Storyworthy by Matthew Dicks

Storyworthy by Matthew Dicks

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Amazing book. By far the most practical book I’ve read on storytelling. Dicks walks you through the exact processes he teaches (and uses himself) to generate ideas, craft compelling stories, and share them with your audience. He does an excellent job of teaching you how to be an awesome storyteller through his own beautifully-crafted stories. Super useful as a writer who wants to master the art of storytelling and just a flat-out fun book to read.

I think this may have been the book I took the most notes on ever, so it’s going to be a big entry. Trust me, it’s worth it.

Book Notes

“No matter who you are or what you do, storytelling can help you achieve your goals.”

Storytelling is an amazing skill that can be taught (and thus learned) and may improve your life in ways you wouldn’t have thought possible.

PART 1: Finding Your Story

What is a story?

💡 A story is not a folktale. You don’t become the life of the party by telling a good folktale.

”Folktales and fables do not create the same level of connection between storyteller and audience as a personal story. No one has ever listened to someone tell a folktale and felt more deeply connected to the storyteller as a result.”

💡 A story is a personal journey. 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.

There are three requirements to ensure that you are telling a personal story (aka the ONLY type of story worth telling):

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. People love a good story about someone making a life-altering change. It helps them believe they’re capable of change too.

2. It must be YOUR story

Don’t tell the story of someone else even if their story is better than your own. Your story will always be better and more vulnerable. It takes zero courage to tell someone else’s story.

If you do tell someone else’s story, you must make the story about yourself. You must tell your side of the story, from your point of view. If you can’t, or if you weren’t there, don't tell it. Your side of other people’s stories can still be interesting as long as you are the protagonist in these tales.

3. It must pass The Dinner Test

Your stories should be very similar to the ones you would tell a friend at dinner. That should always be the goal. A few tips for doing this:

  • Don’t start your story with dialogue. You would never do this at the dinner table.
  • Don’t add weird hand gestures for visual effect
  • Talk or write normally. Don’t go writer-happy with alliteration, for example. People don’t talk like that.
  • It should sound authentic, not crafted. Write like you speak.

How to Come up with Ideas for Stories

1. Homework for Life

Basically, start a daily journal to record your most storyworthy moments from every day. Don’t write the whole thing down — just a sentence or two for you to recall it. Could be something that happened to you that day or something you remembered from awhile back. Do this daily and use a tool like Excel or Notion to record your entries.

2. Crash & Burn

This technique utilizes stream-of-consciousness writing. You kickstart your thoughts with a prompt (like colors) or something random in the room, then continually write down whatever thoughts enter your mind.

  • Don’t get attached to any one idea
  • Don’t judge any thought or idea that pops into your mind
  • Don’t let the pen (or your fingers) stop moving

Set a timer for 5-10 minutes and go.

3. First Last Best Worst

Grab a sheet of paper or a spreadsheet.

Across the top —> 5 columns: Prompt, First, Last, Best, Worst

Across the left side —> 7 prompts (any work but the ones in the example below work really well)

After completing the chart, analyze it with these 3 questions:

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

Mark potential stories (or stories that you’ve already told) with an S.

Mark potential anecdotes with an A.

Part II Crafting Your Story

The Most Important Aspect of Storytelling:

💡 “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 — this is super important — the purpose of the story is to bring that moment to the greatest clarity possible.”

Where to start?

Start with the end.

“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 do you find your story’s beginning?

The beginning of your story should be 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. This is what creates an arc in your story. This is how a story shows change over time. I was once this, but now I am this. I once thought this, but now I think this.”

WHERE you start the story is a very important decision. Spend most of your time figuring out the right moment to start your story. Once you have the ending and the beginning, the rest flows easily.

How to begin your story?

