Cover of Storyworthy

Storyworthy

ISBN: 9781608685486

Date read: 2026-02-15

How strongly I recommend it: 9.5/10

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My notes

The first time I plan to take the stage and bare my soul

As we prepare to embark on this journey together, keep in mind that there are a few requirements to ensuring that you are telling a personal story: ChangeYour 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. It need not reflect an improvement in yourself or your character, but change must happen.

Your Story Only You must tell your own story and not the stories of others. People would rather hear the story about what happened to you last night than about what happened to your friend Pete last night, even if Pete’s story is better than your own. There is immediacy and grit and inherent vulnerability in hearing the story of someone standing before you. It is visceral and real. It takes no courage to tell Pete’s story. It requires no hard truth or authentic self. 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

Don’t tell other people’s stories. Tell your own. But feel free to tell your side of other people’s stories, as long as you are the protagonist in these tales.

The Dinner Test Lastly, the story must pass the Dinner Test. The Dinner Test is simply 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.

[I] needed more stories. If I was going to continue to perform, I was going to have to generate more content. 2. The stories that my friends initially thought would be great — the near-death experiences, the arrest and trial for a crime I didn’t commit, sharing a bedroom with a goat — are all good stories. Audiences love them. But the story about Charlie throwing his food and my wife uncovering my childhood secret — a tiny story that takes place at a dining-room table between a husband and a wife — that’s 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. We know how powerful and painful secrets can be. We all know what hunger feels like. We know what it’s like to want something important and essential — food, friendship, acceptance, love — but never to have enough of it. And we all know what it’s like to feel embarrassed or ashamed of never having enough of something that you so desperately need.

but it turns out even these big stories need to be more about the little moments than the big ones.

I assigned myself Homework for Life. This is what I did: I decided that at the end of every day, I’d reflect upon my day and ask myself 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 my day?I decided not to write the entire story down, because to do so would require too much time and effort. As desperate as I was for stories, even I wouldn’t be able to commit to writing a full story every day, especially if it wasn’t all that compelling. Instead I would write a snippet. A sentence or two that captured the moment from the day. Just enough for me to remember the moment and recall it clearly on a later date.I also allowed myself to record any meaningful memories that came to mind over the course of the day, in response either to something I added to the spreadsheet or something that came to mind organically. Oftentimes these were recovered memories: moments from my past that had been forgotten for years but had returned to my mind through the process of doing Homework for Life.To do this work, I decided to use an Excel spreadsheet. It works well for several reasons. First, it forced me to capture these moments in just a few words. As you can see, my spreadsheet is broken into two columns: the date and the story.

but I believe in simplicity. I believe in strategies that are easy to apply and maintain even on our busiest days. This is the best way to develop a habit.

Not every day contains a storyworthy moment for me, but I found that the longer I did my homework, the more days did contain one. My wife likes to say that I can turn any moment into a good story, and my friend Plato has said that I can turn the act of picking up a pebble from the ground into a great story. Neither of these statements is true. The truth is this: I simply see more storyworthy moments in the day than most people. They don’t go unnoticed, as they once did. I discovered that there is beauty and import in my life that I never would have imagined before doing my homework, and that these small, unexpected moments of beauty are oftentimes some of my most compelling stories

in such force that there are times when I need to brush them away. All of this happens because I sit down every evening and ask myself: What is my story from today? What is the thing about today that has made it different from any previous day? Then I write my answer down. That’s it. That’s all I do. If you do it, before long you will have more stories than you could ever imagine.

She’s calling to tell me that she’s fifty-two years old, and for her entire life, she’d never felt like an important person in this world. She’d always thought that she was just like everyone else — simply another face in the crowd — and that one day in the future, she was going to die and “go out quietly. Unnoticed. ”Then she started doing my Homework for Life, and within three months, it had changed her life. She says that searching for stories in her everyday life and recording them has made her feel like an important person for the first time. She tells me that she has real stories — important and significant moments in her life that she had never seen before — and that she feels that they are a part of a much larger story. She says she feels like a critical cog in the gears of the universe. Her life matters. She tells me that she can’t wait to get out of bed every morning and find out what will be the thing that makes that day different than the last.

But it’s true. As you start to see importance and meaning in each day, you suddenly understand your importance to this world. You start to see how the meaningful moments that we experience every day contribute to the lives of others and to the world. You start to sense the critical nature of your very existence. There are no more throwaway days. Every day can change the world in some small way. In fact, every day has been changing the world for as long as you’ve been alive. You just haven’t noticed yet.

There’s an added bonus to Homework for Life. It’s unrelated to storytelling, but it’s worth mentioning. It might just be the most important reason to do the exercise. 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.

Commitment that you will sit down every night and reflect upon your day. It’s crazy to think that you won’t give five minutes a day over to something that will change your life, but many won’t. Instead, you’ll blindly give two hours of your life over to a television show that you will barely remember a year later.

