Bad Advice Wednesday: The Annotated Table of Contents

categories: Bad Advice / Cocktail Hour


Table of Contents for "100 Famous Views of Edo"

Let’s say you have an idea for a nonfiction book, whether it’s a memoir, an extended personal essay, journalism, or something else.  It’s hard to get started, isn’t it?  Or if easy enough to get started, hard to keep going.  Part of the problem is knowing where to start, and after that, where to go.


Or you’ve finished a draft of a book and the chaptering came willy-nilly as you composed.  There are holes in the narrative or in the stream of argument.  The sections are of all sizes and methods and shapes.  There’s no sense of progression, or if there is, the progression seems to stutter.


Or say you’ve written four essays on a related theme.  Growing up in Nigeria, for example.  Or your life as a teacher and coach.  Or in my case, more than 20 years ago, on my adventures in nature with my then girlfriend (now wife) Juliet.


Or take it a little further–you’ve thought quite a bit on your subject and have some preliminary chapters put together and you want to go ahead and pitch your book idea to editors or agents.


Or back up a little: You haven’t written much at all, but you’d like to explore the possibility of writing a book on your subject of choice.


In each case and many others I advocate the annotated table of contents.  It’s a simple thing.  You give your book idea a title, if it hasn’t already got one, and then you decide arbitrarily on a number of chapters.  Ten or fifteen or twenty–doesn’t matter.  Then you make yourself a table of contents, each chapter with a title of its own followed by a two-or-three line description.

One exercise I give to writers who haven’t written much is to think what book they might write in an ideal world, one in which they had all the time and money and talent and skills they needed.  What would be in chapter one?

Sometimes you can’t quite answer that, but you know that such-and-such an event or idea must be in the middle.  So start there: Chapter 7:  We begin to breed dalmations.  And fill in the annotation (which amounts to a descripton of the contents of that fantasy chapter), as best you can, several sentences or more.  Chapter 7 should begin to suggest what should be in chapters 6 and 8.  So fill those in a little, too.

If you’re the one with the four related essays–declare them chapters.  Where would they each fit in the greater story that links them?  What chapters are missing, and what would be in them?  Your lines of annotation might grow to include research notes, and maybe passages and portions of what you will eventually write–sometimes, the annotations can grow into chapters, practically on their own.

If you’re ready to try a book proposal on editors or agents, an annotated table of contents is a very helpful item to include.  Your writing samples will prove your skills, and your pitch will lay out the nub of your idea, but the table of contents will illustrate the shape of the proposed project, make it possible for potential supporters to picture it whole.

My first book, Summers with Juliet, came about because my friend Betsy Lerner (who at the time was an editor and is now my agent), read four seemingly unrelated essays I’d written in grad school and noticed that all four had to do with a life in nature, and further, that all of them involved Juliet, something a little different.  Betsy suggested I put together a table of contents.  The pieces I’d written all fell into the middle of the portrait of a future book that emerged.  I’d met Juliet in the summer, so that must be chapter one.  We’d gotten married in the summer, eight years later, so that must be the last chapter.  I let chronology rule, and filled in the blank spots with chapters that filled in what was missing, this summer, then that.

Always, the best thing to do is start writing.  The annotated table of contents can help.  The next thing is to keep going: pick a chapter that’s gone unwritten, and get to work.

  1. Kyle Minor writes:

    Bill, you’re a closet Oulipian, or something formalist or French, anyway. I like it.

    And good post, too. Another good post. Lots of them, by now. This is such a nice place to visit.

    • Bill writes:

      My favorite Oulipian is Charles Mingus. But I don’t get why you say this here? We gots to get you to do a guest column on the Oulipians…

      • Kyle Minor writes:

        Not in any specific or rigid way an Oulipian. You’re not doing math stories or random generation or anything. But the spirit of this post — to let a formal machine drive the choices, as in your annotated bibiliography — isn’t as far from that sort of thing as one might think.

        I enjoy hearing more or less naturalist writers talk about their processes with regard to formal concerns, and what they yield for books whose readers would never know.

        Regarding Summers with Juliet, I always thought you were lucky to have a partner with a romantic name that immediately calls to mind Shakespeare’s Juliet. The title of the book (Summers, too!) creates a big generous space in the mind of the reader for receiving whatever follows. I like hearing, here, how the essays preceded the title and the idea of the book, and then the book was knit together out of the title and the idea of the book.

        There are parts of that book — such as the places where the lovers brag about their past lovers, especially that talk about the pool table — that made me realize, when I read that book (and I was very young), that there were more ways to understand love and sex than I had known in my life, and that one antidote for anger and jealousy might well be a generosity that passes for a better sort of love.

        I realize I never talked to you about that book — there’s more to say. Maybe one of these days we’ll be in the same place at that same time, and I can buy you the first of the 73 beers I probably owe you by now.

  2. Tommy writes:

    Bill, this is REALLY good bad advice! I’m guessin’ you’re one hell of a teacher!

  3. Marie Marshall writes:


    Just thinking back… My first novel, I had the story in my head, in fact I had two parallel stories which seemed so obviously linked, but the link instead of resolving at the end became less tangible and dissolved. With that one I simply sat down and wrote, every spare minute I could find, until it was finished. No plan, no chapter headings, no nothing, bish bash bosh, result! 🙂

    My second novel started out that way too. I had always criticised J K Rowling, and my friends said to me, “Okay, if you’re so smart, write a fantasy set in a school that’s better than a Harry Potter story!” So I did. I wrote a weird, inexplicable tale set in a Comprehensive school in the Essex suburbs of London. I wrote it for a friend’s daughter, and my friend drip-fed it to her one chapter per day as a reward for doing her homework. Never had homework been so faithfully done. But when I stepped back and looked at the result – something of novella size – I decided to add two further sections, to re-tell the whole story through the eyes of two of the other characters, and indeed to arrange one of the stories so it was told backwards in order to reveal more of the ‘back story’. It was hard work trying to get the different register of each part of the book, trying to get into the heads of three separate 1st-person narrators, each of which saw the same events totally differently. Work progressed sporadically, but I got there.

    I am currently writing my third novel, and I am stuck. Maybe this is more to do with my physical (and mental) health than any failure of process. However, it is at times like this when process can help bring clarity to a project. So I am now looking with interest at your advice above…

    Many thanks.

    Marie Marshall

    • Bill writes:

      Definitely going to address novel composition in the next post! Definitely different from nonfiction in some key ways…. Your projects sound terrific! It’s all such a strange journey.

  4. Chelle G writes:

    I have been working on short stories recently and thus far have published five of them in small literary magazines. I never pictured myself working on shorts but as a grad student, a mom, and a small business owner these pieces are easier to budget time and effort for than a larger project like a novel. Like your collection of essays my shorts all have related content but I was unsure of what to do with them until now. Thanks for the tips.

    • Bill writes:

      It’s a slightly different game with fiction, I think. When are related or linked stories actually starting to turn into a novel? And how is a novel different from linked stories? For fiction, I like using movie techniques, like storyboarding and sequences of scenes, fun to get out the index cards and visualize–but I’ll save that for future bad advice!