in: People, Podcast, Social Skills

• Last updated: March 25, 2022

Podcast #462: How to Tell Better Stories

This is a re-broadcast. The episode originally ran in November 2018. 

Humans are storytelling and story-listening creatures. We use stories to teach, persuade, and to make sense of the complexities of existence. Being able to craft and deliver a good story is thus a real advantage in all areas of life, giving you a foot up when doing job interviews, going on dates, interacting with friends, or making a sales pitch.

Fortunately, good storytelling is a skill that can learned by anyone. Here to teach us the art of storytelling is Matthew Dicks, a writer, five-time Moth GrandSlam storytelling winner, and the author of the book Storyworthy: Engage, Teach, Persuade, and Change Your Life through the Power of Storytelling. 

Today on the show, Matthew walks us through the nuts and bolts of how to craft a compelling story. We begin our conversation discussing ways to generate story ideas, why good stories don’t have to be about big moments, and why he recommends a practice called “Homework for Life.” Matthew then tells us what we can learn from movies about making a story so engaging that people are waiting to hear what you say next. We also discuss the don’ts of storytelling, including how to never begin a story. And we end our conversation with a five-minute story from Matthew that showcases all the principles we discussed during the show.

If reading this in an email, click the title of the post to listen to the show. 

Show Highlights

  • How did Matthew become, essentially, a professional storyteller?
  • Which moments in life are storyworthy?
  • Why “drinking stories” aren’t the kind of stories that stay with us
  • The difference between anecdotes and stories 
  • Why small moments can make for more powerful stories than big moments
  • Homework for life
  • Why paying attention to storyworthy moments can make your life more meaningful
  • The “first, last, best, worst” framework
  • The first step in turning an idea into a story 
  • How you should never begin a story 
  • Does a story have an ideal length?
  • Should a good storyteller embellish?
  • How do you get a story going at a social event or in everyday life?
  • Why learning to tell better stories can make you a better person

Resources/People/Articles Mentioned in Podcast

Book cover of a Storyworthy by Matthew Dicks.

Connect With Matthew

Matthew on Twitter

Matthew’s website

Matthew’s storytelling podcast: Speak Up Storytelling

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Read the Transcript

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Brett McKay: Humans are storytelling and story-listening creatures. We use stories to teach, persuade, and to make sense of the complexity of existence, but being able to craft and deliver good stories, that’s a real advantage in all areas of life, giving you a foot up when doing job interviews, going on dates, interacting with friends, and making a sales pitch. Fortunately, good storytelling is a skill that can be learned by anyone. Here to teach us the art of storytelling is Matthew Dicks, a writer, five-time Moth GrandSLAM storytelling winner, and the author of the new book Storyworthy: Engage, Teach, Persuade, and Change Your Life through the Power of Storytelling.

Today on the show, Matthew walks us through the nuts and bolts of how to craft a compelling story. We begin our conversation discussing ways to generate story ideas, why good stories don’t have to be about big moments, and why he recommends a practice called Homework for Life. Matthew then tells us what we can learn from movies about making a story so engaging that people are waiting to hear what you say next. We also discuss the don’ts of storytelling, including how to never begin a story. We end our conversation with a five-minute story from Matthew that showcases all the principles we discussed during the show. This show is literally packed with actionable advice, so take notes. After it’s over, check out our show notes at Matthew joins me now via

Matthew Dicks, welcome to the show.

Matthew Dicks: Thank you so much. Thanks for having me.

Brett McKay: You got a new book out, Storyworthy. It’s all about how to tell good stories, and I would say you’re a professional storyteller. You’re an ace storyteller. How did that happen? How did you become a professional storyteller?

Matthew Dicks: It was honestly an accident that it ever happened. The Moth, the large storytelling organization who I owe all my success really to, they put out a podcast back in maybe 2009, and my friends started listening to it and they directed me to it, and we all sort of loved it. We’re all writers or bookish people and we just love listening to people tell stories on stages, true stories from their lives. My friends told me that I’ve had the worst life of anyone they know, so that I should go to New York and tell a story for The Moth, which is not true. I know people who have had far more difficult lives than myself, but I’ve had one of those unusual lives with a lot of odd circumstances.

I told them yes, without any intention of ever doing it. I was terrified. I had no desire to stand in front of 200 New York hipsters with man buns and side-eye and frighten the hell out of me while I’m telling a story. But they didn’t let up, and eventually my friends sort of shamed me into going to New York to tell a story. I told them it would be one and I’d never do it again. It turned out I took that stage that night, and I loved it and I’ve been doing it ever since.

