Learn to tell compelling stories with 12 unusual storytelling exercises.
Humans’ capacity for language and storytelling is one of our species’ defining characteristics. Once upon a time, back before the internet, board games, team sports, or books existed, humans entertained themselves and each other by telling stories. So why is telling a great story and telling it well so difficult?
Part of the problem is that instead of practicing telling great stories well, we practice telling bad stories poorly. We tell stories chopped up into little bits via text message or social media. We tell stories to people who are in a hurry, so we rush the ending. We get distracted mid-story and digress into a lengthy and irrelevant description of a minor character.
- How Do You Practice Good Storytelling?
- 1. Determine Your Purpose
- 2. Identify Exemplars of Your Intention
- 3. Interview A Friend
- 4. Trade Interview Stories
- 5. Turn Your Research Into A Story
- 6. Read Good Descriptive Writing
- 7. Write About Your Favorite Weirdos
- 8. Dive Deeper Into Strangeness
- 9. Identify the Components of Story
- 10. Start From the End
- 11. Write in the Middle
- 12. Focus on A Choice
- The Final Word on Storytelling Exercises
- FAQ on Storytelling Exercises
- Storytelling Resources
How Do You Practice Good Storytelling?
There are two easy answers to how to practice good storytelling: write more, and read more. Of course, writing isn’t easy, and in this context, even “reading” isn’t as simple as it sounds because you need to read like a storyteller.
What does it mean to read like a storyteller? Instead of simply immersing yourself and going with the flow, you should be analyzing the story as you go. Personally, I prefer to read more casually when I enjoy books for the first time. Then if they’re particularly good, I reread them wearing my analytical storyteller hat.
When you do read analytically, for the purpose of improving your storytelling, pay attention to how the story’s constructed. For example:
- Look for passages of descriptive writing that made you feel like you were in the story, and study them to determine why they were so effective. Consider not just what is there but what the writer left out.
- Pay attention to the pacing. Is it a meandering slow-build to a devastating climax? Is it a non stop thrill ride full of cliffhangers? Does it rotate between several characters on converging paths?
- Identify the structure of the story. For example, what is the inciting incident of the novel? Can you identify the “Five Commandments” in your favorite scene? What is the key turning point in the middle of the story?
- Consider how a character or characters develop throughout the story. For example, how did the author set up the character’s strengths and vulnerabilities at the beginning of the story, and how did they matter to the end?
By paying attention to the stories you love, you’ll become a better storyteller.
The following exercises will teach you about brainstorming, researching, creating a character, and structuring your writing, giving you the tools to tell better stories.
Some people get writer’s block, while others (like me) have the opposite problem: decision paralysis due to too many distracting ideas, more than I’ll ever have time to write. Either way, if the blank page scares you, this exercise can help you decide what story to tell. You might also find our guide on the best storytelling books helpful.
1. Determine Your Purpose
In fiction writing, as in nonfiction writing, it helps to consider your purpose in telling the story. Are you trying to educate? Entertain? Amuse? Spook? Titillate? Persuade? Perplex? When the reader puts down your story, do you want them to say “Wow” or “Awwww,” or “Ick” or “Phew”?
Suppose you’re interviewing for a job and are asked about how your personal experiences qualify you for the position. It’s an invitation to tell a story about how you faced an obstacle, triumphed, and learned something relevant to the job. If you need to improvise a scary campfire story, you’d better come up with a creepy surprise for the end. If you’re writing a romance novel, you need a HEA (happily ever after).
That perspective alone might be enough to spark a good idea. If not, try one of the following exercises.
2. Identify Exemplars of Your Intention
If thinking about your desired impact isn’t enough to help you generate a list of good ideas, learn from what you love. Make a list of 3-5 stories you know that provoked the same response in you that you want to evoke in your readers or listeners. Consider how they achieved that effect, and use that in your brainstorming.
For example, if you’re writing a best man speech, your goal is for the guests to feel happy for the couple and confident in the match. Brainstorm 3-5 memories of when you felt happy for your friend and became confident he’d met the perfect partner, and choose one as the centerpiece of your speech.
