SIDEWRITING TAKEOVER: Sidewriting Challenge Roundup

compiled by Anne-Marie Strohman

The authors and contributors we interviewed had so many wonderful sidewriting challenges, we thought we'd put them all in one place. Each exercise will have a link back to the original post so you can learn more about the author and how sidewriting works for them. Enjoy!--Anne-Marie

Start with an Emotion (Erin Nuttall)

1. Pick an emotion you’d like to explore in a scene. It could be anything: hurt, excitement, loss, joy, panic, jealousy, confidence, security, optimism, disgust, gratitude. You get the idea. 

2. If you have multiple POVs, decide which character will be the POV in your scene. Don’t worry about secondary characters, they’ll show up if they need to.

3. Brainstorm your emotion. I like the web kind that can break off into branches as one idea gives way to others, but suit yourself. Set a timer for 3 minutes and just let the ideas flow freely. 

4. Once your timer goes off, take a look at what you have. Look for kernels that can lead to a scene. Sometimes they will be in the same family of ideas and sometimes they will be as disparate as coconuts and peanut butter.

5. Set a timer for seven minutes and write that scene.

That’s it. Ten minutes. I won’t guarantee your scene will make it into your final draft, but if you’re writing about an emotion that’s crucial to your story, there’s a good chance that it will.

Interview Your Character (Karen Krossing)

I brainstorm questions that need to ask my character about my work-in-progress. These are questions that I don’t know how to answer yet, and often my characters don’t either. For example, I recently asked my protagonist, “Who gave you that object you secretly carry in your pocket? What does that person mean to you?”

Once I have a good list of questions, I set them aside, letting my subconscious go to work on them.

A few days later, I’ll interview my character by asking these questions and encouraging them to answer from their point of view.

Travel Through Time (Jennifer Ziegler)

What was your protagonist doing one year before the start of your story? Five years? Ten? Write a scene that lets you peek into their past. It can be a pivotal event – a loss, a triumph, a harrowing or embarrassing event that haunts them still, or the moment they first met someone important to them. Or it could be just a regular day. Perhaps a scene of them at work or school or hanging out with friends or family. Sometimes these “mundane” scenes can show you their default settings – who they were before the inciting incident of your story.

Similarly, you might ask yourself what your protagonist will be doing a year after the end of your story. Or five, ten, twenty years later. Write a scene that shows a glimpse into their future. Knowing where your character will end up in life can reveal all sorts of things, like what they need to learn about themselves and/or the world, what they need to unlearn, what fears they need to overcome.

Personality Test (Aimee Lucido)

For your main characters, or main character and important secondary characters, give them a personality test! Choose any that you’re familiar with: Enneagram, Myers-Briggs, Gretchen Rubin’s Four Temperaments, or the VIA Character Strengths survey (there’s a teen-specific option on this one), for instance.

Spend some time writing: How do the qualities highlighted in the survey already show up in your story? How might you include them in revision?

Gossip Version (Mary Winn Heider)

The sidewriting exercise I rely on most is really simple. I write a messy, gossipy version of my story (or scene or conflict). I handwrite it, like it’s a note I might pass in class, and I allow myself plenty of gossipy digressions. It simultaneously lets me to see what might be going on at the outskirts of my story (feelings and tensions that might affect the main action), and it pares down the main plot itself, so I can very basically tie each important moment to the next. I’ve developed a kind of outlining process I love, but sometimes I really crave the structure of gossip, the way it’s built on cause and effect.

Misbelief Scene and Character Diary (Sarah S. Davis)

• From Cron’s Story Genius, write the scene where your character’s misbelief originates.

• Assign your character the task of writing a diary for a week. Give them space to be as boring and mundane as they wish (e.g. without an agenda). What themes emerge during the week?

Character Relationships (David Macinnis Gill)

Characters are about relationships. This is an exercise that I use in every one of my novels as a way of getting to know my characters better. It is also a way to create endowed objects, but that’s just a happy side effect. 

Write a short scene in which the secondary character gives your main character something she doesn’t have. It can be an object, an emotion, a physical trait, a belief. 

Now write a second short scene in which your main character no longer has access to the thing that the secondary character gave her. How does she react to the loss? What does she realize about herself?

Character's Misbelief and its Origin (Jen Jobart)

Lisa Cron offers a short explanation of how to write your protagonist’s misbelief and origin scene here. I highly recommend reading her explanations and then following her three-step exercise.

Step 1: Ask yourself, what is my protagonist’s misbelief? What one, defining thing does she think is true about the world that is going to be proven false?

Step 2: Brainstorm possible scenes where the misbelief might have first taken hold in your protagonists’ life.

Step 3: Write out your Origin Scene as an actual scene

Questions for Focused Freewriting (Louise Hawes)

Free write questions can be as general as, Why do you want me to tell your story? (This is almost always a good start, a solid relationship-builder for you and your protagonist.) Later in the process, areas of inquiry may be as specific and nitty-gritty as, I’m having a terrible time with this scene. Can you tell me what you feel when X confronts you about Y?

First memory, recurring nightmares, earliest punishment, most respected adult—the list of questions to ask is endless, but often boils down to, “ask it slant.” Like people in real life, most characters can’t verbalize, probably don’t even know, what their personal strengths and weaknesses are, what triggers their deepest fears, what their spirit needs to grow and thrive. It’s up to an author to keep asking heartful questions, to keep building freewrite bridges till the answers—and the story, come clear.

