Storyworthy by Matthew Dicks

My rating: 7.5/10
I've never seen myself as a good story teller, but this book gave me a huge boost in that direction. Totally recommend to anyone who wants to improve their abilities to captivate an audience.
My rating: 7.5/10
I've never seen myself as a good story teller, but this book gave me a huge boost in that direction. Totally recommend to anyone who wants to improve their abilities to captivate an audience.

The Book in 3 Sentences

  1. Story telling can be improved just like any other skill.
  2. Everyone has stories to tell.
  3. Improving your story telling lense will help you to live a more fulfilling life.


The book is filled with advice on how to find your story, craft your story, and tell your story. There are also example stories interspursed throughout the book which are a joy to read, and some story telling theory.

A common theme is the difference between a romp/stand up comedy and a story. The idea is that romp/stand up can be just as engaging with the audience, but it won’t stick with them forever because it doesn’t show change over time. Personally what I was most interested in getting out of this book was how to captivate an audience; I’m more interested in the high energy romp than the story that stays with the audience forever. After improving at the romp I will move to the improving at the forever lasting story.

He put a lot of emphasis on the “5 second moment” where something fundamentally changes forever, but I don’t quite believe when he says that “Every great story ever told is essentially about a five-second moment in the life of a human being… where something changes forver”. Maybe one day i’ll see the light in this regard.

There was some commentary on applying the story telling theory to popular books and films, but I didn’t like this part as much because it was extremely hand wavy.

Who Should Read It?

I would recommend everyone read it. The ability to tell stories well will drastically improve anyones life, and it just takes a few hours to see significant improvement.

How The Book Changed Me

  • Made me more comfortable with telling stories.
  • Gave me a new appreciation for the story worthy moments in my own life. Showed me that events I would typically have completely overlooked can have a great story behind them.

My Top 3 Quotes

  • “When I’m asked a question, I tell a story.”
  • “We tell stories to express our hardest, best, most authentic truths”.
  • “Your story must reflect change over time. You must start out as one version of yourself and end as something new.”

Summary and Notes

Part I. Finding your Story

What Is a Story? (and What is the Dinner Test?)

  • Drinking Stories

    • no one will ever care as much as you
    • don’t impress people that you want to impress
    • good drinking stories don’t do well during the day or at the workplace
  • Vacation stories

    • no one wants to hear about your vacation
    • if someone wants to hear about it, they are being polite
    • if you had a moment that was actually storyworthy during vacation, it should be told, but should not mention the local cuisine or anything related to the charm of the destination
  • Your Story Only

    Nobody wants to hear you tell the story of someone else. You can tell someone else’s story, but it has to be your side of the story.

  • The Dinner Test

    The story that you craft for the stage, board room, or sales conference should be similar to one you would tell a friend at dinner.

    You should also tell it like you would at dinner. No crazy crazy hand gestures, no starting off with dialogue, not too much poetry.

    Pretend it is first time telling the story, but really it is not. Don’t memorize it, but learn the specific beats. The beginning and ending lines. Laugh lines.

Homework For Life

At the end of every day, reflect upon the day and ask yourself one simple questions:

  • If I had to tell a story from today, what would it be? As benign and boring and inconsequential as it might seem, what was the storytworthy moment from my day?

Don’t write the whole story down. Just a sentence or two that captured the moment from the day. Enough to remember the moment and recall it clearly on a later date.

Lots of reasons to do it:

  • Develop a story telling lense. As you reflect on each day of your life, you begin to see that your life is filled with stories. Moments of real meaning that you woul dhav enever noticed will suddenly stare you in the face. You won’t believe how plentiful they are. Not every day will really contain a story worthy moment, but the longer you do your homework, the more days that will contain one.
  • Improve story telling repretoir
  • Therapeutic
  • Slows life down.

Five minutes a day is all it takes. If you want to be a storyteller, this is your first step. Find your stories. Collect them. Save them forever.

Dreaming at the End of Your Pen

Crash and Burn exercise. Talks about the benefits of spending 15 minutes a day writing whatever comes to mind.

Essentially Crash and Burn is a stream-of-consciousness writing. Stream of consciousness is the acct of speaking or writing down whatever thought that enters your mind, regardless of how strange, incongruous, or even embarrassing it may be.


