Storyworthy by Matthew Dicks

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Storyworthy's book cover


Two things you will believe after reading this book:

  1. Storytelling is a superpower,
  2. We all have meaningful stories to tell.

That’s right, the best stories are about mundane events, simple moments of transformation which we usually don’t pay attention to. However, if we start noticing and keeping track of these moments, we’ll see the abundance of stories we could tell. The challenge, then, becomes how to craft a good story.

A story should see the main character (you) change over time, and contain plenty of stakes. It should start with forward movement, and always have clear settings for each story scene. Ideally, it should be told in the present tense so that the listeners can “be there with you”. Ultimately, a great storyteller is able to create a movie in the mind of the audience.

Book Notes

Why telling stories matters

You need not spend time in jail or crash through a windshield or have a gun jammed against the side of your head to tell a great story. In fact the simplest stories about the smallest moments in our lives are often the most compelling. We all have stories. You may not believe this yet, but you will. You just need to know how to find them in your everyday life and then capture them for future telling.

We tell stories to express our hardest, best, most authentic truths. This is what brings thousands of people to hear stories at theaters and bars every night in cities all over the world. They want the real deal.

Example: "This Is Going to Suck", story by Matthew Dicks.

Without my friends showing up in the emergency room when I needed them most, it’s just another car-crash story. Turn on the news at 11:00 PM and you’ll see that they are a dime a dozen. Without my friends arriving at my time of need, there is little for the audience to connect to. But add my friends to the mix, and everything changes. We’ve all felt alone at some point in our lives. We’ve all been let down by loved ones, perhaps even by our parents. We’ve all had moments when we are unexpectedly lifted from pain or despair by the kindness of a friend. This is what people connect to. Few people will ever understand what it’s like to crash through a windshield or awaken to paramedics performing CPR on your body. But feeling alone? Forgotten? Lost? We all know that feeling.

3 rules to tell a personal story

There are a few requirements to ensuring that you are telling a personal story:

  1. Change. 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. The change can be infinitesimal. Stories that fail to reflect change over time are known as anecdotes.
  2. Your Story Only. You must tell your own story and not the stories of others. There is immediacy and grit and inherent vulnerability in hearing the story of someone standing before you. It is visceral and real. This doesn’t mean that you can’t tell someone else’s story. It simply means you must make the story about yourself. You must tell your side of the story.
  3. The Dinner Test. [Craft your story as if you were to tell it at dinner to friends.] It will guarantee that you don’t sound “performancy” or inauthentic.

Find stories worth telling

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. These five-second moments are the moments in your life when something fundamentally changes forever. You fall in love. You fall out of love. You discover something new about yourself or another person. Your opinion on a subject dramatically changes. You find forgiveness. You reach acceptance. You sink into despair. You grudgingly resign. You’re drowned in regret. You make a life-altering decision. Choose a new path. Accomplish something great. Fail spectacularly. These are the moments that make great stories.

Visiting Tanzania is not a story. Your ability to travel the world does not mean that you can tell a good story or even have a good story to tell. But if something happened in Tanzania that altered you in some deep and fundamental way, then you might have a story. If you experienced a five-second moment in Tanzania, you might have something. Think of it this way: If we remove Tanzania from the story, do you still have a story worth telling?

If you think you have a story, ask yourself: Does it contain a five-second moment? A moment of true transformation? Your five-second moment may be difficult to find. You may have to dig for it. So dig. Search. Hunt. Fight for the five-second moment. Allow yourself to recall the entire event. Don’t get hung up on the big moments, the unbelievable circumstances, or the hilarious details. Seek out the moments when you felt your heart move. When something changed forever, even if that moment seems minuscule compared to the rest of the story. That will be your five-second moment. Until you have it, you don’t have a story.

Your five-second moment is the most important thing that you will say. It is the purpose and pinnacle of your story. It’s the reason you opened your mouth in the first place. Therefore it must come as close to the end of your story as possible. Sometimes it will be the very last thing you say.

How to find your 5-second moments

These moments are everywhere. The problem is that we don’t see these moments. We fail to notice them or recognize their importance, and when we happen to see one, we don’t reach out to catch it. We don’t record it. We don’t save it. We fail to keep these precious moments safe for the future.

Years ago, I found a way to recognize and collect these moments, and it has changed my life. It’s turned me into a storyteller with an endless supply of stories. Stories that don’t rely upon near-death experiences or unlawful imprisonment or homelessness to be effective. It’s also made me a happier person.