You may also lack faith, because this change won’t happen instantly, and in this world, most people want their results instantaneously. But this process does not happen overnight. It didn’t happen immediately for me. The stories that I was finding and recording early on were not very good. I couldn’t see the moments of true meaning, nor could I distinguish them from moments that might be interesting, or even amusing, but ultimately carry no weight. My storytelling lens had not yet been focused and refined, but I was so desperate to find stories that I refused to stop. I kept on doing my homework, even when it seemed pointless, because I was desperate to remain on the stage, and I thought that finding even one story would make it all worth it.

Dreaming at the End of Your Pen

Rule #1: You must not get attached to any one idea. The goal of Crash & Burn is to allow unexpected ideas to intersect and overrun current ones,

So, regardless of how intriguing or compelling your current idea may be, you must release it immediately when a new idea comes crashing in, even if your new idea seems decidedly less compelling than the original one. When Crash & Burn is at its best, ideas are constantly crashing the party, slashing and burning the previous ones. It’s in these intersections of ideas that new ideas and memories are unearthed.

Rule #2: You must not judge any thought or idea that appears in your mind. Everything must land on the page, regardless of how ridiculous, nonsensical, absurd, or humiliating it may be. Similarly, grammar, punctuation, and capitalization are meaningless. Penmanship is irrelevant. This can be difficult for many people. For years, writing teachers have demanded that students think about grammar, spelling, and punctuation as they write. They have required students to outline their essays and stories before placing a single word on the page. They have handed their students archaic graphic organizers and insisted that they be completed prior to writing. They have ignored the reality of writing, which is this:Many writers have no idea what their next sentence or paragraph will be. Much of writing is done in the dark. The next sentence is often as much of a surprise to the writer as it is to the reader.

Rule #3: You cannot allow the pen to stop moving. I say pen because, although I do almost all my writing on a keyboard, I have found that engaging in Crash & Burn with a pen tends to trigger greater creativity (and there is some science to support this claim). But if you must use a keyboard, go for it. Either way, your hand or fingers cannot stop moving. You must continue writing words even when your mind is empty. To make this happen, I use colors. When I have no other thought in my mind, I begin listing colors on the page until one of them triggers a thought or memory. For example:Red, green, blue, black, brown ... I tell kids that brown is my favorite color, and it makes them all crazy, which makes no sense, but in truth, I have no favorite color, which makes them even crazier ... Writing down numbers is also a popular strategy utilized by my workshop students, though I recommend that the numbers be listed in word form. For example:One, two, three, four, five ... I have five fingers on each hand, and there are scars on five no six of them, which seems like a lot, but maybe not ... I’ve known frequent travelers to list countries. I had a mechanic in one of my workshops list engine parts. I had a teenager in a workshop list the names of his previous girlfriends (and apparently had more than enough names to work with). It doesn’t matter what you choose. Your list of items simply needs to be long and familiar to you. That’s it. Set a timer for ten minutes, follow these three rules, and go

Once I’ve finished with a session, I look back and pull out threads that are worth saving. Story ideas. Anecdotes for future stories. Memories that I want to record. New ideas. Interesting thoughts.

As I said, Crash & Burn is damn good for the soul. Instead of the five minutes a day that I’ve asked you to dedicate to Homework for Life, this exercise requires about fifteen minutes at a time. Although I think it’s a highly productive exercise, I realize that fifteen minutes every day is asking a lot. So I’m asking a lot. Do it every day.

Author Zadie Smith says, “Protect the time and space in which you write. Keep everybody away from it, even the people who are most important to you. ” She’s right. Storytellers must selfishly guard their time, especially from the people they love most.

Storytellers need to know how to tell a good story, but they also need good stories to tell. Lots of them. Crash & Burn will not only give you the content you will need, but it will change the way you perceive yourself and your life in the process. Give me fifteen minutes a day, and I’ll guarantee you some amazing results.

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

It’s called First Last Best Worst. All you need to play is pen and paper. As you can see from the worksheet that follows, the top row of the page (the x-axis) is labeled with the words “First,” “Last,” “Best,” and “Worst,” along with a column labeled “Prompts.” Along the left side of the page (the y-axis), the prompts are listed. The prompts are the possible triggers for memories. What was your first kiss?What was your last kiss? What was your best kiss? What was your worst kiss?For each of these prompts, you fill in the word or words that indicate the answers to those questions. That’s it.

After completing my chart, I analyze it. Specifically, I ask myself three 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?

I mark potential stories (or stories that I have already told) with an S. I mark potential anecdotes with an A. Below is the same sheet, now marked for possible stories and anecdotes.

