Getting Out of the Labyrinth: Part 2 – Outlining

This is a continuation of my series on The Labyrinth, that monstrous impossible maze so many of us writers get stuck in during our inbetween years.  Last week, I talked about phase 1 of any novel, planning. You can read the five things I learned about planning while writing my first novel (The Deathsniffer’s Assistant, available this summer!) in this blog here.

Today I’ll be talking about the second phase of writing a novel, outlining. This is a long one because I think this stage is so important and I have a whole lot to say about it!

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1. If you are in the labyrinth, you need an outline.

Bear with me here. This one takes a long time to bring together. But we’ll get there.

I used to be one of those writers who preferred working without an outline. I’d rather find out what was going to happen as it developed, I said, and I did! All the books I wrote before my labyrinth years were written outline-free. I figured out how Mary the Mouse and her intrepid band of investigators were going to rescue Tommy the Turtle on the fly, and it was exciting and grand. I told people up until my mid-twenties that I preferred working without an outline. I hadn’t actually worked in ten years, but that was how I’d always done things before. Why change?

Well… because I had to. I don’t think it’s a coincidence that the manuscript I came out of the labyrinth clutching triumphantly above my head was the first manuscript I’d ever written a full outline for.


I had one real attempt before The Deathsniffer’s Assistant that made it to the writing phase. It was a solid concept about clashing cultures and ideologies, the nature of compromise, and it had some amazing women in it! I wrote over sixty thousand words before I realized that I really didn’t know where it was going. I had a beginning and I had an end, but my plans for the middle were tenuous little islands of shrouded concept, and I remember staring across those waters thinking – oh my god. What was I thinking?

The answer is that I was thinking I was eight years old again. Remember Mary the Mouse? Well, when Mary and her rodent comrades scurried into the old factory where Tommy was being held via the ventilation system, I didn’t think that was cliched and overdone. When Wendy the Weasel bit an alley cat’s tail and defeated him, it didn’t occur to me that the cat definitely could have turned around and taken poor Wendy in a heartbeat. When they all walked triumphantly out the front door, I didn’t realize that defeating a few guards wouldn’t have taken down the whole fort. I was eight years old and writing was magically simple. What happened happened because I said it happened. If I got stuck, I deus ex machinaed right out of it.

There’s a sliding scale in creativity. On one side is “innocence.” On the other, “experience.” When a writer is far enough on the innocent side, our writing is weak and our stories are riddled with holes. On the experienced side, our writing is compelling and our stories are well told. Innocent writing has a joy in it that’s impossible to reproduce, but debating the merits of one versus another is moot, because no writer can stay on the innocent side of the scale. You will get older. You will read more books. You will learn literary criticism. You will slowly slide toward experience. And the labyrinth is located right where that scale tips.

the devil's buttcrack
pictured: the worst place on earth

You’ve become experienced enough to recognize all the flaws in your own work, but not experienced enough to know how to fix them. Every word you write is torturous. You hate it all. You read a great book and it inspires you, so you think, yeah! I’m going to write! You try. It sucks. How can it possibly suck this much? Oh my god! I used to be good at this! What happened to me?! The book that inspired you becomes your worst enemy. It haunts your nightmares. You want to finish a project. That will make you feel better. The thought of actually writing feels like punching yourself in the face. You can’t face that disaster you left in your word processor. This is pointless. You’re going to go learn to crochet, instead. Crochet is easy. You can’t screw up crochet.

When you’re in this headspace and you hit a wall in a manuscript, you don’t sit down and brainstorm how your characters are going to get to the next island on your very foggy map. You throw your hands in the air and you walk away, because you already hate what you’re working on and hate yourself and you’re never going to be published anyway so why bother.

(None of this is true. But oh lord, have I ever been there.)

This is why you need an outline.