Brett McKay: Well, I think telling a story, it’s one of those skills that a lot of people wish they had. I wish I was a good storyteller, and this book was really helpful because it shed light on what I do bad with storytelling. Let’s start with this. What makes a story even story-worthy in the first place?

Matthew Dicks: Yeah. I think that a lot of times people think that stories are stuff that happened to me told in chronological order, and that’s just never really a story. That’s not compelling in any way. I argue that a story is about a singular moment in your life. I call them five-second moments because I really do believe that they happen over the course of about five seconds. They’re either moments of transformation or realization so that you’re either I was once one person and now I’m another person, or I once thought something but now I think a new thing. Those are the things that people really want to hear about. They don’t want to hear about the food you ate last night or the vacation you went on or what you did over your weekend unless over the course of those events, something really happened that changed you in some fundamental way. Then you have a story. Then you have something people are going to want to hear and connect to emotionally.

Brett McKay: Gotcha. So, those chronological stories, you call those drinking stories. Right?

Matthew Dicks: Well, I think a good story can be told chronologically, and there’s nothing wrong with it, but, yeah, I think the drinking stories or the romps, those are stories where I did something crazy. I didn’t really fundamentally change in any way, but some crazy stuff happened. And they’re fine to tell, but they’re not the kind of stories that sort of sink into our hearts and minds and stay with us once the storyteller is gone. They’re just fun drinking stories or stories you tell your spouse when you get home at night, that kind of thing.

Brett McKay: Gotcha. One thing, you made a good distinction between stories and anecdotes. I often think after writing the book, I feel like I was telling a lot of anecdotes but not really stories. What do you think the difference is?

Matthew Dicks: Well, an anecdote, first it’s going to be a lot shorter. That’s just a simple thing. But I think anecdotes are really just those moments in our lives when something unusual or something unique or something special happens to us, but at the end of that moment, we’re still fundamentally the same human being. An anecdote, sort of like I climbed a tree and I fell out of it and I broke my leg, you’d tell your friends that story, but if the breaking of the leg doesn’t fundamentally change you in any way, then it’s just an anecdote, and it’s just something you tell your friends to let them know, sort of update your status in life, I am now a person with a broken leg. But it’s not the kind of thing that they’re going to want to tell other people about. They’re not going to want to run to their friends and say, “You’re not going to believe this amazing thing that someone just told me.”

Brett McKay: So, a story, there has to be a change of some sort.

Matthew Dicks: Yeah.

Brett McKay: Now does this change have to be big, like a life and death thing or can the change happen, those five-second moments, can they be like really small thing?

Matthew Dicks: Yeah. Small is great. I prefer the small ones, to be honest with you. I’ve died twice in my life and then brought back to life through CPR. I’ve been arrested and tried for a crime I didn’t commit, and I was homeless for a period in my life. That’s the tip of the iceberg of the big stories that I have in my life, but those are the stories I don’t want to tell so much because people can’t connect to those big moments. If I tell you the story of dying, I don’t meet very many people who can relate to that in any fundamental way. It’s just not going to happen for them, and so I like the little moments. I like the moments where some tiny little thing happens and you suddenly understand yourself a little better than you did before. Those are my favorite ones.

Brett McKay: Okay. Let’s talk about where you get these ideas for your stories. I think a lot of people, they look at their lives, okay, where were those moments that I had those changes where I thought one way, and then I thought something differently? Because I think a lot of people, they’re not very … We really don’t pay attention to that stuff very well. How do you start paying attention and start coming up with those moments in your life where there was a change in yourself that could be the fodder for a story?

Matthew Dicks: Right. There’s a bunch of ways I do it, but the primary way I do it is something called Homework for Life, which is an assignment I gave to myself about five years ago. I’m an elementary school teacher when I’m not doing the other things that I do, and so it made sense to just sort of give myself a homework assignment, and it’s very simple. All I do is, at the end of every day before I go to bed, I sit down and I ask myself, “What was the thing that made this day different than any other?” Sort of what is the most story-worthy moment from my day. Even if that moment isn’t truly story-worthy, even if it’s sort of benign, if it’s something I wouldn’t even tell my wife about, whatever it is, I find the moment and I write it down.

I don’t write the whole thing down because I just don’t think anyone would ever really do that over the course of time. I use a spreadsheet and so I’ve got two columns in my spreadsheet. I’ve got the date on one side, and then I stretch that second column all the way across the screen, and in there I write what my story is, so I can really write only two or three sentences a day about that moment. My goal was to find maybe one story a month that I could keep getting on stages and telling to people.