PromptFirstLastBestWorstKissLaura (S)ClaraElysha (S)Sheila (S)CarDatsun B210 (S)Hyundai Tucson1976 Chevy Malibu (S)Datsun B210 (S)PetMeasleman (S)Toby & Pluto (S)Kaleigh (S)Prudence (S)TroubleCorner in kindergarten (S)Speeding ticketInciting riot upon myself (S)Arrested (S)InjuryMysterious head wound (A)Elbow tendinitisPole-vault pole snapsDatsun B210 accident (S)GiftPuppy12 dates for 12 monthsFriends as family (S)Bath towels (S)TravelPasadena 1988 (S)Lewiston, Maine (A)Honeymoon (S)Disney with Cushman (S)

I’ve given you three tools to find stories. Homework for Life, Crash & Burn, and First Last Best Worst

storytelling, but there is one fundamental truth above all others that must be understood before a storyteller can ever be successful:All great stories — regardless of length or depth or tone — tell the story of a five-second moment in a person’s life. Got that?Let me say it again: 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.

So you’ve got yourself a five-second moment — a moment of transformation or revelation or realization. This is good. You’re already a better storyteller than most people in the world.

You’ve also found the end of your 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

The hard part is finding the beginning, because it involves choosing the right moments from your life, and there is often a multitude of choices. So how do you choose the right place to start a story? Simple. Ask yourself where your story ends. What is the meaning of your five-second moment? Say it aloud. In “Charity Thief,” I might say it like this: “I thought I was alone in this world, facing a lifetime of loneliness. Then I met a man who taught me that I knew very little about loneliness and never wanted to know loneliness the way that man knew it on that day and probably many, many days thereafter. ”That’s my five-second moment. That is what I’m trying to say to you as simply as possible. It’s not a good story on its own, but choose better words to describe the moment, prop it up with everything that comes before the moment, and you have yourself a story. Once you’ve distilled your five-second moment down to its essence, 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. 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. I once felt this, but now I feel this. Stories must reflect change of some kind. It need not always be positive change, and the change need not be monumental. In fact, stories about failure, embarrassment, and shame are fantastic. Stories about trying desperately to achieve a goal and failing spectacularly are beloved. Even when progress is made, the best stories often reflect incremental change. Tiny steps forward. Glacial improvement. Audiences would much rather hear about incremental, tenuous growth than about overnight success. Regardless of whether your change is infinitesimal or profound, positive or negative, your story must reflect change. You must begin and end your story in entirely different states of being. Change is key. The story of how you’re an amazing person who did an amazing thing and ended up in an amazing place is not a story. It’s a recipe for a douchebag.

Simply ask yourself what the opposite of the first fifteen minutes of a movie is, and you will almost always have your ending.

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. The correct beginning makes the rest of the choices seem much more obvious.

I also try to start my story as close to the end as possible (a rule Kurt Vonnegut followed when writing short stories). I want my stories to be as temporally limited as possible. I strive for simplicity at all times. By starting as close to the end as possible, we shorten our stories. We avoid unnecessary setup. We eliminate superfluous details.

I started as close to the end as possible. Simplifying also helps storytellers tell their stories better. When time and space is limited, it’s easier to remember your story. Easier to master your transitions, and easier to remember those favorite lines that you don’t want to forget. But simplification is even more important because of the difference between oral storytelling and written storytelling. A written story is like a lake. Readers can step in and out of the water at their leisure, and the water always remains the same. This stillness and permanence allow for pausing, rereading, contemplation, and the use of outside sources to help with meaning. It also allows the reader to control the speed at which the story is received. An oral story is like a river. It is a constantly flowing torrent of words. When listeners need to step outside of the river to ponder a detail, wonder about something that confuses them, or attempt to make meaning, the river continues to flow. When the listener finally steps back into the river, he or she is behind. The water that has flowed by will never be seen again, and as a result, the listener is constantly chasing the story, trying to catch up. To keep your listener from stepping out of your river of words to make meaning, simplification is essential. Starting as close to the end as possible helps to make this happen. Sometimes the closest place to start is thirty years before your five-second moment. If that’s the case, so be it. But when that beginning can be pushed closer to the five-second moment, your audience will be the better for it.

Here are a couple more practical tips for choosing an opening:1. 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. 2. Don’t start by setting expectations. Listen to people in the world tell you stories. Often they start with a sentence like, “This is hilarious,” or “You need to hear this,” or “You’re not going to believe this.” This is always a mistake, for three reasons. First, it establishes potentially unrealistic expectations. “Hilarious” is an exceptionally high bar. “You’re not going to believe this” is probably an impossible mark to hit. Never start your story by setting expectations for it, realistic or otherwise. No one wants a rubric or an introduction at the beginning of a story. They simply want a story. Second, starting your story with a thesis statement reduces your chances of surprising your audience. When you tell me that the story is hilarious, I’m already primed for humor. When you say, “You’re not going to believe this,” I am prepared for the improbable. Surprise is a beautiful thing in a story. Apart from vulnerability, it may be the most beautiful thing about stories. Letting your audience know that your story is hilarious or improbable hinders your ability to catch them off-guard and offer them a surprise later on. Third, these are simply not interesting

