The 5 Easiest Storytelling Mistakes to Fix.
(Why you’re making them & how to get listeners wanting to hear more .)
You’ve come to the right place.
Story Luck is a nonprofit, 501c3. We’ve been producing storytelling shows for over 11 years.
We’ve seen all the mistakes anyone could ever make! Here’s what separates this guide from
any other on the market. We dig into why people make the mistakes. Once you understand
why they crop up, they are much easier to draft away.
Whether you came across this resource because you subscribe to our newsletter, you ran in
Journey to the End of the Night, you showed up to one of our potluck shows, or cost us 35
cents by clicking on a Facebook ad! Everyone at Story Luck is glad you’re here.
Now, we want to be as transparent as possible.
This is enough to get you started. This guide is not a teaser. It’s actionable and helpful.
You don’t need anything else. If after reading this, you feel satiated, great. But what we are
searching for are those who love storytelling. Who long to write stories which keep readers
up past their bedtime because they need to read one more page. We want to connect and
cultivate a group of people who remember sitting around campfires as scouts making up
totally ridiculous kid stories. Have nostalgia for family kitchen table get togethers where you
just sat listening to your aunts and uncles. Watched as they riffed off the energy in the room
and then got everyone to explode in fits of laughter.
We want to connect, really stay in touch AND work with those of you who catch the
storytelling bug through our cohort classes. That’s Story Luck’s goal.
Personally, I spent 2022 doing over 1k free 1-on-1 coaching
sessions, teaching cohort classes all year long, and have been
producing Live Literature Storytelling Shows since 2011. While
this list of mistakes isn’t exhaustive, if you fix just a handful of
these problems, you’ll be 100x more engaging.
Here’s why getting even a little bit better at this skill is wildly
important.
Your stories matter.
There are people who feel alone in this world. And when you
share your story, do you know what happens? You articulate what they can’t. Your
experiences, no matter how unique, there are other people in this world who’ve been
through them. When you’re better understood, people also learn to understand themselves
better. It’s a virtuous cycle.
Stories give us access to that divine feeling of universal connectedness.
You picking up this quick guide, means you’re ready to start the journey to becoming a
master storyteller.
If you ever need me, I’m an email away Dan@storyluck.org
And if you make it to the end of this guide, and want more, there’s a bonus mistake that we
can help you with now that you’ve signed up to our email list.
Thank you. Because at the heart of every storyteller is someone who wants to inspire the
audience to be better than they were. You’re a good one.
Your Blue Haired Story Lion,
Daniel Andrew Boyd
Mistake #1 Your story isn’t actually a story.
This word “story” gets used to describe an ad for a car, a sculpture sitting outside the
museum, constellations, and a Rorschach blot.
Outside of any other context, I’m happy to let story be all encompassing. The leaf on
the tree has a story to tell. The ant crawling up your leg looking for a crumb of Krispy
Kreme Donut has an epic adventure just waiting to be shared. Your mom telling you
about all the colors that exist on page 44 of her stamp book. It’s all a story.
But when you’re trying to get better at storytelling, it’s best to define it more narrowly.
Constrict the rules, to ferment creativity and growth.
Story Luck defines storytelling this way: “An event told to an audience as a Live
Lit experience that’s meant to be a gift.”
Think critically about live lit, and ask yourself:
1. “What is it I’m trying to achieve?”
2. “What is the most effective way to achieve that goal?”
When you finish telling a story that doesn’t feel like a story. Here is what it normally
looks like:
“And Bill was there, and Toto was barking, and of course Mary had baked a cake
and and and… What was I saying? Ummmm, so yeah I was at that Cubs’ baseball
game and it was like… good. Fun. Ummm, yeah.”
My significant other, McKenzie, likes to prep people when she starts a story - “There
will be no punchline.”