Another helpful exercise is to write a list of your favorite stories in your chosen genre. Identify if there are any clear common elements across all of the stories on your list? If so, then focus on ideas that share those elements when brainstorming your story ideas.
While it may seem either too simple or counterintuitive, or both, starting at the end saves you a lot of time. I’ve spent thousands of hours brainstorming plots, developing characters, and writing early chapters that I threw away because they didn’t go anywhere. So instead of spinning your wheels, start with the destination, then choose the correct characters and plot to get you there.
If you prefer to start at the beginning, and want more brainstorming ideas, check out this compilation of writing prompts.
3. Interview A Friend
Choose a friend or family member and set up a time to talk to them, ideally in person. First, ask for their permission to record the conversation or take notes. Then spend at least a half-hour interviewing them about one interesting experience they’ve had.
In order to conduct a good interview, you’ll want to ask a lot of open-ended questions (not answerable with a simple yes/no). First, listen attentively to show the interviewee you are interested. Take notes if you don’t have permission to make a recording. Then, ask lots of follow-up questions to dig deeper, and let the person go off on a few tangents to ferret out the most interesting details.
Once, when preparing to write a story about a blue-collar worker, I interviewed a friend who’d worked in a cardboard box factory as a teenager, and we ended up discussing it for more than two hours. Another time I interviewed a second cousin about being raised as a Jehovah’s Witness. I learned far more than I could have browsing the internet because I could ask follow-up questions and because they felt comfortable giving me the real dirt.
4. Trade Interview Stories
I use this exercise with students, often early in the semester, to practice interviewing, note-taking, storytelling, and public speaking skills (while getting to know their classmates).
After each student interviews a partner about “the most interesting thing that’s ever happened to them,” they give an oral presentation of their classmate’s story, summarized. The interviewee and the rest of the class then provide them with feedback on accuracy and the storytelling quality.
You could do this same exercise with a friend to practice your storytelling skills in pairs or small groups, like a writing group.
5. Turn Your Research Into A Story
If you don’t have a group or partner, there are still several ways you can use an interview to practice telling a good story.
One is an outlining and story structure exercise. Use the information you gained in the interview to create a concise outline of your friend’s story. This should not be a rehash of the interview but rather organized as a dramatic or comedic story about your friend. Use good story structure and cut out unnecessary details that don’t advance the story.
To take this exercise to the next level, write a fictional short story featuring a character in a situation inspired by the interview. The main character will likely have something in common with your friend, but preferably they should be quite different. To develop your skill at perspective-taking, focus on how your friend’s experience in that situation would differ from your character’s experience, based on their differences in background or personality.
6. Read Good Descriptive Writing
I teach an exercise on writing character and point of view using Susan Orlean’s nonfiction masterpiece The Orchid Thief, which contains particularly compelling descriptive writing. For example, Orlean describes her main character as “pale-eyed, slouch-shouldered, and sharply handsome, in spite of the fact that he is missing all his front teeth. He has the posture of al dente spaghetti and the nervous intensity of someone who plays a lot of video games.”
After reading excerpts from The Orchid Thief, and a few other good examples of descriptive writing, I give my students a two-part exercise. You, too, can get yourself ready to write by reading stories by writers with a gift for writing character.
7. Write About Your Favorite Weirdos
There are two parts to this exercise.
First, write a description of the strangest person you know reasonably well. Be kind, but be honest and unsparing in your description of their strangeness. If you want a challenge, don’t just write descriptively, but tell a completely true story.
Second, write a description of yourself and your own quirks, but from the perspective of the character you just wrote about. For example, I’ve used the first part of the exercise to describe my grandfather. Then for the second part, I wrote in my grandfather’s voice about me, his granddaughter.
8. Dive Deeper Into Strangeness
You can take this exercise to the next level with any of these bonus prompts:
- Write a fictional story about (or from the point of view of) a strange character inspired by the real-life person you just wrote about.
- Write a true story about yourself that is deeply honest about your strangeness.