[Here's how it works:] At the end of every day, reflect upon your day and ask yourself one simple question:

If I 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 benign and boring and inconsequential as it might seem, what was the most storyworthy moment from your day?

Don't write the entire story down, because to do so would require too much time and effort. A sentence or two that captured the moment from the day. Just enough for you to remember the moment and recall it clearly on a later date.

💡 Listen to Matthew explaining the concept further in his Ted Talk 'Homework for Life'.

How to start a story

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. I was once hopeful, but now I am not. I was once lost, but now I am found. I was once happy, but now I am sad. I was once uncertain, but now I know. I was once angry, but now I am grateful. I was once afraid, but now I am fearless. I once believed, but now I don’t.

This change is what makes stories satisfying. It’s how storytellers are able to move an audience emotionally.

The beginning is much harder to find because the opposite of your five-second moment does not happen on the same day or even in the same week.

When we search our past for the beginnings of our stories — which storytellers do quite often — we have a mountain of material from which to choose. Less effective storytellers latch onto the first thing that comes to mind rather than making a list of anecdotes, analyzing them for content, tone, the potential for humor, and connectivity to the story before deciding. I also believe that great storytellers know this: The first idea is rarely the best idea. It may be the most convenient idea. The easiest to remember. The one you personally like the most. But rarely is the first idea the one that I choose. First ideas are for the lazy. The complacent. The easily satisfied. I fight for my beginnings. I struggle to find the correct entry point to a story, and I believe that every story has a perfect entry point. The ideal place to start. More than half of the time I spend crafting stories is spent searching for the right beginning. Once I’ve found it, the rest of the story often flows easily.

Try to start your story with forward movement whenever possible. 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 we’re already on our way, immersed in the world you are moving us through. We’re going somewhere important.

5 ways to infuse stakes in storytelling

If you’re not sure about the level of stakes in your story, simply ask yourself:

  • ​Would the audience want to hear my next sentence?
  • If I stopped speaking right now, would anyone care?
  • ​Am I more compelling than video games and pizza and sex at this moment?

If the answer to any of these questions is no, you need to raise the stakes. I use five different strategies to infuse this story with stakes. These strategies are both easy to apply and almost always effective. [Each strategy is demonstrated through the example of the story “Charity Thief”. Listen to it before you read about them.]

1) The Elephant 🐘

The Elephant is the thing that everyone in the room can see. It is large and obvious. 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.

Example: In “Charity Thief,” the Elephant that I present at the beginning of the story is a simple one: I’m stuck in New Hampshire with a flat tire and no spare. How will Matt escape from New Hampshire and return home without a spare tire or money? Those are the stakes. The problem is clear. Now the audience has a chance to guess. To predict. To wonder.

Eventually the Elephant in my story changes color. The story isn’t really about escaping New Hampshire at all. It’s really a story about understanding the nature of loneliness. I change the color of the Elephant halfway through this story. I present the audience with one Elephant, but then I paint it another color. I trick them. This is an excellent storytelling strategy: make your audience think they are on one path, and then when they least expect it, show them that they have been on a different path all along.

2) The Backpack 🎒

A Backpack is a strategy that increases the stakes of the story by increasing the audience’s anticipation about a coming event. It’s when a storyteller loads up the audience with all the storyteller’s hopes and fears in that moment before moving the story forward.

In “Charity Thief,” I stick a Backpack on my audience when I describe my plan for begging for money before entering the gas station. I say: "So I make a plan. I’m going to beg for gas, because it’s 1991. Gas is eighty-five cents a gallon, so eight dollars is all I need to get me home. I’ll offer my license, my wallet, everything in my car as collateral in exchange for eight dollars’ worth of gas and the promise that I will return and repay the money and more. Whatever it takes. So I rehearse my pitch, take a deep breath, and walk in."

At this point the audience is loaded with my hopes and dreams. They know the plan, so when the kid behind the counter refuses to give me gas for my car, the audience experiences the same kind of disappointment that I felt that day.

By putting a Backpack on them, I allowed my audience to enter the gas station with me, wondering what would happen next. I turned my plan into their plan. They’re now invested in the outcome. These are stakes. The audience must hear the next sentence.

