Writing Workshop: Pre-Planning Your Book

About a month or two ago I asked you all for some topical ointment suggestions. Ointment? Really? That doesn’t seem right.

*checks notes*

Oh, I meant some topical blogging suggestions. (<– that was about as forced as a joke can possibly get. Please forgive me.)

On the whole, the ideas thrown out were more diverse than San Francisco’s Gay Pride Parade, but if I was tied down next to a fire-ant hill, slathered with jelly, and forced to admit to a particular topic you guys were most interested in, it would probably have to do with writing processes. Processes’? Processors?

Gah, words are hard.

Anyways, I live to give the people what they want, so let’s spend a little time this afternoon talking about pre-planning a book. We’ve talked before about the relative benefits of outlining your story and how this can save you a lot of time and heartache in the long run. In a lot of ways I’m a stream of consciousness writer (something you may or may not have noticed if you’ve spent any amount of time on this blog), but I usually go into whatever writing project I’m psychically buried beneath with a rough idea where the whole thing is gonna end up.

Here’s how I do it. I get an idea, whether that be about a character or a situation, and I sit down and pound out about 1,000 words as quickly as my little fingers can fly. Typically this takes me between 15 and 40 minutes depending on how free I’m letting myself be. All I’m doing at this point is vomiting words onto a page. Getting the mental effluvia flowing. Let’s see if we can’t storyboard an idea in real time to give an example.


Forgive any typos, grammatical errors, egregious word misusage, and the like. I spat this out in *checks the timer* 13 minutes.

It was the horns that freaked me out. I’m not sure why that particular feature, above and beyond the rest, was the one that instilled a sense of, Oh, shit, but it was.

There were other disturbing features to be sure. Two fangs protruded from the beast’s lower jaw–an under-bite that would make a bulldog blush. The red skin was weird, too. It shimmered in the final rays of sunlight before that celestial orb dipped below the horizon for the night making the skin appear slick with blood. A tattoo on the Manimal’s left shoulder blade of three sixes pinwheeling around one another, stuck in the infinite loop we call a circle, was kind of like a calling card.

But again, his horns were the thing that was freaking me out. As far as horns go, they were very nice. As far as human-ish looking heads go, it wasn’t so far off. The combination of the two, however, was grotesque.

“You called?” That the Beast spoke English shouldn’t have been surprising, but again, it was. His voice was gravel thrown in a cement mixer with broken glass.

I glanced down at my cell phone and scrolled through my contacts list just to be certain I didn’t, in fact, have the devil’s contact information by accident. This was my first time meeting the devil, by the way. I’m not afraid to admit I wasn’t on my “A” game.

“No, I’m sorry,” I said, backing away with hands raised in front of me. Each step was slow because the man-goat thing fused with a serpent standing before me seemed like the skittish type. Rumors had it he was the ruler of Hell, king of the underworld, eternal tormentor to the millions of souls in his possession..not the sort of guy you want to startle. “I think you’ve got the wrong guy,” I added.

“You’d be surprised how often I get that,” the devil said, waving a clawed hand before him.

“Sorry for the mix-up. Hope you find the guy you’re looking for,” I said, exiting the alley way.

The devil looked puzzled for a moment, regarded a piece of script in his left hand. A hand, which, looked to have been removed from a Falcon and haphazardly sewn onto the Lord of Pain.

“Wait…” he said.

I waited. He didn’t seem like the sort of guy you ignore.

“Are you Daniel McScrooge?”

“Uh…yes,but that’s a fairly common name around these parts.” I lied.

“Do you live on 312 Fairfax Ave?”

“Again, yes, but there are a few of us living over there. Our mail gets mixed up all the time. It’s hell, I swear.”

“Is it really?” the Devil cooed.

“Well, no… not literally hell. I mean, I’ve never been.”

“Hm… Daniel McScrooge, have you ever uttered these words, “I swear to any and all gods above or below, I’ll give you anything, whatever, name your price, if you but grant me this one request: Please, for the sake of all that’s beautiful and right in this world, let me have the last pop-tart.”

Oh, shit.

The Devil must have noted the change in my expression. He smiled the second most malevolent smile I’d ever seen–my Mother-In-Law having easily taken the prize on that account–and said, “I hope you enjoyed that pop-tart, Danny.”