What happened over the course of time in doing this was something really remarkable. I discovered that my life was full of stories. I have more stories to tell than I have time to live at this point, and I think that’s true for everyone. In fact, I know it is because now thousands of people all over the world do Homework for Life, and they report back to me constantly that it’s changing their lives. We just have these moments where we have a beautiful or a terrible or a memorable interaction with another person or we see something and it suddenly changes our mind in some way.

The problem is we just take these moments and we throw them away like trash. We just ignore them instead of collecting them and seeing them for what they are. Those moments, I see them all the time, and so it is rare in a week that I don’t find two or three moments that I could craft into an effective story that people want to hear. But it’s just that process of asking yourself every day, “What is the moment from this day that is the most story-worthy?” Eventually, you’ll just discover by honing that lens that there’s more moments in your life than you could ever begin to imagine.

Brett McKay: Yeah. I thought one of the interesting insights you found that you talk about in the book, that people do this to get ideas for stories. But what your students find, you teach how to tell stories, it’s actually improved their lives. Their life has slowed down. It seems more meaningful whenever they can see this collection of moments or stories in this spreadsheet.

Matthew Dicks: Yeah. I hear that all the time. I did Homework for Life as a TED talk one time, and people will watch that even if they’re not interested in storytelling, and it’s so true. Even if you don’t plan on ever taking a stage to tell a story, even if you’re not planning on telling a story at a cocktail party, once you start seeing that your days are filled with moments of significance, time slows down and you never lose a day anymore. So often you can go to someone and say, “What did you do last Thursday?” And unless they refer to their calendar or they really think hard, that day is forever lost to them, but if you’re doing Homework for Life, you’re marking every day with at least one moment that made that day different.

I did a workshop a few years ago for my school district, actually a bunch of principals, and about three months after the workshop, one of the principals came up to me and he said, “Do you know why Homework for Life works so well?” And I was thinking, “Yeah, I do. I spent a whole day explaining it to you.” But I humored him and said, “No. Tell me why.” And he said since the workshop he had missed three days, and he said, “I feel like I’ve lost those three days forever. I can’t remember a single thing from those days.” And he said, “I’m never going to miss another day again because I understand the value of capturing every day and how it’s already made me feel like my life has more meaning and that time moves by slower than I thought.”

Brett McKay: I love that. Just that idea that it can make my life more meaningful got me. I started like, “I’m going to do this. This is a really cool and it’s so easy.” Besides the Homework for Life, what are some other things you use to help generate some ideas that are pretty easy?

Matthew Dicks: One of my favorite things is something that I actually got from the director of The Moth. She told me that when she’s working with people who can’t find stories or are having a hard time finding stories in their lives, she does this, which is first, last, best, worst, which is the idea that oftentimes the first time, the last time, the best time, or the worst time we ever did something, those are often excellent story-worthy moments. In workshops I use things like your first kiss, your last kiss, your best kiss, your worst kiss. You can do it with almost anything. There are some topics that are much easier than others. If you use pets and cars and vacations and things like that, those are all going to work great. But truly, there’s not a single thing in the world that I can’t play first, last, best, worst with, that I can’t probably find something to talk about, and oftentimes it’s a story.

That’s a game I used to play with my wife, if I’m being honest, and then she got sick of hearing from me. When you live with a storyteller, eventually you don’t want the storyteller to talk anymore. And so she won’t play it with me, but I’ll play it with my students. I play it in workshops, and honestly, sadly, I play it with myself all the time. I find something in the room and say first, last, best, worst and go, and I always find a story.

Brett McKay: Yeah. I can see how that would generate stories. First kiss, there’s definitely a change there. You go into that thinking one thing, but then after it happens you’re probably like, “Well, that wasn’t what I thought it was,” or something like it. I can see how that would be a great fodder for a story.

All right, so you got ideas with these, doing ideas with these games or these tools, but ideas aren’t stories. What’s the first step in crafting those ideas into a story?

Matthew Dicks: I always tell people to start with the end of their story first. They sort of need to know where they’re going or what they’re aiming at. They need to know what that five-second moment is, what is that moment of transformation or realization. If you don’t have it, crafting the story is sort of like walking in a dark room, not really knowing what to do, not knowing what direction you’re supposed to be aiming at. I always say that storytelling is nothing more than the process of making good choices, because I think most people when they tell a story, they just say the next thing that pops into their head and that’s why their stories are oftentimes terrible, frankly. There’s just a lot of terrible storytelling in the world because people just don’t really make choices. They don’t even think that a story is comprised of choices. It’s just sort of the first thing I think of is the first thing I’m going to say.