Three tips:

  1. Start your story with forward movement whenever possible. (Driving down a highway, walking up the street, etc.)
  2. Don’t lead with expectations (”you’re going to love this”, “this is hilarious”, etc.)
  3. Start right with the story, not a summary of the story

5 Ways to Keep Your Story Compelling

Dicks’ uses tools he calls “stakes” to do this. Stakes are the reason audiences listen and keep listening to a story.

1. The Elephant

“Every story must have an Elephant. The Elephant is the thing that everyone in the room can see. It is large and obvious. It is a clear statement of the need, the want, the problem, the peril, or the mystery.”

It should appear as early in the story as possible, preferably in the first minute. Better within the first 30 seconds.

Example: “When I was nine years old, I wanted to disown her. Leave home and never return. Forget she ever existed.”

2. Backpacks

“A Backpack is a strategy that increases the stakes of the story by increasing the audience’s anticipation about a coming event.”

“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.”

3. Breadcrumbs

Breadcumbs are hints (objects, thoughts, etc.) of what’s to come in the story.

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

4. Hourglasses

An hourglass is a method of stalling once you reach a moment in the story that the audience has been waiting for. It builds anticipation.

5. Crystal Balls

Crystal Balls are false predictions that make the audience wonder if the prediction will become true.

“The boss called me into her office this morning, and as I walked down the hall, I just knew I had done something wrong and was getting fired. This was it. The end of the road for me.”

Not mentioned: humor. Note that humor is optional but stakes are nonnegotiable. (Though well-timed humor is usually a plus.)

5 Permissible Lies of Storytelling

Flat-out lying is not good practice, but slight manipulations of the truth are OK (and encouraged) under the right circumstance.

Three important caveats:

  1. Storytellers only lie for the benefit of the audience, not for personal gain.
  2. We want to tell true stories, but memory is a slippery thing. Stories will contain mistakes, inaccuracies, etc. — try to be strategic in some of these inaccuracies (only when it’s done for the benefit of the audience).
  3. Never add something to a story that was not already there. Making things up is cheating.

The five lies:

1. Omission

You can (and should) omit people, objects, details, etc. that distract from or don’t add value to the five-second moment of your story. People are the most common omissions.

2. Compression

You can compress the story in order to make it easier to comprehend, visualize, and tell. Shorten the timeline, cut out days/months/etc.

3. Assumption

You can make assumptions about specific details only when they’re critical to the story. For example, if you want the audience to clearly picture a car you’re about to crash into, you can make an assumption about what make/model/color the car was (even if you don’t necessarily remember).

4. Progression

You can change the order of events to make the story more emotionally satisfying or comprehensible. (This is the least common of lies.)

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.” For example, even though your emotions or feelings on something or someone change over time, you can condense that into a singular moment.

A side benefit of using conflation is that your stories will be shorter, which is almost always better.

A Great Story is Cinema of the Mind

“A great storyteller creates a movie in the mind of the audience.”

Your story should always be the centerpiece of your performance. Don’t do anything that pulls your audience out of the story and back into real life. You want your audience to be able to see the story in their mind’s eye at all times.

💡 Always provide a physical location for every moment of your story. Even if you’re giving backstory information, give your audience a scene to visualize.

Use but and therefore storytelling

Stories that go from beginning to end in a flat line are boring.

💡 Instead of using and, combine sentences with but and therefore as much as possible

This forms a jagged line and a “rollercoaster” for your audience to ride on.

“Matt Stone says it’s this ‘causation between each scene that makes a story.’ This happens, therefore that happens, but then this happens, therefore that happens.”

💡 Use the power of the negative. Negatives are almost always better than positives in storytelling.

For example, “I am dumb, ugly and unpopular.” isn’t as strong as “I’m not smart, I’m not at all good-looking, and no one likes me.”

Another example, “I was lost” is not as good as “I could not find my way home.”

The reason? Negatives contain hidden but’s e.g. “I could be smart, but I’m dumb.”

The Secret to the Big Story: Make it Little

If something crazy happens to you (e.g. a near-death experience, something not many people can relate to), make the story about something little instead.

“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.”