ways to start a story. A thesis statement, a prediction about the audience’s response to the story, or a summary of its theme or mood does not immediately draw us into the story’s time and place. We don’t feel transported to a new and interesting locale. We don’t get the sense that we are traveling back in time. We feel lectured to. We feel cheated. Start with the story, not with a summary of the story. There is no need to describe the tone or tenor at the onset. Just start with story, and whenever possible, open with movement. Forward progress. It’s a simple and effective way of grabbing the listeners’ attention and focusing it somewhere specific. It makes them feel that we’re already off and running. In “Charity Thief,” my opening sentences tell you that I am hurtling down a lonely stretch of New Hampshire highway, headed in the direction of home. In “This Is Going to Suck,” I’m walking out of a record store on a December day, two days before Christmas, with a shopping bag in my hand. Forward momentum. These stories are going somewhere. We are already on the move. Jump aboard for the ride. Pay attention to the opening scenes of movies. So many of them use this strategy as well. We open on the protagonist or someone similarly important to the story. That person will be moving. Walking. Running. Driving. Flying. Climbing. Fleeing. Falling. Swimming. Crawling. Diving. Filmmakers want to immerse you into their world as quickly as possible

Many movies open with simple overhead views passing over an ocean, a cityscape, or a mountain pass. Many movies based in New York City open with an overhead approach of the island over water. This has nothing to do with the film but allows the director to open with momentum. Forward movement. We’re headed somewhere important.

Thirteen Rules for an Effective (and Perhaps Even Inspiring) Commencement Address

  1. Don’t compliment yourself. Don’t praise your accomplishments in any way. It is not your day. Even if you’re delivering the valedictory speech, it’s still not your day. It’s a day for every person in your graduating class. Don’t place your accomplishments ahead of theirs. You’ve already been recognized as valedictorian; that should be more than enough credit for one day. Make the speech about something other than the great things you have done.
  2. Be self-deprecating, but only if it is real. Don’t ever pretend to be self-deprecating. Your audience will see right through you. This is even worse than being self-congratulatory.
  3. Don’t ask rhetorical questions. These questions always break momentum and displace your authority as the speaker onto your audience. Also, audience members will sometimes answer these questions and interrupt you, which is never good.
  4. Offer one granular bit of wisdom, something that is both applicable and memorable. Anyone can deliver a speech filled with sweeping generalities. Most people are capable of offering old chestnuts and choice proverbs. The great commencement speakers manage to lodge a small, original, useful, and memorable idea in the minds of the graduates. It’s the offer of one final lesson — a bit of compelling wisdom and insight that the graduates will remember long after they have tossed their caps and moved into the greater world. Don’t cater any part of your speech to the parents of the graduates. As much as they may think otherwise, this is not their day either. This is a speech directed at the graduates.
  5. Make your audience laugh.
  6. Never mention the weather or the temperature. If it’s a beautiful day, everyone knows it. If it’s not, reminding your audience about the heat or rain is stupid. There is nothing more banal and meaningless than talking about the weather.
  7. Speak as if you were speaking to friends. Be yourself. If your language sounds more formal than your normal speech, you have failed.
  8. Emotion is good. Be enthusiastic. Excited. Hopeful. Even angry if needed. Anything but staid and somber. This is not a policy speech or a lecture. It is an inspirational address.

If you plan on describing the world the graduates will be entering, don’t. It’s ridiculous to assume that the world as you see it resembles the world that this diverse group of people will be entering. Your prognostications will most assuredly prove to be wrong. These graduates’ paths will be multifarious. Some will be moving on to higher levels of education. Others will be hired for jobs that may not even exist yet. Others will join family businesses, travel the world, launch their own companies, or return home to care for aging parents. Telling these people what the world will be like for them requires hubris on a monumental scale. 11. Don’t define terms by quoting the dictionary. “Webster’s Dictionary says” are three words that should be banned from all speeches and essays until the end of time. 12. Don’t use a quote that you’ve heard someone use in a previous commencement speech. Don’t use a quote at all, if possible. Instead, be quotable. Your job is not to recycle but to create something new. 13. End your speech in less than the allotted time.

Boring stories lack stakes, or their stakes are not high enough. Stories that fail to hold your attention lack stakes. Stories that allow your mind to wander lack stakes.There are many ways to add new stakes or increase the existing stakes in a story, but not all stories need to have stakes added or increased. Some stories are naturally infused with stakes. Their content alone is enough to grab an audience by the throat and never let go.

Specifically, I use five different strategies to infuse this story with stakes. These strategies are both easy to apply and almost always effective.

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 signifies where the story is headed, and it makes it clear to your audience that this is in fact a story and not a simple musing on a subject.

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.

Elephants can also change color. That is, the need, want, problem, peril, or mystery stated in the beginning of the story can change along the way. You may be offered one expectation only to have it pulled away in favor of another.Start with a gray Elephant. End with a pink one.

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. The audience knows this almost immediately. It all happens within the first two sentences of the story. At this point, the audience is probably thinking that this is an escape story: 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. Hopefully the audience wants to know how it all turns out. 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. Note that I’m not actually changing the path that the audience is on. It’s the same path we’ve been walking since the start of the story. 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.

