Writing My Novel: When Outlines Fail

Fail Whale When I first started seriously working on my novel, I said that “I definitely want to outline.”  I knew that going into writing something as complex as a novel without a plan would lead to failure.

So I sat down and thought about what I wanted to happen in my novel.  I broke it down into sections and subsections.  I thought about the narrative arc and who was where at what time, and then I sat down with my handy-dandy Moleskine notebook and wrote it all out.

Round Hole, Square Peg

I got about a quarter of the novel outlined before I realized that I was spending too much time writing details into the outline.  Instead of simple path markers, I was writing out whole scenes by hand.  I was basically synopsizing my whole novel as I went.  Which wouldn’t have been a bad thing had I not been doing that with every single bullet-point I wanted to bring up.

It didn’t take me long to realize that outlining just wasn’t for me.  I just couldn’t stick with it because of my inherent wordiness and attention to detail.  I was working with a form that just didn’t fit my style.  My style was the square peg and outlining was my round hole.  No matter how much I wanted them to fit, they wouldn’t.

So I went back to the style that I thought worked in the past: just writing.  Then it failed, too.

I kept thinking of ideas for parts I wasn’t working on, trying to go back or go forward and edit it in, and lose my current train of thought in the process.  I was getting nowhere, and my novel was suffering for it.

Well, Duh!

47e8a_Evernote_Icon_256 I felt like an idiot when I stumbled on a system that actually worked.  I was glad I found it, but in reality, I had been using it all along.  On my iPhone. But not for my novel.

You see, I’m a fanatic about notes.  I jot notes about everything, and since I’ve had a smartphone, I’ve been fanatical about keeping them with me at all times.  I use the Evernote app to sync my notes so that I’m never without them.

Why I didn’t use this particular system to help with my novel initially is beyond me, but once I did, I found things working much more smoothly for two main reasons:

  1. I could write as little or as much as I wanted.  Depending on the need, I could write a sentence.  If I needed a paragraph or eight, I could do that, too, and I wouldn’t be going outside the form’s boundaries.
  2. I could sync them anywhere.  While I didn’t actually use Evernote for my novel, I did use MS Office Online Workspaces (Google Docs was my initial choice, but it gave me a lot of silly problems that added up to be a bigger headache than it was worth).  With Office Online, I was able to keep both my notes and manuscript synced so I could work on them anywhere, when before, I found myself without my Moleskine notebook pretty often.

What I Did

I made two documents.  One was my manuscript file.  I use .docx because of its smaller file size than .doc, which meant easier uploads and downloads on the go.  The other document was my notes file.  It was just a normal MS Word .docx, but I separated it into sections:

  • Backstory Notes (this section included organizational subheadings depending on what part of the novel I was trying to clarify)
  • Structure Notes
  • Plot Notes
  • Revision Notes
  • Unused Text

Under each of these sections sits a series of bullet points that I could append anytime I felt like it.  Some of the stuff didn’t end up making it into the first draft, but a lot of it did.  And that’s okay because I knew by just looking at the document what went where and why.

The biggest boon to this style of planning was that it matched perfectly how I thought about the novel in my mind.  I could visualize my notes document and organize my day’s writing with it.  I could start writing a portion of my novel, refer back to my notes occasionally, and realize that I had left out a major idea I wanted to include.  I would then go back and fix it.  While that’s possible with outlining, the linearity that goes with outlines just doesn’t work for me.  I have notes for sections out of chronological order, and that’s okay—because I know where they go in the novel.

And maybe that’s arbitrary, but to me, outlining was restrictive.  It felt like I was writing a sonnet instead of a novel.  It never felt right.  Notes felt great, however.

Lesson Learned?

Just because other writers do something one way absolutely does not mean that it works for all writers.  I know a lot of people who work very well with outlines.  I don’t see how, but they do; they like the rigid structure, but I don’t.  I know some people who sketch scenes on index cards and arrange them on a corkboard with ideas tacked all around them.  Even for me, that’s a bit disorganized and fluid.  I know of some people who write novels off the cuff and have the whole shebang contained within their noggins.  Kudos to them; their minds can correlate much more data than mine can.

photo I found that the “notes” style of planning worked for me, and I know it will continue to work for me when I start my next novel.  I’ll be one step ahead of where I was when I started this one.  And that’s what writing my novel has been: learning what I can do better next time.

So on the topic of planning and outlining and note taking, my advice to you is simple: do whatever works.  If you are the kind of person who can sketch an idea on a napkin and go home to write a Pulitzer winner from it, then go for it.  You have my blessing.  If not, then that’s okay, too.