Luckily, I had.


Is this a story? Meh, it has a beginning, middle, and an end so I suppose you could make the argument, but the point at this juncture isn’t to have a fully flesh story or even a fully fleshed idea. Honestly, I started with a really simple concept inspired by those old Klondike bar commercials that asked via a catchy jingle “What would you dooooo-oooh-oooh for a Klondike bar?”

I thought, hm… what about a pop-tart. What rules of cultural decency would I break just to have a pop-tart? Would I sell my soul for one? Would the Devil demean himself by even acknowledging such a deal?

So those were the original thoughts bouncing around in my head and, let’s be honest, there really isn’t a story there. But by getting the words onto the paper I’ve started down a road whereby I can shave and sculpt that dung-heap of words into a story.

turd polishing

‘Cause now I know somethings about my story world that I didn’t know fifteen minutes ago:

– My story takes place in a world where the devil is real and is willing to make deals

– My main character carries himself with a lethal amount of snark. These two factors combined tell me this story is going to be Fantasy Humor and I can start thinking along those lines when it comes to figuring out where to go next.

Where do we go next? Well, sometimes I’ll write four or five of these little vignettes, popping around between characters and situations I find interesting, and all I’m really doing is dipping my toes into the story-world. Letting the ideas simmer both in my mind and on the page. Since I haven’t invested much time at this point, it’s still relatively easy to be creatively open to possibilities of where my story might go.

The problem most people run into when story-boarding is that they get stuck on one idea. The blinders go on and they can’t see the trees for the forest. Let me give you an idea:

After writing the above vignette I started wondering about the larger story world and what the point of a tale like this might be. What sorts of hijinks would ensue? The first idea that came to mind was having Daniel go to hell where he would effectively be a telemarketer. Working in a subdivision of Hell’s bureaucracy that deals with managing mayhem in the world and securing fresh soul-trades.

He’d effectively be a soul broker, or something. *shrug* I dunno. To me, juxtaposing Hell with the corporate rat-race wouldn’t be a hard comparison to make. If nothing else it would afford plenty of opportunity for silly shenanigans to take place.

Oh, boy, I love my shenanigans, but there’s got to be more.


I’m sure they are. Truly. But shenanig…


Uh…I mean, those comical situations you throw your character into aren’t enough on their own. One good idea does not make a good story.

You’ve got to bring it to life. Got to figure out what your characters want and then make them go get it. So, what does Danny want (besides pop-tarts)?

Well, it’s probably a safe bet to assume he wants to get out of Hell, right? To do that we have to set up appropriate conditions for this to become possible. Let’s say Hell has an Employee of the Year contest: the person who brings in the most souls for the year gets his or her own soul back. Sweet, that seems like sufficient motivation at this point.

Daniel wants out of Hell and he sets off to be the best soul broker this side of purgatory. He is raking in the souls hand over fist. He’s in tight competition with that bozo three cubicles over and it looks as though it’s going to come down to the final couple souls.

Okay, hit the pause button. Think back on all your favorite stories and I bet you dollars to donuts (what the hell does this phrase even mean, by the way?) that the main character went through a substantial growth arc. Characters have to grow. They have to change. If they don’t, they suck, and we hate them.

Don’t give me a reason to hate your character unless you intentionally want me to hate your character– which is a totally legitimate device, by the way.

We need Daniel to grow out of the selfish desires that made him sell his soul in exchange for a pop-tart to begin with (not to mention the selfish desires that motivate him to damn all those poor people to hell just so he can be free). How are we going to do this?

Shit, I don’t know. And neither do you. And guess what, even if you do know right now at this very moment how the story is going to end, I can almost guarantee that by the time you get there it will have changed somehow. Characters grow organically. You can coax and nudge them along the right path, but they are their own people, they are gonna go their own direction.

Follow them. Trust your character, unless, you know, that character is an untrustworthy bastard who murders children. Then keep him on a tight leash otherwise he’ll kill all your other characters and then you have no story, just corpses. (Sometimes you have to reign in your characters for their own good.)

What does any of this have to do with pre-planning a story? Interesting you should ask ’cause I totally have no idea.

joker plan

Nah, I’m just kidding. Follow me, kid, I know where we’re going.

