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Why Storytelling Mastery Lives in the Middle

Storytelling School

Release Date: 07/16/2025

How Storytelling Can Turn Crowd Chaos into Connection show art How Storytelling Can Turn Crowd Chaos into Connection

Storytelling School

It’s my very first time at Comic-Con. I’m with my dear friend Denise, and it’s her first time, too. The second we arrive in downtown San Diego, we’re hit with a wave of everything - cosplayers everywhere, camera crews darting around, and volunteers all over the place. There are 135,000 people moving in every direction at once. It’s buzzing, massive, and honestly thrilling! Since it’s Day One, we find our way to the convention center and step onto this long escalator. We’re heading up to the top, and I’m trying to act calm - for Denise, sure, but really for myself, too. Inside,...

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200 Episodes In: Your Storytelling Masterclass in 50 Moments show art 200 Episodes In: Your Storytelling Masterclass in 50 Moments

Storytelling School

It’s a Tuesday morning. I am sitting in front of my computer, matcha tea in hand, staring at my podcast dashboard. A little number in the top corner catches my eye. 200 episodes, 200! Part of me can’t even believe it. I think back to those first recordings; I was so nervous, wondering if people would care about storytelling the way I do, yet week after week, I kept going. I didn’t always know if I’d have the time, the stories, or the right guests to keep it fresh. But every single conversation, every solo episode, every moment behind the mic has taught me something. And at each...

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Why Storytelling Mastery Lives in the Middle show art Why Storytelling Mastery Lives in the Middle

Storytelling School

I am standing on a court in Santa Barbara, and it's my very first pickleball lesson. I arrived early and I’m already warmed up, focused and ready to do everything exactly right. In fact, even before booking this lesson, I researched every single coach in town. I landed on Richard Pastoria because he's the real deal: a professional coach for over 25 years, the resident pickleball pro at the Valley Club of Montecito, and - not only that - he also has a military background. That combination of structure and discipline and high standards speaks to me because I've been an athlete my entire life,...

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How Great Speakers Rehearse (It’s Not What You Think) show art How Great Speakers Rehearse (It’s Not What You Think)

Storytelling School

I'm on a Zoom call with one of my private clients. She is a powerhouse executive and is preparing for a TED-style keynote. Her ideas are solid, and her story is incredible; it's emotional, has high stakes and everything you would want in an opening story. And the rest of her Talk? That’s epic as well. Plus, she's done the work and is ready to go.  We start rehearsing and everything… falls flat. Her delivery is kind of robotic, and there's no energy in her voice. Even the transitions between her story and her insights kind of feel like speed bumps. She is reciting her script but isn't...

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The Callback Strategy Every Speaker Should Know show art The Callback Strategy Every Speaker Should Know

Storytelling School

I’m working with my client on a TEDx Talk. In her opening story, she shares a vivid moment from her childhood: She is standing on a stranger's doorstep, completely nervous and uncertain if anyone is going to answer at all. It's a small detail yet it’s emotionally powerful and completely gripping.  After the story, we go ahead and develop the rest of the Talk. And as a whole, her Talk is strong. It's structured and meaningful… except when we get to the end. Something is missing. Her idea and her content are clear, but there isn't really an emotional lift at the end. I suggest going...

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What Knife Fighting Taught Me About Storytelling show art What Knife Fighting Taught Me About Storytelling

Storytelling School

I am standing in the dojo, drenched in sweat. We’re in the middle of a dynamic circle knife drill, and I’m surrounded by fellow black belts, each armed with metal training knives and ready to attack in a simulation of real-life danger - fast, chaotic, and unrelenting.  At first, I hold my own, fueled by adrenaline and a strong desire to prove that I can hang with the best. I move quickly, using flashy moves and relying on sheer speed, but as the drill speeds up, my technique falls apart. I'm rushing transitions, missing critical details, and losing confidence. My partners sense the...

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Why Sharing Difficult Stories Can Change Lives show art Why Sharing Difficult Stories Can Change Lives

Storytelling School

I'm a freshman at the University of Hawaii, living the dream on a full-ride softball scholarship. One night during finals week, my roommate and I decide to take a break from studying and grab a bite to eat. On our way back to the dorms, riding our mopeds, the unthinkable happens and I get hit… by a cement truck.  I wake up five days later in the hospital with massive head injuries and indescribable pain. The doctor tells me that my sense of taste and smell is gone, permanently. For years, I don’t talk about the accident. I think, who wants to hear a story like that? It feels too...

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How Embracing Imperfection Can Transform Your Storytelling show art How Embracing Imperfection Can Transform Your Storytelling

Storytelling School

It's the early 2000s, and I get invited to speak in New York to a room full of tech heavyweights - people and thought leaders I dreamed of being in front of. I am determined to crush it, so I do what any overachiever would: I obsess.  I write, rewrite, and practice endlessly. No improvising. No mistakes. I even buy a stiff, serious outfit that doesn’t feel like me but seems like something a “real” speaker would wear. On the day of the event I deliver my Talk flawlessly, every word in place. The audience claps, though I leave feeling like something is off. It was perfect, yes, but...

