Step #5
Examine the Structure of Your Book

Remember Alice from Alice’s Adventures in Wonderland? She didn’t have a map. No destination. That’s why she wandered around and didn’t care where she ended up. At this point in the Author Training Process you have the information you need to design the creative map for your book. If you’ve left your Alice Attitude behind and adopted an Author Attitude, you can complete Step #5, Examine the Structure of Your Book. Additionally, you can make sure you arrive at your destination: a successful book—one that sells to readers and to a publisher as well, if that is your goal.

You’ve made it halfway through the Author Training Process, and this step asks you to apply your research, evaluations, and training to create the table of contents (TOC) for your book. In a book proposal, this would be called the “List of Chapters,” and it represents the structure of your book’s content. It also represents an important part of the writing guide you are creating. You can consider it a map for writing a successful book because it begins to put all the pieces together—unique and necessary content based on your idea and targeted to your category and market.

If you feel uncertain at all about creating your book’s structure or developing a map to take you (and readers) from its beginning to its end, take a deep breath and drum up your courage. You will find many tips and tools in this chapter to help you figure out what will end up on the pages of your book. What you first thought you would write about may, indeed, have changed by this point in your Author Training. You can firm up your summary, pitch, list of benefits—in fact, your whole book idea—after you have completed your TOC, if need be. (You’ll have another chance to review all of these elements again after you complete Step #6.) Soon you’ll have a well-defined map anyone can understand—you, agents, editors, or readers.

At this stage of the Author Training Process, however, the TOC is just a list of chapters you plan to include in your book, each one named appropriately and listed in an order that seems to make sense from a storytelling or conceptual standpoint. If you provide descriptive chapter titles, such as those found in nonfiction books, anyone can look at your TOC and see the reasonable and effective path you’ve charted to get to your planned destination. Your pitch, summary, and list of benefits provide a description of that destination.

But you should think of Step #5 as a chance to build and strengthen the structure of your idea, changing it from a general overview to a defined map. The TOC holds up your book and gives it form, much like a backbone. Without a strong TOC, your book ends up crooked, bent, or unable to stand. When an agent or acquisitions editor looks at the List of Chapters in a book proposal, they “see” your book—or they don’t. If your TOC is weak or too general, your idea remains amorphous.

The TOC is often the next logical thing for agents or acquisitions editors to look at after the Overview, where they can find a complete and concise description of a book idea. A look at a TOC can help an agent or acquisitions editor determine if your book will have substance, contain pertinent information, tell a complete story, and carry out the promises you made in your Overview. They can tell if it has the strength to hold up all aspects of your content, takes a logical path, and gets your readers where you say you want them to go.

The TOC is particularly helpful for evaluating the soundness of a nonfiction book. These books tend to have chapters descriptive of their content. As such, the TOC easily shows if the creative plan for the book will hold up the proposed content and get readers where they need to go. However, if a novelist writes chapter titles that allow readers to glimpse the storyline (without revealing important twists or climaxes later on, of course), the TOC can provide an agent, editor, or reader with the same ability to gather this information about a novel. Memoirists should keep this in mind because it can help readers (and agents or editors) make early purchase decisions about their books as well.

Think about it: When you go into a bookstore and open a book to its TOC, you know if it appeals to you and if it contains the information you need or want or a story you would like to read. You must prepare your book idea for that prospective reader’s first glance.

How to Create Your Table of Contents

As an author in training, you want to approach your TOC as both a creative and business process. In the first case, writing your TOC offers you a chance to get inspired and help your idea take shape. Have fun when creating the titles of sections and when shaping the bare bones of the content readers will find within your book’s pages. In the second case, you have the opportunity to evaluate your TOC from a business perspective to ensure it lines up with your target market as well as with your angle, theme, purpose, pitch, summary, and benefits. You determine if each section and chapter you have proposed will:

• fulfill the promises you made to your readers—provide them with benefits
• be unique—differ from your competition
• be necessary—answer questions or solve problems
• hit readers emotionally—allow them to relate to what you have written
• tell a compelling story—entice the reader.
• target your intended markets—be written for your readers

Not every writer begins writing with a TOC as a map, although many do. Others like to write “by the seat of their pants,” allowing their books to flow out of their heads with little planning. (Some refer to this as “mappers vs. pantsers.”) I recommend both fiction and nonfiction writers develop a TOC because it provides organization, direction, and focus as you write. It also reduces some need to revise and cut in later drafts of your manuscript.

