Building a Short Story from the Ground Up: Lesson 4

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Welcome to our fourth lesson from Building a Short Story from the Ground Up. We are offering two options for this class:

  1. You can simply read through the class and take it on your own. No strings attached. Challenge yourself with the homework assignments if you like or not. The entire class is on your own, assignments and all.
  2. You can do the lessons and homework and receive feedback for each lesson, along with a critique of your final short story for the price of $47, paid via Paypal. If you choose this option, you will need to send homework assignments to <> along with your name (and if your Paypal contact name differs from your name, include this as well for verification).

Lesson 4: Outlining Versus Winging It

Why outline your story?

What are the benefits of outlining a story? Outlines help the writer to organize plot points and sequences. They help the writer to focus and stay on track. But when it comes to outlining a story plot, one size does not fit all. There are as many ways for detailing your story plan as there are writers—meaning, every writer must find the way that works best for him. Let’s take a look at several methods for outlining a plot.

Methods for outlining your story

Traditional approach. Otherwise known as the basic outlining method all of us were taught in fourth grade English class. For those having trouble remembering, each heading has a Roman numeral, subheadings underneath are indented and labeled with capital letters, and points underneath the subheadings are numbered and indented.

So how can this method be applied to plotting a story? Each Roman numeral is a scene (in sequence), subheadings are the statements of what happens, and any particulars you might want to add underneath the subheadings are numbered.


I. Mary receives a promotion at work.

A. Unsuspecting Mary walks into the boardroom.

B. The boss gives a short speech, announcing Mary’s promotion.

C. Mary’s co-workers whisper behind her back.

II. Mary’s fiancé, Tom, breaks off the engagement.

A. Mary comes home to find Tom at her apartment.

B. Mary shares her good news.

1. Tom doesn’t look happy.

2. Tom begins to pace the room.

Okay, you get the idea. Everything you need to know about the story at a glance. The traditional outlining method works great for writers who are detailed thinkers, highly organized, and love lists. They find comfort in the structure, seeing their ideas on paper. The down side is when the outline becomes a rigid plan the writer feels she must follow, down to the last detail, leaving no room for change if the story should go in another direction. Provided the writer leaves room for plot changes, outline away!

The “And Then” method. This approach is more user friendly. (I admit, I’m partial to this method.) The writer starts at the beginning, plotting line after line with the prompt, “and then.”


Unsuspecting Mary walks into the boardroom.

And then the boss gives a short speech, announcing Mary’s promotion.

And then Mary’s co-workers whisper behind her back.

And then Mary comes home to find Tom at her apartment.

And then Mary shares her good news, but Tom doesn’t look happy, paces the room.


Variation: Omit the words “and then,” which is what I do. The amount of detail in each line depends on the writer. This method works well for those of us who like detail but also like a less structured approach to gathering plot information. Be sure to double space between lines in case further plot points need to be added later.

Free Writing method. Throw out all the structure, set the timer for twenty minutes, and write everything you know about this story.


Mary doesn’t suspect a thing when her boss gives her a promotion at the board meeting. (Mary happens to be wearing her brand new gray pinstriped business suit she saved up for months to purchase, just so she could be taken seriously. Play hardball with the big boys.) Her boss seems to be in a good mood when he tells her about the promotion, but her co-workers whisper behind her back. That slacker Bill Evans even smirks. (Probably because she didn’t go out for drinks with him when he asked her a couple of months ago.) Later, when Mary gets home to her apartment, Tom is waiting there for her. But he doesn’t look real happy and starts pacing around the room. Finally he stops by the window and “drops the bomb” by telling her the engagement is off.


The beauty of this method for the writer is there’s no structure at all. Just write out the thoughts as they come to you, under the wonderful pressure of the ticking timer. I admit to using this method when I’m truly stuck and need the pressure of a mini deadline—which the timer provides. Plus, as the title of the method suggests, I have the freedom to write whatever crazy thought might come to me during my writing frenzy. For me, this method helps clear the log jam in my head, but, afterwards, the structured side of me has to sort through the thoughts, cast off the ones which don’t add to the story and place the ones I keep in a sequence.

Variation: You can throw out the timer!

Winging it without an outline

The phrase “it’s all in your head” comes to mind. Whereas the writer using the traditional outline approach finds comfort in a detailed and orderly plan, the free-spirited writer finds outlines to be highly restricting. The fun and adventure of story making is lost in the planning. These writers require the freedom for their characters to chase butterflies, dodge bullets, and fall in love at the spur of the moment. I have a good writing buddy who works this way. When she’s writing, she can sit and type for long stretches at a time, lost in an adventure, letting her imagination run free.

This non-method is great for writers who are spontaneous, who love discovering anew each writing session what their character will do next. But one problem with this non-method can be the lack of direction. My friend often laments, “I can’t write good endings.” The lack of focus shows up at the worst possible moment—the ending.

While I would never want to advise the free-spirited writer to outline, I would suggest a simple solution. Write a premise. (I promise, it’s not an outline!) A premise is a one-line explanation of your story. A statement you can prove by your story. Let’s revisit Mary.


Unhealthy ambition leads to loss and eventually self-discovery.


A premise keeps the writer from straying from the point of the story. Whatever doesn’t further the premise gets cut.


Outline your story using one of the above methods, or a combination of methods. Whatever works for you. If you fall into the category of the free-spirited writer, write a premise. But don’t rush writing the premise. Give it some thought, as this will be the theme of your story. Again, don’t worry about the writing—yet.



Related posts: 

Announcing Our Build a Short Story from the Ground Up Class

Building a Short Story from the Ground Up: Lesson 1

Building a Short Story from the Ground Up: Lesson 2

Building a Short Story from the Ground Up: Lesson 3




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