And so, if I start at the end and I ask myself, “What is the purpose of this story? What is the moment of transformation and realization?” then from there, I can begin at the start of my story by making choices that will eventually lead me to the end in the best possible way. Because we tell the truth as storytellers, but we don’t tell the whole truth. We leave things out of stories all the time that don’t help the story in any way or confuse the story or just slow the story down in a way that it doesn’t need to be. So, I always say start with the end. You have to know what you’re aiming at before you start moving forward and crafting the thing.

Brett McKay: All right, so the end is that five-second moment of change. That’s kind of what you’re leading up to, right?

Matthew Dicks: Yes, exactly.

Brett McKay: Okay. How do you keep the story compelling? Well, let’s talk about, okay, so you know what the ending is. How do you start a story? Or here’s a better question, how should you never begin a story?

Matthew Dicks: Well, both of those questions are good. I would say that I start the story by asking myself what is the opposite of the ending of the story, whatever my moment of realization or transformation is. Let’s say I have suddenly discovered that my mother was right all along. I should not marry that girl. If that’s the end of my story, the realization that my mother is smarter than I ever thought she was, the beginning of my story, if I really want to show change, is, “I don’t think my mother is very smart. I think my mother is giving me bad advice.” Over time, I will discover that my mother is actually the smart one in our relationship. I find that opposite. It’s not always a clear opposite. Sometimes it’s an approximation of what the opposite is, it’s a cousin of what the opposite would be, but I have to find that because if I don’t have the opposite to start with, I can’t really show change.

Then, once I’ve figured out that spot that I want to start my story in, the thing I always want to do is I want to start the story right away. So often when people start stories, they instead start with lists. So, if the story is about my grandmother, they will start with a list of all the characteristics of a grandmother, which is not compelling in any way whatsoever. It’s just a list about my grandmother. So, I always say start the story, get things moving, and then after things are moving, then start revealing some of the things that we need to know before we get to the end.

Stories are just like movies. The stories that we tell out loud, we’re just creating movies in the minds of our audience. Pay attention to the way movies are constructed. Oftentimes, movies begin with action. Things are moving right away. Someone is chasing another person or someone is walking down a street. Star Wars classically begins with a big spaceship shooting at a small spaceship. It doesn’t begin with someone saying, “Darth Vader is a bad guy and Princess Leia is a good guy, and in a minute we’re going to see this space battle take place.” No. We’re in the middle of the battle, and then we learn about the characters. That’s how stories should be. You want to grab people by starting it right away.

Brett McKay: You talk about how you should never start a story. One tip, and I’ve broken this rule all the time and saying, “I’ve got the crazy …” You never say, “I got the craziest story,” or, “I got the funniest story.”

Matthew Dicks: Yes. It’s terrible because you set such an unrealistic expectation for yourself. You hear it all the time, though. People say, “You’re not going to believe this.” I’ve never heard really anything that I don’t believe after that statement. It’s always something that is going to be less than what you proclaimed it to be. So, don’t start off with any expectations.

Brett McKay: Gotcha. Start right away with the action. Start from one opposite of your ending and, yeah, I love the insight you gave there about movies. You sort of said start paying attention to movies because movies do this. You gave the example of Jurassic Park, of the paleontologist guy. In the beginning, he hated kids and at the end, he liked kids. I was like, “Oh, my gosh, it’s so obvious. Now I get this.” Now you’ve ruined movies for me because I’ve been looking for that.

Matthew Dicks: Well, it’s true. My wife doesn’t allow me to speak during movies anymore. But even that, that’s Spielberg and he’s brilliant because he knows that if I called you up and I said, “Hey, do you want to watch a movie about a man who doesn’t really love children, so he can’t fundamentally be with the woman he loves, but over the course of time he’s going to learn to love children and therefore his relationship will be stable?” You would never go to that movie with me.

Spielberg takes a true and real story that will sort of touch our hearts and he surrounds it with dinosaurs. Those are what I call the stakes of the story, the reason that we want to hear sentence by sentence by sentence, the thing that we’re worried about and concerned about and wondering about. Spielberg understands I have to give you a real story, the story of a man learning to love children, but I can’t give it to you without something to hang that story on. For him, it’s dinosaurs and it works so beautifully, and so many of his movies operate on that level. There’s a real story happening and then there’s the thing that brings you into the movie theater in the first place.

