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How to Outline a Book by Answering 5 Questions

Outlining a book can be a scary prospect. Where do you even begin???

Thankfully there’s a simple answer… actually, five simple answers.

During the last stream, the viewers voted that we go over how to outline a story by answering 5 easy questions.

We’ve done this exercise a few times before, and it’s one of my all-time favorites. Not only is it fun and easy, but it’s super practical too. I use it to help plan all the books I write, and you can too.

Watch the full exercise here or scroll down
for the outline we came up with.

Here’s the five questions, along with two examples, and the story idea that chat voted for.

1) Who is your main character? What makes him/her unique? What does he/she want to do? What is the conflict?
(Harry Potter: An eleven year old orphan boy finds out he is a wizard.)
(Romeo and Juliet: Two teenagers from rival families fall in love.)

A man publishes a book that offends some people in his country so badly that he now has to live in a bulletproof van.

2) What happens at the END of your story? What do you want to SAY with your story?
(Harry Potter: “Love is the greatest magic” – Harry defeats an evil wizard with the power of love.)
(R&J: “The dangers of prejudice and not allowing young love to be explored” – The teenagers kill themselves because their feuding families won’t allow them to be together.)

“Even if you think you’re making a difference, you’re not,” or “The uselessness of ‘rebelling’ online by liking tweets and blogging.”

He lives in the van for years, never daring to go out for fear of being shot, until his driver and food/water-supplier stop showing up and he has no choice but to leave. He break a window, climbs, out, and discovers that no one cares about his book. it was just the government hiding him all along and feeding him propaganda that his book was controversial to keep him quiet and in a prison of sorts. Ending line: “What hurts most is that no one was listening.”

3) What is the first good/bad thing that happens to your main character?
(Harry Potter: Harry is taken to a wizarding school where he makes friends and learns about magic.)
(R&J: The teenagers find out they will not be allowed to be together.)

The man lives in the van because of death threats from extremists. But he doesn’t mind. He is well-fed and posts blog articles online, getting a great response from the people in his country, encouraging him to write more. (He has limited Internet because he doesn’t want to be tracked online.)

4) What is the next bad/good thing that happens to your character? (If #3 was a good thing, then do a bad thing this time; if it was a bad thing, then do a good thing.)
(Harry Potter: Harry finds out his parents were killed by an evil wizard but somehow he survived.)
(R&J: The teenagers get married in secret without their families knowing.)

Slowly but surely, over the course of a year, he starts to notice things that feel wrong. There’s an Internet blackout that his driver talks about, but it doesn’t affect his Internet. The IT guy who comes weekly to “update the Internet security” carries a gun. The comments on his blogs start to feel less and less human, less and less consistent, they don’t get the same jokes/ideas that he talked about with them before (because they’re run by new people now). Finally he decides to break into the “real” Internet, and he discovers that his book was not on any bestseller list, in fact it was never even published

5) How is it resolved? How will you connect #4 to your ending? How will your character(s) grow/change?
(Harry Potter: Harry confronts the evil wizard and the shield of love that his mother gave him by sacrificing her life allows him to win.)
(R&J: The teenagers’ families find out, and the teenagers kill themselves rather than be separated.)

He decides that he needs to escape the van. When the IT guy comes one week, he surprises him and steals the gun, shooting him and the driver, and stealing their phones, which he immediately uses to go on the full Internet. To his horror, he discovers that he was right. No one cares about his book, there weren’t any extremists hating him to even begin with.

At some point, the guy needs to say: “Now I know how the ship in the bottle feels.”

After that, chat voted that we write this prompt: A person suffering from severe depression is in the subway on their way to their monotonous job. As their train approaches they consider jumping in front of it. At the last second they change their mind and go on a train in the opposite direction.

Here’s what we came up with:

It hurt more than anything to climb onto that train. Just moving my body into the door felt like my bones were cracking in half. It was more painful than getting out of bed in the morning, wrapped in sheets of steel, tears burning as I thought about another miserable day that lay ahead.

But I placed one heavy lead foot in front of the other. I walked through the train door, my head cracking open with thoughts of despair. My boss was going to be mad at me for not showing up. I was going to lose my job at the bookstore. I was going to lose my apartment. I was going to lose my girlfriend of three years.

Losing all of that was better than losing my life.

Inside the train, my heart slowed. I could almost hear the blood draining from my head. Breathing was harder, nearly impossible, so I sat down on a cushioned chair to regain myself.

I was doing the right thing. I knew that, but still, everything hurt. It was like there was a ten-ton weight on top of me, crushing me into a pulp. This had to be my own brain fighting against me. It was addicted to misery, and it knew it wasn’t going to get its fix. I had to break it cold turkey.

Trying to distract myself, I looked around on the train. New train. New passengers. New people to see. A pale woman sat perfectly still, arms folded over her purse in her lap. A man and his child stared away from me out the window. A young girl stood hanging onto a leather strap. Her arms covered in slices of blood.

The pain was excruciating now. I physically couldn’t breathe. My panting must have caught the attention of the man and his child. They turned to me and grinned. Both their faces were burnt crispy and black.

I looked down to my own hands. They were flattened, veins and knuckle bones bulging out like hairs and twigs from wads of old flesh-colored chewing gum. All the way up my arms, red and purple dead roots throbbed dewdrops of blood in a slower and slower rhythm. I could just make out my reflection in the darkened window across from me, my face a garbage bag of expired ground meat with an eyeball popping out.

As the train lurched forward, I saw a body on the tracks. A familiar silhouette against the darkness. Like a mirror, my own face looked back at me.

I had jumped.

If you want to join us and help write a story by trolling in chat, or share your own writing for feedback, then we’d love to have you. We stream on Twitch every Sunday, Tuesday, and Thursday.

And you missed the stream, you can still watch them on the YouTube channel or watch the full stream reruns.

Hope to see you next time, friend!

Featured image: GAHAG

Published inExercises/WritingGenres/StoriesGrimdarkOutlining