October 30, 2024
By now, I’ve coached thousands of people on storytelling, given workshops for companies like Google and MetLife, and published a #1 bestseller, The StorySelling Method.
The insights you’re about to learn have taken me years to figure out, but I’m here to save you time.
In 20 lessons of this free storytelling training, I’ll share everything you need to tell insanely good stories.
A few weeks ago, during a storytelling workshop in the Netherlands, a participant started his story by saying, “Let me tell you a story.” I interrupted him with, “Wait a second. Can you start over without using the ‘S-Word’?” Confused, he asked, “What’s the S-Word?” I replied, “It’s ‘story.’ Avoid starting your story by announcing, ‘Let me tell you a story.’”
Why? For some people, hearing the word “story” triggers negative expectations. They think, “Oh great, here comes a 15-minute fairy tale.”
A simple fix is to replace “story” with “experience,” “example,” or “case.” For instance, if you’re sharing a story with friends, say, “Two weeks ago, I had a crazy experience.” At work, try, “Let me share an example that makes this clear.” It’s a subtle shift, but it helps.
Seven seconds.
You have seven seconds to grab your audience’s attention.
If you spend those crucial seconds setting expectations or giving too much context, this is what happens: “Ah, what should I eat tonight? Do I want pasta or pizza? Wait, what’s that guy talking about?”
Now, let me share three ways to start your story strong:
1. Jump into the Action
Start with a scene where something is happening. Have the character doing something—talking, biking, stepping, reading—anything that brings forward momentum.
Example: “I stood in front of the manager’s door, took a big breath, knocked three times, and slowly opened the door. As I peeked in, I saw my manager and the head of HR. I immediately knew this wasn’t good.”
2. Ask a Question
Ask a question that resonates, one that makes your audience reflect on their experiences or feelings.
Example: “Have you ever wondered what it would be like to walk away from everything you’ve ever known and start over? That’s exactly what I did when I packed my bags and moved halfway across the country.”
3. Use a Cliffhanger
Start your story as close as possible to the most crucial moment. Show your listeners that this moment is going to be huge but don’t reveal everything just yet.
Example: “I was standing in my room with a letter in my hand. I knew this was it. I knew this letter would change my life forever. But let’s go back to when it all started.”
If you start strong, they’ll be fully present. But even a strong start needs the right foundation to keep attention, which brings us to the next lesson of this storytelling class.
When I started on my storytelling journey, I took an expensive storytelling course that taught me the Hero’s Journey—a 17-step structure used in blockbuster films like Star Wars and Lord of the Rings. I loved it and thought, “I’m going to use this at work.” So, next day, I’m in a meeting with a customer, launching into my breathtaking story, expecting the client to be blown away.
But halfway through, I could tell they’d tuned out.
After talking with my sister, I realized the problem. She said, “Your stories are too long and dramatic. This isn’t a TED talk; it’s a casual conversation.” That hit me. Most storytelling courses teach structure for big stages. But for casual stories we tell in everyday life, we need something simpler.
That’s why I developed a structure called CART: Context, Adversity, Resolution, Takeaway—a four-step structure that works for almost any story you want to tell.
Think of it like a shopping cart holding all the elements of your story together. Here’s how it works:
Step 1: Context
Set the scene. Where and when does this take place? Who’s the main character, and what do they want?
Example: “It was October 2019, I was in Amsterdam, rushing to the train station. I had to be there on time for a job interview with a company I’d always wanted to work for.”
Step 2: Adversity
Introduce the conflict or challenge. This is where things go wrong, and tension builds.
Example: “As I reached the station, I realized I’d left my wallet at home. Panic set in: ‘How am I going to pay for the train? What if I miss the interview?’”
Step 3: Resolution
Describe how the character deals with the adversity. What decisions do they make? How does the story resolve?
Example: “Just when I thought I’d miss my train, a woman who saw my panic approached me and offered to buy my ticket. I couldn’t believe it! I made it to my interview just in time.”
Step 4: Takeaway
Share what you learned from the experience.
Example: “What I learned is that unexpected help shows up when you need it most—and to double-check my pockets before leaving the house.”
Mastering this four-step structure—Context, Adversity, Resolution, Takeaway—will give your stories a solid foundation.
With that, let’s move to the next lesson of this free storytelling training.
One golden rule of storytelling is to “show, don’t tell.” Instead of directly telling your audience how the character feels, show how it looks.
