The storytelling lie we’ve all believed - and how it’s costing you conversions
Sara paced her living room, laptop balanced on the arm of the couch, the glow from the screen lighting her face.
She had spent weeks perfecting the story she was about to share with her audience.
It followed the ‘Hero’s Journey’ formula to a ‘T’:
She started with a relatable struggle - her failure to land clients in her early freelancing days.
The middle consisted of descriptions of sleepless nights and mounting bills.
Then came her turning point: a strategy that changed everything.
Ending with walking readers through her success and the lessons she learned.
Hitting “publish”, Sara felt nothing but pride. This was storytelling done right. Every piece of advice she’d read on it had told her so.
Across town, Jamie was sitting at her kitchen table, half-empty coffee mug by her side, her toddler babbling in the background as she randomly grabbed her phone.
Her story was much different from Sara’s - much less formulaic:
“Yesterday, I pitched a new client. I thought I nailed it, but they ghosted me. I know I’m supposed to be learning from this, but honestly? Right now, I just feel stuck. I’m questioning everything.
Anyone else ever feel this way? What do you do when the self-doubt creeps in?”
Jamie hit “post” without rereading or editing.
Both women were trying to connect with their audience through storytelling.
But over the next six months, their paths unfolded quite differently.
While Sara’s posts were beautifully designed - her engagement was trash. People rarely engaged, instead choosing to simply admire a success they just didn’t see themselves in.
Jamie’s stories, on the other hand, were messy AF.
Each post organically created engagement. Her followers were regularly offering advice, sharing their own experiences, and coming back the next day to see what had happened next.
The difference?
Sara’s audience saw her as a finished product.
Jamie’s audience saw her as a work in progress - just like them.
My Problem with the Hero’s Journey
The ‘Hero’s Journey’ assumes life follows a clean, linear arc:
A problem arises.
The hero struggles but overcomes.
The story ends with triumph and resolution.
But life doesn’t work that way anymore… if it ever did.
In today’s world, people experience life in fragments:
A win here.
A setback there.
A ‘don’t even know if I’m winning or losing right now’ everywhere else.
In a 2025 world, success and failure don’t follow a straight line.
They loop, overlap, and circle back.
Sara’s stories felt distant because they didn’t reflect this reality. Her audience just couldn’t see themselves in her neat, pretty narratives.
Meanwhile, Jamie’s approach reflected her audience’s own lives.
In sharing her struggles in real time, Jamie allowed people to step into her shoes.
Not as spectators. But as participants.
The Case For Iterative Storytelling
Jamie didn’t know it at the time, but she was using a powerful strategy called iterative storytelling.
Rather than presenting a finished, resolved story… Jamie shared moments from her journey as they happened.
She let her audience see the messiness of her process, the questions she was still asking, and the lessons she hadn’t yet learned.
Here’s why it works:
Unfinished Stories Create Curiosity
When Jamie shared a setback without a resolution, her audience wanted to know what would happen next. They stayed invested in her journey, looking out for updates.Raw Moments Build Trust
By sharing her struggles in real time, Jamie showed vulnerability. Her audience felt like they knew the real her, not a curated version.Engagement Became a Dialogue
Jamie didn’t just tell stories; she invited her audience into the process. Her posts ended with questions that sparked conversations. Her followers weren’t just readers - they were collaborators.
Because Storytelling Is a Conversation, Not a Performance
Six months after they started, Sara and Jamie’s results were telling.
Sara’s audience respected her, but they didn’t feel connected to her. Her stories were something to admire from a distance - not something to engage with.
Jamie, on the other hand, had built a community. Her followers didn’t just cheer her on - they rooted for her success as if it were their own.
The difference wasn’t effort.
Both women were hardworking, creative, and talented.
The difference was how they told their stories.
How Can You Use Iterative Storytelling
If you’re ready to ditch the outdated ‘Hero’s Journey’ and connect with your audience for real… here’s how to get started:
Start in the Middle
Share a raw moment from your journey without waiting for a resolution. Let your audience see you mid-struggle or mid-discovery.Invite Reflection
End your story with a question that invites your audience to share their thoughts or experiences.Follow Up
Keep your audience updated on how the story evolves. This creates an ongoing story they can invest in.Focus on Moments, Not Milestones
Instead of waiting for a big win to share, focus on small, relatable moments that highlight your process.
Let’s Put It In Action
Imagine if every story you told didn’t need an ending. This week, share a single, unfinished chapter with your audience:
Describe the tension you’re feeling.
Ask a question you’re genuinely struggling with.
Let your audience share their own “chapters” in response.
Then… do this:
1: Collect and Highlight Responses
Turn the audience comments into a key part of the story:
Pick 3-5 unique responses that stand out.
Highlight their contributions in a follow-up post or thread, crediting the audience members who shared their chapters.
Example: “[Name] suggested [comment]. It made me think about [reflection].”
2: Explore the Possibilities
Use the feedback to create a collaborative continuation:
Write a post exploring how your story could evolve if it ended with their ideas.
Example: “What if I took [audience suggestion]? Here’s how it might play out…”
Take it to the next level by reaching out to them for a collaborative post.
Example: “This idea was too good not to have a conversation about. Here’s what we built together.”
3: Turn It Into a Series
Create a multi-post story that documents:
Your original chapter.
The audience’s responses.
A hypothetical or real resolution based on their ideas.
The lessons learned from the collaboration.
When you stop trying to tie every story up with a pretty bow, you create space for others to join in.
Share your unfinished chapter today.
Then invite your audience to write the next part with you.
Today’s Mega-Prompt: "Master-Level Storytelling Engagement"
Paid members get to use today’s mega-prompt to design an advanced, interactive storytelling experience that seamlessly incorporates audience input into an evolving, dynamic content series. This prompt equips you with the ability create real engagement that drives seamless conversions.
Here’s a sneak peek:
"Adopt the role of a master story series architect and community engagement innovator, responsible for designing immersive storytelling experiences that captivate and convert… your task is to design an intricate, multi-dimensional interactive storytelling series based on my unfinished personal story and my audience’s input."