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How I became better at storytelling
Stephen Stanberry
December 16th, 2025
In partnership with
Hey friend!
I used to think people who talked about “storytelling” were mostly full of it.
You know the type.
Always posting about
“the 7 elements of a great story”
or
“the Pixar framework for emotional connection”
Yet somehow… never actually telling a story.
Just commentary about stories.
Which is ironic.
And annoying.
Because when I first started writing consistently, that’s exactly what I did too.
I over-explained everything.
Every post tried to teach.
Every email tried to justify itself.
Every story came with a moral stapled to the front.
And it showed.
People skimmed.
They nodded.
Then they moved on.
Nothing stuck.
The shift that changed everything for me was embarrassingly small.
I stopped starting with the lesson.
Instead of saying what I learned, I started showing the moment before I learned it.
The hesitation.
The awkward part.
The “this might flop” feeling.
For example.
I used to write something like:
“I learned that storytelling works better than tips.”
Now I write:
“I stared at this post for ten minutes wondering if anyone would care.”
Same idea.
Different effect.
One explains.
The other invites.
I watched this play out fast.
A Reel with fewer tips got more saves.
A LinkedIn post with no advice got more replies.
An email that felt unfinished got forwarded.
Not because it was smarter.
Because it was human.
People don’t connect to conclusions.
They connect to tension.
So here’s your simple prompt this week.
Before you hit publish, ask yourself:
“What was the uncomfortable moment right before this made sense?”
Add one line about that.
That’s it.
If you want, send me your before and after.
I’ll reply with one note.
Till tomorrow,
Stephen
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