How to Tell Stories So Good Even Your Boring Days Sound Interesting

December 12, 2025

12 Storytelling Secrets I Wish I Knew Sooner

This morning, I woke up and asked myself:

If I could go back in time and give my 20-year-old self advice on how to become a master storyteller, what would I say?

Here are the 12 storytelling secrets I wish I had known much earlier.

Lesson 1: Share Your Rock Bottom

Back in May 2025, I had a coaching call with the famous entrepreneur and YouTuber Dan Martell. And early on into the call, I said:

“Dan, I watch your keynote. It’s amazing, right? Beautiful. Your wonderful speaker. But when you mentioned your teenage years, the part about the drugs and crime, well, you just skipped right past it. Why?”

He said, “You know what? Because it always gets emotional.”

And so I asked, “Well, Dan, what’s your number one goal with your business?”

And he said, “Well, to inspire millions to live a better life.”

And I said, “Then why are you being selfish?”

He looked a little bit confused at me. And I told him, “When you skip over the dark parts of your life, you make it harder for people to see themselves in your story. Sure, your success impresses them, but your struggle is what changes them.”

Once I told him, he’s like, “Oh, yeah, I don’t like it, but you’re right.”

Which brings me to the first lesson:

Share your rock bottom.

Don’t be afraid to revisit the pain, the failure, the dark night of the soul. The story that scares you is usually the one people need to hear the most.

Lesson 2: Start Close to the Challenge

This summer, I ran a storytelling workshop for this big tech company in Amsterdam. And early on in one of the exercises, one of the guys stands up to share his story.

10 seconds in, he’s talking about his job title.
30 seconds in, where he grew up.
60 seconds in, past responsibilities.
At 93 seconds, he finally got into the story.

I looked around. Pretty much everyone in the room had mentally left the building.

And the crazy thing is, once he went into his story, it wasn’t even that bad.

After he finished, I pulled him aside and said, “I actually loved your story. It was so honest, so vulnerable, so inspiring. Such a shame that you lost everyone before you even started.”

I said that with a grin, not to tear him down, but to help him grow.

He laughed and asked the right question: “Okay, so how should I start?”

Here’s what I told him: 

Start as close to the challenge as possible.

Draw us right into the moment before things go wrong — the meeting, the phone call, the silence in the room.

Don’t warm up your audience. Wake them up.

The faster you reach the tension, the faster your story grabs people.

Lesson 3: Zoom Into the Moment

Now, imagine you’re watching a war movie.

It opens with a big helicopter shot. Battlefield from above. Tanks rolling. Smoke in the distance. Cool for three seconds.

Then you’re like, “Okay, bring me in. I want to feel the action.”

Then the camera zooms in: trenches, bombs, mud, fear in the soldiers’ eyes.

When most people tell a story, they stay in helicopter view. They say things like, “I faced a big challenge,” or “I wanted to improve the customer experience.”

Too high-level. Too vague. Too forgettable.

Great storytellers zoom into the moment.

They take us into one specific scene.

They share the exact words of the frustrated client. They show the look on your face at 2 AM. They reveal the doubts running through your head.

The good news is you don’t need to be a poet to do that. All you have to do is relive the moment and then just describe what was happening like you’re back in it.

So think of that moment and then picture it clearly in your mind and just ask yourself:

  • Where am I?
  • What am I doing?
  • What am I thinking?
  • What am I feeling?
  • What am I hearing?

Whatever comes up – those are the details that you want to include in your story.

So, don’t just hover across the ground, but drop us into the moment.

Lesson 4: Share Actual Dialogue

If I had to choose just one storytelling technique to use for the rest of my life, it would be this one.

Imagine I said:

“Well, in that moment, my boss informed me that he wasn’t impressed by my presentation and that I should prepare more.”

That is so boring, right?

Now listen to that same story, but this time with dialogue:

“My boss looked at me and said, ‘Phillip, what the hell was that? You were all over the place. Did you even look at the slides before?'”

Voom, now you feel it. You can see it.

Share the actual dialogue.

Say the exact words that person said in that crucial moment of the story. The moment that you quote that person, the story comes to life and a movie starts playing in your listener’s mind.

Lesson 5: Share Your Inner Dialogue

Here is what separates an average story from a great story:

An average story sounds like this: “I was worried my manager didn’t like me.”

You just explain what happened. That’s okay, but it’s not great.

The best storytellers don’t just tell us what happened. They let us hear what you were thinking in that moment.

So instead of saying: “Oh, I was worried my manager didn’t like me.”

Say: “I thought, **** how am I going to turn this around? My manager hates me.”

See the difference? Now we’re in the story. We can feel the fear, the pressure, the stakes.

Share the inner dialogue.

Share what was running through your mind. Share the hopes, the dreams, the plans, the fears. Because the moment you do, your story stops sounding flat and starts feeling real.

Lesson 6: Share the Why Behind the What

Here is how you can tell the difference between a beginner, amateur, and pro.

  • A beginner just shares a random story without a goal or direction: “I once spent a couple of months preparing for a marathon.”

  • An amateur storyteller does it a bit better. They at least share the goal: “My goal was to finish the marathon under 4 hours.” Now we know what they’re aiming for.

  • Pro storytellers go one step further: “I wanted to run a marathon so that I could prove to myself that I can do anything in life.”

