The Cure For Long-Winded Storytelling
“When I hear, ‘share your story,’ I think: ‘Do you have three hours? lol’”
I laughed along with my client when she messaged me that last week.
Every storyteller has been there.
You start writing.
Then, to make sure people “get it,” you add some background.
Then a little more.
Then a side note for impact.
Then—wait, this part is important too.
Before you know it, you’re 200 words deep.
And you haven’t even gotten to the good part.
At that point most people would have stopped listening.
Not because your story isn’t good—but because there’s too much padding around the parts that make it compelling.
That’s what this week’s newsletter is about.
By the end, you’ll know how to tell a personal brand stories that resonate—without the weight of excess words.
The 5 Second Rule of Storytelling
A friend once told me about a taxi ride that changed his life.
He was in a foreign country, on a routine ride to the airport.
The driver was chatty, asking the usual questions—where he was from, how he liked the city. Then, out of nowhere, the driver said:
"You know, the hardest part about life is deciding who you want to be."
Something about the way he said it hit differently. My friend had spent years feeling stuck, waiting for clarity.
And in a single moment, he realized—clarity isn’t something you wait for. It’s something you choose.
That’s a story.
Not the conversation with the taxi driver.
That was just context for the real story: a perspective shift. A change.
This is what most people miss.
“Stories” are often told as a series of events.
"I went on vacation to The Azores."
“Our room was overlooking the ocean.”
"I went skydiving."
None of these qualify as a story.
Not on their own anyway.
Story is change.
Every story is about a five-second moment of our life—a decision, realization, or shift that changes everything.
Without a transformation (internal or external, but ideally both), you’re just recapping events—and if you ever listened to someone recount their vacation you know that’s about as exciting as tax season.
The number one rule for concise, compelling storytelling:
Start the story close to the 5 second moment.
What Context to Include (And What to Cut)
Once you identify the five-second moment, the next step is knowing how much background to include.
Context—the who, what, where, when—sets the stage for the moment of change. These details make us care enough to keep reading.
But context is where most storytelling goes off on a long-winded tangent.
People spend too much time on setup, usually for two reasons:
Over-explaining out of fear the reader won’t “get it.”
Overly descriptive, thinking more detail makes it immersive.
While it’s true that details draw people into a story. Too much detail has the opposite effect.
The reason to be concise isn’t short attention spans. It’s resonance.
The more detail you pack in, the harder it is for someone to see themselves in your personal stories.
Instead of stepping into it, they’re watching from the outside.
That’s because our brains engage most with stories when we have to fill in the blanks—a cognitive process known as the generation effect.
When we actively make connections, we engage short-term and remember better long-term.
But when a story is overloaded with personal specifics, it does all the work for the listener.
There’s no space left for them to insert their own experience, no way to become emotionally engaged.
The right amount of detail doesn’t mean painting a complete picture—it invites the audience to complete it.
And that’s what makes a story feel personal, even when they aren’t the main character.
Moreover, we don’t have the luxury of time, space, or undivided attention on social media.
We have to say a lot without saying a lot.
The trick in short-form storytelling is to deliver context and stakes like a one-two punch close to the start.
What happened? (context)
Why does it matter? (stakes)
This gives your story momentum:
The ability to pull the reader forward from one line to the next.
The Right Amount of Detail (Storytelling Example)
Here’s how most people start a story:
"I’ve always struggled with pricing. I remember my first sales call back in 2018, sitting at my desk with a nervous knot in my stomach, wondering how to justify my rates."
The problem? It’s not immediately clear what is going on or why it matters.
It’s all context—no stakes.
Here’s the same story, but starting closer to the five-second moment where everything changes:
“'We like your work, but $7,500 is steep. Can you do $5,000?'
They might as well have asked: "Will you stay true to yourself or fold like every time before?”
That sets up the moment when I’m forced to make a choice—
Will I stick to my guns or cave?
The next pieces of context I choose for this story need to add to the weight of my choice to get emotional buy in quickly.
❌ Bad Example: Details That Don’t Add Tension
"I had spent months researching pricing, reading every blog post I could find. Every time I saw someone else charging more, I felt like I was behind. So when this client asked me to lower my price, I panicked. My mind was racing, and I didn't know what to do."
Why this doesn’t work:
It explains the backstory but doesn’t add urgency to the decision.
It tells us the narrator is panicking instead of making us feel it.
✅ Good Example: Context That Adds Pressure to the Decision
"My throat went dry. I had turned down work before, but never at this price. A ‘yes’ meant more money in my pocket—but also meant I was still the person who always folded under pressure."
Why this works:
It keeps us inside the moment rather than looking backward.
It makes us feel the tension—the push and pull between the easy choice and the right one, a universal experience we all relate to.
StoryCraft Storytelling Framework
A story isn’t everything that happened—it’s the moment that changed everything. This week's storytelling framework helps you cut what’s unnecessary, focus on what adds weight, and pull people straight into the moment that matters.
Before you share your next story, run it through this quick test:
✅ Is the five-second moment clear?
Does the story hinge on a decision, realization, or shift? If there’s no change, there’s no story.
✅ Does every detail add weight to that moment?
If it doesn’t build tension or stakes, cut it.
✅ Have you started close to the moment of change?
Trim the background for immediate emotional connection.
Try This At Home
Take a story you’ve told before (or one you’re about to share) and cut everything that happens before the five-second moment except for details that make the stakes clear. Then, rework the opening so it drops us into the moment of change faster. If you can do that, your stories will be tighter, more compelling, and, frankly, easier to write.
In search of storytelling content ideas? Here are seven for March.
Moral of the Story: Kill Your Darlings
There’s a rule writers live by: Kill your darlings.
That means cutting the details you love if they don’t serve the point of your story. This is hard in practice, but it'll make you a better storyteller.
If the details don't build tension or make it easy to understand why the change at the center of the story is meaningful, it’s just a wedge between you and a deeper emotional connection with your audience.
In personal brand storytelling, the right details matter more than more details.
That’s all for this week. Thank you for reading and…
Happy Storytelling!
Cyndi
