Your Story isn’t Actually a STORY. Here’s Why.

1 mistake I see new Medium writers making.

Daniel Andrew Boyd
6 min readOct 13, 2023
Easy to fix mistakes are ruining your stories. Follow me and your stories will sing
This artwork was created by Daniel Andrew Boyd in collaboration with ai.

To the writer who feels they suck at the storytelling part of the game!

I’ve spent the last decade Absolute-Unit-Style dedicated to the art, craft and science of oral storytelling. Through the non-profit Story Luck, I’ve done over 1k free 1 on 1 consultations. Helped ten times that through our podcasts, live shows, classes and social media writing life.

So I know from experience, the vast majority of people, even good writers, struggle with storytelling.

Part of why is because 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 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 Crispy Krème Donut has an epic adventure just waiting to be shared. Your mom listing all the colors that exist on page 44 of her stamp book? It’s all a story.

But when you’re trying to go from 0 to 1, it’s best to define it more narrowly. Constricted rules 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.”

-Story Luck

Listening to stories. Told live
Photo by Story Luck

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. This is what it normally looks like.

“And Bill was there, and Toto was barking, and of course Marry had baked a cake and and and… What was I saying? Ummmm, so yeah I was at that Cub’s Baseball Game and it was like good. Fun. Ummm, yeah.”

My girlfriend, McKenzie, likes to prep people when she starts a story, “There will be no punchline.”

Stories that don’t feel like stories, peeter out.

When you start, you and your audience feel there’s a destination everyone is headed to… but somewhere near the middle you and your audience realize, nobody knows where that train is going to stop. Usually storytellers just keep talking, hoping to reach a station eventually. Grasping and sputtering into and over random details till the audience moves on, or exasperated, the storyteller just stops talking.

“Ah, I guess I don’t know where this is… going.”

3 Tips so Your Story Never Peters Out

There’s no new advice under the sun, but you need to hear the best advice over and over again to keep you on the right track. New people saying the same old same old in new ways can create personal unlocks.

Click follow immediately, because over the course of the year I’ll be sharing my ultimate guide to the 101 storytelling mistakes that are easy to fix.

Now, you’ve heard this advice before but here are key things people miss:

  • Have a 3 act structure: beginning, middle and end.

Classic advice! But people get it wrong because it’s simple, not easy.

All stories start and stop thus making a middle inevitable.

What makes a story FEEL like a story is the start & stop are placed intentionally. Choose where you’re going to stop the story train before you start, so if you get lost in the messy middle, you’ll still land your audience in the last act.

  • Your story needs to illustrate a moment of change.

Kindra Hall, in her book Stories that Stick, calls this 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 audience get access to that a-ha moment too. Now, we can change our lives, just like the protagonist.

So when you’re telling a story, your theme will connect to the moment of change.

  • Go small in scope to control your audience’s tendency to mentally wander.

Remember, you’ve come up with a single goal, with the questions, “What am I trying to achieve,” and, “How do I attain that goal?”

When stories don’t feel like stories, your scope is too big. This can happen for two main reasons.

  1. Everything is important!
  2. 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. I trust you. But understand, your super fans can’t take everything in right now. They have room for one change moment per Live Lit story. They have room for one important fact. And when you put more in, though your fans are incredible listeners, all of the extra details, themes, and change moments will dilute your main reason for telling the story.

This is a photo of email testimonials saying daniel andrew boyd is a master storyteller.
This Testimonial Graphic was Created by Story Luck CC

Concise emails are best, here’s why.

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 most of the time, you don’t open their emails. It’s overwhelming. You’d be better off getting the main ideas one email at a time.

You want Live Lit 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 issue, 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 struggle at this point. We meet up in secret groups and say things like, “This story is wobbly Jello.” (I first heard this said by Toastmaster 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 in, then it’s time to check in with yourself and ask, “If the audience was going to leave tonight with just 1 take away, what would I want it to be?”

If you still don’t know the answer try these questions to massage it out.

  1. “What draws me to this story?”
  2. “What did I learn from this story?”
  3. “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.

Art provided by our friend from Deviant art Sole One

Congratulations! You’ve done it. Finished this article. THANK YOU for getting this far. Your attention is valuable and I am grateful. Now to prove it!

After I get to 100 subs and make Medium Partner I will be combining the top 10 storytelling mistake into a slick PDF guide and sharing it with all my subscribers for free. (Wait! There’s more. 😁 Everyone who gets the guide will also receive a coupon for Story Luck’s next class.)

In the comments, tell me the storytelling mistakes you see on Medium and out in the world. Why do you think people make them?

Understanding why is better than understanding the formulas.

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Daniel Andrew Boyd
Daniel Andrew Boyd

Written by Daniel Andrew Boyd

Nice to internet meet you. | Named after an Irish ballad, destined to spit yarn & listen to you with delight. Subscribe & I'll email you a storytelling guide!

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