Part I. Finding Your Story

No one ever made a decision because of a number. They need a story.
— Daniel Kahneman

Chapter 2. What Is a Story? (and What Is the Dinner Test?)

• Tell your own story, not the story of others.

  • People would rather hear what happened to you — there’s immediacy, grit, and inherent vulnerability in hearing the story of someone standing before you. It’s real.
  • If you have to tell the story of someone else, make it about yourself. Tell your side of the story.

• Stories are personal narratives. True stories told by the people who lived them.

• A few requirements to ensure that you are telling a personal story:

  • Change

    • Your story must reflect change over time. You must start out as one version of yourself and end as something new. It can be infinitesimal. It might not even be an improvement in yourself or your character, but change must happen.

  • Your Story Only

    • Tell your own story. Not another person’s story. But it’s fine to tell your side of another person’s story — as long as you are the protagonist.

  • The Dinner Test

    • Any story must pass the Dinner Test: is the story similar to a story you would tell a friend at dinner?
    • No poetry and no gestures.
    • No unattributed dialogue.
    • If you wouldn’t tell it at dinner that way, don’t tell it onstage that way.
    • Be planned and prepared but be off the cuff and extemporaneous- don’t make it a performance, make it something like telling a story over dinner

Chapter 3. Homework for Life

• The audience wants stories they can connect to.

• To generate stories, ask yourself at the end of each day what story the day held: “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?

  • Keep track of your answers. Just write down a snippet. A sentence or two that capture the moment from the day.
  • This is the Homework for Life. Do this every day. It takes only 5 minutes.
  • By practicing the act of finding stories, you’ll find more of them.

Chapter 4. Dreaming at the End of Your Pen

• Crash & Burn

  • It’s an exercise of stream-of-consciousness writing. “dreaming on the end of your pen”

    • Write down whatever enters your mind — no matter how strange, incongruous, or embarrassing it may be.

  • This allows you to generate old ideas and resurrect old memories.

  • Apply these three rules:

    • Don’t get attached to any idea.

      • The goal of the exercise is to allow unexpected ideas to intersect and overrun current ones.
      • Release the idea you’re holding immediately when another one comes in. No matter how good it is.

    • Don’t judge any idea or thought that appears in your mind

      • Everything goes on the page. Don’t worry about what it is.

    • The pen cannot stop moving.

• This is also a daily exercise. Do it daily.

Chapter 5. First Last Best Worst: Great for Long Car Rides, First Dates, and Finding Stories

• First Last Best Worst exercise

  • Label the top row (x-axis) of a page with the words “First”, “Last”, “Best”, and “Worst” along with a column labeled “Prompts” to the leftmost side. The prompts are listed on the y-axis. The prompts are the possible triggers for memories.

  • Fill in some prompts and fill out the rest of the cells. For example, what was your first kiss? Your best kiss? Worst kiss? And so on.

  • After completing the chart, analyze it. Ask yourself these 3 questions:

    • Do any entries appear more than once (the signal of a likely story)?
    • Could I turn any of these entries into useful anecdotes?
    • Could I turn any of these entries into fully realized stories?

  • Mark potential stories with an S. Anecdotes with an A.

Part II. Crafting Your Story

The most powerful person in the world is the storyteller. The storyteller sets the vision, values and agenda of an entire generation that is to come.
— Steve Jobs

Tell me the facts and I’ll learn. Tell me the truth and I’ll believe. But tell me a story and it will live in my heart forever.
— Ancient proverb

Chapter 7. Every Story Takes Only Five Seconds to Tell (and Jurassic Park Wasn’t a Movie about Dinosaurs)

• “All great stories — regardless of length or depth or tone — tell the story of a five-second moment in a person’s life.”

  • The moments in your life when something fundamentally changes forever.
  • These are the moments that make great stories. The moments we seek when we are doing our Homework for Life.

• If you don’t have a five-second moment, you don’t have a story.

Chapter 8. Finding Your Beginning (I’m Also About to Forever Ruin Most Movies and Many Books for You)

• You know the ending of your story now. Your five-second moment is the most important thing you will say, so it should be as close to the end of your story as possible.

  • The ending informs all the choices we make as we craft the rest of the story. Everything must serve our five-second moment.

• How, then, do you find the beginning?

  • Simple: Ask yourself where your story ends. What is the meaning of your five-second moment?
  • Then ask yourself: what is the opposite of my five-second moment?

• The beginning of your story should be the opposite of the end. Find the opposite of your transformation, revelation, or realization. This is where your story should start.

  • Remember: Stories must reflect change.
  • The change is what makes stories satisfying.

• Start as close to the end as possible.

  • When time and space is limited, it’s also easier to remember your stories.

• Your stories should be simple. When telling stories, your audience cannot just jump out and back in again. It’s like a river — always flowing. Make it easy to catch up if they fall off.

• Practical tips for choosing an opening

  • Try to start your story with forward movement whenever possible.

    • You see this very much in movies. We open on the protagonist (or someone else important to the story) moving.

  • Don’t start by setting expectations.

    • Don’t start with “This is hilarious” and so on. It ruins the story.

Chapter 9. Stakes: Five Ways to Keep Your Story Compelling (and Why There Are Dinosaurs in Jurassic Park)

• Stakes are the reason an audience wants to hear your next sentence. They’re what makes a story compelling.

• Five strategies to infuse a story with stakes

  • The Elephant

    • Every story must have one. It’s the thing everyone can see. Large and obvious. It’s the clear statement of the need, the want, the problem, the peril, or the mystery. It signifies where the story is headed.

    • It tells the audience what to expect. It gives them a reason to listen.

    • It should appear as early as possible. In the first minute or 30 seconds is best.

    • They can change color — the need, want, problem, peril, or mystery stated in the beginning can change along the way.