To develop a TOC, however, you must organize your story or information into chapters.

Delineating Chapters

Whether you are starting from scratch or have your research at hand, you are at the right place in the process (as long as you previously have completed Steps #1 to #4) to begin breaking down your book idea into the steps (or chapters) needed to fulfill your promises to the reader. You can create your TOC in a variety of ways. For nonfiction, which often has about ten to fifteen chapters, for example, you can:

• Create a list of ten to fifteen topics you know you want to cover in the order you want to cover them. Write a compelling title for each topic; later you can refine what you come up with, but for now this becomes the chapter title.
• Think of ten to fifteen common questions you want to answer for your readers. Then write creative chapter titles for each one of those questions; another option is to leave the titles as questions.
• Think of ten to fifteen pressing questions you want to answer for your readers. Then write creative chapter titles for each one of those questions; these could be “how-to” titles.
• List ten to fifteen benefits you want to offer readers. Write titles that draw readers into those chapters by explaining what’s in it for them—the added value that speaks to their interests.

To create a TOC for a memoir:

• Create a time line. Draw a line with the start and end date of the period about which you plan to write; place dates that indicate major events you want to include in your story on the line. Then organize these into chapters.
• Plot vignettes on a storyboard. Storyboards are graphic organizers most often combining both images and descriptions of a scene. Some writers simply describe scenes on them. Once you have organized them in chronological order, identified themes, and determine the narrative arc, write your TOC.
• Create an outline. List the events you plan to include, and then organize them logically with lesser events placed after more important events. (In all these cases, add in flashbacks in the places you feel appropriate to recount them, not necessarily in real time.)
• Organize your memories into topics of interest.
• Make a list of ten to fifteen significant moments or turning points in your life, and relate them to your themes; locate them on a time line. Write each turning point in a scene, creating chapters from these core stories.

To create a TOC for fiction:

• Profile your characters. Give them backstories and motivations so you get to know them before you set them within the dramatic or comedic arc of your creation. Then outline your storyline. Place the scenes you plan to include on that story line (like a time line) with your characters. Consider how your novel’s themes play out on that storyline and where the dramatic arcs occur. Then break this down into chapters, and create a TOC.
• Create a storyboard. Break this down into chapters and then a TOC.
• Number the lines on a sheet of notebook paper, and put one word (be it an action, place, person, object, or symbol) that best represents what you want to happen in each chapter. That becomes the working chapter title. Then make notes about specific events that will occur in that chapter as well.
• Use an Excel spreadsheet to block out chapters and the scenes within them. Move events around as necessary. (You can also write character biographies as part of this exercise.) Then create a TOC.

Speaking of Excel, you can find lots of proven creative tools to help you organize your research and, later, your work. Some can be used on your computer or online. For example, you might explore these programs:

• Scrivener
• Evernote
• Dropbox
• Box.net
• Google Drive

Most Internet browsers, like Firefox, Internet Explorer, and Google Chrome, allow you to bookmark pages into folders you create and save them in those browsers. You can then organize your online research into folders named for each of your book’s chapters, which makes it easy to find the websites and web pages you have used for your book research.

You can also create a folder on your computer in which to save and organize research. Use your book’s title as the name of your primary book project folder. Create subfolders within that one for research, your manuscript (and separate chapters), book design, or anything else related to your book (including your business plan). You can save information you find online to the research folder by copying and pasting links and information to Word files. You can even scan research into files and save them into these folders. The same holds true for audio and video files and other snippets of information, including screenshots of web pages.