Here are three simple but effective techniques to help with this:
1. Use Dialogue
Instead of saying what someone felt or thought, share their exact words.
2. Show Through Action
Actions reveal more than words. Use physical movements to convey emotion and tension.
3. Show Through Metaphors
Metaphors, analogies, and comparisons are powerful for making stories vivid.
By showing instead of telling, you let your audience experience the story firsthand.
For my book Public Speaking with Confidence, I interviewed the 2019 world champion of public speaking, Aaron Beverley. I asked him, “How do you prepare for your speech?”
His response was simple but mind-blowing: “I have a story file where I note down anything that could be interesting. Once I’m invited to give a speech, I review my story file and pick one that works for that audience.”
It changed everything. Before, I used to rely on memory and forget most of my stories. That all changed about four years ago when I started a story bank.
Now, I have 141 stories saved and still counting.
Here’s what I track in my story bank:
Where should you store your story bank? Wherever is most convenient for you. I use Notion because I can access it anywhere, but Google Docs, Evernote, or even a physical journal works. Just make sure it’s easy to update.
A story bank is like a savings account for your stories. Each time you add a story, you’re investing in your ability to tell more impactful stories in the future.
Onto the next lesson of this storytelling training.
When I started my storytelling journey, I thought great stories had to be big TED-style stories. I’d focus on moments like when I almost died rock climbing in Rio or meeting “God” in an Ayahuasca ceremony in the Amazon.
But after studying the best storytellers, I realized this isn’t the case. In fact, big stories can often disconnect you from your audience. They’re too far removed from everyday life. Storytelling is about connection, and the best storytellers focus on smaller, relatable moments.
So how can you spot these small moments? There’s an exercise called Homework for Life, created by Matthew Dicks. It’s the only exercise I’ve done daily for four years, and it’s life-changing. Here’s how it works:
At the end of each day, ask yourself, “If I had to tell a story from today, what would it be?” You’re not looking for something huge—just a small act of kindness, a funny conversation, or even a minor annoyance. Once you find that moment, write it down:
For example, today my storyworthy moment was feeling proud after cooking curry for dinner—a big deal because I hadn’t cooked in 14 months. I felt like a grown-up.
What about you? What was your storyworthy moment today? Let me know in the comments.
Over time, you’ll notice more storyworthy moments in your life, and your stories will feel natural and relatable. Stick with this exercise, and soon, you’ll have a suitcase full of stories ready to share.
Though I knew how to tell stories, I used to struggle with actually sharing them. Often, I’d realize hours later, “Ah, Philipp, you could’ve told a story in that moment.”
This changed when I developed a simple habit: Instead of waiting for the perfect moment, I began telling tiny stories whenever someone asked, “How are you?” Before, I’d say something boring like, “Good, thanks.” Now, I share a tiny story instead.
Example: If someone asked, “How are you?” I’d say, “I feel like such a grown-up! Today I cooked vegetable curry. I know it sounds like nothing, but I haven’t cooked in 14 months. It felt like it was time to be an adult. What about you? When was the last time you tried something new?”
Instead of talking about the weather, I respond with a story. It could be:
At first, it felt awkward, but after years of telling small stories, I can tell you—it’s worth it. Not only will you become a better storyteller, but you’ll also spark more meaningful conversations with coworkers, friends, and even strangers.
Imagine you’re super hungry and just ordered from your favorite restaurant. Every minute, you check your phone to see where your food is. You’re so excited. This sensation of waiting and craving is due to dopamine. You want to create this same sensation for your audience when telling a story.
So, how do you build anticipation?
1. Sell Your Story
Before you dive in, say a sentence that gets your listeners excited, something that makes them want to hear more.
Examples:
2. Drop Mini-Cliffhangers
Hook your audience at the start, and keep adding small hooks throughout the story.
Examples:
Including small hooks throughout your story keeps your listeners on the edge of their seats. If you don’t, they’ll look for other sources of dopamine, like checking their phone.
Last week, I watched Star Wars Episode II for the fifth time. At one point, as in every Star Wars movie, dozens of stormtroopers were killed. Watching the bodies pile up, I noticed I felt happy—no sympathy for the stormtroopers. Why?
Because they’re faceless, nameless creatures. I know nothing about them. And while that makes sense for villains, it’s a problem when we do the same to our protagonists. Often, we don’t share anything about the main character that makes our audience care.
So, how can you bring characters to life?
