“Outlining is an important part of writing, but no one ever buys anything off the NYT Bestselling Outlines list.” ~ Me

A question from writer Mike Cummings spawned the little quip above. After thinking about it for quite a bit, this afternoon I figured I ought to back it up with some actual writing of my own.

If you’ll recall (and most of you will not because it was more than five years ago), the original concept for HNTW was to run my own writing through the sieve of popular how-to writing books and see what came out. The first book I profiled was Writing the Blockbuster Novel by Albert Zuckerman, and I still think his examples of outlining are among the best I’ve found.

Now, before you get all click-happy on the link, you should know that the post is thousands and thousands of words long. So, rather than make you wade through all of that, I’ve taken the little outlining section and posted below.

Meet you at the end of the post for more… Enjoy!


In the introduction to this chapter, Zuckerman points out the tried and true of outlining: no one builds a bridge without a set of plans. He goes on about skyscrapers and such, but really you can boil it down to my little statement.

What is really important though are the following points:

There are authors who commence a novel without working up an outline. They say it inhibits their creativity, takes the joy out of writing, removes the joy from discovering the hidden gems of plot and character that only come while writing the prose itself.

I’m paraphrasing again, but I’m also quoting too. Unfortunately, I’m quoting myself. My god how I hate to outline.

To me, outlining is all that is said above and more. Much more. Outlining is a huge time sink, it is addictive, and what’s more, outlining has caused me to rub out many a good story by just getting bored with it.

But you know, there’s something painfully obvious to be learned from statements like this. If you, as the author, get bored with your subject, how is your reader going to feel?

I don’t care if you are writing the greatest literary masterpiece the world has ever seen. If you are so gung-ho fired up about it that you just simply cannot be bothered with planning and must write then you are a hobbyist not a professional writer. I can say this with some authority because I have never been paid for my work and I’ve written two novels, perhaps several hundred short stories, maybe a thousand poems, and I have over 1MM (that’s million) words in my journal. I’ve been writing steadily, daily, for almost fifteen years now and not a penny. If this isn’t the definition of a hobbyist (and a maniacal one at that), then perhaps we should consult the OED again.

hobby – a favorite subject or occupation that is not one’s main business; a spare-time activity followed for pleasure or relaxation. Cf. earlier hobby-horse (this means it’s derived from the longer “hobby-horse”).

hobby-horse – (among other definitions) a topic to which a person constantly recurs or in which he or she shows and obsessive interest. “He also had a tendency to be down-right boring once he climb aboard his hobbyhorse.”

I don’t know about you, but that quote really hammers it home. How often do you rail on to others about the passion and pleasures of writing? And yet, when it comes to doing it you don’t want to take the measured approach, the professional approach, and just get on with it?

I write each day before I go into my day job. If, for some reason, I get interrupted or I have to cut it short, I become surly and moon for the dream world where all I do is write all day and how wonderful that would be.


The writing I do and have done on a daily basis is a hobby. If idea that you are not working professionally in your writing makes you angry (and just the idea of the word professional sends me into a rage), then you are a hobbyist pure and simple. There is nothing wrong with this though. You might enjoy this hobby for years and years. And then, like many hobbyists, you want to turn around and make it your business. If you do, you will find out what all hobbyists and amateurs discover when turning their passions to profit – it is hard work.

Alright already! What the Hell is an Outline?

Ok, so what the hell does an outline look like?

Like a lot of young writers, my first outlines looked like the sort you are taught to make in high school. Proper headings and subheadings, bulleted all the way down, etc. However, as I’ve read through a number of actual outlines written by successful authors I find this is not what comprises an outline for a novel (or anything else for that matter, unless you are following the MFA guidebook).

So many writing books and courses tell you to show not tell. Well, this is where the good news comes in. Outlining is the one place where you want to do exactly the opposite. Outlining is telling the story, over and over again until you flesh out the plot to such a degree that is crackling with deep connections between the characters and all non-essential details are pushed far into the background. Zuckerman describes it as a process that is defined by layering. No author should be remotely satisfied with the first attempt, or the second for that matter. And most importantly it takes time.

Outlines in the Book

Zuckerman provides not one, but four examples in the chapter on outlining and they are all for the same book The Man from St. Petersburg by Ken Follett. This is a valuable resource as it demonstrates the evolution from a terrible and trite plot to one that is rippling with excitement and fun. It also gives a good idea how to take a hugely complex historical setting (in this case the run-up to World War I) and turn it into a narrative drama.

As you might expect, this is incredibly tedious to read. The first outline introduces an interesting but rather weak story. I found it a reason to take heart though. You see, though I claim to hate it I have in fact written many outlines for books. I just didn’t realize it. Like the hobbyist described above, I generally start writing a story by focusing on a character or a scene. From there, it sort of grows organically, which is swell if you are only doing it for fun, but hell if you want the plot strands to work out properly.

For example, I started writing a book for my son a couple months ago. The general idea was to write a kind of Alice in Wonderland as told by Tim Burton though with a bit of Narnia tossed in. I am now seven chapters into the thing and I’m stuck. I know sort of where I want to go next, and I know how it ends, but I don’t have a map to get there. Problem is, I’ve been letting my son read each chapter as they rolled off the fingers, and so I have a little boy asking very pointed questions about what happens to this character or that. How does such and such get away? When do these characters get back together? Kids are great. They will tell you what they think without reservation or concern for your feelings. I love it, and I am terrified.

The reality is, I need to stop working on this now that I have the flavor of it and try to figure out the real way this ought to go together. In the past, I’d see this as a failure on my part, that I’d failed to finish the work and just dribbled away into writing about the story instead of writing the story. Zuckerman notes that this is often what writers do. They bang out some prose in order to get a feel for the characters or the setting and then set all that aside to do the heavy lifting of outlining. So, perhaps what I was doing all along wasn’t so bad.