Stories that don’t feel like stories, just sort of peter out. When you start them, you
and your audience feel like there’s a destination point… but somewhere near the
middle you and your audience realize, nobody knows where that train is going to
stop. Usually people just keep talking, hoping to reach a station eventually. Grasping
and sputtering into random details till the audience moves on, or exasperated, they
just stop talking.
3 Tips so your story never peters out.
1. Have a 3-act structure: beginning, middle and end.
Aristotle let us know that all stories start, and stop eventually. It’s inevitable that
somewhere in between is a middle. What makes a story feel like a story is that those
3 moments are intentional. When you follow the Story Luck 5L1K method, you focus
most of your attention on the ending. We believe that if you know where you’re going
to stop the train, you’ll get there.
2. Your story needs to illustrate a moment of change.
Kindra Hall, in her first book on storytelling, calls this change moment framework,
“The moment after which everything was different.”
In a movie script it usually comes at page 75. An unexpected twist that pops around
the protagonist’s nadir moment. When everything looks bleakest, they realize the
strength was in them all along, or they get a magic sword or they realize the girl
they’ve been chasing isn’t the one!
With this new knowledge the protagonist gains an a-ha moment which they use to
change the course of their life. And we, as the audience, get access to that a-ha
moment too. Now, we can change our lives, just like the protagonist.
3. Go small in scope to control your audience’s tendency to mentally wander.
Often, when stories don’t feel like stories, your scope is too big. This can happen for
two main reasons.
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Everything is important!
You don’t know your main reason for telling the story, so you don’t know what
is or isn’t important.
For the first issue, you’re right. Trust. But understand, your audience can’t take
everything in right now. They have room for one change moment per story. They
have room for one important fact. And when you put more in, even if they are
incredible super listeners, the second and third point gets diluted.
Think about email.
People send you huge value packed emails filled with facts and figures that are
important to you and your work. You love those people, and they love you! But you
don’t open their emails. You’d be better off getting the main ideas one email at a
time.
You want your live literature stories to feel like a personal story, not a novel, and
certainly not a dissertation. Stick to one theme statement and one moment of
change.
For the second bullet point, know that’s where 90% of stories start. We don’t know
what the meaning of the story is, until we’ve told it a few times. For those of you who
tell stories that ramble - take heart, all of the professional storytellers I know start
there. We meet up in secret groups and say things like, “This story is wobbly Jello.” (I
first heard this said by Kory May.)
Play with your story in safe places. Tell friends who don’t mind a little ramble. Meet
up in Zoom storytelling workshops like Story Luck’s Feedback Loop. And after you’ve
got a couple tellings under your belt then it’s time to check in with yourself and ask:
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“If the audience was going to leave tonight with just 1 take away, what would I
want it to be?”
“What draws me to this story?”
“What did I learn from this story?”
“What is this story about?”
These sorts of questions will help you find that golden nugget. That’s how you
wrench meaning from the random plot of life. If you’re asking those questions and
still struggling after a few tellings. Ask one of those friends who were listening,
“What’s something you learned from this story?”
Know that a good storyteller makes it look easy. But when you’re struggling, that’s
the sign it’s going to be a great story, because it’s one you’re invested in. Eventually
when it looks easy, it will be all the more glorious for the work you put in.
Mistake #2 You don’t airdrop us into the action.
Rule of thumb: Start with the inciting incident.
A personal narrative story, whether it’s told around a Thanksgiving table or on stage
to a live audience at a show, lasts 3-10 minutes. That’s not a lot of time. Knowing
brevity is appreciated, start as close to that moment of change as possible.
3 Mistakes that slow you down and bore the audience:
1. Apologizing for your story.
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I’m sorry, this is going to be a little long winded.
I’m sorry, I don’t know where this is going.
Bear with me, this is…
Stop. You’re making it Worse.
These are examples I’ve heard over and over at Live Literature shows. Many novice
storytellers apologize because they are humble.
They desire to be honest with the audience AND want to set low expectations so
they can beat them. Worse, they want sympathy. That’s not what the audience is
there for. You are there for them, to present them a gift in storytelling form. Not to be
comforted. For that, join a writer group and work it out in a workshop. (You’re
welcome to work with me for free and 1-on-1 here.)