1. Describe Physical Characteristics
Describe their appearance—clothes, body type, or anything memorable.
Example: “She had a bright, infectious smile that could light up a room. And her curly red hair always looked like she’d just stepped out of a wind tunnel.”
2. Reveal Their Quirks and Traits
Share habits or traits that make your character stand out.
Example: “He couldn’t start his day without making sure every item on his desk was perfectly aligned.”
3. Share Their Dreams and Fears
Show what drives your character and what they’re afraid of.
Example: “Her biggest dream was to open a small bakery to bring joy to her community, but the fear of failing kept her from taking the plunge.”
When you bring your character to life, your audience connects with them and cares about their journey.
Onto the next lesson of this storytelling training.
Think of a childhood memory.
Maybe a birthday party, a school performance, or a family holiday. Why do you remember that moment?
Because of the emotions you felt. Compare that with how much you remember from a meeting last week. You’ve probably forgotten 99 percent of what was discussed.
If you want to connect with your listeners and be remembered, tell a story that touches them emotionally.
Here are two techniques to bring out emotions:
1. Share the Thoughts
Let us in on what the character is thinking or feeling during key moments. What do they fear, worry, dream, or hope? Sharing raw thoughts makes the story more emotional.
Example:
2. SHOW the Emotions
Rather than just telling emotions, show how they look on the body and face.
Example:
By sharing thoughts and showing emotions, you make it easier for your audience to visualize, feel, and remember your story.
How do you use your voice, body, and emotions to tell your story? There are different styles—some storytellers use very little, relying 100% on the story itself, while others act out their stories quite a bit. Personally, I like to use my voice, body, and emotions to make a story more engaging. I’m not an actor, and you probably aren’t either, but a few techniques can bring your stories to life.
1. Show an Action
If you say, “I bent down to pick up the orange,” actually bend down and mime picking up that imaginary orange. Or, “I walked across the hall and opened the door”—take a few steps and pretend to open that door. Show the action rather than just describing it.
2. Show Reactions
In real life, we react to events. If we’re angry, we raise our voice; if we’re happy, we laugh; if we’re sad, we speak softly. When telling stories, don’t suppress these reactions to seem “professional.” Show your reaction during the key moments. If it was a joyful moment, let that joy come through in your expression and tone. If it was sad, show it. Visualize that moment as if it’s happening again, and let your audience see it in your face and hear it in your voice.
3. Impersonate a Character
Most stories involve more than one person, and dialogue is a great way to bring a story to life. When you include a conversation in your story, try impersonating the characters involved. If you’re sharing a conversation with your mom, mimic her tone of voice, posture, and body language to capture her personality.
Example:
“In that moment, my mom said, ‘Philipp, why did you do that? You had one job—to take care of the dog, and you couldn’t even do that?’”
It may feel awkward to act out parts of your story at first, but trust me—doing so makes your stories much more vivid and compelling.
Imagine you live in the countryside and drive to work every day. You pass fields with cows grazing. You don’t even notice them because it’s routine. But one day, you see a pink cow. You’re so shocked you tell everyone about it—and probably remember it forever.
This is the essence of breaking expectations. Humans are great at spotting patterns, but as soon as something is predictable, we tune out. If your audience knows where the story is going, they’ll start thinking about other things.
To capture their attention, share something unexpected. It could be an unusual action, event, or reaction. Here’s an example of a story with surprising elements:
Example:
This story comes from Nordstrom and shows the company’s dedication to customer service.
“Back in 1978, Craig Trounce was working as a store associate at a Nordstrom in Fairbanks, Alaska. One day, he noticed a man rolling a pair of tires into the store. Craig walked up and asked if he could help. The man replied, ‘Yes, I want to return these tires.’ Craig explained, ‘Sir, we’re a clothing retailer. We don’t carry tires.’ But the man insisted, ‘No, no. I bought these tires in this building years ago.’ It turned out he’d bought the tires from a previous tenant.
Craig was initially overwhelmed, but he decided to do what felt right. He called a local tire company to estimate the value of the tires, then took them and gave the man a refund. He gave a refund for a product that Nordstrom didn’t even have. That’s what it means to put the customer first.”
The story takes unexpected turns: first, the customer brought tires into a clothing store, then Craig decided to give a refund on a product Nordstrom didn’t even sell. Breaking expectations like this makes your story unforgettable.
