Nate Medina

So how does Matthew pull off captivating stories? Here’s my summary of his book Storyworthy.

What is a story? 

A story is like a diamond with many facets. Everyone has a different relationship to it. If you can find a way of making your particular facet of the story compelling, you can tell that story as your own. Otherwise, leave the telling to someone else.

Your story must reflect change over time. A story cannot simply be a series of remarkable events. You must start out as one version of yourself and end as something new.

Don’t tell drinking stories or vacation stories unless you underwent change. 

Only tell your story and not the stories of others unless it affected you to change. But feel free to add your side of other people’s stories, as long as you’re the protagonist. 

Your story must pass the dinner test. The dinner test is this:  Is the story that you craft for the stage, the boardroom, the sales conference, or the Sunday sermon similar to the story you would tell a friend at dinner? This should be the goal. Storytelling is not theater. It is not poetry. It should be a slightly more crafted version of the story you would tell your buddies over beers. This is what the audience wants. They want to feel that they are being told a story. They don’t want to see someone perform a story.

How do you collect storyworthy moments? 

Matthew recommends doing homework for life to collect moments from your experiences that you can use to turn into stories. 

Your stories don’t have to be extreme moments

Yes, audiences love these stories. But a tiny story that takes place at a dining-room table between a husband and a wife is the kind of story that audiences love best of all. Here’s why: “If I tell the story about the time I died on the side of the road and was brought back to life in the back of an ambulance, it’s going to be challenging for an audience to connect with my story and with me. It might be exciting and compelling and even suspenseful, but audience members are probably not thinking, “This is just like the time I died in a car accident and the paramedics brought me back to life!” There’s nothing in the horror of a car accident for an audience to connect to. Nothing that rings true in the minds of listeners. Nothing that evokes memories of the past. Nothing that changes the way audience members see themselves or the world around them. But if I tell you about my secret childhood hunger, that story is much more likely to resonate with you. Why? We all have secrets that we hold close to our hearts. Maybe it’s a secret that you never want anyone to know, or maybe it’s one that you desperately wish someone would uncover. Or maybe, like me, you had a secret that was discovered by a friend or loved one. Either way, we all know what it’s like to have a secret like mine.”

Homework for life

At the end of every day, reflect upon your day and ask yourself one simple question: If you had to tell a story from today — a five-minute story onstage about something that took place over the course of this day — what would it be? As boring and inconsequential as it might seem, what was the most storyworthy moment from your day? What is your story from today? What is the thing about today that has made it different from any previous day? Then write your answer down.

You’ll start to notice moments of real meaning that you’ve never noticed before. As you begin to take stock of your days, find those moments — see them and record them — time will begin to slow down for you. The pace of your life will relax.

How to find hero stories

“There is nothing wrong with sharing your success stories, but they are hard stories to tell well. The truth is this: failure is more engaging than success.”

If and when you want to tell a success story, make sure that you malign yourself and marginalize your accomplishment. This is because humans love underdog stories — they’re universal. 

How to craft a story

Find your 5-second moment

All great stories — regardless of length or depth or tone — tell the story of a five-second moment in a person’s life. Every great story ever told is essentially about a five-second moment in the life of a human being, and the purpose of the story is to bring that moment to the greatest clarity possible.

Anything in the story that doesn’t help bring that moment to the greatest clarity possible is marginalized, shaded, or removed entirely. Anything that helps bring clarity to that moment is strengthened and highlighted.

For example, in Raiders of the Lost Ark, the 5-second moment is when Indiana Jones finds faith when he needs it most. It’s a story about a scientist who finds God. 

Your 5-second moment should be a realization about something in your life, typically in understanding why something matters to you and how you’ve changed because of it — a moment of true transformation. 

You might not know your 5-second moment right way. That’s Ok. Just start telling your story, and the meaning of the story will come out.

How to find the beginning of your story

The 5-second moment should be the end of your story. It’s the most important thing that you want to say. It’s the reason you opened your mouth to tell the story — which means it should come near the end of your story. Always start by knowing your 5-second moment (or ending). 