With an outline, it’s something like 1000% harder to get stuck. It can happen! But it’ll probably happen a lot later in your work and a lot less messily. You’re never going to face a situation where you’re looking at where you want to be from across a thousand foot deep ocean trench. You know where you’re headed next. You have an actual map. You can get there.

It took sixty thousand words into a decent book idea before I realized I needed outlines after all. I was so depressed about losing that book up its own butt that I didn’t write again for a year. Let me try and save you the realization. You need an outline. It can be sketchy, it can be meticulously detailed, it can practically be a first draft, but you owe it to yourself to at least try.

It was my key out of the labyrinth. It could be yours, too.

2. Experiment and find a structure that works for you.

Wow. I told you that was going to be a long one. I know it’s controversial to insist that every writer needs an outline, but I’ve seen too many authors both amateur and professional get completely lost because they didn’t have one.

Now that I’ve hopefully convinced you to try one, here the bad news: I don’t have a one size fits all solution for how to make one.

I know what works for me. I write my outlines chapter by chapter, bullet point style. I go through everything I want to happen in the chapter. If I have a particularly good line come to me while I write, I scribble it down. My outlines are written in a casual rambling tone that matches the way my train of thought works. When I reread, this makes it a lot easier to fall into the state of mind I was in when I wrote it. They’re incredibly unprofessional. I call my characters names and swear a lot. and  I would be super embarrassed to show them to anyone. But an outline is for you and no one else. Make it in a way that you want.

This way doesn’t work for everyone! There are a lot of different methods. Here are just four that I know of and that have worked for people:

A) Randy Ingermanson’s famous Snowflake Method is well regarded and works really well for a lot of people. His write-up here is great! I don’t use this method but I see the value in it for a more compartmental approach to writing.

B) Build three or four different “set piece” style scenes that will be cornerstones of your book. (This is in addition to a beginning and end scene.) Go through all the major things you want to happen in these scenes. They’re great places to have different plot threads collide and new conflicts to be born as old ones are resolved. Then, outline between these scenes to create a spiderweb that eventually is a full, detailed outline.

C) Treat your outline as an incredibly loose and rough first draft. Let the scenes unfold in your mind and scribble down what’s happening. I used a combination of this and my usual method for my second book, and it brought a lot of joy to the outlining process that I used to feel when I wrote without outlines. You might hit some walls, but without actually having put effort into the writing, it’s a lot easier to course correct.

D) A lot of my writer friends use a method inspired by a different Randy Ingermanson article, Writing the Perfect Scene. They use Ingermanson’s fantastic scene writing tips to string together a full novel. The Goal/Conflict/Resolution model can be used in both micro and macro scales. You can divide scenes, chapters, acts, arcs, and entire books this way.

There are so many ways to write an outline. There is no right way. There’s only a right way for you. Try different things. Have fun with it. Experiment Don’t let it be something you hate doing. You might have to do a few outlines for your first book until you find a method that works for you, but that will give you a clearer picture of the book… and it’ll be worth it to find a method that works for you.

3. Do as much in one sitting as you can.

Regardless of how you outline, an outline always has the potential to be… fun. That sounds like a lie,  I know. You think I’m just telling you that to make you outline. But I’m telling the truth! You’re looking at someone who loathed outlining so much I had a good long cry when I realized that I needed to do them. And now I outline every single thing I write, no matter how short. You’ll discover your story while you do it and it can really feel like writing.

You’ll get a lot more out of it if you clear a few hours and work at it with dedication. Writing a good outline should be an experience. You can actually feel and live some microcosm of your book while you’re working on it. I’ve been so immersed in planning some of my bigger and more detailed scenes while outlining that I feel like I’ve actually been in that empty house, that grand ballroom, that country estate – all scenes I haven’t actually written yet!

The trick is to get a flow going. Don’t stop until you have to. The longer you go at it, the more immersed you’ll find yourself. Doing it in segments is just going to mess up your flow. You’ll need to gather together all your thoughts again to get back into it. In my experience, so long as you did a good, thorough planning phase, even a really detailed outline shouldn’t take more than three to four hours to get through. And that’s nothing. One night of Netflix, sacrificed for the greater good!