Just don’t go into writing a novel as thinking that there’s a right way and a wrong way to do it.  I thought originally that there was.  I learned quickly and harshly that wasn’t true.  Every writer is different, and what works for one may not work for another.  The right and wrong dichotomy has no place in the process of writing; it’s all far too subjective.  Give all the methods and styles a try, see what fits, and when you find a method of planning your writing that works for you, stick with it. It’ll pay dividends when you have that finished manuscript in your hands.


  1. Longasc

    The way you write novels is very much the way I wrote my theses. I think it is your academic background that influences the way you write enormously. Interesting that you rather used Office than Google Docs for that. I prefer it over Docs, too! Unlike Picasa which I learnt to love, Google Docs and me simply do not get together. I usually save in .doc format, never noticed .docx is smaller. I do it for compatibility reasons, there are still many people who user older office versions or other word processors that still can’t read .docx properly.

    • I don’t doubt it is my academic background coming out and influencing that. I write completely differently than my wife. When she gets done with a project, she has very little revision to do because she pores over each word. I write until I’m done and then go back and can fix whatever I want. Outlines don’t work for that very well, but notes do.

      With the circles I’m in generally, .docx has been accepted. My main thing is that Kindle can’t use a .docx format yet, so I have to convert to keep documents as ebooks.

  2. I didn’t start outlining my novel until I was about 100 pages in. I found that the editor in me needed to know at that point that I wasn’t just wasting my time writing superfluous scenes. Each chapter synopsis consisted of only a couple of sentences, enough to let me know where I was supposed to start and end. It was a lifesaver for me and actually got me back on track. Of course, the outline changes as I write more and more, and I scribble little things here and there, and it’s turning into a little bit of a mess, but I don’t know what I would have done without it.

    • I’ll probably have something more along those lines when I start my next novel. That is, a couple of sentences that let me know where it starts and ends or who’s doing what. But I can’t have a lot more than that. Even that might be too much micromanagement for me. I will most likely just map out the major events I want to happen in the book and let the other pieces fall where they will. In my mind, too much control of the initial draft was harmful. Now that it’s finished, I can go back and screw with it until its perfect.

  3. I actually use a student’s notetaking program for this sort of thing… are you familiar with Microsoft OneNote? It’s a series of notebooks (heh, I keep actual class notes in only one of mine) divided into various tabs — mine are things like chapters or sections of story, character profiles, outlines, names, bits of clever phraseology I’m (stealing) inspired by, and so on and so forth. You can create separate pages on each tab, and within pages you can drag any particular bit of text around in its own little textbox. I get these neat little word clouds going that help me associate ideas with each other. You can also screenshot bits of anything, including pdfs and paste them into the notebooks, and it has a full set of highlighters and brushes and chart/table sort of tools.

    Has made an enormous difference to my ability to find things I would once have just jotted down on the back of an envelope and then never seen again. I actually have a separate notebook for blogging too.

    • And since I seem to be full of OneNote praise tonight… it’s also a godsend for organizing a tabletop campaign! I keep all my character sheets in there as well as screen snips for important things like XP/level information or what exactly the magic item the party is carrying does. Since I use PDF copies of game books whenever possible, the screen snip method is awesome, and everything I need for a game is in my laptop, handy and portable.

      Plus all the characters, background info, everything is fully editable, without destroying a paper copy with a million eraser marks…. /sigh I love.

    • I’m incredibly interested in OneNote now. I’ve had it installed since, well, forever, but I’ve never actually used it. If it’s as robust as you say it is, I’m going to go in a few moments and check it out and see if I can get my notes for this novel copied into it. The various tabs very well could make my life a lot simpler than just having headings I keep copying into. I’m an anti-clutter junkie, though, so one incredibly minor thing that might keep me from really utilizing it is not having the window for the program stack with MS Word in Windows 7’s taskbar. I’m kind of nutty about stuff like that.

      I really do appreciate the info, though; OneNote never cross my mind, but what you’re describing sounds pretty near perfect for me.

        • The thing is that MS Office online doesn’t really work with my iPhone, either. I’ve set up a notebook for my novels and figured out tabs and pages, so I’m going to give it a shot. I need to email myself the .one file and see if I can open it on my iPhone. If not, it loses a little bit of functionality, but not a lot since I couldn’t edit them outside of Evernote or Mail anyway, and the programs never synced to begin with. I copied/pasted a lot.

  4. I have encountered the exact same problem. I’m not sure that I’ve hit on the right method for me yet, but this is helpful information. Thanks!

    *PS/ If you have a Mac, you may find Scrivner a very useful tool. It is designed especially for novel writers, and I love it…