Brett McKay: Well, you mentioned that idea of stakes. That’s what keeps people engaged with the story. You have your beginning, which is the opposite of how you’re going to end. You have your ending, and then the stakes in the middle can be things that you think things are going to go a certain direction, but then they just fall flat. It just keeps you going on edge, right?

Matthew Dicks: Exactly. I’m always asking myself, “Is my audience wondering about something right now?” And if they’re not wondering, if they’re not worried or concerned or in suspense, that means I’m losing them. And so whenever I think that my audience has stopped wondering about something, I have to find a way to create that drama, that suspense. There’s lots of tricks that I talk about in the book to just sort of punch up moments, to make the same moment just more appealing and more filled with wonder than how it might normally be presented.

Brett McKay: Gotcha. One of the tactics that I like was the backpack where you have all … You pack a metaphorical backpack full of things that you could possibly use to solve the problem, and you start unpacking them in the story, but none of them work.

Matthew Dicks: Right, exactly.

Brett McKay: You want to keep seeing what’s the next thing that’s not going to work.

Matthew Dicks: Right. All the Ocean Elevens movies, they’re all just backpacks, which is we’re going to tell you how we’re going to rob the casino and then we’re going to go rob the casino, but it’s not going to work in the way we planned. But if we don’t know what the original plan was, then we can’t experience the fear and the frustration and the agony of our characters when the plan starts to go wrong. Any time in a movie when sort of a group of people regroup after a disaster and make a plan, really what’s happening is the writers are putting a backpack on the audience. We’re letting the audience know what the characters’ hopes and dreams are, so now you carry those hopes and dreams as well, and as those things start to go wrong, you feel something akin to what the people in the movie are feeling. That’s just the best kind of storytelling is when your audience’s feelings match your feelings from the moment you’re describing.

Brett McKay: Now there’s a lot more high-level things that people can do to really make stories engaging. Just the things we’ve talked about now, like knowing your ending, that five second moment of change, beginning with the opposite and then adding stakes in the story, that can make your stories better 90% of the stories out there, right?

Matthew Dicks: Yes. I fully believe that if you choose a good beginning and a good ending and it’s actually a moment of realization or transformation and you think even just a little bit about making sure that your audience continues to be interested in what you’re saying, you’re better than 95% of the storytellers in the world. I really believe that, because most people just never consider any of these things before they start telling a story. If you practice it in the way that I have, now it’s just automatic for me. If I’m going to play golf with my buddies, I don’t get up early and plan my stories for the golf course. When someone says, “What happened yesterday?” I automatically land on a moment of realization or transformation, and I automatically think about what the opposite of it is and that’s where I start my story. It’s become a process that is just totally normal for me because I practice it so much.

Brett McKay: How long should a story be? Or does it just depend on the situation you find yourself in?

Matthew Dicks: Yeah, it does. Ideally, a story of five to six minutes is fantastic, and that’s the length that The Moth uses in their SLAMs, but sometimes I have a story that is two minutes long because it’s only worth two minutes. It’s not something meaningful and huge. And then there are stories … There’s a guy named Ron who told a story in our show recently. We produce a show here in Connecticut. His story was about in the 1980s, he had to go to Russia to help refuseniks who were starving because the Soviet Union wouldn’t allow them to have jobs, but wouldn’t allow them to leave the country.

So, he had to buy VHS tapes and give them to the refuseniks because that was what was valuable in the Soviet Union in the 1980s. That story was 14 minutes long because it needed to be, because I didn’t know anything about the Soviet Union in the 1980s without Ron giving me a lot of background. So, a lot of it depends on what you’re saying, whether your story requires more time or not, but I always say the shorter story wins. People who can speak concisely will always be preferred over someone who is long-winded.

Brett McKay: You referred to this a little bit earlier, but the idea of embellishing stories, should a good storyteller embellish or lie, some people would want to call it that, for the sake of a good story?

Matthew Dicks: I always say that I have never in my life added something to a story that was not already in the story. What I do instead is I remove things from stories all the time. People especially, people come out all the time if they don’t actually play a role in the story. By removing things that are unnecessary, they allow the things that still exist in the story to shine. I just think that so often people feel like they have to say everything, and really, we only have to say the things that get us to that five-second moment.

Embellishment for me is the removal of material that my audience doesn’t want to hear and doesn’t serve my story very well, or it might be sort of the compression of time. A story that takes place on a Saturday and a Sunday for me, I might jam into one day, just a Saturday, because it’s easier for an audience to understand a story that takes place on one day versus two. And they don’t need to know that I went to bed and then I woke up the next morning and things continued. That’s the kind of embellishment that I believe in.