- If you have a current fiction project (or even some nonfiction projects), use this as a character development tool. Write a series of short narratives in which one or more characters do the two-part exercise. For example, your protagonist writes about your antagonist, then writes about themselves from the antagonist’s perspective. As a result, you may discover new depths in the relationships between your characters.
9. Identify the Components of Story
There are a lot of approaches to breaking down story structure. One example, Shawn Coyne’s book The Story Grid, proposes that all stories (and all sub-components of story, such as chapter or scene) contain five parts, which he calls the Five Commandments.
- Inciting Incident – the event that starts the protagonist’s story in motion
- Progressive Complications – the obstacles and events that challenge the protagonist
- Crisis – the protagonist faces a decision
- Climax – the protagonist makes and executes a decision
- Resolution – the outcome
Consider the story Goldilocks and the Three Bears. In it, Goldilocks’ mother sends her into the forest to pick blackberries, where she discovers a cottage. (Inciting incident.) Nobody is inside. Goldilocks samples a variety of porridge and beds and finds most of them unsuitable. Eventually, she eats, makes a mess, and falls asleep. The bears find her in their child’s bed and wake her. (All progressive complications.) Goldilocks must decide whether to face the bears or run away. (Crisis.) Goldilocks escapes through the window and runs home. (Climax.) The friendly bears are puzzled at how strange and inconsiderate humans are. (Resolution.)
Take your stories to the next level by combining this structure with the other exercises. In other words, take the stories you wrote in response to the other exercises, and check to make sure they follow this structure. If they don’t, revise them until they do.
10. Start From the End
This is both a brainstorming tool and a revision too. In other words, you can use this basic framework to structure any kind of story, and you can start building your story with any of the parts. My favorite is the ending.
For example, if you’re invited to be a guest blogger or a podcast guest, you know you’ll be expected to talk about the accomplishment that got you the invitation. Your achievement is the resolution.
Now that you know the ending, work backward. What was a difficult choice you made that was instrumental in that accomplishment? That’s your climax. Keep moving backward.
11. Write in the Middle
Conversely, you might start with a progressive complication. Perhaps you’re sitting at a coffee shop, brainstorming short story ideas, and you look up from your laptop to see three people riding by on bicycles, completely nude, singing Queen’s We Are The Champions. A minute later, a cop car drives by, fast, in the same direction. ‘
You start wondering who the bicyclists were, how they came to be in that situation, and what might happen when the police catch up to them. You’ve started constructing a story by identifying a pretty interesting progressive complication, now you have to work forward and backward.
12. Focus on A Choice
One of the insights of Coyne’s approach to framework is that good stories virtually turn on a tough decision by the protagonist. A great true story isn’t really about what happened to you; it is about how you reacted to what happened to you. Often when an ending fizzles, or people don’t understand the point of your story, it’s because it didn’t turn on a decision with consequences.
The Final Word on Storytelling Exercises
Even the most gifted natural storyteller can get better with practice, and the rest of us always have room to improve. These exercises will help hone your storytelling skills and give you the confidence to tell your own stories and tell them well.
FAQ on Storytelling Exercises
What are the Five C’s of Storytelling?
There are many helpful writing mnemonics, and several of them are referred to as the Five C’s. For example, the Five C’s of Communication are a list of five qualities to aim for in any oral or written communication: clear, cohesive, complete, concise, and concrete.
I’ve seen several variations specifically focused on storytelling. For example, one source lists circumstances, curiosity, characters, conversations, and conflict. Indeed, all of those are vital elements of a story. Another source offers a different list of the Five C’s of Storytelling: characters, conflict, cure, change, and carry out the message. There are many others.
In the story structure exercise above, you use the so-called Five Commandments of storytelling to craft a story, so you could consider those elements (inciting incident, progressive complications, crisis, climax, and resolution) the Five C’s.
You don’t have to pick one. Any framework like this can help you craft your story.
What are the Five Acts of a Well Structured Story?
You will find them given different names in different circles, but they all mean the same. In classic story structure, you have 5 acts. These are:
1. Inciting incident
2. Progressive Complications
These can take many forms and guises, but if you make sure your story has these five crucial components you will be well on your way to creating a strong story.