Once you have your 5-second moment, ask yourself what’s the opposite of that moment? “Simply put, the beginning of the story should be the opposite of the end. Find the opposite of your transformation, revelation, or realization, and this is where your story should start. This is what creates an arc in your story. This is how a story shows change over time.” Change is key. You must begin and end your story in entirely different state of being. 

For example: 

• I was once this, but now I am this (I was once hopeful, but now I am not). 
• I once thought this, but now I think this (I once believed, but now I don’t). 
• I once felt this, but now I feel this (I once was afraid, but now I am fearless).

The beginning can be hard to find because the opposite of your 5-second moment could be years before the event happen. But don’t start there. Try starting as close to the end as possible to shorten the story and avoid unnecessary setup. 

Practical tips: 

1. Start your story with forward movement: Establish yourself as a person who is physically moving through space. Opening with forward movement creates instant momentum in a story. It makes the audience feel that they’re already on the way, immersed in your world. 
2. Don’t start by setting expectations: Don’t say “This is hilarious” or “You need to hear this.” Just start your story. 

How to make your story compelling

You need to raise the stakes. Answer questions like: 

• What does the storyteller want or need? 
• What is at peril? 
• What is the storyteller fighting for or against?
• What will happen next?
• How is this story going to turn out?

“Stakes are the reason an audience wants to hear your next sentence. They are the difference between a story that grabs the audience by the throat and holds on tight and one that an audience can take or leave. Stakes are the difference between someone telling you about their mother and someone telling you about the time they wanted to disown their mother.”

Introduce the elephant — the thing that everyone in the room can see. It’s large and obvious. It’s a clear statement about the need, the want, the problem. The Elephant tells the audience what to expect. It gives them a reason to listen, a reason to wonder. It infuses the story with instantaneous stakes. The Elephant should appear as early in the story as possible. Ideally, it should appear within the first minute, and if you can say it within the first thirty seconds, even better.

Make your audience think they are on one path, then when they least expect it, show them they have been on a different path the whole time. The audience just didn’t realize that it’s a much deeper, more interesting path than first expected. Don’t switch Elephants. Simply change the color.

Build up your backpack — Make the audience wonder what will happen next. And Make your audience experience the same emotion, or something like the same emotion, that the storyteller experience in the moment about to be described. 

For example, tell your audience about your plan, your hope and dreams so that they know what you’re trying to accomplish. Movies like Ocean’s Eleven explain almost every part of the robbers’ plan before they make a move. You’re instantly hooked to see them succeed. But what makes the story more interesting is when things don’t go according to plan. That’s when you’re pulled in even more. Perfect plans executed perfectly never make good stories.

Use breadcrumbs — hint at a future event but only reveal enough to keep the audience guessing. For example, “I see my McDonald’s uniform on the backseat, and I suddenly have an idea.” Breadcrumbs are great to use to get your audience guessing what will happen next but you know that the unexpected is coming. 

Use the hourglass — Find the moment in your story that everyone has been waiting for, then flip that hourglass and let the sand run. Slow things down right before big moments. When you know the audience is hanging on your every word, let them hang. Drag out the wait as long as possible. Right before you’re about to reveal what happens, stop. Don’t do it. Describe something else for a bit. This is because your audience wants to know what’s happening next — but you’re in full control. 

Use crystal balls — offer a false prediction to cause the audience to wonder if the prediction will prove to be true. You can do this by verbally predicting the future of your story, which makes your audience wonder about what’s to come. Use crystal balls that are reasonable. 

How to use humor

Humor a way of keeping your audience’s attention through a section of your story  that you think might be less compelling. Remember that the goal of the storyteller is not to be funny. Your goal is to move the audience emotionally. Like every other emotional response, laughter is simply a well-cultivated surprise.

When to use humor

1. Start with a laugh. Get your audience to laugh within the first 30 seconds. 
2. Make them laugh right before you make them cry. 
3. Make them laugh after the incident to break the tension. 
4. Don’t end on a laugh. End with movement. 