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How to Make Numbers Unforgettable Through Story show art How to Make Numbers Unforgettable Through Story

Storytelling School

It’s 2006. I am sitting in the audience at TED surrounded by visionaries, innovators, and thought leaders. The energy in the room is electric and everyone is buzzing with anticipation about who’s going to take the stage next and what new insight we’ll walk away with. When the next speaker, a Swedish professor specializing in global health and data, is introduced, I brace myself for a dry, academic talk full of statistics and charts. Instead, the speaker starts moving across the stage with visible, infectious enthusiasm, pointing at animated visuals and telling a story through data....

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Why Many Stories Fall Flat in the Final 10 Seconds show art Why Many Stories Fall Flat in the Final 10 Seconds

Storytelling School

I am coaching a speaker as she prepares for one of the biggest keynotes of her career. Her story is powerful, full of resilience and triumph. As she runs through her story, I am captivated... until it just... stops. She smiles, says thank you, and that’s it. There is no call to action and no invitation. I deliver the news, gently: her ending isn’t serving her or the audience. She pushes back because she doesn’t want to  sound salesy. And while I do definitely understand her concerns, I explain that, while her story hits hard, her ending needs to hit home. So we roll up the sleeves...

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I am standing on a court in Santa Barbara, and it's my very first pickleball lesson. I arrived early and I’m already warmed up, focused and ready to do everything exactly right. In fact, even before booking this lesson, I researched every single coach in town. I landed on Richard Pastoria because he's the real deal: a professional coach for over 25 years, the resident pickleball pro at the Valley Club of Montecito, and - not only that - he also has a military background. That combination of structure and discipline and high standards speaks to me because I've been an athlete my entire life, and I take performance seriously, so I want to work with someone who brings that level of excellence and who understands focus like I do. I'm thinking we are going to be perfectly aligned.

A few minutes into the lesson, we are already deep into a drill, and Coach Richard feeds me a ball. I move the way I think I'm supposed to and swing the way I think I'm supposed to… and I completely miss. Instantly, I feel my entire body tighten. I start analyzing. What did I do wrong? Was it my grip, or maybe it was my footwork? Or it could be my timing…

I replay this moment in my mind, and I start getting mad at myself because I'm doing what he's telling me to do. I can feel myself spiraling faster and faster. I am an athlete. I should be able to do this. I should be able to pick this up. 

I want so badly to get this right. It’s at this moment that Coach Richard can see me spiraling. Across the court, I hear him yell out, “Kymberlee!” Okay, here it comes. I'm bracing myself, thinking that it's going to be a technical adjustment, another drill, and he says, “It's just pickleball.” That's it. No lecture, no overanalysis, just those three words.

At that moment, I laugh. My shoulders drop, and I stop holding my breath because he's right; it is just pickleball. All of a sudden, I think, what if this were fun? Everything shifts. I keep playing, but now I feel lighter, looser, still focused but not robotic. I start laughing when I miss. I reset faster and strangely start hitting the ball better, and I realize that I don't have to choose between working hard and also having fun. I can actually care deeply and enjoy myself at the exact same time, and that paradox, that is where the power is.

In this episode of the Storytelling School Podcast, I discuss what you can do to make your story truly land, why too much control kills connection, and so much more. You’ll get answers to questions like:

How can you be both serious about your performance and still have fun at the same time? What elements need to be in alignment in order to deliver a memorable Talk? How can you tell a compelling story without sounding robotic or rehearsed? 

What you will learn in this episode:

  • How mastery over your Talk is in the balance between effort and ease
  • Why your energy should be in sync with your story 
  • Why perfection is not persuasive
  • Why letting go just enough creates the necessary space for authenticity, flow, and real impact

A little about me:

Hi there. I’m Kymberlee.

As a Speaking Strategist and founder of Storytelling School, I’ve had the pleasure of working with over 500 speakers, business leaders, and entrepreneurs worldwide for over a decade. No matter if those folks were getting ready to take the TED or TEDx stage or preparing for a high-stakes presentation with everything on the line, my specialty is High Stakes Short Form Communication. I’ve seen what works when influencing change and what doesn’t. It turns out storytelling is one of the most powerful tools you can have in your arsenal. That’s why I’m building a movement of master storytellers to affect change in the world on a global scale to help people tell real stories that have influence and impact. With effective storytelling, you change people’s lives.

Since competition for potential client attention is fierce, a story can make the difference between being memorable or irrelevant. You’ll find me sharing my matcha tea mishap to discuss perfectionism, my quest for Bruce Lee and Hello Kitty art to explore kindness, or, as I discuss in this episode, the six months of live blade training I underwent to illustrate presence. I spend my days showing the power of using stories to help cement ideas and bring lessons to life and teach my clients to do the same.

If you think business owners can’t tell stories or don’t have stories to share with their clients, staff, donors, followers, or investors, I invite you to reconsider your perspective. There’s no better place than in business to tell your stories so audiences, no matter how big or small, can understand how you think and what you value.

Now it’s your turn... If you’re ready to become a master storyteller and effect change in our world, you’ve come to the right place.

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