4. It’s never going to sound fun.

Or at least, it never has for me. I’m making it out like I relish outlining now, and let me make this clear: I dread outlines. I look at them like they’re bears in the woods and we’re having a standoff. It doesn’t matter how many successful outlines I write. Every single time I have to write one it’s like realizing I need to go to the dentist or have a really uncomfortable conversation with a friend. I’ve never found a way to make myself want to do them. All I can do is make myself do them. And I do this by kicking my own ass. Come on, stupid. Let’s go write that outline. It’s not going to write itself.

Maybe you’re different and you’re going to get to a point where your favourite part of the process is outlining. But I have a feeling most writers are more like me. An outline is a necessary evil. Writing outlines, if you will forgive the crudeness, is very much like pooping. It has to be done, you’ll feel better once you finish, and it can even be incredibly satisfying when done right. However, nothing on earth can make you want to do it.

If you wait for that mythical moment when you’re in the mood to outline, you’re never going to get past this point. So as soon as the date you set at the end of planning rolls around, make the time. Sit down. Power through. Once it’s done, it’s done, and then you can start writing.

5. Don’t leave blank spots.

This is a lesson I learned in The Deathsniffer’s Assistant. It’s also a lesson I’m learning right now. Again.

I have this line in the outline I’m using for my second book: “She knows he DID SOMETHING THINK ABOUT THIS LATER and so she springs a trap!” Well. I’m at that point in the book, now. I still don’t know what he did. I can’t come up with anything, especially not something so salacious that it could be used to bait a trap. Guess what I’m doing tonight after this blog goes up? It’s not going to be writing my book, I’ll tell you what. I’m going to need to take writing time while I’ve got a lot of writing momentum and turn that into outlining/planning time. Yuck.

You’re going to have moments where you’re not sure exactly what happens at a given point. And what you’re going to want to do is write something like I did in your outline.“FIGURE THIS OUT LATER.” Please don’t do that. Figure it out now.

Because outlining can seem like such a chore – even when you find you enjoy it! – once it’s finished, you’re not going to want to look at your outline again except as what it’s meant for, a roadmap. Those notes to figure something out later are probably only going to resurface once you actually reach the scene in question, and you’re not going to know what to do. The point of an outline is to prevent those moments that turn a great writing session into staring blankly at your laptop.

I did it on my first book. It took a week of backtracking and editing and brainstorming to fix. And then, like a kid told not to touch the stove, I did it on my second book. It’s all right, I’m a pro now. I can handle this. I couldn’t, and you probably can’t either.

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Last week, I let you all in on my deep dark secret. The Deathsniffer’s Assistant began as a project for NaNoWriMo (National Novel Writing Month.) I said I’d talk about the details later. Well, here it is.

I wrote up to the end of what is now the fifth chapter. And then I stopped. Can you guess why?

Of course you can: The Deathsniffer’s Assistant did not originally have an outline.

What always happens happened. I hit a wall. I had characters and concepts. I was writing the fantasy murder mystery I’d been dreaming of all my life. I knew who did it. But once again, I couldn’t get there. Thankfully, it didn’t take me sixty-thousand words and being written into a corner to realize it the second time. At ten thousand, I put the book in a chest for a rainy day. I knew I was going to need an outline to get any further on it. A year later, I was working again. All I needed to turn yet another failure into my greatest success was an outline.

My outline was more than just a blueprint for my book. It was the map I’d been waiting a decade for, the one that pointed me in the right direction to get out of the labyrinth.

I started writing the next November. Again. One of the rules of NaNoWriMo is that you’re not supposed to work on something you already started. Screw that. I needed yet another unfinished manuscript like I needed a hole in the head. But that fifty thousand word goal would put me sixty thousand words into this project, and if I could do that, it would be a strong enough start to springboard into something real.

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