Brett McKay: Yeah. Think of a movie, movies don’t do that. Sometimes you don’t even … Days could pass and you have no clue because they just got to the, three days later and you don’t know it’s three days later, but it is three days later.

Matthew Dicks: Right, exactly.

Brett McKay: But, yeah, I guess embellishment becomes unethical when you start adding stuff that didn’t happen. If you didn’t die and you said you died, that would be unethical.

Matthew Dicks: Yeah. It doesn’t make any sense to me either. I’m a novelist, I write novels for a living, and those are all completely fictional. When I think about storytelling, stories from my life, I always think of it as a puzzle, which is kind of why I love it, because I’m forced to work with the material that is in front of me. I can’t make up any information. I’m stuck with what I’ve got, and so I love how I have to fight with that material and get it into the order that works best for the purpose of the story. Whereas when I’m writing a novel, anything is available to me. I’m not saying writing a novel is easy. There’s a lot of challenges in writing a novel, but the one challenge I don’t have is I’m not limited by the content that is available to me. I have an infinite amount of content available to me when writing a novel, so I don’t know why anyone would want to embellish a story that way. I just think it’s so much fun to fight with what you’ve got.

Brett McKay: You said one of the downsides, though, of embellishing your stories or changing your stories, that if someone was there with you when it happened, they can ruin it for you because they’ll be like, “No, that didn’t happen like that.” You’ve ruined the story.

Matthew Dicks: Right. Even if you’re doing what I’m doing, which is dropping people out of stories or compressing time, that’ll annoy your friends. They’ve heard me tell stories, and someone will come up to me and say, “But I was there, too. You didn’t even mention me,” and I’ll say, “Well, you didn’t do anything. You want to be in my story, be interesting. Otherwise you’re just a third wheel that’s not necessary in my story.” Even if you’re not adding things, people don’t like it when they’re left out of stories either, but that’s just something they have to deal with.

Brett McKay: Just got to deal with it. Do stories need to be funny or sad, or should you even think about that when you’re crafting a story? Because I think a lot of people think stories need to be funny or really poignant to be worth telling.

Matthew Dicks: Right. I don’t think they have to be funny. I tell a lot of stories that are not funny at all, and I also tell many stories that are very funny. I don’t think that any of those things are necessarily required. Ultimately, I want to be entertaining. That is the first thing I want to do with every story I tell. Then I want to connect with people. I want to find something that they will consider interesting or make them feel closer to me or reveal some part of themselves that they didn’t see before. Then, after that, if it’s funny, that’s great, and humor, I think, in storytelling is a strategy.

I do standup as well, and when I do standup, I have to be funny all the time. Everything I say has to be working towards a laugh. But in storytelling, I always use humor strategically. In fact, my funniest stories are the stories I least like to tell because there’s no emotional journey in those stories. They’re just funny all the way through. People love them, but I don’t feel like people connect with me as deeply as they do in the stories that move them in a variety of emotional ways. So, you don’t have to be funny. I work with a lot of people who are tragically not funny in any way whatsoever, but they’re still great storytellers and they can be really effective.

Brett McKay: Let’s say you got the story, you start crafting these stories. You have them in your pocket. How do you get a story going? Say you’re at a party or you’re at dinner and you have a story that’s related to the topic of conversation, you just say, “I’ve got a story.” What do you do for that? Because with The Moth, it’s, okay, you’re just there to tell stories, but I’m talking about just storytelling in everyday life. How does that work?

Matthew Dicks: I think the best thing to do is to actually be a great listener. The thing that I say to people most is, “Tell me a story.” Or so often in life, people have stories they want to tell, but for whatever reason, they’ve been convinced that no one has the time to listen to them or the inclination to listen to them or worst of all, they don’t think they have anything good to say, and I think they do. I’ve sort of learned to listen for those cues. When someone says, “Oh, that happened to me once,” and they trail off, that’s a moment when I jump in and I say, “Really, tell me that story.” If you sort of get other people telling stories, if you open up a space for them and allow them to speak for as long as they need to speak, oftentimes that will then create a space for you as well, and suddenly you’ll have a chance to tell a story, too. Start by being a good listener. Start by being someone who wants to hear stories, and then people will want to hear your stories as well.

Brett McKay: And how do you think telling better stories can make people better parents, better teachers, better business owners, et cetera?

Matthew Dicks: Well, in a myriad of ways, really. The number of people or the variety of people who I work with now consulting and teaching workshops, you just can’t imagine the people who walk into my workshops or who call me and ask me to work with them. If you’re a business leader, I was just working with the CEO yesterday, being able to communicate the mission of your company and talk about what your people are doing in an engaging and entertaining way, a way that doesn’t force you to stick a PowerPoint up on a wall every time you speak, that’s a tremendous skill.