Many writers prefer old-school organizational methods, such as putting their research or ideas on 3 × 5 index cards and keeping them in those little index card boxes, putting papers in folders in a filing cabinet, creating piles, or saving information in boxes. Dan Poynter, author of How to Write Nonfiction, talks about creating the content for books with a “pile method”; each pile later becomes a chapter.

As you organize chapters for a nonfiction book, consider placing them in order like this:

For fiction (or memoir), consider something like this:

Whatever method you use to organize your TOC, make sure it is clear, well-defined, and as categorized as it needs to be for someone who doesn’t know anything about your book to look at your TOC and immediately see—and understand—what you are trying to accomplish.

How to Mind Map Your Book to Create a TOC

Another method I like to use to create a TOC is called “mind mapping.” Although quite creative, writers—especially nonfiction writers—tend to think in a linear fashion. Mind mapping allows you to move out of the left side of your brain, where you might develop an outline for your book (or write a business plan), and tap into the right side, where you can inspire the free flow of thoughts.

Also, mind mapping provides an exercise for brainstorming chapter ideas and storylines as well as content within nonfiction chapters, scenes within fiction chapters, and subheadings that delineate nonfiction. It allows you to drill down beneath your chapter titles to the actual content. You end up with a clearer idea of what you actually will write about in each chapter and what will appear in your completed manuscript.

You can purchase mind-mapping software or download free software, such as: xmind.net, mindmeister.com, freemind.sourceforge.net (http://freemind.sourceforge.net/wiki/index.php/Main_Page), and mindjet.com.

The easiest way to complete the exercise, though, involves purchasing a large posterboard and some colored sticky notes, such as Post-it Notes. I like the square or rectangular Post-its you can use to mark pages in a book as you read. You need ones made of a material you can write on.

Write your topic or title on a larger Post-it Note and place it in the middle of the board. Then start writing related topics, events, memories, or characters on the smaller sticky notes. I like to use one color for this part of the exercise. Just stick them all over the board. Don’t worry about where you place them unless you are certain they are related topics. In that case, you can group them together.

I call this a “brain dump.” Simply allow yourself to put everything you can possibly think of onto the board. Free-associate. Empty your mind. Fill the board to capacity without thought of organizing anything. When you think you are finished, think again … and again.

When done, organize the notes. Look for related topics, time periods, events, themes, or storylines. Pick up the notes and move them around. See which groupings are well suited to become chapters. More than likely, the ones with the most information or most scenes will work as chapters, but you may have to break some of them into more than one chapter if you have an overabundance of notes. Use a different-colored Post-it Note at the top of each grouping to delineate it as a chapter, and place a title on that note. As you group the Post-it Notes, you might get additional ideas. Add these into an appropriate group or chapter. (You might even brainstorm a whole new chapter in the process.)

As you complete the exercise, you should have created a number of chapters—hopefully ten to fifteen, if you are writing nonfiction. If you are writing a novel or memoir, you might have more. Now type each chapter name or subject into a TOC. Each of the sticky notes in the groupings below the chapter title becomes a topic, event, scene, or issue to cover in that particular chapter. (Hang onto this information for Step #6, when you flesh out your TOC into chapter summaries.)

As indicated above, you can mind map a novel using the same basic process. Place all the events or ideas for the story on various Post-its, and then move them around, combine them into scenes, and organize the scenes into chapters. Basically, you mind map a storyline.

One writer I know told me she does a modified mind-map exercise prior to writing her novels. She gets a bunch of blank paper and cuts each sheet in half. She then blocks in what will happen in each chapter on different-colored sticky notes and puts them on the pages—one blank page for each chapter. “This way I can move events around, add new ones, or get rid of things,” she says. “These pages are my outline. It’s a bit bulky and messy looking at times, but boy, oh boy, does it ever work for me.”

Once you’ve typed up your fiction TOC, evaluate if each chapter has a dramatic arc, carries out your themes, shows character development, etc. In Step #6, you will use this additional information you accrued during the process in Step #5 to write your synopsis or chapter summaries.

