On Writing: When Outlines Attack

Back in my early days of novel writing, I was addicted to reading how-to books. I raced through one after another with barely a breath between them, let alone time to apply what I’d just read. Eventually, I became disgusted with my lack of progress after eight years of working on the same novel and decided to read a book and actually do the exercises in it. That book was The Weekend Novelist by Robert J. Ray:

“A dynamic 52-week program to help you produce a finished novel…one weekend at a time.”

I can already hear the groans of the writers in the audience who sit down to a blank sheet of paper and start writing a novel with not one bit of a plan in mind. Bear with me. 🙂

On Weekend 1, I started with character sketches and completed one for each of my characters. I progressed to the characters’ back stories, their dreams, the contents of their closets, and then it was time for storyboarding, sketching out scenes, and setting the stage. I’ll admit I was having fun in those early weeks, exploring and discovering.

Soon I had a 3-column table listing every scene that would eventually be in my novel in excruciating detail. I was ready to sit down and write. And that I did, right up to the last quarter of the book where I stopped dead and lost all interest in finishing.

The following year, I showed up for a writing workshop at my local library. We were told to bring our in-progress novels and any other materials that we had created to facilitate the writing process. As we went around the table, each person held up a chapter or two and told a similar tale about how they had sat down to a blank page, begun writing, and hadn’t gotten very far. Then, it was my turn. I pushed my hand truck up to the table and started unloading my specimens. [click on graphic to enlarge]

The shock and horror on the faces of the other participants will never leave my memory. It was like I was the star of a circus freak show.

When I finished my spiel, the instructor stood up and said something so simple and obvious, it’s hard to believe I hadn’t thought of it before. But it was truly a light-bulb moment for me [click on graphic to enlarge]:

Then she turned to the others and said, “She needs to do less plotting and outlining, but you need to do a bit more.”

I barely heard the rest of it because my brain had jumped into high gear. I realized she was right. I had already written the novel in summary form and dreaded writing it again. A few years later, I would study personality typing tools like Myers-Briggs and realize that I am an unstructured person by nature who had been forcing myself to operate in a super-structured way for an extended period of time. That mistake had sucked the creativity and fun out of the writing process.

“If I had a plot that was all set in advance, why would I want go through the agony of writing the novel? A novel is a kind of exploration and discovery, for me at any rate.”  —Chaim Potok

From that point on, I did away with the tomes of reconnaissance on my characters. When I had an idea for a new novel, I’d jot down some notes and play with the idea like it was a piece of clay, mushing it this way and that until I saw something I liked. Over the course of the writing process, I’d record a bare-bones list of scenes, maybe 1-2 sentences for each scene. Sometimes the scene had already been written. Sometimes it hadn’t and I didn’t want a good idea to slip through the sieve that is my brain.

The skeletal structure of my outline made it extremely flexible. I could delete or add ideas whenever the mood hit. It was also helpful as a Cliff Notes-type tool to remind me what I had already written, so I didn’t have to waste time rereading chapters before getting down to the task of writing. Perhaps the best part of such an outline is that it makes the dreaded synopsis, a submissions requirement of many publishers, much easier to write because it is already in “tell/don’t show mode,” which is how a synopsis should be written unlike the novel itself.

I’ve seen debates online where writers claim their approach to writing is the better method. Writing organically, or not, is a good thing only if that is how you write best. If it’s not, forcing yourself to work that way is a major chore. And let’s face it, writing is hard enough when you’re doing it in a manner that is true to your personality type.

With that said, I do think it sometimes helps to sprinkle a pinch of “opposite function” into the stew. For example, when you’re flying by the seat of your pants and you feel yourself floating off into space, maybe a bit of a plan would help. And if you’re recording every last detail in an outline before you even begin writing and find that you’re stuck, maybe it’s time to put away the outline, take a notebook outside and just start writing whatever comes into mind. These kinds of tricks often help to awaken the part of your brain that’s having a long siesta.

In 2009, I participated in NaNoWriMo (National Novel Writing Month), an exercise in which you write a 50,000-word novel in one month. I started on November 1st with the barest hint of an idea and had to come up with 1,667 words of pure, unthought-out originality every day. I managed to churn the words out for about half the month until my novel The Benefactor was published and book promotion took precedence. However, I did end up with about 28,000 words of a novel that I was looking forward to continuing. I planned to proceed in the same manner—without a plan—but because of the complexity of the story, I repeatedly found myself in a labyrinth of dead ends. I wasted a lot of time before I gave in and wrote out a brief outline to make sense of the various twists and turns and to gear up for an equally complex second half.