If you’re a teacher and you can tell stories throughout the school day, whIch is something that I do with my students all the time, then you’re an engaging person who people are going to want to listen to. I work with clergy members on their sermons so that they can be more interesting. I work with politicians who are trying to craft stories and are really … Politicians are the worst. They’re the worst in terms of storytellers. They’re the ones who need the most work, but whoever you are …

Dating is a big thing now, storytelling for dating. People take my workshops because they can get a first date with someone, but it turns out that whatever they’re saying on the first date is so terrible that they can’t get the second date. If you can tell a good story about yourself, something that demonstrates humility and humor and self-awareness and it’s just engaging and entertaining, people are going to want to spend more time with you. Whatever you are, whoever you are and wherever you are, storytelling can help you. It’ll make you a better human being to spend time with.

Brett McKay: Matthew, this has been a great conversation. Is there someplace people can go to learn more about your work and what you do and the book?

Matthew Dicks: Well, if they go to my website,, they can learn about all the things that I’m doing there. They can find my book wherever you get books. It’s available on Amazon as well. Wherever you’re buying your books, you can probably find it there as well. My wife and I also produce a podcast called Speak Up Storytelling, and in that podcast we air one of the stories from the shows that we produce, and then we pull that story apart and tell people what’s working in the story and what could be improved, and we talk about Homework for Life in every episode. I give one of my Homework for Life moments from the week and talk about how that could be crafted into a story. It’s a good way to sort of take a deep dive into storytelling once a week with us as well.

Brett McKay: Fantastic. I don’t know if you’re up for this, but you tell a really short story. It’s okay if you’re game for it, but I’d love for people to get a sample of a story, sort of an example of what we’ve been talking about.

Matthew Dicks: Sure. How long do you want it to be?

Brett McKay: Oh, up to five minutes. It could be shorter than that.

Matthew Dicks: Yeah, all right. I’ll give you the quick version of something.

Brett McKay: Okay.

Matthew Dicks: Okay, great. All right, so I’ll tell you, I’m going to choose a very small moment. This is about the smallest moment that I can think of to illustrate the point. I’m leaving the gym. Just a few months ago this happened. I’m leaving the gym, and as I’m coming down the stairs and I’m feeling really good about myself because I’ve just exercised for 45 minutes and I have not yet eaten a cheeseburger. It’s this unique time in my life where I have done something really good for my body and have not defiled it with fat and carbohydrates yet. I will. I’m on my way, actually, to a cheeseburger on this day, but this little time in between, I feel good about myself. I’m heading towards the door and my keys fall out of my hand. My hands are all sweaty so they slip out, and as they fall, they sort of land on my foot, half on my foot and half off.

Before I can even bend over to pick them up, this woman coming into the gym, walking in the opposite direction, bends over, picks my keys up off my foot, puts them in my hand, and then just keeps walking, and I can’t believe it. I would never pick the keys up off someone’s foot. I would never pick up anyone’s keys, I don’t think. I have a friend who’s in a wheelchair, and if he dropped his keys, I honestly would do sort of the trigonometry to determine if he can get his own damn keys or do I have to help him. And this woman has done this for me. She picks up my keys and then she goes into that little room where she’s going to ride a stationary bike to nowhere while some authoritarian in Spandex is going to shout at her for not going nowhere fast enough, and she hasn’t waited for a thank you or a gift or a parade, all of which I would have expected had I done something so selfless.

I’m standing there in front of the smoothie bar with my keys in my hand and I am thinking about what a horrible person I am and how just in the last hour how horrible I have been. Before I got to the gym, I went to the supermarket to get a Gatorade, and as I was walking in, the Boy Scouts were set up at a little table by the door selling candy bars, and I hate that. I hate that they sell candy bars because there’s already candy bars in the grocery store, too. It’s like putting a hat on a hat. Why are you selling me something that I could get for cheaper inside the store?

So, when I walk up to them, I used to be able to tell them I don’t have any cash on me. I would say, “Oh, sorry, I only have a credit card,” but now they have phones and they say, “Oh, no, we can take your credit card. No problem.” Now, what I do is I pretend that I’m on a phone call. This is what I did on this day. I put the phone to my ear and I pretend I’m talking to my wife and that I’m in this really serious conversation. So, as I walk by them, I can sort of wave them off by pointing at the phone and and letting them know this is really serious. Then when I leave the grocery store, I actually leave from the opposite way and I walk all the way across the parking lot. I do a full circle just to avoid these kids, and I was a Boy Scout for all of my childhood. Boy Scouts saved my life in a million ways, and yet, I’m not willing to give these kids $1 so they might get to a summer camp someday.