Backpacks are most effective when a plan does not work. It’s an odd thing: The audience wants characters (or storytellers) to succeed, but they don’t really want characters to succeed. It’s struggle and strife that make stories great. They want to see their characters ultimately triumph, but they want suffering first. They don’t want anything to be easy.

3) Breadcrumbs 🍞

Storytellers use Breadcrumbs when we hint at a future event but only reveal enough to keep the audience guessing. In “Charity Thief,” I drop a Breadcrumb when I say: “But as I climb back into the car, I see my crumpled McDonald’s uniform on the backseat, and I suddenly have an idea.” All I care about is that my audience is wondering what will happen next.

4) The Hourglass ⌛

There comes a time in many stories when you reached a moment (or the moment) that the audience has been waiting for. The sentence you’ve been waiting to say. This is the moment to use an Hourglass. It’s time to slow things down. Grind them to a halt when possible. When you know the audience is hanging on your every word, let them hang. Drag out the wait as long as possible. In “Charity Thief,” that moment occurs as I am knocking on that blue door. [Minute 2:35, when he describes the McDonald uniform, then describes the man's appearance]

5) The Crystal Ball 🔮

A Crystal Ball is a false prediction made by a storyteller to cause the audience to wonder if the prediction will prove to be true. In “Charity Thief,” I say: "[The man] points his finger at me and says, “You stay right there.” Then he walks back into his house, and I know what he’s doing. He’s calling the police, and they will come and arrest me for stealing money from McDonald’s." This does not happen, of course, but when I present this very real possibility, the audience wants to know if it will happen. By predicting my future arrest, I’ve established wonder in their minds about a future event.

In storytelling, deploy Crystal Balls strategically: Only when your prediction seems possible. Only when your guess is reasonable. And only when your prediction presents an intriguing or exciting possibility.

5 permissible lies in storytelling

We lie in our stories only when our audience would want us to lie — only when the story is better for our doing so. We want to tell true stories of our lives, but no story is entirely true. Intentionally or otherwise, our stories contain mistakes, inaccuracies, slippages of memory. All I am asking you to do is to be strategic in some of your inaccuracies, and only when it’s done for the benefit of the audience.

  1. Lie #1: Omission. [e.g. of peope who were there with you but do not add to the story.]
  2. Lie #2: Compression. If the first scene of your story takes place on a Monday, for example, and the next scene happens on Friday, and you are concerned about the audience wondering about Tuesday, Wednesday, and Thursday, you simply push time together and turn your Monday-through-Friday story into a Monday-through-Tuesday story.
  3. Lie #3: Assumption. [e.g. of a detail you can't actually recall, like the color of a car or the name of a person]
  4. Lie #4: Progression. A lie of progression is when a storyteller changes the order of events in a story to make it more emotionally satisfying or comprehensible to the listener.
  5. Lie #5: Conflation. Storytellers use conflation to push all the emotion of an event into a single time frame, because stories are more entertaining this way. [e.g. Oceans Eleven's heist happens in 3 days instead of 3 years, which would probably be more accurate for planning it.]

Storytelling is movie-making

A great storyteller creates a movie in the mind of the audience. Listeners should be able to see the story in their mind’s eye at all times. At no point should the story become visually obscured or impossible to see. As the title of this chapter suggests, effective storytelling is cinema of the mind. In order to achieve this lofty goal, storytellers must do one thing, and happily for you, it’s exceedingly simple: Always provide a physical location for every moment of your story. That’s it. If the audience knows where you are at all times within your story, the movie is running in their minds.

  • [If possible use the present tense to tell your story] The present tense acts like a temporal magnet, sucking you into whatever time I want you to occupy.
  • Instead of memorizing your story word-for-word, memorize three parts to a story: 1. The first few sentences. 2. The last few sentences. 3. ​The scenes of your story. If you’re following my advice and placing every moment of your story in a physical location, then your story will be composed of scenes: places where the action, dialogue, and internal monologues are taking place. If you remember these places, you will remember what happens there, even if every prepared word of your story suddenly flees your mind. I try not to have more than seven scenes in a story.

I like to think about storytelling in terms of superheroes, because I believe that a person who can speak in an entertaining and engaging way to a group of people possesses a superpower that is sorely lacking in the world today. As people’s gazes continue to fall to their screens and communication is truncated into bite-size text messages, the human beings who can still hold the attention of an audience and teach and speak in an entertaining way possess enormous power.

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