Starting this way wastes time. You’re reading this, which means you’re interested
in craft, and you’re better than you think you are! Think of it as a 1st date. You don’t
blurt out all your red flags right away.
This sort of start is putting your worst foot forward. Don’t give the audience a reason
to stop ignore you. If you tell people that you suck, some will believe you.
(Worst case scenario? You internalize that false story.)
2. Adding preamble or backstory before you start.
This is work you want to do inside your story.
Most of the time, no one needs to know that backstory to understand the story. And it
will offer up fun moments of conversation once you’re done telling.
3. Telling people you’re about to start telling a story.
“So, this is a story…” Stop.
We know and on the off chance someone doesn’t, they will pick it up very quickly!
Don’t tell the audience what they already know.
These mistakes happen because we have the correct feeling that we should be
setting audience expectations, which is an important part of storytelling.
Unfortunately, these mistakes misalign expectations and start you and your audience
off on the wrong foot.
Your first sentence is your hook.
You want it to shimmer and shine. To grab attention. To be vivid and make the
audience think, “Oh, I need to know what comes next.” If you don’t have a good
opening line, you’ll lose your audience to cell phones and their own imaginations.
So don’t open with boring preamble, telling people that you suck, or explaining the
obvious. You’ve got more important work to do, you’ve got a story to tell!
Mistake #3 You Don’t Anchor Your Story in Scenes.
When your audience is confused, this is why.
In Story Worthy, Mathew Dicks pushes the idea that when he’s telling a story, he’s
trying to create a movie in the listener’s mind. If you think about how you listen to
podcasts, it’s almost as if your eyes are closed. The images fill your mind, and you
FEEL present. You're there with the storyteller, seeing what he sees.
Anchoring your story in scenes is hard.
When you are telling a story that you’ve lived through, your mind does all that work.
So it doesn’t feel necessary to say it out loud.
When you tell someone about the first time you jumped off the high dive, your
imagination takes you back to that place. You feel the diving board under your feet.
You remember the color of the board and how it contrasted to the water below. Your
imagination is so powerful you feel the air and the sun on your skin.
Since you’re feeling all those lush, vivid, sensorial details it seems ridiculous to
repeat them aloud.
Live literature storytelling is about accessing your imagination and then speaking it
into existence for the audience. That’s when the magic happens. That’s when you
transfer the scene from your mind, into the minds of the audience. Suddenly, not
only do they see it, but they are there, standing on that diving board with you. They
feel what you feel.
Through the power of story, they discover it with you!
Set these 3 details so your audience is comfortable
following the story.
1. Set the story in a specific time and location.
You aren’t driving in a car.
Instead, you’re sixteen and driving a 75 silver Cadillac South on 94 because you’re
heading into Chicago with your friends for the first time.
Giving your audience a snippet of detail, anchors them in the scene and then their
imagination can fill out the rest of the details without you having to give them all the
rest. Some of them will imagine the window is down. Some will imagine you blasting
music. That’s okay. It makes it richer for them.
But what happens when you simply say, “I’m driving a car,” is different. Instead of
filling out the details with their imagination, your audience ends up with questions.
What kind of car? When is this? How old are you? Etc.
2. Center your scenes in action.
You’re the protagonist of your own story. Set a strong desire right off the bat and
your scenes should be placed so we feel it. Maybe the desire leads to conflict. But
we are seeing you striving to get what you want.
Cut scenes where your motivations seem confused.
3. Scenes need to serve the dramatic arc.
Arlene Malinowski in her class on Goddesses & Storytelling hammered home that
stories need to have two arcs. There’s the news and what we think about it.
(If you are ever looking for 1 on 1 storytelling coach, or to build out a full length solo
show, seek her out.)
