Funny Fingers


Storytelling: How to Be Funny

An excerpt from Stories Sell by Matthew Dicks


Posted 7/28/24


You don't need to be funny in the business world in order to be perceived as funny. You just need to be amusing. Occasionally funny. Sparingly hilarious.

This is great news because humor is an exceptionally powerful tool in communication. When we make someone laugh, chemicals are released in their brain that cause them to like us, think of us as intelligent, trust us more, feel better about the world, feel better about the moment they are experiencing, and enjoy improved cognition.

What Makes Something Funny?

There are three esssential ways to make people laugh.

1. Surprise

We assemble words or actions in such a way as to surprise someone and produce a laugh. Lester Maroney's decision to call my brother Little Dickus was funny because that collection of words is surprising given the word Dickus, the size modification (little), and the fact that a teacher was speaking those words.

2. Anticipation

We cause an audience to see a future unfolding that will result in a funny circumstance, and that anticipation about future buffoonery can often produce a laugh. When I tell the story about leaving my three-week-old daughter home alone because I forget that she exists, the audience begins laughing as I start looking for my keys, suddenly understanding what is about to happen. Even though I haven't said a word about leaving the house to purchase a Big Gulp at the 7-Eleven and nothing terrible has happened yet, they are already giggling. I'm just a man looking for his keys, but the audience plays the future out in their minds, and that future, via anticipation, is funny.

3. Empathy

An audience will laugh if we describe a scenario that also rings true to them and so inspires their empathy, having experienced or witnessed it at least once themselves. When I talk about stripping in the break room of a McDonald's restaurant and describe pulling a button-down dress shirt over my head while forgetting to unbutton my sleeves — thus creating a reverse straight jacket of sorts — the audience howls because they know how impossible it is to unbutton those buttons on the sleeve after the sleeve is turned inside out. They have empathy for my impossible situation because they have experienced it themselves, and that recognition causes them to laugh.

It's All Surprise Or…

Those three ways of making people laugh can essentially be boiled down to one thing: surprise, since anticipation and empathy are simply forms of surprise.

The audience is surprised by what they anticipate is approaching.

The audience is surprised to discover that their lived experience is more universal or better understood than they ever realized.

Then again, almost all these surprises can also be boiled down to a simple construct.

…Contrast

Two things are pushed together or compared in such a way as to create contrast, thus producing a surprise for the listener. In each case, the surprise is produced because an expectation was pushed against the unexpected.

The more lenses you possess when looking for humor, the more opportunities for humor you will see. Think about humor as surprise, anticipation, empathy, and contrast. They may all boil down to one or another thing, but this is not an academic study. This is your chance to look at the world through a variety of lenses to increase your chances of finding the funny thing.


Where and When to Be Funny

Here's a fact that some people find hard to swallow:

We should not always try to be funny.

Businesspeople almost never try to be funny in their work lives, but in their personal lives, people want to be funny all the time. People take my storytelling workshops solely for the purpose of learning how to be funny because they (almost always men) want to be hilarious all the time. I actually teach classes specifically designed for humor because the demand is so high and the desire to be laugh-out-loud funny all day long is so strong.

But this would be disastrous.

Funny people — people who know how to effectively deploy humor regardless of the situation — understand that strategically locating humor is far more effective than constantly being funny.

This means that for every joke I tell, I've probably left three jokes on the cutting room floor. Every time I make a group of people laugh at a dinner party, I've probably kept my mouth shut half a dozen times, knowing that timing is everything. Every time I make the people in a meeting laugh, I've probably allowed half a dozen other jokes to slide right by, understanding that a meeting is not the place to dominate the conversation with humor.

That would stop being funny very fast.

People may want to be funny all the time, but people who attempt to do this are obnoxious and exhausting. Instead, funny people place humor where it can serve them best. Here are those places and times:

☺ The First Minute of a Story

That first laugh alters an audience's brain chemistry by triggering the release of dopamine, oxytocin, and endorphins.

Dopamine enhances learning, motivation, and attention, priming an audience to receive our message. Oxytocin is considered the "empathy hormone" and the "bonding chemical." When it enters the bloodstream, it creates feelings of relatedness and connection with the source of that release.

So audiences will instantly feel more connected to us.

Endorphins trigger feelings of pleasure, making audiences feel better about themselves and the world around them.

We make our audiences laugh as early in our performance as possible so that they are chemically primed to love us and our story.

This receptiveness is important when telling an especially difficult story. The story of the armed robbery that I experienced in the office of a McDonald's restaurant ("The Robbery") is the most difficult story for me to tell, and it's probably the most difficult story to hear. A gun is pressed to the side of my head and the trigger is pulled in an effort to get me to open a portion of the safe that is locked.

It's horrific. It's led to a lifetime struggle with post-traumatic stress disorder.

But I open this story with my children's ridiculous, hilarious magic show. The disappearing dime trick, for example, features my daughter telling me and my wife to close our eyes while she makes the dime disappear. Then, without warning, she violently jams the dime into my ear.