  1. You must not get attached to any one idea
  2. You must not judge any thought or idea that appears in your mind
  3. You cannot allow the pen to stop moving

This process will help uncover stories from your past. Finding potentially new stories is thrilling. Even better, recovering memories from the past that had been last until you sat down to write. Forgotten moments that will remain with you now until the day you die.

First Last Best Wost

Great for long car rides, first dates, and finding stories.

List a few prompts that are possible triggers for memories, and for each prompt you fill in the word or words that indicate the answers to those questions. Example:

Prompt First Last Best Worst
Kiss Laura Clara Elysha Sheila
Car Datsun 210 Toby & Pluto Kaleigh Prudence
Trouble Corner in kindergarten Speeding ticket tInciting riot upon myself Arrested
Injury Mysterious head wound Elbow tendinitis Pole-vault pole snaps Datsun B210 accident
Gift Puppy 12 dates for 12 months Friends as family Bath towels
Travel Pasadena 1988 Lewiston, Maine Honeymoon Disney with Cushman

Finding Your Story Overview

You now have three tools to find stories:

  • Homework for life
  • Crash and Burn
  • First Last Best Worst

Do all three with regularity and fidelity, and you will find yourself drowning in stories before long. Now it’s time to learn how to craft a story.

Part II. Crafting Your Story

Every Story Takes Only Five Seconds to Tell

All great stories, tell the story of a five-second moment in a person’s life. The 5 second moments are the moments when something fundamentally changes forever.

A romp is an entertaining and amusing anecdote - often longer than you might imagine an anecdote to be - not something that will move an audience emotionally. It was fun and exciting and surprisng, but it was unlikely to remain in the hearts of the audience in the way a good story can.

Even when the ending is all but certain, a good storyteller can grab the audeience by the throat and make them temporarily forget that they know damn well how this movie will end.

Finding Your Beginning

You have your five-second moment. This gives you the end of your story. It must come as close to the end of the story as possible.

To find the beginning of the story ask yourself: what is the opposite of your five-second 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.”

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

    Establish as a person physically moving through space. It creates instant momentum in a story.

  • Don’t start by setting expectations.

    Don’t start with “This is hilarious” or “You need to hear this”. I raises the bar and reduces the chances of surprising the audience.

Thirteen Rules for an Effective Commencement Address

Each rule summarized in one line:

  1. Don’t compliment yourself
  2. Be self-deprecating, but only if it is real.
  3. Don’t ask rhetorical questions. They break momentum.
  4. Offer one granular bit of widsom, something that is both applicable and memorable.
  5. Don’t cater any part of your speech to the parents. Speech should be focused on graduates.
  6. Make your audience laugh.
  7. Never mention the weather.
  8. Speak as if you were speaking to friends.
  9. Emotion is good. Be enthusiastic. Excited. Anything but staid and somber.
  10. Don’t attempt to describe the world that the graduates will be entering.
  11. Don’t quote the dictionary.
  12. Don’t use a quote you’ve heard someone use in a previous commencement speech. Don’t use a quote at all, if possible. Try to be quotable instead.
  13. End your speech in less than the allotted time.


Stakes are the reason an audience wants to hear your next sentence. Strategies for increasing the stakes (i.e. better captivating the audience):

  • The Elephant

    The thing that everyone in the room can see. It tells the audience what to expect. Gives them a reason to listen and wonder. It should appear as early in the story as possible.

    Elephant can change through out the story. In his example he starts with elephant of wondering how he is going to get out of new hampshire, and then moves to focusing on the idea of loneliness. Excellent story telling strategy to have audience think that they are on one path, and then show them its a different path all along.

    The “laugh laugh laugh cry forumula”.

  • Backpack

    Put the audience in your shoes, so that when they learn what happens next, they experience similar emotions that you did. Give the audience a way to guess about what will happen next. Backpacks are most effective when a plan does not work.

    Perfect plans executed perfectly never make good stories.

  • Breadcrumbs

    Hint at a future event, but only reveal enough to keep the audience guessing. Most effective when the truely unexpected is coming.

    Example: “But as I climb back into the car, I see my crumpled McDonald’s uniform on the backseat, and I suddenly have an idea.”

  • Hourglasses

    Eventually you reach a (or the) moment the audience has been waiting for. This is the time to use an hourglass. It’s time to slow things down. Grind them to a halt. Drag the wait out as long as possible. You own the audience.

    • describe things that don’t need description
    • describe more things that don’t need description
  • Crystal Balls

    A false prediction made by a story teller to cause the audience to wonder if the predicion will prove to be true.

