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The 3 levels of storytellers (and how to move up)
Let’s break it down.
Stephen Stanberry
November 11th, 2025
In partnership with
I realized something recently, friend!
Most entrepreneurs don’t have a storytelling problem.
They have a platform mismatch problem.
They’re trying to tell one-size-fits-all stories across four completely different ecosystems
Instagram, TikTok, Threads, and LinkedIn
and wondering why their content falls flat.
After watching hundreds of founders and creators “storytell their way to sales,”
I’ve noticed there are 3 levels of storytellers online.
Each level thinks differently, writes differently, and connects differently.
If your stories aren’t converting, you’re probably stuck at one of these.
Let’s break it down.
Level 1 – The Over-Explainer (Beginner)
Beliefs
“If I share enough details, people will care.”
“My story needs to sound professional.”
“All platforms want the same thing.”
Skills
You write to inform, not to connect.
You explain everything instead of building tension.
You post the same caption everywhere and hope it lands.
Traits
Nervous about being too emotional.
Obsessed with information instead of insight.
Thinks good stories require dramatic life events.
👉 How to level up:
Start with one conflict line.
That messy, imperfect “before” moment that shows you’re human.
Example:
Instead of saying “I teach coaches how to attract clients,”
say “Last year, I sent 42 DMs and got ghosted by every single one.”
Same topic. More tension. More truth.
Level 2 – The Consistent Creator (Intermediate)
Beliefs
“Stories are for engagement, not sales.”
“I already told that one people will get bored.”
“If it doesn’t go viral, it didn’t work.”
Skills
You hook attention but can’t sustain it.
You’ve found your voice but not your platform rhythm.
You tell stories but don’t connect them to your offer.
Traits
Overthinks what fits where.
Hesitates to show vulnerability.
Keeps rewriting instead of publishing.
👉 How to level up:
Repurpose smart.
Keep one story, but adapt how you tell it.
Here’s the Story Platform Checklist I use myself:
Platform | Style | Goal | Example |
|---|---|---|---|
Visual + Personal | Emotion | “Here’s what burnout looked like for me.” | |
TikTok | Fast + Dramatic | Curiosity | “This one client almost made me quit.” |
Threads | Bold + Punchy | Truth | “Nobody’s talking about this part of freelancing.” |
Reflective + Strategic | Trust | “Here’s what firing my first client taught me about leadership.” |
Example:
Share a story about a failed launch,
On Instagram, it was a raw “behind the scenes.”
On TikTok, it was a dramatic one-line intro: “I lost $2,000 in 48 hours.”
On Threads, it became a mini-rant about mistakes.
On LinkedIn, it turned into a leadership lesson.
Same story. Four versions. Four audiences.
Level 3 – The Story Strategist (Advanced)
Beliefs
“Every story is an asset.”
“Each platform deserves its own angle.”
“Emotion builds authority faster than education.”
Skills
You adapt your message to context.
You use pacing, silence, and conflict intentionally.
You connect story to offer without sounding “salesy.”
Traits
Intentional. Patient. Data-aware but not data-ruled.
Reflects before reacting.
Treats every story as a test, not a performance.
👉 How to level up:
You start writing like a director, not a creator.
Every detail, pause, and visual cue has a purpose.
Example:
An advanced storyteller could take the same “fired client” story
and turn it into:
A LinkedIn post that attracts leaders who value integrity.
A TikTok video where the emotion sells the lesson.
A newsletter story that transitions into an offer without pitching.
A podcast clip that turns a single mistake into an evergreen narrative.
You’re not chasing attention anymore you’re building connection equity.
Here’s your Tuesday prompt 👇
Add one conflict line to your next story.
That one honest “before” moment that makes your lesson matter.
Send me your before + after.
I’ll reply with one note to help you sharpen it.
Till tomorrow,
Stephen “stories > strategy” Stanberry
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