That is to say, there’s the plot, the scenes and the action that ensues, but there’s
also an emotional core to every story. Each scene, each setting should be placed
intentionally into the story so that it serves both those arcs.
This is most famously explained in the rule of Chekhov’s Gun. If the audience sees a
gun in act 1 then that gun must go off by act 3. Don’t introduce details or scenes that
are superfluous to the plot and the emotional core of the story. If the story is about
how you overcame your fear of heights and jumped off the high dive! Skip the scene
where you’re driving with your friends to Chicago for the first time.
If your story is about how you felt freedom by stealing your grandpa’s 75 Cadillac,
skip the scene of you on the high dive.
Once you get good at rendering scenes, they will become seductive to the audience.
Especially those that want to help you workshop your stories. Make sure you’re
always checking in with yourself to see if the scene fits with your theme statement.
#4: Your audience gets lost because you don’t
use transitions.
Transitioning a story looks harder to fix than it is.
Tiktok, YouTube, and movies have popularized the jump cut, and audiences look forward to
them. They can follow from one scene to the next and their brains are quick to latch on to
specific details that tell them, “Oh, we aren’t in Kansas anymore.”
Use this to your advantage.
3 cues to help anchor your scenes in time and place.
1. Tell the audience how old you were and give details that were emblematic of that
time.
While you want to have a hook, and jump into the action. You also want to set the time and
place within the first paragraph of your story. So, you might open with a quick heart stopping
line like, “The headlight shattered as it slammed into the stop sign, and shifted the
momentum of my car, spinning me completely out of control.”
After you stop the mental scroll and have the audience’s attention, you need to quickly add
details that answer these anticipated audience questions:
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How old is the protagonist? (How long ago was this story?)
Who are the other characters?
Where is the setting?
At the beginning of each scene, think about what questions the audience is going to
immediately have, and try to answer them, or let the audience know, those questions don’t
matter for this story.
2. When telling stories out of order, use transition phrases like, “Three weeks ago…”
Flashbacks and time jumps are effective at allowing you to start the story inside the inciting
incident. You can backfill details via scene changes later.
In a movie, they have wipe transitions and dissolves as well as audio ques to help the
audience understand that we are moving to a new scene of the story that’s also at a different
time. Don’t be afraid to use these terms to help guide a media savvy audience as to what’s
going on.
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“Flashback to 7 weeks ago, I hadn’t even bought my first car.”
“Four months later, I was still in jail, and hadn’t heard from Susan.”
“Now I’m twenty-two, standing at the edge of the Grand Canyon’s splendor.”
When you change the scene, make sure you’re following the tips in Mistake #3above. You’re
anchoring the audience in scene, not just once, but every time you move in time or place.
3. Use sensory ques and repetitive language to help the audience keep track of
scenes.
If you are moving back and forth to the same places and times throughout a story or you can
color code them, to help the audience understand.
As examples, you can focus the audience on a specific object in each place. Perhaps it’s a
clock, or a woman’s bright red hair. Maybe it’s the grating lilt of a professor’s voice in
contrast to your father’s husky wisdom bombs.
If you always go back to the same image or sound, and only use it in a specific scene, your
audience will catch on, and be able to follow you from place to place.
What’s the number 1 reason people struggle with transitions?
That’ll be answered in Mistake #5.
# 5 Your story spans too much time.
Your life is expansive.
You are who you are because of generational trauma, because of joys not known by mere
mortals, because of Issac and Abraham, Adam and Eve, Zeus’s capricious goodwill and
Budha’s penchant for excellent advice to strangers.
It often feels like the audience needs to know all that nuance. They don’t.
With a short personal story, it’s much better to go deep than it is to go wide. When you are
crafting and workshopping your story, always take a minute while you’re in the state of play,
just messing around with the story for fun… to try and tell the whole story while staying in 1
place.
What does the story look and sound like if you never switch scenes? How can you jam the
moment of change, and all there is for everyone to know into a single scene?
Here’s some advice I got from the podcaster and comedian Sydney Davis Jr. Jr.
