Are You Too Cool for School?

Why Learning to Be Your Own Best Cheerleader Is the Warrior’s Hidden Skill

The Movie, The Ocean, and The Scar-Sharing Ritual

Summer of ’75, Waikiki.

I was 9 years old.

My cousin took us to see Jaws at a theater on Kalākaua Avenue—right across the street from the ocean. The sun was hot, the waves were gentle, and the scent of salt filled the air.

That all changed after the movie.

As the credits rolled and we stepped outside, the ocean suddenly didn’t look so inviting. I remember staring at the water, half-expecting a dorsal fin to slice through the waves.

But you know what stuck with me more than the shark?

It was that scene on the boat—three men, late at night, drinking, laughing, and showing each other their scars.

It was part locker-room banter, part tribal storytelling. They weren’t bragging. They were bonding. Each scar had a story, and each story built trust.

They were letting each other know, “I’ve been through hell too—and I’m still here.”​

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That moment taught me something I wouldn’t fully understand until years later: sometimes, talking about your scars is how you earn your seat at the fire.

It's how you signal to others that you belong—not because you’re perfect, but because you’ve survived.

Fast forward to today.

Let me ask you something,

"How comfortable are you talking about how badass you are?"

I don’t mean being a blowhard or pretending to be a big shot. I mean being real. Being proud. Being your own best cheerleader without cringing or minimizing your wins.

Because the truth is, most young men either hide their greatness out of fear of being judged… or inflate themselves to cover up insecurity.

There’s a third way—and it’s the way of the warrior.

Let me show you what I mean.

The Lost Art of Self-Respect

Insecure people mistake confidence for arrogance.

Why?

Because they don’t know what earned confidence looks like.

They’ve only seen the loud, shallow kind—the influencer kind. But true warriors, real leaders, the ones you want in your foxhole?

They’ve got scars. And stories.

And they know how to carry themselves with quiet power.

But even quiet power must be seen.

Too many young men suffer in silence, not because they’re weak, but because they’ve never learned to speak about their strength.

I used to be like that.

I was part of a men’s group back in West L.A., just before and during COVID. We used to meet in person, but during lockdown, we moved online.

Every few Saturdays, the host—Ken—would toss us into Zoom breakout rooms and prompt us to share our “Too Cool for School” stories.

We’d each have to tell a story that made us sound kind of badass.

But there was a twist: it had to be true. No exaggeration. No overcompensating. Just real stories, told with humility and power.

It felt awkward at first. Brag? On purpose? With strangers?

But something clicked.

Ken was teaching us how to stand tall in our own stories—how to practice strategic vulnerability. How to stop downplaying our gifts and start owning our wins. Not to posture. Not to dominate. But to connect.

Because if you can’t talk about your wins, who will?

This is a critical skill most men were never taught.

We were told to be humble. To be quiet. To “let our work speak for itself.”

But what if your work is invisible? What if no one’s watching?

You have to learn to speak.

And you don’t have to be loud to be heard. You just have to be honest, embodied, and present.

That’s why I teach my clients and students something I call the High–Low–High framework—a three-part story arc you can use in job interviews, dates, networking events, and anywhere else people ask, “So, what do you do?”

High: Share your wins. “I’ve led billion-dollar construction projects, taught martial arts to hundreds of students, and retired in my 50s with financial freedom.”

Low: Share your struggle. “But it wasn’t always like this. I grew up surrounded by bullies and barely graduated high school. I was an alcoholic who had zero direction. Zero confidence.”

High: Share the turning point. “Things changed when I found the mat. Martial arts taught me how to lead myself. That bled into my work, my relationships, and my life. Now I teach others how to do the same.”

Simple. Clear. Impactful.

It’s not bragging. It’s storytelling.

You see the difference?

Being your own best cheerleader isn’t about inflating your ego—it’s about owning your evolution.

Let me tell you one of my favorite humble brags.

Back in ’88, I bought my first motorcycle, a Honda Hawk NT650, with a driver’s permit and no clue how to ride.

Seriously. I had never driven anything with a clutch. The salesman at Honda of Glendale had to show me how to shift gears. I clumsily made my way to the quiet residential street of Glendale to practice.

Then to the Rose Bowl parking lot to hit second and third gear.

Then—like a true genius—I hit the 134 freeway.

Wind screaming in my face. White-knuckled on the handlebars. I was alive.

But the real story?

Getting off the freeway at Brand Boulevard, I stalled at a red light. Embarrassed by the line of cars behind me, I overcompensated—too much gas, popped the clutch, and did an unintentional wheelie through the intersection.

Then I crashed.

Right there on Brand and East Doran. Bent my shifter. Skinned my pride.

A few strangers helped me up. Asked if I was okay.

I limped home.

But I kept riding. And I’ve loved motorcycles ever since.

That’s a humble brag. Not because it’s impressive. But because it’s mine.

It’s real. It’s earned. And it reminds me that bravery doesn’t look like perfection—it looks like showing up and trying again.

This is what being your own best cheerleader is about:

• Recognizing your evolution
• Sharing your stories with presence
• And reminding yourself (and others) of who you really are

If you don’t do this, you stay invisible.

And there’s no valor in hiding your strength.

The world needs more real ones. More warriors who know how to speak without barking. Who can inspire without performing. Who can lift others simply by telling the truth about where they’ve been.

Don’t let false humility rob you of real connection.

Don’t let insecurity keep your gifts hidden.

Don’t be “too cool for school” and miss your own damn graduation.

Putting It On the Mat:
Tell Your Damn Story

There’s something powerful about a scar shared in the right circle.

A few years ago, I was on the mat with a younger training partner at Meraki BJJ. He was strong, fast, and skilled. But something held him back.

After we rolled, I pulled him aside.

“You’re good,” I said. “But you’re hiding. What’s that about?”

He laughed nervously and shrugged. “I don’t want to come off like I think I’m better than anyone.”

I nodded. I’ve heard that before. I’ve felt that before.

I told him the story of my motorcycle crash.

I told him about Ken’s men’s group.

I told him that humility isn’t about hiding—it’s about holding your story with both hands and sharing it when the moment is right.

Later that week, I saw him talking with another white belt. He was coaching. Encouraging. Sharing a story about a mistake he’d made—and what he learned from it.

That’s how it starts.

You don’t need to “brag” to be seen. You just need to speak.

So here’s what I want you to do this week:

1. Write down one of your humble brags. A time you were scared but acted anyway. A time you failed but kept going. A time you showed up when others didn’t.
2. Practice telling it. Say it out loud. Don’t minimize. Don’t exaggerate. Just speak.
3. Share it with someone. A friend. A peer. A mentor. Or email it to me. Seriously—I’d love to hear it.

Because if you can’t be your own best cheerleader, how can anyone else know how badass you really are?

This is how we build the tribe.

This is how warriors rise.

By telling the truth.

By owning the story.

And by showing up, again and again—with scars, with strength, and with the courage to be seen.

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