There Is Only One Way to Make Someone Cry

“When it comes to storytelling, I believe that surprise is the only way to elicit an emotional reaction from your audience. Whether it’s laughter, tears, anger, sadness, outrage, or any other emotional response, the key is surprise.”

“Common mistakes that storytellers make that ruin surprise include:

  1. Presenting a thesis statement before the surprise
  2. Failing to take advantage of the power of stakes to enhance and accentuate surprise
  3. Failing to hide critical information in a story”

“The strategies for preserving and enhancing surprise in a story:

  1. Avoid these statements in storytelling
  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 bombs).

This is done by:

  • Obscuring them in a list of other details or examples
  • Placing them as far away from the surprise as possible
  • When possible, building a laugh around them to further camouflage their importance"

Simple, Effective Ways to be Funny in Storytelling (Even If You’re not Funny at All)

Effective times to use comedy:

  1. Start with a laugh
  2. Make them laugh just before you make them cry - “Contrast is king in storytelling”
  3. Take a breath - Make them laugh immediately after you make them cry to break the tension
  4. Stop crying so you can feel something else - A laugh is a good separator when you want the audience to stop feeling one way and start feeling another

Two easiest ways to be funny:

“Laughter is simply a well-cultivated surprise.”

  1. Milk Cans and a Baseball
  2. Milk cans are the setup, and the baseball is the punch line
  3. Use more milk cans to achieve a greater potential laugh
  4. Example: “I was rescued from the streets by a family of Jehovah’s Witnesses. I sleep in a pantry off their kitchen that they’ve converted into a tiny bedroom. I share this room with a Jehovah’s Witness named Rick, a guy who speaks in tongues in his sleep, and the family’s indoor pet goat.”
  5. Babies and Blenders
  6. The idea of putting together two (or more) things that rarely or never go together
  7. Example: “Family, pineapple-flavored ham, and despair”

💡 Reminder that “Humor is optional. Heart is non-negotiable” in storytelling.

Part III: Telling Your Story

Some Important Notes on Using the Present and Past Tense

The present tense is awesome for submersing your audience in a scene with you.

The past tense is good for providing backstory (since it’s in the past).

Stories can’t have two or more events that take place at different times happen in the present. Once you identify where/when your present tense is, stick with it.

Good storytellers shift tenses often. Again, keeping the most powerful moments in the present.

A Few More Do’s and Don’t’s


  • Write and tell stories about things you haven’t fleshed out yet. Sometimes you rediscover hidden meanings you forgot.
  • Limit your stories to having only ONE meaning. A good story cannot have two meanings.
  • Tell stories about your greatest failures (”failure is more engaging than success”)
  • Steer clear of profanity unless it’s very well-timed or executed


  • Tell success stories unless you:
  • Malign yourself
  • Marginalize your accomplishment(s)
  • “Address the audience or acknowledge their existence whatsoever.” This pulls the audience out of your story and back into the real world. (E.g. don’t say something like “you guys aren’t going to believe this!”)
  • Use anachronisms
  • Mention the word “story” (e.g. “That’s a story for another day”)
  • Use vulgarity - it’s very rarely a good idea to repulse, offend, or disgust your audience
  • Use the real names of people in a story (you never know when this could bite you in the butt)
  • Use pop culture references (the goal of a story is to relate with your audience, these references alienate)

Tips for Telling Stories on Stage / In-Person

  • Don’t memorize your story word-for-word
  • Memorize these three parts:
  • First few sentences
  • Last few sentences
  • The scenes of your story
  • “Try not to have more than seven scenes in a story.” Otherwise it’s too long and easier to misstep
  • Avoid the use of props
  • Make eye contact

Ending Notes

Storytelling is a superpower that can enhance almost every aspect of your life and help you connect with all kinds of people.

💡 “Storytellers have a superpower. They can make people feel good and whole and right. They can inspire and inform. They can make people see the world in a new way. They can make people feel better about themselves.”