“The laugh laugh laugh cry formula,” she calls it. The audience thinks they are in the midst of a hilarious caper, and then they suddenly realize that this story is not what they expected. This method of storytelling is especially effective when the end of your story is heavy, emotional, sorrowful, or heartrending. To keep an entire story from being filled with weight and emotion, I try to find a way to make the beginning light and fun, hilarious and joyous. I present an Elephant that is happy, adventurous, and amusing to contrast with the weight, the sadness, and the solemnity at the end.Start with a pink, polka-dotted Elephant and end with varying shades of blue.

Backpacks 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. It’s an attempt to do two things:

  1. Make the audience wonder what will happen next.
  2. Make your audience experience the same emotion, or something like the same emotion, that the storyteller experienced in the moment about to be described.

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. Perfect plans executed perfectly never make good stories. They are the stories told by narcissists, jackasses, and thin-skinned egotists.

in the absence of possible stakes, humor can substitute for a time. But also remember that the goal of a storyteller is not to tell a funny story. The goal is to tell a story that moves an audience emotionally. That means a story can contain humor, but if it’s all funny, then the story operates on a single emotional plane and is ultimately forgettable.

Stakes are essential in a story. Stakes are the gears that make stories work. If your story lacks stakes or lacks meaningful stakes, there is nothing you can do to make that story great. Humor is optional. Stakes are nonnegotiable.

As storytellers, we only lie for the benefit of our audience. We never lie for our own personal gain. We don’t manipulate the truth, alter the fabric of reality, or shift time and space for our own benefit. We’re not in the business of making ourselves look better, appearing more noble, or mitigating our shame or failure. We lie in our stories only when our audience would want us to lie — only when the story is better for our doing so.

The Five Permissible Lies of Storytelling

Lie #1: Omission: People are the most frequently omitted aspects to stories: third wheels and random strangers who distract audiences from the matter at hand. If a person doesn’t fill a role in your story, simply pretend that person wasn’t there.

Lie #2: CompressionCompression is used when storytellers want to push time and space together in order to make the story easier to comprehend, visualize, and tell. 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. Placing scenes closer together also heightens the drama and suspense of a story. It makes the world seem more visceral and cinematic.

There is never room for needless complexity in a story. Remember that stories are like rivers (not unlike the river I dammed up to empty the Basin). They continue to flow even as your audience struggles to understand a time line or attempts to construct a complicated mental map in their minds. For this reason, simplicity should be prized at all points. Compression can often be helpful in this regard.

Lie #3: AssumptionStorytellers use assumption when there is a detail so important to the story that it must be stated with specificity, so the storyteller makes a reasonable assumption about what the specifics may be. This does not mean that a storyteller should assume all details. It is only when the forgotten detail is critical to the story that an assumption should be made.

I'd love to say it was a cherry-red Corvette instead of a station wagon, because it would make the story more interesting, but when I assume (and I don’t very often), I always make the most reasonable and likely assumption.

Lie #4: ProgressionA 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. In my experience, this is the least common lie told, and I have never done it myself, but I’ve recommended that other storytellers use it from time to time.

Change the order of the story if the real-life order did not adhere to narrative expectations. The world does not always bend to serve our stories best, so we must sometimes bend reality instead.

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. Rather than describing change over a long period, we compress all the intellectual and emotional transformation into a smaller bit of time, because this is what audiences expect from stories.

That is conflation. I conflate the emotions of the moment. I transform a moment into the moment.Movies do this all the time. If you track the number of days that pass over the course of the average movie, the number is small. A lot of stuff is often jammed into one or two days of movie time, when in real life, no one ever has days so packed with action.

Rather than describing my grandmother in essay form or cracking a series of jokes about her, I set the moment in a location, and therefore I create a scene. I start to make a movie in your mind. One version is a story. The other version is an essay. The only difference is that I provided a location for one but not the other.

A clear majority of human beings tend to connect their sentences, paragraphs, and scenes together with the word and. This is a mistake. The ideal connective tissue in any story are the words but and therefore, along with all their glorious synonyms. These buts and therefores can be either explicit or implied. “And” stories have no movement or momentum. They are equivalent to running on a treadmill. Sentences and scenes appear, one after another, but the movement is straightforward and unsurprising. The momentum is unchanged. But and therefore are words that signal change. The story was heading in one direction, but now it’s heading in another. We started out zigging, but now we are zagging. We did this, and therefore this new thing happened.

Do you see the way the sentences, paragraphs, and scene work against each other? They either oppose the previous sentence (it was this, but now it’s this) or they compile the previous sentences into a new idea (this plus this equal this). This is effective storytelling. It’s a way of making a story feel as if it’s constantly going someplace new, even if the events are linear and predictable. 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.

The first example has a single sentence that accomplishes much more than the two sentences in the second example. That single sentence:

  1. Climbs to the summit of a hill (I loved Heather since sixth grade ...).
  2. Rests at the top for a moment (... but as much as I loved her ...).
  3. Falls down the backside of that hill (... she was never mine).It zigs and then zags. It says this and then that. The two clauses work against each other, creating

principle, a student directed me to an online video of Trey Parker and Matt Stone, the creators and writers of South Park. They had joined a college writing class at NYU and described stumbling upon this principle as well. Parker and Stone explained that as they storyboard each scene in their show, they have found that they must be able to connect the scenes (they refer to them as beats) with a but or a therefore for the next scene to work. If the words and then can be placed between any two scenes, Parker says, “You’re fucked. ”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.