Riff on Your Influences (Jasmine A. Stirling)

Words and sounds: Come up with lists of words relevant to motifs in your story and play with how they might be incorporated into your book. Think about the kinds of sounds you want in your sentences and eliminate words from your list that don’t have these sounds. Keep the list handy as you write to keep you on track.

History: Research the history and biographies of people loosely connected with motifs in your book and see if you can incorporate aspects of their stories to your characters. For example, I’m looking at the lore around the inspiration for various Edward Lear poems, which often includes people Edward knew. I’m researching those people and then adding references to them in my characters.

Literature, etc: Study literature, games, news, scientific discoveries, or other aspects of motifs or a time period connected with your story and explore how to bring those influences into your current project. For example, I’m exploring how to bring specific creatures and references from nonsense poetry directly or indirectly into my novel.

Symbols: Brainstorm symbols that are relevant to motifs in your story and that also communicate the personalities of your characters or make tangible the inner struggles that your characters are going through.

Look for double or triple duty: You’ll come up with lots of ideas when you sidewrite, but use only the ideas that are relevant to your protagonist’s internal or external struggle in your story. These are the ideas that do double or triple duty: they’re not just interesting, they’re interesting and meaningful. Discard the rest.

Audition Your Characters (Jasmine A. Stirling)

Hold “auditions” for the characters you’re considering for your story. Play the casting director and  run your prospective characters through a series of exercises to see if they are a good fit. (For example, have them read lines of dialogue or act out a specific scene). You can find out how each character performs under pressure, how they relate to the casting director (you) and their fellow actors (other characters). You decide who gets called back and cut. You can also do reference calls on the finalists, and put two characters together to see what their chemistry is like. 

Start with a Glimmer (Sarah Aronson)

Recently, I tried something new: I started some side-writing by starting with a glimmer. I pulled out the BEST line of the chapter (it’s always a line that speaks to theme or character) and began sidewriting from there. 

By focusing on a line that resonated on more than one level, I started with confidence (yay) as well as my reasons behind writing the book in the first place. That helped me open some new doors—or maybe some old doors in a new way. 

An "I Am From" Poem (Beth Mitchell)

Write an “I am from” poem for your main character inspired by George Ella Lyon’s “Where I’m From.” Of the dozens of “who am I?” assignments that my two kids completed in elementary school, this one sparked the deepest reflection for both of them. As a writing exercise, it helps me focus on the small details that make a character’s experience unique.

Process Journal (Evan Griffith)

I’m a big fan of getting personal with journal-style sidewriting exercises. When I’m feeling discouraged about a story, I write about why I want to tell this story—what I want to communicate with it and why it matters to me.

Travel Brochure (Evan Griffith)

Here’s an especially fun creative exercise: If you’re writing a fantasy or science-fiction story, create a travel brochure to your fictional world! Bonus points if you illustrate it. (Yes, I developed this for kids, but aren’t we all kids at heart?)

Collect Words (Kristi Wright)

I listen to audiobooks while I’m on the treadmill and jot down random words on a 4X6 card. Words that are pretty. Words that fit the mood of my story. Phrases that are just really excellent at getting across some random action. Words that have no bearing on my book or on my writing that I’ll never use and have no reason for why I’m writing them down. It doesn’t matter. I just randomly jot down words.

Suddenly, I’ll randomly think of something I need to fix or add in my book, even though it doesn’t have anything to do with the words or the story I’m listening to. I jot down a note about my story on the same 4X6 card and just keep going.

Ask "Why?" (Margaret Chiu Greanias)

My favorite sidewriting exercise (and the simplest) is to continuously ask myself “why?” questions. I ask and write out answers until I have a better understanding of whatever character, problem, situation, etc. I’m struggling with. Give it a try!

Journaling and Alternate Points-of-View (Amber Lough)

My two favorite sidewriting exercises are:

1. Journaling from the MC’s POV. This never fails. 

2. Writing about the story/character/world from a side-character’s POV to get a wholly different perspective. This helps a lot when I feel like there’s not enough depth, especially in the worldbuilding.

Dream Team of Defenders (Anne-Marie Strohman)

 I started writing down all the accusations and doubts from my Critics (those really loud voices in my head). But when I wrote them down, I didn’t have any answers for them.

I decided that Anne Lamott might have a better answer than I would. So I let her defend me. On paper. Then I decided Oprah might have some wise words. My high school English teacher. Even Sarah Silverman. Just thinking through how those people might answer the criticisms gave me a freedom to answer them, to reduce their power.

Freewrite the Story from Another Point of View (Especially for Picture Books) (Anne-Marie Strohman)

When I get stuck, I freewrite the story from another character’s point of view. It helps to open the story, helps me see the problem in a new light, and helps me prioritize the relationships between characters. I’ve had more than one picture book recover from stuckness because of this technique.

It works for short stories and novels, too. I once heard a lecture by Rita Williams-Garcia where she recommended that if you get stuck, you should figure out what a secondary character is doing while they’re off-stage. Sometimes that exercise can kick-start the story by bringing new material or conflict into the main storyline when the character shows up again. So write about a secondary character off-the-page, and write their perspective on the storyline and the world. It can help you as a writer see the story in new ways too.

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