after some time has passed. I find that leaving my outlines overnight provides enough distance that I can spot problems I missed during my initial planning; leaving them for several days works even better if I can muster the patience to wait that long. You may find that you need more time or, if you’re working under a tight deadline, may only be able to walk away for half an hour before your final revision. With practice, you’ll learn the optimal time for you.

If you’re fortunate enough to have colleagues, ask them to review your outline. They have distance you lack, and see things you can’t. For example, the first draft of my novel Jester flowed in simple chronological order, but my writers’ group unanimously agreed that the 3rd chapter was the ideal starting point. It quickly became apparent they were right. The published version of the novel now starts with a more dramatic scene that also provides a hook to draw you into the protagonist’s world. This approach is called in media res—literally, jumping “into the middle of things.” In my case, the original first chapter was still important, and examining the outline let me quickly find an appropriate new location for it later in the novel.

I’m mostly known for my non-fiction, and I find that despite my best intentions to outline before I begin, I’m often not 100% sure of the heart of my message until I’ve actually written a draft of the article and tried to fit all the raw facts together. This approach is impractical for book-length projects because it involves too much work, although you can still use it for individual chapters or problematic parts of chapters. The writing process is my way of exploring all the components of that message until I create a gestalt that lets me understand the real story I’m trying to tell. As a result, my outline shifts over time as I move parts of the argument into more effective locations.

Fiction is even more fluid. Though I always start with a detailed outline, I find that my best characters gradually develop minds of their own. The things they want to do often prove more interesting than my plans for them. I’ve learned that what works best for me is to outline the overall story arc, itemize the key scenes I want to include in the journey, and then set my characters loose to explore the itinerary I’ve created for them. Over time, that path shifts as I come to understand them better and as we negotiate a story that we both want to tell. An advantage of maintaining this kind of flexibility is that the overall outline keeps you on track to accomplish what you’ve set out to accomplish, while still providing freedom for experimentation and occasional detours.

For simpler stories or stories that just seem to flow naturally and pour forth like a fountain, you may be tempted to work without an outline, as I sometimes do. That can work, but when it comes time to revise the result, you’ll often find that this free-form approach created structural problems. Don’t despair! One of the better-kept secrets of outlining is that you can also create an outline after you’ve finished your first draft. That outline concisely summarizes what you’ve done, and that summary often reveals structural problems that would otherwise be concealed by the details. For example, you may have packed in too many or redundant waypoints, repeated information better left to a cross-reference, or failed to clearly establish the flow between waypoints. Creating this outline can also rekindle your excitement in the story by revealing new and potentially more interesting alternative routes through your story. A post-writing outline can additionally reveal overwritten parts that need tightening or may need cutting altogether. Harrison Demchick’s article, “Word Count Woe,” provides some additional thoughts on how to decide whether your manuscript is too long and what to do about it.

At this stage in your outlining, you’ve created the itinerary for a successful journey. But a journey must be more than a series of destinations.

Fill in the Details

Outlines are often described as “plot skeletons,” and like their bony cousins, they provide a frame on which you hang the muscles and viscera of your story. In fiction, that skeleton may be Freytag’s structure  or “the Hero’s Journey”; in nonfiction, you may need to work with a prefabricated structure that everyone must use, such as journalism’s pyramid structure: the point of the article appears at the top, with a broader mass of supporting information at the bottom. Or you may have designed your own structure to support the unique needs of a specific story, as in the case of my nonfiction books.

Your fleshed-out outline takes your elevator pitch a few steps further and is a great tool for pitching your story to an editor and getting them up to speed quickly on what you’re trying to accomplish. This will both interest them enough to take a look at the actual story and focus their attention on key points so they can tell you whether you’ve achieved what you set out to achieve.

In each case, your outline represents a functional skeleton in which all the pieces work together well. But the next step is to flesh it out. And this is where most outliners go astray: they’re tempted to take shortcuts and rely on generalities. Instead, it’s crucial to be specific: a generic phrase such as “the climax goes here” is useless because it says nothing about how your story differs from every other story. Instead, emphasize the details that make your story unique. For the climax of Jester, the relevant line was this: “Morley can no longer equivocate, and is forced to decide just how much his soul is really worth.” I followed this with a list of the considerations that I forced him to ponder, each reflecting the events of one or more previous chapters, before he makes his choice. (I’ve drawn the spoiler curtain over those details for those who might want to read the novel.) Needless to say, I had to walk him through those considerations in a logical order—so I created a micro-outline that helped me do so.

That fleshed-out skeleton, like Frankenstein’s monster, looks somewhat like a real human, but it isn’t breathing yet. You’ll still need to identify and describe the telling details that make your creation live and breathe. Even when the outline represents a compromise between what we want the characters to do and what they want to do, many characters will be unhappy about following this path. When they aren’t happy, they are going to complain about it to anyone willing to listen—even if only to themselves. Embrace those complaints. They’re the kind of detail that adds life and breath to your outline.

Start Writing!

When you’ve completed this step, your outline tells the whole story that you’re planning to tell. You can think of that version as the TL;DR (“too long, didn’t read”) summary for readers who don’t have the patience to read anything longer. Indeed, I’ve used this approach in the workplace when a manager asked me to provide a summary document on short notice and there wasn’t enough time for anything more complete. Of course, that version wouldn’t be very satisfying for a really tasty topic that you want to explore at length and in depth in a book. More often, there’s still a ton of work you’ll need to do. In fiction, you’ll want to write and then hone the dialog, plus add the details that make each character and each setting unique; in nonfiction, you’ll want to craft your conclusion and ensure that you’ve mustered all the supporting details needed to lead the reader to that conclusion and persuade them. In short: you’ll need to start writing.

At this point, the outline becomes your plan of action: it keeps you on track as you write, and removes much of the stress that comes from not knowing what you need to write next or how you should write it. It also helps you relate what you’re currently writing to what came before and what will follow, thereby letting you craft smoother and more effective transitions. Best of all, if you get stuck on one part, you can skip ahead to find something that you are comfortable writing, so that you’re constantly making progress. (For some other thoughts on conquering writers’ block, see my article “Writer’s block: different causes have different solutions”). A bonus of this approach is that the parts you skipped tend to linger at the back of your mind so your subconscious can wrestle with them while your conscious mind deals with the section you’re currently writing. Often, by the time you finish that writing, you’ll find that your subconscious has already found a solution, and you can return and write what you skipped.

Writing isn’t always a simple or stress-free exercise, but a strong outline eliminates or greatly simplifies many of the harder aspects and makes the whole experience less stressful. That being said, never let an outline become a Victorian corset that slowly strangles you and forces you into unpleasantly contorted shapes. Rather, think of it as a modern high-performance sports garment that shows off your shape to best advantage while making your exertions much easier.

Interested in learning more about outlining than I can fit into this article? Have a look at K.M. Weiland’s books: Outlining Your Novel, Structuring Your Novel, and Creating Character Arcs. Need a little help visualizing your manuscript’s structure in a less linear way than the approach that I’ve described? Have a look at Martin Page’s Storyteller Tools.