      • Never switch elephants — only color.

  • Backpacks

    • 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.

    • It’s an attempt to

      • Make the audience wonder what will happen next.
      • Make your audience experience the same emotion — or something like it — that the storyteller experienced in the moment.

    • Backpacks are most efficient when a plan does not work.

      • The audience wants the storyteller (characters) to succeed — but they want to see struggle and strife first. It should never be easy.
      • “Perfect plans executed perfectly never make good stories. They are stories told by narcisists, jackasses, and thin-skinned egotists.”

  • Breadcrumbs

    • Hinting at a future event but only reveal enough to keep the audience guessing.
    • Particularly effective when the truly unexpected is coming.

  • Hourglasses

    • Just before the moment the audence has been waiting for.
    • An Hourglass slows things down. Grinding them to a halt.
    • Stop the story cold. Bring everything to a halt. Describe things that don’t require a description.

  • Crystal Balls

    • A false prediction made by the storyteller to cause the audience to wonder if the prediction will prove to be true.

Chapter 10. The Five Permissible Lies of True Storytelling

Important Caveat #1

Only lie for the benefit of your audience. Never for personal gain.

Important Caveat #2

Memory is slippery. No story is entirely true. That’s OK.

Important Caveat #3

Never add anything to the story that wasn’t already there. You can manipulate it in many ways, but never add something that wasn’t there.

Lie #1: Omission

Lie #2: Compression

Compressing your story to a smaller timeline is fine.

Lie #3: Assumption

Lie #4: Progression

Changing the order of events to make the story better.

Lie #5: Conflation

Rather than describing change over a period of time, you can compress it a bit.

Chapter 11. Cinema of the Mind (Also Known as “Where the Hell Are You?”)

Always provide a physical location for every moment of your story.

Your goal is always to create a cinematic experience in the minds of your listeners.

Chapter 12. The Principle of But and Therefore

• Use “but” and “therefore” (or synonyms) to connect elements of your story.

• Using “and” provides no momentum.

• The negative is almost always better than the positive when it comes to storytelling. It’s better to say what someone is not.

  • “I am dumb, ugly, and unpopular” as compared to “I’m not smart, I’m not at all good-looking, and no one likes me.” The second sentence is better. It presents possibility. The first is binary.
  • By saying what you are not, you are also saying what you could have been. There’s a hidden “but”.

Chapter 14. The Secret to the Big Story: Make It Little

The goal of storytelling is to connect with your audience.

Big stories can get in the way of connecting. Not everyone can relate to your insane stories.

Chapter 15. There Is Only One Way to Make Someone Cry

• We cry because of surprise.

• You need to build surprise into your stories.

• It’s common to ruin surprise. Here are some common mistakes:

  • Presenting a thesis statement prior to the surprise

  • Failing to take advantage of the power of stakes to enhance and accentuate surprise

  • Failing to hide critical information in a story

    • Hiding the Bomb in the Clutter

      • You can hide important information by making it seem unimportant. Hiding it among other details.

    • Camouflage

      • Camouflage the bomb with laughter. Laughter is the best camouflage. People assume you just wanted to be funny.

Chapter 16. Milk Cans and Baseballs, Babies and Blenders: Simple, Effective Ways to Be Funny in Storytelling (Even If You’re Not Funny at All)

Stories should never only be funny. The best ones use humor strategically.

Chapter 17. Finding the Frayed Ending of Your Story (or, What the Hell Did That Mean?)

Stories can never be about two things.

You already know the ending of your story: your five-second moment. That’s what it’s about.

Chapter 18. The Present Tense Is King (but the Queen Can Play a Role Too)

Present tense makes the audience feel that they’re with you in the moment.

Chapter 19. The Two Ways of Telling a Hero Story (or, How to Avoid Sounding Like a Douchebag)

When you want to tell a success story, there are two strategies you should employ.

1. Malign yourself
2. Marginalize your accomplishment

Don’t attempt to be grandiose about yourself or your success. You have to undermine both you and it.

Why? People love underdogs. And people prefer stories of small steps over large leaps.

So just talk about a small step of your path to success.

Chapter 20. Storytelling Is Time Travel (If You Don’t Muck It Up)

Another goal as a storyteller is to make the audience forget that the present moment exists.

But that bubble is easily burst. Here are a few ways to avoid it:

• Don’t ask rhetorical questions.
• Don’t address the audience or acknowledge their existence whatsoever.
• No props. Ever.
• Avoid anachronisms
• Don’t mention the word story in your story.
• Downplay your physical presence as much as possible

Chapter 21. Words to Say, Words to Avoid

The words you choose will play a part in how the audience perceives you.

Profanity

Don’t swear much.

Sometimes, it’s fine to swear:

• Repeated dialogue
• When a swear word is simply the best word possible
• Moments of extreme emotion
• Humor

Vulgarity

This is the rule. If you’re speaking about a topic that would be awkward to talk about with your parents or grandparents, tread lightly.

Other People’s Names

When you choose a name, make it similar. That way it’s easier to remember. (Sally becomes Sandy)

Celebrity / Pop Culture References

Don’t do it. Don’t refer to celebrities.

You’ll alienate those who don’t know who you’re talking about.

It breaks your time-travel bubble. If you say someone looks like x, people will imagine that person there.

And it’s just lazy.

Accents

Don’t.

Chapter 22. Time to Perform (Onstage, in the Boardroom, on a Date, or at the Thanksgiving Table)

• Make eye contact
• Control your emotions
• Learn to use the microphone

Don’t memorize your story

It’s hard to be authentic and vulnerable when you’re reciting lines. Memorize these 3 parts:

1. The first few sentences.
2. The last few sentences.
3. The scenes of your story.