How to lie as a storyteller

Matthew recommends only lying if it benefits the audience (not for personal gain) and, if your memory is slippery, piece it together strategically. But, never add something to a story that was not already there. Here are the five permissible lies: 

1. Omission: You can’t possibly tell everything from 0 to 100. You need to omit elements from your stories so that your story is easier to understand and more concise. Omit people, like third wheelers and random strangers who distract the audience from what matters. Pretend they aren’t there. Omit places that aren’t building your story up. Omit redemption. For example, just like in Inception,  the spinning top continues spinning at the end, don’t give the full resolution to the audience. Stories like these linger in the hearts and minds longer. “Audiences don’t want redemption. Redemption cleanses the palate. It ties up all loose ends. It makes the world whole again. It allows your audience to sleep well at night. I want my audience tossing and turning over my story.”
2. Compression: This is used when you want to push time and space together in order to make the story easier to comprehend. For example, you turn a Monday-through-Friday story into a Thursday-through-Friday story. Place scenes closer together to heighten the drama and suspense of the story.
3. Assumption: Make assumptions about details. For example, if you can’t remember the make and year of a car, make your best assumption. 
4. Progression: Change the order of events in a story to make it more emotionally satisfying or comprehensible to the listener. 

How to make your story flow like a movie

Your audience should be able to see the story in their mind’s eye. Your story should be visual and easy to see. To do this, always provide a physical location for every moment of your story. That’s it. All your audience needs to know is the location of the action at all times for them to run the story in their minds. 

Don’t use “and” too often

The better connective tissue for stories is the word “but” and “therefore.” “And” stories have no movement. “But” and “therefore” signal change. It’s a way of zigzagging through the story. It’s the difference between these two statements: 

• “I loved Heather since sixth grade, but as much as I loved her, she was never mine.”
• “I loved Heather since sixth grade. She was never my girlfriend.”

This happens, therefore that happens, but then this happens, therefore that happens.

Use the negative: “The negative is almost always better than the positive when it comes to storytelling. Saying what something or someone is not is almost always better than saying what something or someone is. For example: I am dumb, ugly, and unpopular. I’m not smart, I’m not at all good-looking, and no one likes me. The second sentence is better, isn’t it? Here’s why: it contains a hidden but. It presents both possibilities. Unlike the first sentence, which only offers single descriptors, the second sentence offers a binary. It presents the potential of being not smart, good-looking and not good-looking, popular and unpopular.”

More examples: “Heather is my ex-girlfriend” is not as good as “Heather is no longer my girlfriend.” “I was penniless” is not as good as “I didn’t have a penny to my name.”

How to tell your big story

“This is the trick to telling a big story: it cannot be about anything big. Instead we must find the small, relatable, comprehensible moments in our larger stories. We must find the piece of the story that people can connect to, relate to, and understand…Little moments hidden inside big moments. That’s what we need to find to tell a big story well.”

Shorter stories are always better

Try saying less than saying more. Who likes long meetings or long speeches anyway? As Blaise Pascal first said, “If I had more time, I would have written you a shorter letter.” Brevity takes time because brevity is always better.

How to make someone cry

Use surprise. It’s the only way to elicit an emotional reaction from your audience. 

That means you must keep your story unexpected. 

Don’t lead with a thesis statement about what your story is about. 

Don’t forget to explain your plan before you do something. Heighten the contrast between the surprise and the moment just before the surprise. 

Don’t forget to hide critical information. Obscure your audience in a list of other details. Place them as far away from the surprise as possible. Build a laugh around them to camouflage the surprise. 

Use the present tense

“It creates a sense of immediacy. Even though you are reading these words in bed or by the light of a roaring fire or perhaps naked in your bathtub, a part of you, maybe, is on this train with me, staring at a little boy who desperately needs to pee. The present tense acts like a temporal magnet, sucking you into whatever time I want you to occupy.”

You can use the past tense to tell backstory or to help you fast-forward. 

How to interact with the audience

Don’t ask rhetorical questions.

Don’t address the audience or acknowledge their existence. 

Don’t use props. 

Avoid anachronisms. 

Don’t use the word “story.”

Don’t use costumes. Be as simple with your clothing/aesthetic as possible. 

How to present your story

Don’t memorize your whole story as it could throw you off if you forget a word. Instead, memorize the first few sentences so that you start strong. Memorize the last few sentences so you end strong. And memorize the scenes of your story.