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How To Tell a Story Worth Hearing with Matthew Dicks

How to Tell A Story Worth Hearing!

Whether you’re a fiction writer or a content marketer, your goal as a storyteller is to capture and keep your audience’s attention. 

And the best way to do that is by telling a story your audience can connect with on a personal level. 

Matthew Dicks, an internationally bestselling author and an expert storyteller. 

Also a record 55-time Moth StorySLAM and 7-time GrandSLAM champion, Matthew has performed for audiences all over the globe. 

In this episode, Matthew shares why stories are so important, and how to breathe life into the stories you choose to tell.

Show Topics

  • Connect with other people’s experiences
  • Tell relatable stories
  • Keep your audience curious
  • Give your audience information in the right way
  • Make every moment essential
  • Start with the story
  • Tell stories to yourself
  • Don’t be afraid of vulnerability
  • Be available for others
  • Value your time

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Key Takeaways

Key Takeaways

7:18 – Connect with other people’s experiences

If you want people to be able to relate to the story you tell, you must work to connect your story with their personal experiences.

“That story is actually not about the car accident, but about my friends showing up later on, when my family fails me. And people understand that. They understand what it’s like to be let down, and they understand what it’s like to have someone pick you up in an unexpected moment. When I tell that story, people cry at the end all the time when my friends show up, after my parents have failed me. People cry every time I tell that story. No one has ever cried, not even once, when I describe the death that I experienced before the paramedics bring me back to life. I go through a windshield. I bleed to death. I stop breathing. My heart stops beating. People just blink at me. They’re completely unmoved. And the reason is because they don’t understand it. That’s not an intelligible thing that they can relate to. So to find a good story, you have to find something that other people will feel, ‘Maybe that has not happened to me, but I’ve experienced the feelings that you are describing and therefore I can now connect you.’”

9:17 – Tell relatable stories

The problem with the hero’s journey is that stories don’t always need a hero. More often than not, people prefer stories that are about relatable people rather than heroes.

“I hate the hero’s journey for a whole bunch of reasons. One is that it implies that a story requires a hero. Whereas many of the stories I tell, I am not the hero. I have actually discovered my failings over the course of the story. It is a story about me possessing hubris, and in the end, discovering that I’m not worthy of the hubris. So I’m not out slaying dragons. I’m out discovering truths about the world and myself that I did not see before. And it’s not always positive. In fact, many of the stories I tell are not, ‘I’m the hero,’ because people don’t want to hear stories about you being the hero. They want to hear more relatable stories where you are going to be vulnerable, where you are going to share something that most people would not share.”

18:30 – Keep your audience curious

Your audience should always be wondering what you’re going to do next. By using misdirection, you can create wonder by surprising your audience.

“I want the audience always wondering, and I will often misdirect. So I want the audience wondering what’s going to happen next at all times, but I also sometimes want to lead them down the wrong path. So in workshops, for example, when I tell that story, ultimately I put my McDonald’s uniform on and pretend to be a charity worker collecting money. I steal money from people pretending to be a charity worker, which is not great, but it happened when I was 19. So forgive me. But what I do in that story is, in the workshops I’ll tell the story all the way up to the moment I put the uniform on, and I stop and I say, ‘What do you think I’m going to do right now?’ And what people mostly say is, ‘You’re going to go work in a McDonald’s for a while to earn the money you need to put gas in your car.’ And I always say, ‘Well, look, you understand how ridiculous that is.’ Just because you’re driving around with a McDonald’s uniform doesn’t mean you can walk into some random store in a different state and say, ‘Hey, I’m going to work here for a couple hours, because I need some gas money, and also you have to pay me in cash.’ None of that makes sense, but I love it because they’re wondering about something, and they’re never wondering about the thing I’m really going to do.”

20:10 – Give your audience information in the right way

Surprises are only effective if they are built on information your audience already has. You have to lay the groundwork for the surprise during the story if you want to get the best payoff.

“Almost always, a surprise is predicated on information that you already have. You have to have the audience be aware of things in order for the surprise to pay off. What people often do is they take that information that the audience requires, and they put it right up against the surprise and they light it up, they put it on fire so that the surprise is always ruined. So I have all these strategies that I use where you layer information into a story in such a way that the audience knows it, but does not recognize its importance. That’s the trick. What can I teach my audience? What can I make sure they know? And then how can I make it seem completely unimportant so that the surprise can be preserved? If we can do that, then the audience can genuinely feel that beautiful moment when the world flips.”

25:23 – Make every moment essential

Every moment in your story needs to be essential. If you have arbitrary scenes, your story won’t hold up to the audience’s scrutiny.

“When a story is told, what an audience wants to feel is that every moment was essential, and that nothing was said just because the storyteller wants to share a part of their life that wasn’t relevant to the story, but felt important to them. Or in a movie, there was an extraneous scene that was funny, but was not tied into the plot in any way. Things like that can happen. And that’s always disappointing to an audience, because we really do want to feel like this is a causal chain that’s being built and every link is essential. And if one link broke, the story would not hold up anymore. And that’s a good way to determine whether your story is too long or even good. Can we take a scene out and is the story still making sense? Well, then take the scene out. So yeah, it can be disappointing when things don’t link together.”

