“You’re never going to kill storytelling because it’s built into the human plan. We come with it.”
—Margaret Atwood
No, it’s not a story about pockets. That said, I keep a curated list of women’s clothing that has pockets so you can send me a message privately if you would like access and I will hook you up. But that’s not what today’s article is about. Do I have a funny pocket story about pockets? Yes, I do. I’ll tell you that one some other time. Today we’re talking about how to cultivate and prep your own pocket story: The anecdote you keep handy at all times, to bring out whenever you need to impress or amuse a bunch of people.
I talk about storytelling in Shelf Life all the time, but I’m usually talking about written forms of storytelling whether they are short (a poem) or long (a novel), or meant to be read versus meant to be viewed and heard. Scripted writing that becomes a television show or a movie is still written storytelling. Even if actors deliver the lines you wrote, it’s not quite the same thing.
Oral storytelling has a couple of things in common with written storytelling but for the most part, it’s wildly different. Not everyone who is a good oral storyteller can write a story well, and not everyone who can tell a story in writing can do the same thing aloud. They’re separate and different—though related—skills. Consider:
You have to be able to see your audience. This might mean you’re physically in the same place, or you could be on a video call (as I have lately learned).
You need to be concise. People do not have the same attention span for your story as they have for a book.
You’ll get an assist from both nonverbal communication and audience interactivity.
You have to be able to think on your feet and react to audience input. Your story isn’t set in stone. You can make modifications each time you tell it.
If you have a pleasant voice or natural charisma, those will help engage your listeners. But telling a great story is a skill just like any other. If you break it down, learn its components, study them, and practice, you can improve your storytelling game just like you can improve your writing game.
There was a time—and it was not too terribly long ago—when we used to be able to put large quantities of people in the same building at the same time with music and alcohol and I believe that used to be called “a party.” All my friends will tell you that I’m the person to make sure you invite to your party. I don’t drink alcohol and only rarely consume intoxicants of other kinds and in fact I’m not actually very fun. I make the guest list because I always have a hilarious story in my pocket to obliterate an uncomfortable silence or draw a reticent partygoer into the mix.
To clarify, let’s just make sure we’re all on the same page about what an anecdote is. It’s not just any old story. It’s different from a tale or a yarn. According to the dictionary, it is:
“a usually short narrative of an interesting, amusing, or biographical incident”
Thanks, Merriam Webster. I’m going to break that out just a little bit differently and say, for our purposes, that an anecdote must be:
Short.
Narrative.
Interesting or amusing.
About a biographical incident.
Those are our parameters. Does the story take more than a few minutes to tell? Not an anecdote. Put it aside. Not actually amusing or interesting? Not an anecdote. Throw it away. Totally fictional tale you’ve been cooking up in your mind? Not an anecdote. You need an account of a real event, involving real people, and you need it to be short and interesting and you need to be able to tell the heck out of it.
In my considered opinion, there are five elements that unite in great oral storytelling. These are:
Ammunition
Embellishment
Misdirection
Commitment
Brevity
Let’s look at how to put them together into one unforgettable anecdote.
1. Ammunition
First up, you have to have the ammo for your story. This is the sandy grain of truth at the center of the pearl. It’s not going to be your whole story—just the foundation. The ammunition doesn’t need to be especially interesting in itself but you have to be able to make it interesting. For that, you need something unexpected. Importantly, this story need not be solely yours. In fact, it doesn’t need to be yours at all. You can tell an anecdote about something that happened to a friend. You need a biographical incident. It doesn’t have to be an autobiographical incident.
Start by taking a look back through your own life story and then, if you truly don’t find anything you want to use, expand to the life stories you’ve heard from people you immediately know. Look for the most improbable events and incidents you can find, those are great to mine for anecdota. An ordinary day that turned extraordinary in some way. An everyday event with an unexpected twist that made it different from any other day. If you can start your anecdote off with “so I was eating a salad” and then turn it into something incredible, that’s a winner. Do I have an utterly enthralling story about an unremarkable Cobb salad from the Burbank Airport Cantina? Yes, I do.
2. Embellishment
Now that you have your real-life event figured out, you have to embellish the bejeezus out of it. The lifeblood of an anecdote is its concrete details. The trick is knowing which ones to include, which ones to cut, and which ones to exaggerate.
An anecdote told in real time requires comic timing. Consider the pacing as you plot out the details you’ll use. You might add dialog to draw out the suspense, or you may condense the five people who were really there down to one or two so the story doesn’t get too long and complicated. Don’t fabricate the core facts of the actual events, but go wild with the details. For example: Does the story hinge on a character being absent for part of the action, but back when it actually happened you didn’t know where she was? Make something up, make it outrageous. Plug any possible plot hole with a fabulous detail. Don’t leave your audience any loose threads to pull on. At the same time, omit any detail that doesn’t directly contribute to the story. No tangents. Chekhov has his eye on you.
If I’m telling a quick story, for instance, about a quest to replace a missing Jeep with a second, identical Jeep before the Jeep’s owner arrived in town to notice it was missing, someone will naturally wonder what she was coming to town for. I can’t remember why she was coming to town. So I just casually mention that she was flying in for a drag competition. If it’s not material to the story that you report the detail faithfully, then make it fun. Do I have a totally true anecdote about a car that just up and disappeared into the ether one day? Yes, I do.
