3 storytelling exercises to find captivating stories

November 14, 2022

“I’d love to tell stories, but I just can’t think of any I could use.”

If that sounds like you, don’t worry. You’re not alone.
When I started my storytelling journey, I thought that to tell effective stories, I’d need to talk about extreme events. Stories like “how I saved the rainforest”, “how I almost killed myself climbing Mount Everest,” or “how I built a multi-billion dollar company”.
Disclaimer: I haven’t done any of those YET ;).

However, after coaching thousands of people on storytelling, I’m certain that you don’t need to have extreme events to be able to tell great stories.
That’s not necessary and, in fact, can be counterproductive.
Storytelling is about connecting with your audience.
However, the moment you tell a story that is too outlandish or sounds too crazy, you’re distancing yourself from the audience. Sure it can be entertaining, but if you truly want to touch your audience emotionally, it’s better to share a relatable experience.
So in this article, you’ll learn three exercises to find relatable stories from your life.
The exercises will give you a pool of stories that you can start using to captivate your friends, coworkers, or customers.

Finding Stories Exercise #1: Homework for Life

Homework for Life Tweet

The best way to gather an abundance of stories is to train your mind to spot storyworthy moments every day. My favorite exercise to do that is called ‘Homework for Life’ by Matthew Dicks (Author of Storyworthy).

How does it work?
Each day, you reflect upon the one storyworthy moment of the day.
You ask yourself: “If I had to tell a story from today, what would it be?”
It doesn’t have to be a big, life-changing moment.
It can be any moment that stood out, warmed your heart, or taught you something.
For instance, the moment someone complimented you, the moment you noticed something unusual, or the moment you hit a milestone.
Anything that stood out.
It can be work-related and personal.

Once you’ve found that moment, go ahead and write down:

  • Date
  • Your storyworthy moment (One sentence summary of your moment)
  • Your lesson (Optional, as not every moment has a major realization)

Here’s a snapshot of my Homework for Life:

Homework for Life Philipp

You see in the image that a few moments come from my private life, others from business interactions. Some days, nothing exciting happens; other days, I have deep insights.
I completed the exercise on most days, but skipped one (after enjoying too much wine the night before).
For me, this exercise is as if I was writing in a diary every day.

What’s in it for you?
At first, it may not feel too exciting. For example, your entry could look like, “The best thing that happened today was the cereal for breakfast” or “PowerPoint presentation that I worked on”.
Don’t worry. At the beginning, it can be difficult because your mind is not trained to spot more meaningful storyworthy moments.
However, after doing it consistently for a few weeks, you’ll observe fascinating changes:

  • You’ll realize that, actually, you experience dozens of situations that would make for interesting stories every day.
  • You’ll go through life more mindful, observing and appreciating any small moments
  • You’ll recognize patterns in your thoughts (good or bad) that you have not been aware of

It is a very simple but super powerful exercise.
Spending 1-2 minutes daily on this activity will give you a pool of stories.

Finding Stories Exercise #2: First, Last, Best, Worst

Another brilliant exercise to help you find stories is the exercise “First, Last, Best, Worst”.
The exercise (also by Matthew Dicks) is an exercise to go through a set of prompts that trigger memories from your past.

How does it work?
Take out a piece of paper or open an excel sheet and draw a table with five columns.
Note the column titles “Prompt”, “First”, “Last”, “Best”, and “Worst”.
Lastly, fill in the prompts. Potential prompts can be any category that trigger a memory. Popular ones include Gift, Travel, Job, Teacher, Book, Trouble, Car, Hobby, Injury, Pet, and Kiss. You get the idea.

Once you’ve written your prompts, go row by row and ask yourself:

  • What was my first [Prompt A]?
  • What was my last [Prompt A]?
  • What was my best [Prompt A]?
  • What was my worst [Prompt A]?

At this point, don’t fledge out any story yet.
Just write down a few words that will help you remember that event.

Here’s my exercise sheet to give you an idea:

First, Last, Best, Worst Philipp

Once you’ve gone through all the prompts, review your entries.
This time, ask yourself: Do any of these memories stand out? Anything that is very entertaining, emotional, or surprising?
If you answer “Yes” to any of these, that’s a story you could tell.

Not sure how to tell your story? Check out our article on the 6 Steps To Craft A Powerful Story.

What’s in it for you?
Doing this exercise is a great way to remember memories you’ve long forgotten or not thought about —memories that make great stories.
You can use these stories and share them with your family and friends or keep them to yourself.

Bonus: You can also do that exercise with another person. In that case, each of you would share a memory for some prompts. It’s a great exercise to get to know each other better.

Finding Stories Exercise #3: Crossroads

Another awesome exercise to find more stories is “Crossroads”.
Crossroads is an exercise by Jack Maguire (author of The Power of Personal Storytelling) that will help you identify the bigger moments in your life.

How does it work?

  • Take a piece of paper and draw a line from top to bottom. This represents your life. The bottom represents your birth, and the top is your current age.
  • Divide the line with short crosslines into five-year segments.
  • For each segment, look for any turning points. Times when you chose between two alternatives or times the choice was made for you. That could be, for instance, moving, getting into or out of a relationship, or changing jobs.
  • Once you have a turning point, jot down what could have happened (but didn’t) and what did happen.
    • An arrow pointing to the right with what you actually did
    • An arrow pointing to the left with what you did NOT do


Here’s my shortened lifeline to give you an idea:

Philipp's Lifeline

For each turning point, ask yourself:

  • What was the “main reason” for my decision back then?
  • How did I feel about the decision back then?
  • What might my life have been like had I taken the other road instead?
  • How has the decision impacted my life?


By going through that exercise, you’ll have plenty of ideas that could be turned into a great story.

What’s in it for you?
This exercise will help you understand the turning points in your life and will give you a few ideas of the big stories that you could tell.
It often also helps us bring meaning to our lives and helps us appreciate what we have and who we are.

Conclusion

That’s it. These are three exercises to help you find more stories in your life.
While Homework for Life is a great exercise to spot future storyworthy moments, First, Last, Best, Worst and Crossroads are great exercises to help you tap into past memories.

Each one of the exercises is relatively quick. So, give it a try. Ten minutes of doing any one of these exercises will give you a pool of stories you can use. Let me know how it goes.

Want to truly master the art of storytelling? Then, check out this next article in which I share How I’d Learn Storytelling If I Could Start Over.

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