One other aspect to the but-and-therefore principle: the power of the negative. 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. For example:I am dumb, ugly, and unpopular. I’m not smart, I’m not at all good-looking, and no one likes me.

saying what I am not, I am also saying what I could have been, and that is a hidden but.

“I was lost” is just not as good as “I could not find my way home. ”“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. ”This isn’t always true, of course. A short, positive statement at the end of a paragraph of description can often serve as an amusing button to a scene. Heather laughed at me when I wasn’t trying to be funny. She refused my offer of a birthday cupcake, claiming she’d already had a cupcake that day, even though it was only 9:30 AM. She chose to walk five miles home from school, even though I offered her a ride and she lived next door to me. Heather despised me. That short, positive statement at the end of the paragraph serves to summarize all that came before. Inflection and timing can make that simple sentence amusing. It might even get a laugh. But did you notice the three sentences before that last one? Each one of them contained an implied hidden but. Heather laughed at me when (but) I wasn’t trying to be funny. She refused my offer of a birthday cupcake, claiming she’d already had a cupcake that day, even though (but) it was only 9:30 AM. She chose to walk five miles home from school, even though (but) I offered her a ride and she lived next door to me. Three sentences embracing the power of the negative, followed by a single, positive statement to summarize.

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. Storytelling is not about a roller-coaster ride of excitement. It’s about bridging the gap between you and another person by creating a space of authenticity, vulnerability, and universal truth.

For you as a storyteller, this means that you need to build surprise into your stories. There must be moments of unexpectedness so that your audience can experience an emotional response to your story.

Storytellers often mitigate or even ruin surprise by making some simple mistakes or failing to accentuate or enhance the potential surprise of the moment. Common mistakes that storytellers make that ruin surprise include: Presenting a thesis statement prior to the surprise. This often takes the form of an opening sentence that gives away all that is surprising about the story. “This is a story about a time in my life when my friends became my family. ”“This is a story about a car accident so serious that it took my life, if only for a moment. ”“This is the story of a waiting room full of surprise guests. ”It sounds ridiculous, I know, but this is done all the time, both onstage and in less formal situations. People feel the need to open their stories with thesis statements, either in an effort to grab the audience’s attention with a loaded statement or (more likely) because this is how they were taught to write in school: thesis statement, followed by supporting evidence and details.

But storytelling is the reverse of the five-paragraph essay. Instead of opening with a thesis statement and then supporting it with evidence, storytellers provide the evidence first and then sometimes offer the thesis statement later only when necessary. This is how we allow for surprise.

Hiding the Bomb in the ClutterWe hide these important moments by making them seem unimportant. We do this by hiding critical information among other details. We make the important information seem no more important than the rest of the information by pushing it all together. In the case of “This Is Going to Suck,” I turn my all-important request for the nurse to call McDonald’s into just another detail by placing it amid a series of doctors’ and nurses’ interactions with me. Rather than highlighting the encounter, I add it to a long list:Nurses picking glass from my foreheadDental surgeons wiring teethDoctors prepping my knees for surgeryA nurse asking for contact informationSee what I did? It’s a critical moment in the story, essential to all that is to come, but I portray the nurse as just another medical professional doing another job. Oftentimes I will load a portion of a story with superfluous information simply to hide the one important bit of information that I need the audience to know but not yet recognize as important. I clutter the landscape so that the audience can’t tell what is important and what is not.

CamouflageI also camouflage the bomb within a laugh. Laughter is the best camouflage, because it is also an emotional response, and audience members assume that the laugh is the result of the storyteller’s wanting to be funny. This is never the case. Comedians want to be funny. Great storytellers want to be remembered. For this reason, they deploy laughter strategically. I’ll talk more about this in the next chapter, but when it comes to preserving surprise, laughter is an excellent way to hide something important that needs to surprise the audience later on.

To review, the strategies for preserving and enhancing surprise in a story:

  1. Avoid thesis 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.

1. Start with a laugh

Make ’em laugh before you make ’em cry. The second time I make the audience laugh is just before the actual accident. Describing my mother’s car as the size of a box of Pop-Tarts often generates a giggle, but the real laugh comes a few seconds later, when I tell the audience that I’ve always been told to steer into the skid in situations like this, but I don’t know what that means. I want my audience to laugh here because we are seconds away from the collision. The contrast between their laughter and the approaching horror heightens the shocking and visceral nature of what is about to happen. I often say that I like to make people laugh before making them cry, because it hurts more that way. That is my goal here: Make them laugh so the collision and the resulting violence hurt more. Contrast is king in storytelling, and laughter can provide a fantastic contrast to something authentically awful. 3. Take a breath.The third time I make the audience laugh is immediately following the accident. One of the kids from the pickup truck looks me over, leans in, and whispers, “Dude, you’re fucked.” This almost always causes the audience to laugh, but I tag the boy’s dialogue with “It is the most accurate medical assessment that I will receive that day.” Big laugh

want my audience to laugh here because they have just endured the details of a horrific car accident, and I need to break the tension. The audience needs to take a breath. Whenever a story has become exceptionally tense and the audience needs to reset, a laugh is the best way to do this.