Imagine watching Who Wants to Be a Millionaire. At first, the stakes are low—the contestant can win a few hundred dollars. But as the show progresses, the stakes get much higher, with questions worth thousands and the million-dollar prize looming. Each question builds tension, and we become more invested in whether the contestant will succeed.
To make your story more engaging, raise the stakes. Share what big thing the character stands to win or lose in a specific situation. Here are three ways to do this:
1. Share the Character’s Goals
Reveal what your main character wants to achieve—their hopes, dreams, or plans. Share emotional goals that really matter to them.
Example:
“I want to finish a marathon to prove I can do anything. I don’t need to play it small anymore.”
2. Show Impact on Others
Increase the stakes by showing how others are affected by the hero’s actions. What will happen to them if the hero succeeds or fails?
Example:
“I have to get this job. If I don’t, I won’t have the money to send my daughter to college. She’s counting on me.”
3. Introduce Time Pressure
Adding a deadline or time limit increases urgency and tension.
Example:
“I had just two hours to prepare a 30-slide presentation for the board of directors.”
When you show what’s at risk, your audience cares more about the outcome and becomes more invested in the characters and their journey.
During my MBA at Columbia, I had a friend who was a great storyteller. Every time we went out, he’d share a story about getting super drunk and doing something wild. But recently, I tried to remember his stories and couldn’t recall any of them. Why? Because there was no change.
His stories went, “I was this person before, did something crazy, and was the same person after.” No transformation, no growth—just the same old him. Change is the difference between a forgettable story and one that sticks. In almost every movie or book, the main character undergoes some kind of transformation.
For your story, show a change or transformation:
Show the change.
For my book The StorySelling Method, I wanted to understand the language used in the best stories, so I analyzed 97 of them. I listened to each story, rated it, then transcribed it and ran the transcript through readability software. Here’s what I found:
the highest-rated stories could be understood by a 5th grader.
Great stories don’t try to be fancy or intellectual; they focus on connecting with the audience.
To make your story easier to follow, aim for simple language.
Here’s how:
1. Break Down Long Sentences
Instead of one long sentence, use two or three shorter ones.
2. Avoid Jargon or Fancy Words
Use everyday language. Even if your story is in a business context, don’t complicate things to sound “smarter.”
3. Keep It Conversational
Write like you’re talking to a friend, not giving a lecture. This applies whether you’re sharing with one person or an audience.
If you want to check whether your story is simple enough, use a free readability software to measure it. Aim for a level that a 5th to 7th grader could understand.
Simplifying isn’t about dumbing down your story; it’s about ensuring your message is clear and accessible.
When I first began my storytelling journey, I sat down and tried to count how many stories I had.
After two hours, I came up with just six stories. And I was proud of that number—I thought, “Philipp, well done. You’re a wonderful storyteller.”
But now, I realize the number could be much, much higher. If you’re in your 20s, you probably have hundreds of stories.
If you’re in your 30s or 40s, you likely have thousands. And that’s without living a particularly wild life.
To uncover these hidden memories and stories, think of yourself as an archaeologist, digging through your past to uncover experiences that can become stories.
Here’s a storytelling technique I often share in my storytelling classes called Stream of Consciousness Journaling:
1. Choose a Prompt
Pick a prompt to spark ideas and get your thoughts flowing. These can be based on locations, themes (like travel, sports, or relationships), or more specific experiences. For example:
2. Set a Timer
Start with a short timeframe, like 5 minutes, to avoid feeling overwhelmed. You can increase the time as you get more comfortable with this exercise.
3. Start Writing
Once the timer is set, begin writing down any memories that come to mind related to that prompt. Keep writing without stopping, editing, or second-guessing. Let your thoughts flow freely, even if they seem random.
Stream of Consciousness Journaling isn’t about crafting perfect stories immediately. It’s about discovering the “storyworthy” moments in your life. This technique, which I regularly teach in storytelling training sessions, will reveal forgotten experiences and emotions that can be turned into powerful stories.
Have you ever noticed how some stories come alive, while others fall flat? One secret to engaging storytelling is to use specific, descriptive words instead of generic ones. Imagine two scenarios:
Scenario 1:
“I was driving in my car down the highway.”
What does this tell us? Not much, right? You know I was driving, but you don’t get a feel for who I am or what the scene is like.
Scenario 2:
“I was driving 120 miles/hour down the German autobahn in my 10-year-old Toyota Prius.”
Now you have details that make the story vivid and memorable. You get a sense that I might be a risk-taker, and maybe also a bit frugal.