    “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 doesn’t happen, but when presenting a very real possbility, the audience wants to know if it will come true.

    Deploy Crystal Balls strategically: only when the prediction seems possible, the guess is reasonable, and the prediction presents an exciting possibility.

  • Humor

    Doesn’t add or raise stakes, but helps keep the audience’s attention.

    Remember though that the goal of a story is not to tell a funny story. It is to tell a story that moves an audience emotionally.

  • Stakes Overview

    The best way to ensure that a story has stakes is to choose a story that has stakes. Elephants, Backpacks, Breadcrumbs, Hourglasses, and Crystal Balls will only get you so far.

    In order to gauge the level of stakes in your story, ask:

    • would the audience want to hear the next sentence
    • if I stopped speaking right now, would anyone care
    • am I more compelling than video games and pizza and sex?

The Five Permissible Lies of True Story Telling

Only lie for the benefit of the audience; not our personal gain. Not in the interest of making ourselves look better in the story.

We can manipulate the story in ways, but never add something that did not already exist. Not fiction. Trut tellers. Making something up is cheating. Permissible Lies:

  • Omission

    If a person doesn’t fill a role in a story, pretend that person wasn’t there. Cut out events. Make it seem like the third try was the first if the others aren’t important. Audiences don’t want redemption. It allows your audience to sleep well at night.

  • Compression

    Why stretch out a story over two days if nothing of consequence happens between the planning and execution? Helps with simplicity. Simplicity should be prized at all points.

  • Assumption

    Make assumptions when there is a detail important to the story that must be stated with specificity. Helps the audience see what you are seeing.

  • Progresssion

    Change around the order of events if it makes the story flow better. Better to make people laugh before they cry. It hurts more that way.

  • Conflation

    Rather than describe a change over a long period, we compress all the intellectual and emotional transformation into a smaller bit of time. Helps keep stories shorter. Shorter stories are always more entertaining.

Cinema of the Mind

Great storyteller creates a movie in the minds of the audience.

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

He gives two versions of the same passage, one where the location is set, although unimportant to the passage, but it still helps ground yourself in the story better. In the movie.

Backstories should be told as thoughts after giving a location.

Let’s you convey thoughts and ideas from the perspective of your past self rather than your present day self.

The Principle of But and Therefore

And stories have no movement or momentum. They are equivalent to running on a treadmill.

But and therefore are words that signal change.

Make a story feel as if it’s constantly going someplace new, even if the events are linear and predictable.

Ideally all scenes are connected with a but or a therefore. It’s causation that makes a story.

Recounting a vacation is not a story. It is a meangful stroll down memory lane.

Oddly, 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.

  • I am dumb, ugly, and unpopular
  • I’m not smart, I’m not at all good-looking, and no one likes me.

By saying what something is not, you are also saying what something could have been, and that is a hidden but.

Sometimes a quick positive statement fits better.

The Secret to the Big Story: Make It Little

The goal of storytelling is to connect with your audience, whether it’s one person at the dinner table or two thousand people in a theater.

Big stories can get in the way of connecting; most people can’t relate to the big story.

The trick to telling a big story: it cannot be about anything big. Instead we must find the samll, relatable, comprehensible moments in our larger stories. We must find the piece of the story that people can connect to, relate to, and understand.

There Is Only One Way to Make Somone Cry


Storytellers often mitigate or ruin surprise by making simplemistakes or failing to accentutate or enhance the potential surprise of the moment. Common mistakes:

  • Presenting a thesis statement prior to the surprise

    Often takes the form of an opening sentence that gives away all that is surprising about the story.

  • Fail to take advantage of the power of stakes to make something that is potentially surprising truly surprising
  • Failing to hide critical information in a story

    Hiding the bomb in the clutter. You don’t want to let your audience guess that you are foreshadowing. Clutter the landscape so that the audience can’t tell what is importnat and what is not.

  • Camouflage

    Laughter is the best camouflage.

    Make a moment feel like a joke instead of the conveying of a critical bit of information.

  • Surprise Techniques Overview

    1. avoid thesis statements
    2. heighten the contrast between the surprise and the moment just before the surprise
    3. use stakes to increase surprise
    4. avoid giving away the surprise in your story by hiding important information that will pay off later (planting bomgs)
      1. obscure them in a list of other details or examples
      2. place them as far away from the surprise as possible
      3. build a laugh around them

Effective Ways to Be Funny in Storytelling

  • Stories need not be funny
  • Even if you aren’t funny, you can craft a story that conatins funny moments
  • Some of your stories will be funny even if you aren’t funny at all
  • Stories should never only be funny. Use humor strategically.