3. Misdirection
Something about the story needs to be unexpected and, whatever that is, you need to play that aspect up to the absolute max. Audiences want to be surprised. Maybe a character doesn’t react in the way you’ve been building up to all along. Maybe your story is low-key confusing, but when you flip it around to a new perspective, everything suddenly comes clear. Maybe there’s a key detail that takes your story from interesting to incredible, but you withhold it till the last possible second. A word of caution, though. The goal is to surprise your audience—not to make them feel they’ve been hoodwinked.
No story can succeed without raising some kind of stakes. As I discussed in Get Your Reader to Pony Up, you need your audience to invest (their interest) in the story you’re telling, and then you need to pay them out in a satisfying way. The longer they listen to your story, the more invested they are. Literally, they’ve invested their time and attention into your story. You can’t lead them straight from point A to point B or they’re going to be disappointed. If I make you listen to an elaborate story about the time I got lost in the labyrinthine halls of the Fortune 100 aerospace company I used to work at and I end with “and then I found my way back to my desk,” you’re going to be disappointed, because I took you right where you expected to go and that’s not fun. If I end with “and then I stumbled into a room full of mannequins in lacy bras and posters of topless women,” you’re going to be much more invested. Do I have a story about a Fortune 100 Aerospace Company’s Secret Boobie Room? Yes, I do.
4. Commitment
You’ve got to commit all the way to telling your story. You have to know, all the way down in your bones, that it’s entertaining. If the story doesn’t entertain you, it won’t entertain anybody else. Give the story all of your attention while you’re telling it. Tell it energetically. Use the full range of your voice. Get loud. Get quiet. Do voices. (Warning: Impersonate accents only with extreme discretion, if at all.) Get your facial muscles working for you. Bring your eyebrows in on the action. Gesticulate wildly with your hands. Be excited about your story.
Try to get a commitment from someone in your audience. As I’m telling a story and I state something that I think of as a truth universally acknowledged, I tap or gently punch someone on the shoulder and say, “I mean, right?” I’m inviting them to agree with me, to put themself on my side, and buy into the story in front of their peers. I might say: “Office supplies, right? Honestly, is anything simultaneously more boring and more fun than office supplies?”
A rule of thumb: The enthusiasm and commitment with which you tell your story can be inversely proportional to the inherent interest of the story itself. That is to say, the harder you can commit to the story, the less interesting or amusing the story itself has to be. Do I have a story about office supplies that I’ve been telling for fifteen years and that has never failed to get a genuine crowd laugh? Yes, I do. More like office surprise. Right?
5. Brevity
Science has a lot to tell us on the subject of human attention spans. The human attention span ranges from about 5 to 20 minutes, depending on a large number of factors including age (children typically can’t focus as long as adults can) and how much time one spends scrolling through their phone, probably. It also depends on what it is someone is trying to pay attention to. When it comes to listening to someone talk in a social setting, there’s good guidance available. Most people can comfortably pay attention to your story for 5 to 10 minutes. You should aim to tell it reliably in 7 minutes—max. Does your story require a complex backstory or contextual information to understand it? Toss. It’s not anecdote material. The clock starts ticking when you start talking—not when you have finished providing all the necessary background information.
In any gathering or party scenario, every person has a responsibility not to monopolize the group’s attention for a long and uninterrupted period of time. It doesn’t matter how funny or charming you are, no one is going to remember you as “the person who told the hilarious story about the grapefruit” if you kept talking all night. You’ll be “the person who didn’t let anyone else get a word in edgewise.” You don’t want to be that guy. You want to be the grapefruit guy. Do I have a hilarious story about a literal grapefruit? If you don’t know the answer by now you can probably guess.
When I think about the person in my wider social circle who I love to run into at a party, it’s some dude named Thomas. I guess he’s a friend of my partner’s work friend? I’m not sure how everybody knows each other. That guy is hilarious and the great thing about Thomas is you never get sick of talking to him. He’s the anecdote ninja. He’ll find you at a party, spend a few minutes catching up on what’s new since the last time he saw you, drop some incredibly funny story on you for about five minutes, and then say, “Oh, hey, look, there’s so-and-so, let me go see how they’re doing,” and he’s gone. He leaves everyone wanting more Thomas.
Keep it brief. Maunder at your peril.
That’s it, that’s all you need. You’ve picked out your real-life event or incident and determined the perfect details to flesh it out while dumping the unnecessary ballast details. You’ve thought about how to tell the story—in what order to place the elements, what perspective you’ll give, and so on—to employ an element of surprise to delight your audience. Now you just need to practice telling it a few times to get your commitment down and time yourself to make sure you’re able to tell it efficiently. I promise I’ll be back in the new year with pro tips for workshopping your story and adding some ad lib.
Coming up Thursday, just in time for xmas eve: A listicle. I talk a big game about waging a guerilla kindness war, but what does that look like in practice? I’ve got a stock list of little acts of kindness—that don’t cost a a single penny—for you to commit today. Well, Thursday. See you then!
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