  1. Stop crying so you can feel something else. The last time I make the audience laugh is near the end of the story, when I say that the betta fish is the only fatality of the accident. This laugh is another opportunity for the audience to take a breath and reset. Many begin crying upon learning that my friends are piling up in the waiting room. I sometimes do too.I need the audience to collect themselves for the final few lines, because I know they might cry again. Rather than weeping through the end of the story, I want them to cry twice, because each time it’s for a slightly different reason. They first cry upon realizing that my friends are piling into the waiting room, filling in for parents who should be there. Then they cry again when I explain, “Pat is wrong. You can give your friends surprise Christmas presents, because they give me the best one I’ve ever received. ”The audience cries the first time because my friends have arrived when I needed them most. They cry because they are back in 1988, witnessing events firsthand.

The two easiest ways to achieve these humorous surprises are through Milk Cans and a Baseball, and Babies and Blenders. Milk Cans and a BaseballMilk Cans and a Baseball refers to the carnival game where metallic milk cans are stacked in a triangular formation and the player attempts to knock them down with a ball. In comedy, this is called setup and punch line. The milk cans represent the setup, and the ball is the punch line. The more milk cans in your tower, the greater potential laugh. The better you deliver the ball, the more of that potential will be realized. The trick is to work to the laugh by using language that carefully builds your tower while saving the funniest thing for last. Sadly, the instinct of most people is to say the funniest thing first. They can’t wait to get to the funny part, and in doing so, they ruin it.

Babies and BlendersBabies and Blenders is the idea that when two things that rarely or never go together are pushed together, humor often results.

In the story about the way that my grandmother pulled my loose teeth, I refer to her as a sadist. Grandmother and sadist are rarely seen together, so it’s funny.

These are not the only two ways to create humor in a story. There are others, of course. But I would argue that almost all humor boils down to one of these two strategies, and really down to surprise.

There is nothing wrong with telling a story from the past — even five minutes in the past — using the past tense. You will not be a terrible storyteller if you do. In a lot of ways, this is the most intuitive, logical, and expected way to talk about the past. It makes a lot of sense.But try the present tense. See if it’s something you can fall into naturally. If you can, great. You’ll have a much better chance of drawing your audience into your story and perhaps seeing your story as well. You’ll have more choices to make in crafting your story, and they will give you an additional strategy for your toolbox.

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

there are two strategies that I suggest you employ.

  1. Malign yourself.
  2. Marginalize your accomplishment.

Rather than attempting to be grandiose about yourself or your success, you must undermine both you and it. This is because of two realities:First, human beings love underdog stories. The love for the underdog is universal. Underdogs are supposed to lose, so when they manage to pull out an unexpected or unbelievable victory, our sense of joy is more intense than if that same underdog suffers a crushing defeat. A crushing defeat is expected. An unbelievable win is a surprise.You already know the importance of surprise in storytelling. If you cast yourself as the underdog, your audience will enjoy your success. They will root for you. They will expect you to lose and hope for you to win. This is why Bruce Willis is outnumbered and barefoot in Die Hard. This is why Star Wars opens on a massive star destroyer attacking Princess Leia’s tiny rebel ship. This is why Jack is from the wrong side of the tracks in Titanic.

human beings prefer stories of small steps over large leaps. Most accomplishments, both great and small, are not composed of singular moments but are the culmination of many small steps. Overnight success stories are rare. They can also be disheartening to those who dream of similar success. The step-by-step nature of accomplishment is what people understand best. This is how to tell a success story: Rather than telling a story of your full and complete accomplishment, tell the story of a small part of the success. Tell about a small step. Feel free to allude to the better days that may lie ahead, but don’t try to tell everything. Small steps only.

In the end, it’s a success born from good fortune, but it was just one student. So many others had already passed through my classroom quietly. That is what my story is about. I maligned myself by admitting I’d thrown a shoe at a student. I marginalized my accomplishment by pointing out that while I may have saved Lisa, I had failed to save the many who came before her. I know. It’s not the easiest thing to do. Sometimes we are so proud of our hard-fought success stories that we want to tell every bit of them. Sometimes we want to be the hero, damn it. But the line between hero and insufferable person is a thin one. Caution is advised.

I know it sounds crazy to turn the summiting of Mount Everest into something other than the summiting of Mount Everest, but if I can turn a story about putting my head through a windshield and dying on the side of the road into a story about my friends taking the place of my family, why not?If the successful climb taught Tim to trust others, listen to his gut, accept failure, find inner peace, believe in himself, or uncover a strength he never knew he possessed, that would make for a story with much greater universal appeal and potential connectivity.