At this point you have all the story elements you need to sit down and write an outline. It can be real friggin’ simple. Something like this perhaps:

Act 1

– Danny is a fuck-wit living off the kindness of his sister who has continually sacrificed her personal comfort to help take care of him ever since their parents died tragically in a rhinoceros related attack.

– Danny continually takes advantage of Big Sis, what with his propensity for eating all the pop-tarts and other foods without ever contributing to the grocery shopping.

– Danny does a bunch of selfish things. We dislike Danny, but we find him funny and relatable. Eventually he accidentally invokes the devil and sells his soul in exchange for a pop-tart.

Act 2

– Danny goes to Hell Inc.

– Danny hates Hell Inc.

– Danny works his ass off to get out of Hell Inc.

– Something really big and horrible happens at the end of Act 2, it changes the game and now we have more to lose than ever before. Maybe Big Sis accidentally sells her own soul just to have her little bro back for one night. Maybe Danny’s arch-nemesis at Hell Inc. cashes in on Big Sis’ soul and lords it over Danny.

Act 3

– Danny continues trying to get out of Hell Inc while trying to save his sister as well.

– Other stuff happens.

– Danny is faced with the option of saving himself or saving his sister. Climactic shit happens here. This is where the story wraps up.

– Denouement


Above is one of the worst outlines I’ve ever created, but you know what? It’s totally enough to get you off to the races. You take those individual scenes and start flushing them out. Add in details, supporting characters, quirks, the world. This is usually when I take a couple steps back from the story and let it percolate in my sub-conscious. Little ideas will bubble to the top of my pond scummy’esque mind and when they do, BAM! I write them down into Evernote.

Come back after a little mental fugue and start plugging your ideas in. Then expand the outline, keep going until you have a relatively good idea how you’re gonna get little Danny from beginning to end in more or less one piece.

What’s that? You don’t have all the details? Danny keeps falling through those pesky plot holes? Leave them. Come back to them. You can only do so much planning before you have to hop into the story and start writing it for reals.

It’s a good idea to pop back in occasionally and touch base with your outline as you go. Fill in some holes, cut out some parts that didn’t work how you thought they would. Outlines should be organic which means if they ever stop growing, they’re dead.

A dead outline is about as useful as a dead horse. Emphasis here being on the word “about”. You can at least beat a dead horse.

stop stop

Here’s some real down and dirty, nitty gritty details you more anal minded individuals should also maybe consider.

– Figure out how long you want your book to be. 70,000 is low end for a novel (in my opinion). 110,000 is high end. Anything above 110,000 better be Epic Fantasy, Holmes.

– Most novels have anywhere between 50 – 150 scenes. A scene is like that vignette I wrote for you above. A chapter should be, at minimum, one scene. There is no limit on how many scenes you cram into a chapter but here’s something to consider.

Shorter chapters make the story feel faster.

This can be a good thing if you’re writing action-adventure, mystery, or thriller. Chapters that stay under 3,000 words feel quick and readable which can make all the difference when it comes time for the reader to put down your book or to stick it out for just oooooone more chapter before hitting the hay.

If you’re writing fiction, literature, or a story where the pace is generally slower, maybe consider longer chapters, but honestly I wouldn’t go much over 6,000. Those chapters tend to drag in my opinion.

– Use the above word length estimates to figure out how many scenes your book will have and then figure out how many chapters. Once you got that down it’s simply a matter of connecting the story dots.

For myself, I rarely write a chapter under 1,000 words and almost never go over 3,500. That’s a function of my genre and writing style which may, or may not, be the same for you.

Wowsers, this is a really long post and honestly I don’t know if I actually shed any light on the topic, but hopefully this has given you some brain fodder for how you tackle your next writing project. If not, well… uh… here’s a picture of a cat!

cat in box

Love forever and always, (please don’t kill me for having wasted your time)


8 thoughts on “Writing Workshop: Pre-Planning Your Book

  1. Reblogged this on wwannwrites and commented:
    Although I pressed this once, I thought you all might get a kick out of it, while learning a little something in the process. Happy reading and writing, and let me know what you think.


    • One of my favorite scenes from that entire movie! Now get out of here, Matt. Go do your taxes. But then definitely come back once your finished and we’ll have ourselves some more shenanigans!


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