Then when I got to the gym, I was walking in and I saw this woman coming sort of diagonally to me towards the door, and I realized that I was going to get to the door about 10 seconds before she was, which was going to require me to hold the door for her, and I hate this, too. I hate when I’m ahead of people in the world and then I have to stop and hold doors for them. It makes me crazy. And so what I did to avoid this, I did again some mental trigonometry, and I realized if I quicken my pace, I can get to the door maybe 15 or 20 seconds before her and then I won’t be required to hold it anymore. So, that’s what I did. I walked faster and slipped through the door and avoided holding a door for another human being.

Then when I was done on the treadmill that day, I had to wipe the treadmill down, which makes me crazy. I feel like I’ve just run for 45 minutes. I’ve done God’s work. I don’t want to have to wipe this thing down and honestly, according to the Golden Rule, you’re supposed to do unto others as you’d have them do unto you. I don’t care if anyone ever wipes the treadmill down, and so if I don’t want people to wipe down the treadmill, I do it either, the Golden Rule. But I know I have to because I know there’s people watching, and there’s probably no one watching, but in my mind everyone is always watching me. So, I wipe the treadmill down that day, but I do a bad job of it. I do like a passive aggressive slight wipedown just to make myself feel a little bit better about doing the thing that I don’t want to do that I should do.

And then, I leave and drop my keys and this angel picks them up off my shoe, and I think about what a horrible and selfish person I am, just in that last hour, all those bad things I’ve done. And so I leave the gym feeling terrible about myself. So, the next day, I pull into the gym and it’s pouring, it’s cats and dogs, and as I’m pulling in the spot closest to the gym door, there’s someone backIng out of it and I’m so excited because I’m not going to get wet. My kids call it the best spot in the lot. And so I stop and I wait for that car to back out so I can take the best spot in the lot.

As I’m waiting, I see headlights behind me, another car who’s pulling in, waiting for me to move out of the way so that they can park probably nine miles away at the back of the parking lot. Then as I look back down, I see my keys in the ignition and I think about the day before, the angel who picked them up. I swear I can still see some of her angel dust on my keys. So, when that car clears the parking spot and it’s my turn to take it, I drive by the parking spot and I park nine miles away and I give that spot over to whoever’s behind me. Probably a serial killer, but whoever it is, they get the spot that day because I decide to be a slightly better person.

It doesn’t mean I’ve changed my life in any way. I still hate wiping down treadmills and I still hate holding doors and I still dodge the Boy Scouts at every chance that I get. But when I’m holding my keys in my hand, when I’m looking at them, I want to be a slightly better person, and for me, that’s at least a good start.

That is a story of a tiny little moment that when it happened a few months ago, as soon as it happened, I ran home and I told my wife, “I have a great story because some woman just picked my keys up off my shoe and it made me realize what a jackass I am.” She said, “Okay, that’s great.” But it’s a story that I just love to tell because it’s a tiny little moment where I’m illustrating something about myself and when I tell that story, I won a Moth SLAM with it, and I thought I would because when I tell about the things that I’ve done that are especially terrible, people love those stories because everyone’s sort of going through life being terrible in some way, being selfish and not being their best self, but not often do people talk about it.

So, when they hear someone talking about it, it just makes you feel a little more human, like, “Oh, I’m not the only awful person. Other people are doing awful things too that they’re kind of ashamed about. I’m not really as bad as I once thought I was.” People love those kinds of stories, and it’s a tiny, tiny little thing that happens to us all the time.

Brett McKay: Matthew, that was great. Thank you so much for your time. It’s been an absolute pleasure.

Matthew Dicks: Thank you. I really appreciate it.

Brett McKay: My guest today was Matthew Dicks. He’s the author of the book Storyworthy. It’s available on and bookstores everywhere. You can find out more information about his work at Also check out his podcast with his wife, Speak Up Storytelling. Find that on iTunes or wherever else you listen to podcasts. Also, check out our show notes at You can find links to resources where you can delve deeper into this topic.

Well, that wraps up another edition of The Art of Manliness Podcast. For more manly tips and advice, make sure you check out The Art of Manliness website at We’ve got over 4,000 articles there. You haven’t been there, check it out. As always, thank you for your continued support. Until next time, this is Brett McKay telling you to stay manly.

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