Stories are different from stand up comedy; for stand up comedy a week later you can’t remember a single thing from the show. Stories stick with you forever.

  • Start with a laugh

    Good to get audience to laugh in the first thirty seconds of the story because

    1. signals that you are a good storyteller
    2. in less formal situations, it serves as a stop sign for potential interruptions; you have the floor. When interrupted repeatedly you can say: “I made them laugh. I’ve got the floor. Let me finish, damn it.”
    3. Let’s the audience know that whatever horror there was in the past, i’m okay now
  • Make em laugh before you make em cry

    Contrast between laughter and approaching horror heightens the shock. It hurts more that way.

  • Take a breath.

    Use humor to help break the tension. Fore example following the details of a horrific car acident. The audience needs to take a breath. A laugh is the best way to do this.

  • Stop crying so you can feel something else

    You don’t want your audience weeping for long periods of time. It’s not pretty. Use a laugh to stop the weeping.

  • End the story with heart

    Do not end on a laugh. That is not why we listen to stories. We like to laugh; we want to laugh. But we listen to stories to be moved.

  • Humor Tricks

    • Milk Cans and a baseball

      Build up some cans and then knock them down with a strong “throw”.

      Some words are just funny. Oddly specific words are funny.

    • Babies and Blenders

      When two things that rarely ever go together are pushed together, humor often results.

      Common to play one of these things is not like the other. List three things, the last one being different.

      Exaggeration is another form.

Finding the Frayed Ending of Your Story

Advice: tell your story. Don’t worry about the stakes or the lies or anything else. Spill out the details. You’ll come to understand the important of your five-second moment.

You have to be open up in order to tell powerful stories.

Part III. Telling Your Story

The Present Tense Is King

Say important events in the present tense so that the audience can feel as though it is happening in the present. It feels more real that way.

The Two Ways of Telling a Hero Story

No one likes a braggart. Avoiding bragging can make storytelling difficult. In general tell failure stories, not success stories. But if you must, follow these two tips:

  1. Malign yourself
  2. Marginalize your accomplishment

Humans love the underdog.

Surprise is important. If you cast yourself as the underdog, the audience will root for you.

Human beings prefer stories of small tesps over large leaps. Small steps only.

Storytelling is Time Travel

  • Don’t ask rhetorical questions

    This breaks the fourth wall and takes them out of the film.

  • Don’t address the audience or acknowledge their existence.

    This breaks the fourth wall and takes them out of the film.

  • No Props. Ever.

    This breaks the fourth wall and takes them out of the film.

  • Avoid anachronisms.

    An anachronism is a thing that is set in a period other than that in which it exists. A microwave in the middle ages.

  • Don’t mention the word story

    This breaks the fourth wall and takes them out of the film.

  • Downplay your physical presence as much as possible

    This breaks the fourth wall and takes them out of the film.

Words to Say, Words To Avoid

  • Swearing

    In general don’t swear. It is a cheap laugh. Sometimes it is okay:

    • repeated dialogue
    • when a swear is simply the best word
    • moments of extreme emotion
    • humor. don’t rely solely on profanity for humor though
  • Vulgarity

    Don’t be weird.

  • Names

    Be careful

  • Pop culture references

    Not everyone is going to get it.

  • Accents

    Don’t except maybe if it is a close friend / family member.

The Weather Sucks, So Don’t Talk About It

Conversations about the weather are the antithesis of the ideal of an entertaining, connected, meaningful world. Death of good conversation. Enemy of interesting.

Avoid these conversations at all costs. Change the subject. Walk away if necessary.

Time to Perform

  • Don’t Memorize Your Story

    Instead memorize three parts:

    1. first few sentences. Start strong
    2. last few sentences. End strong
    3. the scenes of the story
  • Make eye contact

    Suggestion is find three people and switch between them.

  • Control your emotions
  • Learn to use the microphone

    See a professional, but some general tips:

    1. project to the back of the room in to the microphone
    2. take your time to adjust the height properly
    3. always say yes when offered a microphone

Time Spent Reading

Total time: 6:02

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Time Spend Reviewing/Writing

Total time: 1:46

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