The Question Every Writer Gets Asked
Somewhere in the middle of every conversation about writing, someone asks whether you are a plotter or a pantser. A plotter plans everything in advance. A pantser writes by the seat of their pants, discovering the story as they go. The question is usually posed as if these are the only two options, and as if the answer reveals something fundamental about a writer's personality.
My honest answer is that the distinction is not particularly useful. Every writer I know who claims to be a pure pantser has some sense of where they are going before they start. Every writer who claims to be a pure plotter has had the experience of a character doing something unexpected that changed the plan entirely. The real question is not whether you outline, but how much, and at what level of detail, and how rigidly you hold to it once the writing begins.
What follows is an account of how I actually outline — not a prescription for how you should do it, but a description of the process that has worked across more than twenty books in several different genres.
Why Outlining Matters More for Nonfiction
For fiction, the case for outlining is contested. Some novelists produce their best work by following characters into situations they did not anticipate. The outline, for these writers, can feel like a constraint that prevents the story from finding its natural shape.
For nonfiction, the case is much stronger. A nonfiction book is an argument. It has a thesis, a structure of evidence and reasoning, and a conclusion. The reader follows a logical path from the opening question to the final answer, and if that path is not planned in advance, the book tends to meander — accumulating material without building toward anything.
Most of my books are nonfiction, and for all of them, the outline is the most important document I produce before the first draft begins. It is not a rigid script. It changes substantially as I write. But it gives me a structure to work within and, crucially, a way to identify structural problems before I have written 60,000 words in the wrong direction.
The Three-Stage Process
My outlining process has three stages, and each one produces a different kind of document.
Stage one is the premise statement. Before I write a single outline entry, I write a single paragraph — sometimes a single sentence — that describes what the book is about and why it matters. Not the subject, but the argument. Not "this book is about John Bowlby" but "this book argues that Bowlby's theory of attachment, developed against the grain of mid-century psychology, explains more about human relationships than any subsequent framework has managed to improve upon." The premise statement is the north star for everything that follows. Every chapter, every section, every piece of evidence either serves that argument or it does not belong in the book.
Stage two is the chapter map. Once I have a premise statement I believe in, I map out the chapters. At this stage, I am not writing chapter summaries — I am identifying the structural moves the book needs to make. What does the reader need to understand before they can understand the next thing? What is the logical sequence of the argument? Where does the narrative need to breathe, and where does it need to accelerate?
The chapter map is usually a list of ten to twenty entries, each with a title and two or three sentences describing what the chapter does. Not what it contains — what it does. "Chapter three establishes the institutional context that made Bowlby's work controversial" is more useful than "Chapter three covers the history of the Tavistock Clinic."
Stage three is the section outline. Once the chapter map is stable, I break each chapter into sections. This is where the outline starts to look like a real document — each section has a heading, a brief description of its content, and notes on the key sources or evidence I plan to use. At this stage, I can see the book's full architecture, and I can identify gaps: places where the argument jumps without sufficient support, or where I have accumulated more material than any single chapter can reasonably hold.
How Scrivener Changes the Process
All three stages of this process happen in Scrivener, and the application changes the experience in ways that are worth describing specifically.
The corkboard view is where the chapter map lives. Each chapter is an index card. The card title is the chapter title; the synopsis field holds the two or three sentences describing what the chapter does. I can see the entire book on a single screen, and I can rearrange chapters by dragging cards. When I realize that chapter seven needs to come before chapter four — which happens on every project — the reorganization takes about ten seconds.
The outliner view is where the section outline lives. Each chapter in the Binder contains a set of sub-documents, one per section. The outliner displays these in a hierarchical list with word count targets, status labels, and any custom metadata I have defined. I use a "source density" label — high, medium, low — to track which sections have strong evidentiary support and which ones I still need to research.
The split-screen view is where the actual writing happens. I keep the outline document open in one pane and the draft in the other. When I finish a section, I update the outline to reflect what I actually wrote, which is often different from what I planned to write. The outline and the draft stay in conversation with each other throughout the process.
I have written a full review of Scrivener that covers these features in more detail, including the research folder, the compile settings, and how the application fits into a complete author workflow: Scrivener Review: Why Every Serious Author Needs This Writing Software [blocked].
The Outline Is Never Really Finished
The most important thing I have learned about outlining is that the outline is a living document, not a blueprint. It changes as I write, and the changes are not failures — they are the outline doing its job.
When a chapter refuses to work as planned, the outline tells me why: the argument is not ready to make that move yet, or the evidence does not support the claim I thought it would, or the chapter is trying to do two things that belong in separate chapters. The outline makes these problems visible before they become 10,000-word dead ends.
When a chapter works better than planned — when the research turns up something unexpected that changes the direction of the argument — the outline absorbs the change and shows me what needs to be adjusted downstream. A discovery in chapter three that reframes the thesis means revising the chapter map for chapters four through twelve. That revision takes an hour in the outline. It would take weeks in the draft.
The writers I know who resist outlining usually have had the experience of an outline killing the spontaneity of their writing — of feeling like they were just filling in boxes rather than discovering something. That is a real risk, and it is worth taking seriously. The solution, in my experience, is to hold the outline loosely: to treat it as a map rather than a contract, and to be willing to tear it up and redraw it when the territory turns out to be different from what you expected.
The map is not the territory. But you still need the map.
A Note on Research and Outlining
For research-heavy nonfiction, the outline and the research process are deeply intertwined. I do not finish all my research before I start outlining, and I do not finish outlining before I start researching. The two processes run in parallel, each informing the other.
What the outline gives me is a set of questions I need the research to answer. What the research gives me is material that changes the questions. The outline at the end of the research phase looks substantially different from the outline at the beginning — not because the premise has changed, but because I understand the subject well enough to make a more precise argument.
Bird by Bird by Anne Lamott has a useful chapter on research and the way it can become a form of procrastination — a way of avoiding the writing by always needing to know one more thing. The discipline the outline imposes is partly a discipline against this tendency. When the outline says "this section needs three pieces of evidence," I know when I have enough to write the section and when I am still looking for something I may not find.
The Outline for This Book
Every book I have published began with some version of this process. Searching for Bowlby had a premise statement about the undervaluation of Bowlby's contribution to psychology, a chapter map that went through four complete revisions before the first draft began, and a section outline that grew to nearly forty pages before I was confident enough in the structure to start writing.
The Chinese Room — which is a more philosophical work — had a looser outline, because the argument was more exploratory. The premise statement was clear, but the chapter map stayed fluid longer, and several chapters that appeared in the final outline did not exist in the first draft at all.
The outline is a tool, and like all tools, its usefulness depends on how you use it. The version of the process I have described here is the one that works for me, across the kinds of books I write. Your version will be different. But having some version of it — some document that describes where the book is going before you start writing — is, in my experience, the difference between a book that gets finished and a book that does not.