As a storyteller, I seek a similar goal. I attempt to encircle my audience in a time-traveling bubble. I want to thrust them back to a time and place of my determination. If I’m doing it right, and my audience is in the right frame of mind, and the conditions are ideal, I believe it can happen.

Here are some rules to avoid popping this mystical bubble:Don’t ask rhetorical questions.

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

No props. Ever.

Avoid anachronisms. An anachronism is a thing that is set in a period other than that in which it exists. It’s a microwave in the Middle Ages. A refrigerator during the Renaissance. The internet during the Inquisition.

truth, I’ve been talking about my parents’ failures for a long time. There is very little that I don’t share with the world, but this is me. It might not be you. I’m a big believer in the words of novelist Anne Lamott: “You own everything that happened to you. Tell your stories. If people wanted you to write warmly about them, they should have behaved better.”For this reason, I also name my former

Don’t memorize your story. Actors are required to memorize their lines. You are not, nor should you. Actors also have fellow actors on the stage or in the wings to help them when they forget a line. Actors are also pretending to be other people. It’s hard to be authentic and vulnerable when you’re reciting lines. It’s also obvious to an audience when a storyteller is simply reciting a story instead of telling a story. Instead of memorizing your story word-for-word, memorize three parts to a story:

  1. The first few sentences. Always start strong.
  2. The last few sentences. Always end strong.
  3. The scenes of your story. If you’re following my advice and placing every moment of your story in a physical location (chapter 11), 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. In “This Is Going to Suck,” for example, my scenes are:
  4. On the sidewalk outside the record store
  5. Driving in my car through Mendon, Massachusetts
  6. The accident scene immediately following the collision
  7. The ambulance
  8. The emergency room
  9. The waiting room outside the emergency room
  10. The other side of the emergency room

I don’t memorize my stories. I memorize the places where my story takes me, so even if I can’t remember how I want to tell it, I can still do so. I may lose some laugh lines, clever transitions, and “golden sentences,” but I’m still telling my story. It may not sound as good as it could, but I’m not trapping my audience in awkward, story-killing silence.

I try not to have more than seven scenes in a story. The phone company uses seven digits in our phone numbers because they determined that seven bits of information is the most that the average person can retain at one time. Seven feels right to me. I have some stories that only have three scenes — even better. I have a story composed of just one scene. But seven is my max.

Make eye contact. There are many times when I am standing onstage and I can’t see a thing. A spotlight is shining in my eyes, and I am enveloped in a curtain of black. In those cases, eye contact is impossible. But when you can see your audience — in a classroom, a conference room, your aunt’s kitchen, a reception hall, or a faculty meeting — eye contact is important. You can’t speak to the middle distance and expect your audience to connect. That said, you also need not make eye contact with each and every person. You have enough to do without inventorying your audience. My suggestion is this: Find a person on your left, a person on your right, and a person dead center who likes you. These will be the people who are smiling. Nodding. Laughing. Use these three people as your guideposts. Make eye contact with them, and the people in each of those areas will feel you are attending to them as well. Choosing people who like you will make you feel great.

Learn to use the microphone. Learn to use a microphone from someone who uses a microphone professionally. I could discuss proper microphone use here, but there are many kinds of microphones, and it’s the kind of thing learned best while doing it. Most people use microphones poorly. Don’t be that person. The audio engineer at The Moth once complimented me on my microphone use. “You can cut right through the laughter when you want,” he said. “That’s so great.”It is. When I can cut through laughter or applause and return to my story, I control the pacing of the performance. I dictate how the story will be told. I learned how to use a microphone effectively by working as a wedding DJ for two decades. Just try to guide a bride through a bouquet toss while music plays, single girls scream, and photographers call out for the ideal pose. You learn quickly about how to cut through the noise with your voice. You think you know how to use a microphone, but you probably don’t. Find an expert and practice. That said, here are three universal tips that apply to almost all microphone situations:

  1. The microphone is not a magical device. Many people believe that once they are speaking into a microphone, they can speak as softly as they want. It’s not true. Even when you’re speaking into a microphone, you should be trying to speak to the back of the room. Think of the microphone as the guarantee that your voice will reach the back of the room, but you must do the work first. You must push your voice through the device.
  2. If you’re speaking into a microphone set on a stand, be sure that the microphone is perfectly adjusted before you speak. Don’t rush this process. Every second that it takes you to adjust the microphone will feel like ten minutes, but to the audience, it will feel like less than a second. Take your time. There is nothing worse for you or the audience to be thinking about a poorly set microphone as you speak.
  3. If given the option to use a microphone, do so regardless of how booming your voice may be. In speaking

When I can teach my son and daughter a lesson using an entertaining story from my past, not only is that lesson more effective and enduring, it’s often requested again and again. Rather than nagging my children about something that I feel is critical to their development, I find them demanding that I teach them the lesson over and over again. That is a superpower.