Getting back to the Follett outlines, the second draft blows. I fell asleep reading it, and this was at 9AM after three shots of espresso. However, outlines three and four were great. In between each outline, Zuckerman recaps the high points and the low. He explains how Follett tightened up the drama and why. After reading the fourth outline, I now know this book backwards and forwards but I also want to read the actual book in a bad way, in a way I didn’t after reading the first outline. That says something to me. Outlining can be powerful if you actively engage in it and do not become frustrated.

The Goal of Outlining

Sometimes the last thing should be the first thing. This is true in editing where often the last sentence of a paragraph makes a much stronger first sentence. I’ve even seen this sort of thing happen within a paragraph where a series of internal sentences have more impact when arranged in a different order (often the last appearing first). This section is no different. The Goal of Outlining really belongs at the of the section – see, this sentence would work better as the first sentence of the paragraph.

But it isn’t going to happen that way.

There are a few core lessons to be absorbed from the outlining chapter, and I think, dry as it can be, you really should read the chapter and all of the outlines by Ken Follett. But if you can’t be bothered with that, and if all of my prattling up to this point hasn’t convinced you, here is the goals of outlining…

Focus on your primary characters: While building out the first few outlines, Follett keeps adding in minor characters to supplement the major players. It’s almost as if he doesn’t realize who the key characters are, or is unsure of their depth. Alright, let’s make it simple. In the first few passes, all of the main characters are cardboard versions of their roles. They do not have any depth whatsoever. As Follett moves through the revisions, he absorbs minor characters into the bodies of the majors. The result is a core of powerful entities whose interactions are deep, complex, and continuous.

That’s it. Sort of. You have to read through the rest of the book to see how this principle fits in with the body of fiction-making.

[Back to the present…]

Now way back at the top of this post I said that this is one of the best techniques for outlining that I’ve found, so you would be within your rights to ask whether I’ve used it with success.

As a matter of fact, I have.

It took me awhile to rummage through my writer’s brain but in fact this is how my last published story came to be. I wrote the story in an almost code-like manner, by hand. Scraps of story put down in pen and ink. After doing that, I went about daydreaming a bit and then I sat down and typed it out in a rough fashion. After a little more daydreaming and thought, I went back and rewrote it from the beginning.

I did that five times…

When I was done, I had the story. I went back and rewrote it one last time to make it fit the word count and then rewrote it again to tighten it up some more.

In total, I wrote the story at least eight times though for some reason the number ten sticks in my head.

Does this happen with every story? Does this happen with every writer?

To some degree, I think it does. At least it does with stories that are successful (i.e. finished and sent out and hopefully accepted). If a story doesn’t have a strong enough hold on the writer, this process will fizz out sooner or later because it’s really intense.

And perhaps that is the the real reason we outline… to get down to that intense bit of story that keeps us slogging through rewrite after rewrite.

6 thoughts on “Outlining

  1. For me, I find that the most natural form of “outlining” comes with writing down questions. I start with some character or situation or whatnot and then I start thinking like a 5 year old and writing down all the questions that might need answers.

    I find it’s a lot less stressful than trying to write down a plot right away. (Especially in those situations where you want to start writing but have no freakin’ idea where the story is going to go.)

    The questions spiral out into all sorts of themes and craziness. Then once I’m all out of questions, I can start organizing things and deciding which questions need answers and in vaguely what order. 🙂

  2. @E Yep. I call that sketching. I usually begin with a sketch and see if it holds onto me. Then, I take it a bit further and try to see if there is anything else in there worth writing about.

  3. This is terrific, Jamie, and it’s so good to see your posts on a semi-regular basis again!

    I’ve always been one of those grumbling, crotchety, anti-outlining writers, too, until I decided to take the intro to Slaughterhouse-5 seriously and realized that outlines can take any form they need to (including Vonnegut’s crayon line graph). One of my problems with outlines–aside from the traditional (and sometimes legitimate) “it’s too limiting” complaint–is that I never feel like I can see the whole story at once. I can’t see it all at once in my head, either, but at least in my head, I have a general sense of The Big Picture. Now, that’s what I actually do with my outlines: I map it out as a Big Picture. Right now, for instance, I have all the elements of my current book spread out across the gallery wall of our long central hallway–each story or plotline gets a full sheet of paper, with notes and dates and plot points and characters scribbled all over each sheet, and then all the overlapping elements (characters, settings) are highlighting in corresponding colors. It’s a little childish (or a little Vonnegutesque, though that might be saying the same thing), but at least now I can step back away from the wall and see all the connections and interactions in one sweep of the eyes. It’s not a numbered, ordered outline, but it’s an outline nonetheless.

    Of course, I usually feel silly when I do stuff like that. Professional, but very silly, each attitude competing with the other. Now, I still feel silly, but I feel silly AND professional simultaneously, which means I can not only get back to the work but also enjoy it. So thanks for the post!

  4. Okay, this is wrong. I’m the most active commenter on here and I’ve only posted three (now four) comments. Like this one, none with an outline.

    I am very much a non-outlinining seat-of-the-pants author, and I don’t see that changing. I bust a gut setting up characters and conflict, and writing chapter one. It can take months. Then, when I’ve got all my little dominoes set up just right, I roll a big ole bowling ball through them and see how they fall.

    The one exception to the above was Mom’s bio. Scribbled down an outline on hotel stationery in about four hours. Back home, one month later, I’d typed an 80,000-word first draft. So okay, fine, perhaps I’d work better with an outline. Ah well. I wonder how my new novel’s going to end…

  5. I agree with Samuel – it’s nice to see your regular posts again. I outline somewhat and find it helpful in the long run when I am doing a longer piece (novel). Thanks for the reference – I will check it out.

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