“Sometimes you have the worst day of your life. And it just so happens you
saw a flower that was the most beautiful flower you’ve ever seen. It brought
you all this joy and it was a genuinely happy moment.
“If you want to tell the story that focusses on a happy moment seeing a
flower, without mentioning that it was amid literally the worst day of your life,
that’s okay. Likewise, if you don’t want the audience to know that during the
worst day of your life, you had a moment of reprieve, that’s also okay. Those
cuts are important steps to becoming a better storyteller.
“No matter how expansive your story is, you’ll have to make cuts. The
audience knows this. And you, as an author and storyteller, need to embrace
that reality. You’re not trying to be nuanced and explain everything that ever
happened to you. You’re trying to tell one specific story that’s got a specific
theme.”
It isn't an act of dishonesty when you make cuts to your story.
Instead, it’s an act of care and intention. You make cuts for the reader. You have an agenda.
You have a theme, a nugget of truth that you want the audience to walk away with, and it’s
your job to stay focused on that goal. Make sure the audience follows the story.
This allows for maximum impact.
Your audience can be trusted to know you aren’t giving them all the details. They trust you to
make artistic decisions.
You have an infinite number of stories to tell. And you’ll have a of time to get through them.
But take care to tell one story at a time. Your audience will appreciate getting one deep and
meaningful message, unmuddied by extemporaneous details.
Instead, it's an act of care and intention. You make cuts for the reader. You have an
agenda. You have a theme, a nugget of truth that you want the audience to walk
away with, and it's your job to stay focused on that goal, to make sure that the
audience follows the story.
This will allow for maximum impact.
Bonus Mistake #6 You aren’t practicing.
Here’s the pitch.
I’m Daniel Andrew Boyd, and I’ve had the pleasure of dedicating my life to the art of
storytelling. I was six years old, sitting in a basement watching my older cousins play
Dungeons and Dragons. A collaborative storytelling game where all of them were playing
characters and choreographing the most epic fantasy story I’d ever experienced.
I was too young to play but golly gee wizos did I ever want to join.
Man, to tell stories and have a group of my friends be captivated.
The next morning, my Uncle Bob, while making us all breakfast, told the most hilarious story
I’d ever heard. The whole table was laughing so hard our French toast was getting cold.
It was then I realized, this love of storytelling would be eternal. The form didn’t matter. It
wasn’t about tabletop games or being a movie star, or anything grandiose. Let’s just sit,
friends around a table and tell the best stories anyone has ever heard. Because when you
truly know your friends, the world’s suddenly the BEST place.
And from that sense of peace eventually came Story Luck.
There’s a storyteller in your life, who inspired you. A mom who read you fairy tales before
you fell asleep. Whatever it is. You can affect others, the way they put a spell on you.
I want you to share this feeling of friendship, of being heard, being understood, and in being
understood… help OTHERS feel seen. Be Seen.
There’s a world of lonely people out there, who need you and your storytelling skills.
I want to help you find and grow your audience.
Creative people like you and me. We get sold a myth of a writer all alone.
That’s not how bestselling novels are created.
It takes teams of people. All the books and guides that inspire and teach you how to write in
the first place. Friends, family, draft after draft, beta readers, developmental and copy
editors. Then there’s marketers and jacket cover writers. Finally, fans write you notes
because they know, “You’re the type of author who wants to fix typos in the 2nd edition.” 😂
So, thank you for being part of the audience for this guide to storytelling mistakes.
To get this free download you gave up your email address. You’re part of the Story Luck
Crew now. We will be sharing fundamental tips and tricks that every English major knows
but also, we all need reminding.
We hope you’ve been inspired by this, to refine your craft.
But more than that, we hope, over the coming weeks and months, you decide to join us and
actively encourage us to write more, write better, and make the world a better place.
Because you agree, writing together is how the best writing gets done.
Your friend in the writing life,
Daniel Andrew Boyd
Dan@storyluck.org