It's a sweet, funny moment that is relevant to the story (the robbery affects the way I see my children to this day), but it's also an intentionally light and joyous moment. A couple minutes later, I am describing how my face was pressed into a greasy tile floor as I listened to a man slowly count down to what I think is my death. The experience resulted in an ongoing, relentless existential crisis. It's one of the darkest moments in my life by far. But opening with something light invites my audience in and lets them know that as violent and disturbing as events are about to become, I have a beautiful little girl in my life who jams dimes into my ears as a part of her magic show.

It's all good.

An early laugh also provides the storyteller with an all-important auditory signal of approval.

Oh good. My audience likes me. They're on my side.

It's a fine way to feel as we begin to tell our story.

In a larger theater, where I often can't see my audience because of the glare of a spotlight, that auditory response is especially reassuring.

Oh good. The audience is still there. They didn't quietly leave while I was adjusting the microphone.

Early laughter relaxes everyone and makes the next few minutes of storytelling supremely easier.

☺ Right Before Describing Something Terrible, Painful, or Traumatic

To enhance the awfulness of a particularly awful moment, contrast it with humor. In my story "This Is Going to Suck," about my head-on collision with a Mercedes-Benz, I make the audience laugh just before my head crashes through the car's windshield in order to enhance the degree of the horror.

By contrasting humor with horror, the horror seems even more horrific.

☺ Right After Describing Something Terrible, Painful, or Traumatic

I also make my audience laugh right after the car accident. One of the first people on the scene was a teenager riding in the back of a pickup truck. He laid me down on the ground, looked me over, leaned in, and whispered, "Dude, you're f*cked."

This almost always causes the audience to laugh, then I tag the boy's dialogue with, "It's the most accurate medical assessment that I receive that day."

Big laugh.

I 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. They need to know that I'm okay. Whenever a story has become exceptionally tense and the audience needs to reset, a laugh is the best way to do this.

☺ During Any Boring Parts

This is where humor can be best deployed in business. Because a lot of business is inherently boring, humor helps make it less boring. When Slack was introducing Canvas to their platform — a persistent layer on every channel similar to a whiteboard in a brick-and-mortar — I knew we needed humor in order to punch up this otherwise dry content.

So when we talked about the value of whiteboards in an office for holding information that people would want access to at all times, the list from the marketing team included items like burndown lists, sales projections, meeting times and locations, and office birthdays.

All good, realistic examples, but in order to add humor to what I thought was a boring part of this presentation, I proposed adding additional things to the list of whiteboard possibilities, like these:

  • A countdown of days left before Phil finally retires
  • Requested pizza toppings for Friday (including bizarre and quirky toppings and combos)
  • Number of days since our last accident (a crossed-out numeral 2 with a scribbled note beside it reading, "Thanks a lot, Phil! Learn to use a stapler, dummy!")
  • Various doodles, including at least one derogatory drawing of Phil

Slack chose to use none of this, which was fine, and more than a year later, I am absolutely sure that everyone remembers that particular keynote with great clarity. They've probably told friends about it at dinner parties.

That was sarcasm.

Which is a form of humor appreciated by many but admittedly despised by some.

Use with caution.

☺ When a Story Momentarily Lacks Stakes

Sometimes a story hits a point where the next stake is not yet evident. This is dangerous because a stakeless story — even for a moment — can be ignored.

Perhaps you or your team or your company have overcome a problem or found a solution, but before the next problem or disaster presents itself, you have time in between where the audience is no longer worried or wondering. In these stakes-free moments, humor will keep the audience listening, at least for a while, and this is critical to the success of the story.

☺ Never at the End

We tell stories in an effort to say something — about ourselves, our company, a product, a theory, a belief, a passion, or something similarly meaningful. We undermine these efforts by ending with a joke, a pun, a play on words, or a laugh of any kind. Audiences love to laugh, but they do not want to laugh in the final seconds of a story. That precious real estate should be dedicated to moving our audience emotionally, convincing them of a universal truth, upending their beliefs, changing their minds, or being vulnerable.

Humor is a fantastic tool that can be used to increase the enjoyment of a story. It can keep an audience engaged. It can improve the likability of a storyteller.

We like to laugh. We want to laugh. We love stories that contain moments of humor and hilarity. Sometimes an entire story can be funny. But those last few precious sentences — the space where we will land our story — should end with heart. Close with meaning. Conclude stories with something greater than a laugh.

This is how we ensure our stories linger in the mind of an audience, by ending in a place that is moving, vulnerable, or revealing or that establishes a connection.


Next: The Secret to Storytelling


Copyright ©2024 by Matthew Dicks. All rights reserved.


Matthew DicksMatthew Dicks is the author of Stories Sell and an award-winning slam storyteller with a record-breaking fifty-nine victories at the Moth StorySLAM competition and ten victories at the GrandSLAM.


Stories Sell

Excerpted from the book Stories Sell: Storyworthy Strategies to Grow Your Business and Brand ©2024 by Matthew Dicks. Published with with permission from NewWorldLibrary.com.