As you might have guessed, those writing memoirs can also use the mind map successfully. Brainstorm all the different events that happened during the time period you want to cover in your book. Let your mind wander so you can remember as many events as possible. Put them all on the board. Include the flashbacks you plan to write about. This exercise may even jostle some new memories. Then organize these events into a time line. Place the flashbacks in places that enhance your storytelling. Look at the time line for a narrative arc, a dramatic arc, themes, and, most important, transformational events. Then break the time line into chapters. Type these up into a TOC.

Some people like doing mind maps on a posterboard by writing down their ideas with colored pens or pencils; this is the traditional methodology that requires going though the same basic exercise described above, except when you are done brainstorming, you circle items and link them with lines. I find this rather confusing in the end; it can be hard to follow all of those lines and circles. You can do it more neatly on a white board using colored markers because you can erase items and move them around.

Evaluate Your Book’s Structure

Once you have completed your TOC, it’s time to continue your Author Training by looking at what you’ve created from a publishing business perspective—as if you were an acquisitions editor. You already have some training in this particular type of evaluation because you purchase books based on a TOC. Put this ability to use and evaluate your book’s TOC.

First, take a step back and imagine you are a potential reader of the book you want to write. Imagine that it already exists and you have found it in a bookstore or on Amazon.com. You pick it up or click to download it.

Go back and read what you wrote in Step #2: your book pitch, summary, and list of benefits. These are your promises to the reader. This is what you are trying to accomplish. Imagine this is the back-of-the-book copy; i.e., what you see written on your book’s back cover. Maybe it is more condensed and polished, but it’s something close to the marketing copy you view when you click on the “Look Inside” feature on Amazon.com or when you turn over the book in your hand. Reading this material, you know what the author promises will be inside the covers.

Now flip to your TOC, and see it through the lens of agents or acquisitions editors. They will consider what you wrote in Step #2, your promises and premise, and determine if your TOC follows logically, if you have followed through on everything you said you would while also targeting your market and providing unique and necessary content in your chosen category. Will a publishing professional think your TOC carries out everything you described in your Overview?

To see your TOC through the lens of an agent or editor, evaluate if your TOC:

• easily shows what your book is about, why it is unique, and why it is necessary
• provides an order that reflects a beginning, middle, and end of your subject or story
• illustrates a compelling, unique topic or story with depth
• keeps your promises to the reader and matches your Overview

Books need structure. Plenty of room exists for creativity, but a book without a clearly defined TOC won’t get readers where you want them to go and won’t fulfill the premise laid out in your Overview. Remember: The TOC provides the map for your book as well as its structure. You’ll use it to ensure you get to your destination. Write the book you set out to write, get your readers where you want them to go, and make sure they receive the information you promised they would receive.

When you have a strong TOC, you have an essential part of the writing guide you are creating during your Author Training Process. If your TOC evaluation proves you’ve accomplished that step, move on to the next one, where you will learn to provide directions—summaries—to go with that map.

But if your TOC evaluation proves that you do not have a strong enough idea, that your proposed steps don’t align with your Overview, or that have holes in your proposed TOC, go back through the steps in this chapter again—or revisit Step #2, Find Out If You Know What Your Book Is About and Why Someone Would Want to Read (Buy) It. You might need to get more clarity on your idea. Remember that each step builds on the next; you are involved in a process. Run back through the process with the research you have accumulated, if necessary. If you must repeat steps a few times, so be it—this is what you need to do to create a successful book and achieve your goal of successful authorship. That means you have trained yourself to have an Author Attitude. WOOT!

Suggested Reading:

Finish What You Start: How to Set Priorities, Organize Your Thoughts, Defeat Procrastination, and Complete Outstanding Projects by Kerry Gene
Mind Mapping for Writers: How to Improve Productivity, Overcome Procrastination, Get Creative and Finish Writing That Book Using Your Lack of Focus as an Advantage by David Lynch