So, how can you make your stories more specific? Here are a few storytelling techniques:
1. Replace Generic Words
Use specifics to paint a clearer picture.
2. Add Unique Details to Characters
Highlight traits that make your characters more relatable.
3. Use Metaphors
Comparisons and metaphors can create powerful mental images.
But remember, use details strategically. Too many can overwhelm or distract from your main point. When I cover this in a storytelling class, I emphasize sprinkling in a few details to transform your story.
When sharing a story, the last thing you want is to sound like a robot reciting lines. But you also don’t want to stumble through the story, searching for words, or forgetting key moments. So, what’s the solution?
Instead of memorizing your entire story word-for-word, focus on memorizing SME—Start, Moments, and End.
1. Memorize Your Start (S)
Think of the best speeches you’ve ever heard. They often start with a bang—an action, a provocative question, or a cliffhanger. Memorizing the first few lines by heart allows you to launch into your story confidently. This “hook” sets the tone and gives your audience a reason to keep listening.
2. Memorize the Moments (M)
For the middle of your story, don’t try to remember every single word. Instead, focus on the key moments or scenes. Each moment is a snapshot of a place or action, like knocking on the manager’s door, receiving unexpected news, or reacting with surprise. Visualizing these scenes will help you remember what happens next.
3. Memorize Your End (E)
Many people focus on the beginning and middle of their stories but overlook the ending. The end is crucial because it’s what your audience will remember. This is where you deliver the takeaway or the core message. Memorize your closing lines so you can end with impact.
In storytelling training, I always emphasize SME as an alternative to memorizing every word. Using Start, Moments, and End, your story will feel alive, natural, and real.
Practicing your story a few times—2 to 3 times—is usually enough to get comfortable. But to take it further, share your story with someone and get feedback. At first, I asked friends and family to listen. This worked for a while, but eventually, I felt awkward about repeatedly asking them.
So, I started looking for a storytelling coach. But that’s when I hit a wall: storytelling coaches are expensive. Good ones charge at least $200 an hour, and top-tier ones charge even more.
That’s when I discovered an effective storytelling hack: I hired an English language tutor. And instead of practicing English, I used the tutor to rehearse storytelling techniques. Platforms like Preply or iTalki have private tutors for as little as $3 per hour. In these sessions, I share 2-3 stories and get feedback. The tutor doesn’t need to be a professional storytelling coach—they can still tell me how the story made them feel, where they got bored, and where they were engaged.
Rehearsing with a tutor has been a game-changer for me, and I highly recommend this approach if you’re serious about improving your storytelling skills.
I owe much of my success to one simple mantra: “Commit now, figure it out later.”
Let me share how I discovered this approach.
In November 2021, I decided I wanted to try stand-up comedy. I’d never read a book on comedy or taken any classes, but I didn’t let that stop me. I found an open mic night in Amsterdam and signed up. I didn’t know much about comedy, but I thought, “I’ll figure it out.”
Fast-forward three weeks, and I’m standing in front of 180 people, delivering my first stand-up routine. It was terrifying. My legs were shaking the entire time. I wish I could say I crushed it, but that wouldn’t be true. I wasn’t terrible, but I wasn’t amazing either. What mattered, though, was how much I learned. Those three weeks of preparation taught me more about comedy than a year of passive learning.
The key is this: the biggest growth happens when you go after something that seems far beyond your current abilities. What I did with comedy, you can do with storytelling. Most major cities have storytelling open mic nights. In the U.S., The Moth and RISK are two popular organizations that hold storytelling nights. Submit an application and set a date—it’s the same commitment strategy I use in my storytelling classes.
Or, if there aren’t storytelling nights in your area, ask your boss if you can share a story during the next team meeting. If that’s not an option, ask a friend if you can tell a story at the next family gathering.
Yes, it’ll feel terrifying, and yes, you might feel underprepared. But once you commit to a date, you’ll do whatever it takes to avoid embarrassing yourself. Even if you mess up, that itself could be a great story to tell in the future.
That’s it. Those are my 20 lessons from 5 years of storytelling.
Actually, which lesson was your favorite? Let me know in the comments.
Today, we went deep into storytelling.
But when you speak in front of friends, give a presentation, or speak on stage there are also a few other public speaking techniques that you need to master.
For that you may wanna check out this next article in which I’ll share How to become a Better Speaker than 99% of People.
Enjoy!
Are you ready to transform your storytelling skills?
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