Share the why behind the what.

The what gives us information, but the why gives us emotion.

So the next time you tell a story, don’t just share what you wanted. Tell us why it mattered so much to you.

Lesson 7: Show the Moment of Change

You’ve probably listened to thousands of stories from co-workers, speakers, and friends, and you’ve probably forgotten 99% of them.

Why? Because most stories are missing one key ingredient.

They say: “Well, I was this kind of person. I did this crazy stuff and I was pretty much the same person after.”

There’s no shift, no growth, no change.

But the best stories all have this one moment of change. It’s this instance where something clicks. Before it, you’re one person. After it, you’re someone completely different.

Maybe you were terrified of speaking in public. After that, you love being on stage. Maybe before that, you hated your brother. After that, you’re having your first call with him and you start to get along.

Show the moment of change.

It’s where the story goes from an interesting story to a beautiful story.

Lesson 8: Say Yes to Fear

Now, if you want to tell more stories, but you just don’t have enough stories to tell, this is for you.

Earlier this year, a friend from Brazil called me and he said, “Oi, Philippe, do you want to come to my millionaire mastermind to give a workshop?”

And I said, “Yeah, sure.”

But then he added, “Well, uh, one thing, it’s in Portuguese.”

And I mean, my brain is like, “Oh, Portuguese? Really? I mean, I lived in Brazil like 10 years ago, but I haven’t spoken since that.”

But I said yes anyway.

Why? Because I knew that me being scared of it and going for it anyway, well, that will make a great story.

Say yes to fear.

The moments that scare us, those are the moments that often turn into the greatest stories. That awkward conversation, that project you didn’t feel ready for, or that thing that you have been pushing out because you’re too scared—those are wonderful stories.

Every time you say yes to fear, you’re not just living life, you’re also creating your next great story.

Lesson 9: Find Magic in the Mundane

The number one blocker that stops people from telling more stories is that they think they don’t have enough cool stories.

I thought the same. I used to believe that every great story had to be this big TED-talk type of story.

Like the time when I almost died climbing in Brazil or when I met God during an Ayahuasca trip.

But here’s what I learned: Most people can’t relate to those extreme experiences, but they can relate to those small day-to-day struggles.

The best storytellers don’t chase the extraordinary.

They find magic in the mundane.

They take those tiny everyday moments and tell them with honesty, emotion, and detail.

If you think you don’t have any stories, you do.

You just haven’t noticed them. Start one simple habit called Homework for Life by Matthew Digs.

Every day, ask yourself, “If I had to tell a story from today, what would it be?” Then write down the date and that small moment that touched your heart.

After a few days or a week, you’ll realize your life is actually full of stories—you just haven’t noticed them yet.

Lesson 10: Make Your Life The Arena

If you want to become a great storyteller fast, this is the best way I know.

Every single day, people ask you one question: “How are you?”

How do most people respond? They’re like, “Uh, good. Yeah, busy. Nothing special.”

Nothing wrong with that, but it’s a missed opportunity.

Great storytellers don’t wait for the perfect stage or a big speech to tell a story.

They use every moment to practice.

Make your life the arena.

Next time someone asks you, “How are you?” tell that tiny story. It doesn’t have to be epic. It just needs to be real.

Here’s how I replied today:

“Uh, I’m good. I just wrapped up my longest video ever. 90 minutes. I’m exhausted. My voice is gone. And honestly, we’re a mix of terrified and excited to finally put it out there. What about you? When was the last time you finished something that was a little bit bigger?”

It doesn’t have to be a fancy story, instead share short, simple, human stories.

Lesson 11: Show, Don’t Tell

Boring stories feel like summaries. Great stories feel like movies.

When people tell stories, they often say things like, “Yeah, I was stressed,” or, “It was awkward. It was the best day of my life.”

That’s fine, but it’s vague because we can’t see it.

Show, don’t tell.

Show how that emotion looked on your body, on your face, in the room.

Instead of saying, “Oh, it was awkward,” say: “No one—but really, no one—said a word. We just stared at each other over cold coffee.”

That’s how you turn your story into a seed.

Lesson 12: Build a Story Bank

The best storytellers aren’t necessarily the ones with the best stories. They are the ones who have the most stories.

If you only have three stories, you won’t have many options for when to tell them. But if you have 30, 50, 100 stories, you’ll always have the right story for the right time.

Start a story bank.

A story bank is a central place where you store, save, and classify your stories so you can track the title, the lesson, a quick bullet-point summary, and maybe a theme.

By saving your stories in that story bank, you’ll never run out of stories again in your life.

Final Thoughts

These are the 12 storytelling lessons I wish I had discovered years ago. Each one has the power to transform the way you share your experiences, connect with others, and inspire action.

The good news is it is never too late to start applying them. Your next story could be the one that changes someone’s life, including your own.

If you want to take your storytelling even further, check out this next article where I dive into some of my favorite advanced techniques. 

See you there!


Enjoy.

P.S. Want to become a stronger communicator?

Here are two ways I can support you:

👉 Want to tell more engaging stories? Join our next Storytelling Workshop.
👉 Want to speak with confidence and clarity? Check out our Communication Skills Training.

Both are fun, practical, and designed to help you grow fast.

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