As a technical writer in a my day job, I’m happy to plan out the details in advance to be sure my documentation covers all the bases. At night, I prefer to be a bit more creative and meander the various paths that could lead to the end of a novel. But I’m most comfortable doing that with a crude map in hand, just in case I get lost along the way. That’s who I am.

I’d love to hear about your light-bulb moments in writing or self-discovery.


36 comments on “On Writing: When Outlines Attack

  1. Kaitlin on

    Wow, that workshoper was brilliant! I find that I do just about that – I plot just enough to always have a direction, but never so much that I wind up getting bored. Hooray for Nanowrimo!

  2. rebecca @ altared spaces on

    Love, love this story and the love you offer yourself. Laughing at ourselves is potent. You do it so well! It must bring you and your family great joy. I am you. Stacks of journals well writen….the memoir…not so much.

    Lightbulb: 10 years after arriving at Mother T’s convent and realizing the cab driver let me off blocks from there because he was frightened. I didn’t know any better so I remained unharmed. This is one of my gifts. I charge forward, unaware I should be afraid. (It’s gotten me into heaps of other trouble as you can imagine 🙂 )

    • Margaret Reyes Dempsey on

      OMG, thank you for reminding me of your Mother T story. I had forgotten about that until now. It’s true…if you didn’t know enough to be afraid, you weren’t giving off a victim vibe. Plus, I’d like to think that given your purpose in being in that neck of the woods, someOne had surrounded you with a veil of protection…or maybe a cloak of invisibility, depending on your views. 😉

  3. Brenda on

    Yes, a thought provoking post that I’m sure other writer’s who learned similar and operated outside of their parameters (failed) and then figured things out. It seems like a right of passage for writers – doing everything that seems unnatural. Followed by writing 10,000 words and taking workshops and reading books on how to before finally sitting down to write. At some point (assuming the person hasn’t given up) everything comes together. For me, my lesson was to trust my gut and be true to the characters and the story. I agree with your comment about letting the creative withing roam free.

  4. Kemi on

    Great insight, Margaret! And what a relief to know that there’s no one way to write.

    I started my last and only novel just knowing my main character, her fears and dreams. I also had a vague idea of the key people in her life and that was it! I believe in this world, and especially in novel-writing world, anything can happen to anybody… Thank you for sharing your experience – fab!

  5. suzicate on

    I find I work much better without a plan. When I plan things out I put too much expectation on myself and the fear wins every time. Thank you sor sharing your process and giving us all hope.

  6. Richard on

    Funny post, as ever, Maggie. You make clip-art fun. And that takes some doing. 😀

    I think you’ve identified another important point in here; that the amount of planning you should do also depends on the kind of story you’re writing. Whodunnits and labyrinthine mystery stories are going to require a lot of planning, whether you like it or not. Which is why I don’t write them. 😉

    However, there is nothing like the feeling of having a eureka moment while you’re in the thick of writing. No plan, no forethought, just the moment when the right line or the right event comes to you on the fly. It makes you want to know what happens next and that feeling is the very essence of a good story. To have it while you’re writing the story is ideal. 🙂

    • Margaret Reyes Dempsey on

      So true, so true. I love those moments. A great idea is like a ball of energy that dissipates in the telling, whether the telling is verbal or on the page. I need to learn to sit quietly with those “great ideas” and get them down on paper while the energy is high. If I blurt them out to someone before that happens, the writing is never as pleasurable.

  7. Lisa Creech Bledsoe on

    This. Explains. Everything.

    And it even uses pictures. My God, I feel so inspired!

    I too am a “structured” writer by day (for that I get paid), and an “unstructured” writer by night. Or weekend. Or whenever I put a few hours into it. And I while I wasn’t too worried about this “novel in my closet”, I have been wondering what the hell was going to happen with 4 zillion misc plot dramas that are going on. Dead ends everywhere! This is JUST the prescription I need to get back into it. A simple outline will help so much, I think.

    Note to self: Be sure to add “Thank Heaven for Margaret D” in the acknowledgements (of this book which may never see the light of day, but which is once again engaging…)!

  8. Cynthia on

    Chuckling as always after one of your posts, Margaret. Forgetting writing for a moment, I have a little of this problem in my design work – i like to solve design problems in my imagination, and if I do too much of it before I sit down with the fabric, yarn or semi-precious stones, then, as you say, I am too familiar and bored with the solution process to get the doing of it done. I need to clear space and time in my life to be able to act on those things in the moment, rather than constantly shelving them… ooooh I feel a new year coming on…

  9. Mark Petruska on

    I have always believed that the best approach is whatever works for eac individual writer. Take me, for example: I have never been able to outline a story in advance. I have only a rough idea of where things are headed, and it’s locked away in my brain. This approach has led to some unexpected plot twists and turns and, I fully believe, contributed to a better novel in the end. Obviously though, this fly-by-the-seat-of-your-pants style of writing doesn’t work for everybody.

