I heard Matthew Dicks on a podcast and it changed how I tell stories.
What is a story to you?
I used to think it was a coherent retelling of facts with a punchline or lesson.
But somehow that was never enough?
Why didn’t it drive the point home?
Why didn’t it connect?
Why don’t people remember?
The difference:
Cotton candy = Anecdote - retelling of a situation, that crazy or funny thing that happened, it satisfies you in the moment, doesn’t linger and doesn’t change you.
Best meal of your life = Story - something that people will love to repeat and think about for days or weeks.
You don't remember cotton candy.
But you remember the best meals of your life.
So, I tried to apply his storytelling principles to one of the most emotional decisions I’ve made - selling my side hustle - that you read in my last blogpost.
🎙️ Part 1: The Theory - What Matthew Dicks Taught Me
👆 Here is the full podcast.
I can guarantee you, you’ll be HOOKED 9 minutes into the podcast.
Here is my full summary of the podcast.
Rule #1 - ❌ Don’t Report - nobody wants to hear you report about your life.
Rule #2 - ✨ Stories = Change – they’re about *change over time*, if you know the ending, the starting point is the opposite.
Structure
🕰️ Flow ≠ Chronologically - don't tell stories chronologically.
▶️ Start at the tension, from the appearance of an interesting element
Key Tools
⭐️ Tell YOUR own story - to lead with vulnerability, nobody cares about you retelling someone else's
😂 Front-load humor - make the audience laugh in the first 30 seconds, it puts everyone at ease that you know what you're doing
🌅 Use scenes and locations, not full detailed descriptions
🎒 Backpack of emotions - load up people with a stake and your hopes and dreams, raise the stakes
⏳ Slow down the Key Moment - when you do get to the suspenseful part, slow it right down, then you can start describing and talking slower
Language
❤️ BUT - is the most powerful word of every story
❌ Ditch adjectives, let imagination fill in the rest
🤗 Make it emotional—what you felt, did, said
✨ Keep it relevant - keep it focused and don't distract
🔥 Contrast is more powerful than Comparison - don't tell me what things are like, but what they are NOT like, dynamic rather than flat language
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✍️ Part 2: In Practice - The Story I Told
I knew I wanted to share the story of selling Puddle Pod.
It was tied back to a very personal and emotional moment, us expecting a child.
So I tried to apply the lessons from Matthew Dicks.
Here it is, as a refresher and if you want to see the theory in action.
🔍 How I Applied the Rules
Started at the peak moment: “Two pink lines.” (✔ tension upfront)
Personal stakes: Becoming a dad, letting go of something I loved (✔ emotional backpack, although I could have loaded the backpack more)
Concrete scenes: Day 1 at Startmate, posting on LinkedIn, walking out of coworking sessions (✔ scene-based storytelling, without too much detail as we can all imagine ie a coworking space)
Own Story: Shared fears of miscarriage and letting go (✔ own emotional story)
The Magic word “BUT”: Moments of hope vs fear, energy vs fatigue (✔ contrast and conflict)
Time manipulation: Slowed down the decision-making moment (✔ pacing)
Avoided fluff: Every detail moved the story forward and avoided adjectives (✔ relevance)
🛠️ Where I Could’ve Done Better
Not enough humor upfront – could have added a light or quirky moment early
Missed a strong “ending scene” – the heartbeat line was good, but could I have closed with a more vivid scene?
Could’ve used more “what it’s NOT like” language – stronger comparisons and contrasts, this is the one I struggle with the most, as it doesn’t come naturally
Chronological creep – a few sections slipped back into timeline-style narration
Why am I sharing this with you?
The best way to learn is to do all three:
someone teach you - Matthew Dicks podcast
share it with peers and discuss it - I’ve been telling everyone about this
you teach someone else - this blog post + additional bonus of distilling it in writing
And I really want to get better at storytelling.
So the next time you hear me tell a story, tell me what I could have done better!
Great story = 5 second moment of change