26:29 – Start with the story

How you handle the first minute of your story says a lot about you as a writer. You can’t assume your audience wants to hear what you have to say, so you must capture their attention quickly.

“The first thing I always notice is how they handle the first minute, let’s say, of a story. It’s the most precious territory in a story. It’s your opportunity to engage your audience, put confidence in them that you’re going to do a good job. It’s the promise that the time we’re about to spend is going to be worth it. And oftentimes the beginning of stories contain lots of exposition, which should not be in the beginning of a story. And they contain these weird non-story philosophies. Someone starts a story with, ‘There are two kinds of people in the world. There are people who look at a tree and think it’s a tree. And then there are people who look at a tree and know it’s something more.’ And then they start their story. And I think, ‘Well, you wasted the first two sentences of your story.’ I’m not going to remember it. It means nothing to me. It’s almost like, you know the cleverness of it, but I don’t know your story. So I will never know the cleverness of. And I also didn’t ask for it. I asked for a story, not for some weird bit of philosophical wisdom at the top of the story.”

30:02 – Tell stories to yourself

You are your own most important audience. Telling yourself stories can help you become a better storyteller.

“I actually think the most important audience is yourself. I think you are the first audience for every story you tell. And if you can get a sense of the qualities of good story and what sounds like a good story, I actually think you can be a hermit who is telling stories about yourself to yourself, and there’s enormous value in that as well. I think the finding and crafting of stories from our lives can do great things in terms of finding meaning and making sense of our lives. And then if we want to take those to our audiences, even if your audience is, most of my audiences are not 500 people on a stage. It’s not every night that I’m on a stage. Most of my audiences are 24 fifth graders, my wife and two kids at the dinner table, my in-laws, my buddies on the golf course. Ninety-five percent of my audiences are those audiences, too. And I’m still trying to entertain them and do all the things that I do for an audience when I’m sitting in front of a thousand people.”

35:35 – Don’t be afraid of vulnerability

In a professional setting, most people don’t want to place themselves within the story, but vulnerability is what will capture your audience’s interest.

“This is a problem I find so often when I’m working in corporate America is everyone wants to take themselves out of the story. They could place themselves within the story keenly, in a very specific way. And yet, somehow everyone thinks that round, white, and flavorless is the way to go. Don’t put any edge of color into this thing. I don’t want to be in the thing. Why would I want to be in the thing? I don’t know, because if you were in the thing, people go, ‘Wow. Now I know who you are, as well as the content you’re delivering.’ Somehow people think in marketing that it’s what they’re saying, the actual message that they have, that is going to be relevant to the audience. And it’s never the case. How many times have you ever gone and listened to someone speak, and you’re in the hallway afterwards and you use the restroom and by the time you’re to the car, you’re never going to think ever again about the person who was speaking to you? It happens all the time, and it’s because they never take a moment to express vulnerability.”

1:03:16 – Be available for others

When you open yourself up and speak vulnerably, other people feel like they can also be vulnerable with you.

“I make myself available to people. So I’m the bearer of more secrets than you could ever begin to imagine. Five times in my life, I’ve had a woman come up to me and talk to me about her miscarriage, even though my story had nothing to do with miscarriages or babies or anything, just, I chose to be vulnerable. And the woman who had a miscarriage who had never told anyone in her life about it, decided I’m going to tell that man, whose name I’m not quite sure of, about my miscarriage. And that’s happened five times. So it’s very strange that once you start telling stories, people feel like they know you, and they feel like you are a receptacle of the things that they haven’t shared with anyone else before.”

1:14:06 – Value your time

Don’t wait until you have a full hour to start writing. Make use of every moment and value your time, even if you can’t spend a lot of it writing.

“Most people say that they value time and no one really does. And what most people see time as, they see it as increments of 60 or 120 minutes at a time. They often think, ‘Well, if I don’t have an hour or I don’t have 30 minutes, I’m not going to get anything done. So I’m not going to use the time.’ My wife wrote the forward to the book actually, and I heard her read it today. She was there with me, and she describes what I do is finding the little black holes in our lives that most people ignore and taking advantage of them. And so I view minutes as precious when most people view hours as precious. So most people say, ‘Well, I can’t write unless I have an hour.’ And I say, ‘I can write in two minutes, I can write three good sentences in two minutes.’ And if a book is comprised of somewhere between 5 to 10,000 sentences, every time I write two or three good sentences, I get a little closer to the end. And I view the value in that, where I think most people throw all that time away.”

Join us for Office Hours on May 18th. Karl Hughes started to help companies create authentic technical content that resonates with software developers. 

Karl will show you exactly how to replicate his process on:

  • Finding and recruiting subject matter experts and technical writers
  • Developing engineers within your organization to become writers
  • Motivating and managing creators
  • Paying contributors and the tax/legal implications 


Karl Hughes Office Hours
Alex Birkett

Alex is a co-founder of Omniscient Digital. He loves experimentation, building things, and adventurous sports (scuba diving, skiing, and jiu jitsu primarily). He lives in Austin, Texas with his dog Biscuit.