    Oh, and like you, I have a bookshelf full of “how to write” books with similar exercises. None of which I have ever completed. Oops!

  10. Barb on

    I have a friend who outlines every scene in every chapter before she starts. It doesn’t work for me,,, but then we’re all different. I’m with you. I need some twists and surprises that only come with being flexible. Thanks for the discussion here.

    • Margaret Reyes Dempsey on

      If the basic ideas are in her outline, it may well be that she experiences the twists and surprises as she goes deeper in the writing. She may even edit her outline several times along the way to reflect the new paths she takes in the process. That’s how it usually turns out for me.

      Thanks for stopping by, Barb.

  11. bronxboy55 on

    I agree with you completely, Margaret. “Writing organically, or not, is a good thing only if that is how you write best.” I read articles all the time that claim to offer the best approach to writing. But we’re all different. And as you also said, sometimes we need to change it up, and apply different strategies at different times. What works is simply what works.

    • Margaret Reyes Dempsey on

      There’s something wildly quirky about being a writer. Maybe it’s not too far off from being a major league baseball player with a host of rituals and superstitions when you step up to the plate…or sit down to write. I’ve never heard people in other occupations question how to get down to the business of their job. My accountant most likely doesn’t show up at a CPA convention and ask what type of pencil the other CPAs use or whether they lock themselves in their offices at a set time and complete a certain number of tax returns before exiting. 😀 We seem to focus as much on the ritual as on the content. Maybe too much on the ritual at times. There must be an explanation for that, but I haven’t figured it out yet.

  12. CCIFW on

    First of all I want to say superb blog! I had a quick question in which I’d like to ask if you don’t mind. I was curious to find out how you center yourself and clear your mind prior to writing. I have had a hard time clearing my mind in getting my thoughts out. I truly do enjoy writing but it just seems like the first 10 to 15 minutes are lost just trying to figure out how to begin. Any recommendations or hints? Many thanks!

  13. Debra Colby-Conklin on

    This reminds me of how I realized I need to write. I tend to sketch out a brief summary of what I want to happen in a chapter in order to keep the flow of the story going, then I go ahead and write. Keeps me focused and on track and keeps the story from going in a hundred different directions (which is something I tend to do). Thanks for your insights.

  14. silver price on

    Wow… that is a complex question. I think that if you ask that question to a dozen writers you will end up getting thirteen answers.I do what works for me. I know a couple of actually published writers and when I tell them how I outline they look at me as if I had suddenly grown horns. But here goes…For me an outline is a continually developing and ever evolving document. I have about two thirds of my current WIP written but yesterday I was in my outline making changes and adjusting things. As I write the story subtly shifts and new areas that beg to be covered emerge, sometimes later in the story and sometimes in passages I’ve already written.All my outlines start out as a brainstorming session. My brainstorming is done sitting in front of my computer and it comes out as a long rambling letter to myself about the story I’m thinking about. I just let my mind go and put down all the fun ideas I have and the problems that are cropping up. And then I just play with those problems and ideas. I’ll ask a question about a particular plot feature and just write on it until I figure out what I’m going to do…sometimes that takes a couple pages. For my current WIP I have 14 brainstorming documents each run form 12 to 20 pages. I brainstorm a lot.Once I have the basics brainstormed out that’s when the actual outlining starts. The story structure is put in place. I use the lessons of writer Dan Wells in making the basic structure. He has a series of very entertaining lectures on YouTube that I refer to often: http://www.youtube.com/watch?v=KcmiqQ9NpPE&feature=relatedThen it is a series of brainstorming sessions followed by filling in the spaces of my outline. I don’t use a formal outline style, to restrictive; in the end it’s just a numbered series of short paragraphs. Each chapter gets a paragraph. My current WIP’s outline is 4 pages long and I’m happy with that length. Just enough detail I can tell what’s going on, but short enough I can find things in it if I want to.

    • Margaret Reyes Dempsey on

      Thank you for your comment and the link to the lectures. I am a brainstormer, too. I also find that speaking my thoughts helps my process. I don’t even need the other person to comment. There’s something in just speaking the words aloud that allows me to hear them in a different way and helps me break through the tough patches.


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