Live the Adventure—Before Life Passes You By

In the late 90s, I used to spend my evenings at a Borders bookstore on Westwood Boulevard in L.A., now it's a 99 Ranch Market.​

Back then, I was still trying to figure out who I was.

I’d browse the shelves for wisdom—business, philosophy, martial arts, leadership—and linger in the café long enough to sip two cups of coffee while pretending not to be lost in life.

I wasn’t pretending well.

But there was one person who never seemed lost—Birgit.

An older woman, probably in her late 60s or early 70s, who exuded elegance without a trace of pretense.

Simple but high-quality clothes.

A quiet strength in her presence.

One day, we struck up a conversation that led to another, and then another.

Over time, she became a kind of unofficial mentor, not in any formal way, but through her stories and perspective.

She was from Copenhagen. Former art gallery curator in Paris. Spent half the year in Beverly Hills, the other half back home.

I still remember the first time I shook her hand—firm, grounded.

She laughed and said, "I do power yoga."

She once told me,

I never got the chance to tell her I planned to.

She passed away a few years after we met.

Her son told me, casually, at the café one day. I nodded, held back the emotion, and remembered her voice urging me toward adventure.

Now, decades later, I'm approaching the port of Copenhagen.

It’s been 25 years in the making.

And as I disembark off the Celebrity Eclipse, I carry her with me—because this isn’t just a vacation.

This is a promise kept.

This is the adventure I almost forgot to live.

The Myth of “Someday” and the Cost of Waiting

Most men live their lives thinking “someday.”

• Someday, I’ll take that trip.
• Someday, I’ll start that business.
• Someday, I’ll learn the skill, have the conversation, ask the question.

But “someday” is a seductive lie.

The problem is, life doesn’t wait.

Adventure isn’t an accessory to life—it is life.

And when you delay it, defer it, or deny it, you start dying a slow death.

Not physically, but emotionally, spiritually.

• Your soul shrinks.
• Your joy fades.
• Your edge dulls.

And over time, you become just another man who buried his fire under responsibilities, fear, and the illusion of stability.

Ask any older man what he regrets. It’s never the things he did—it’s the things he didn’t do.

Living the adventure isn’t about running off to Europe or climbing mountains—though those things are awesome.

It’s about saying yes to life.

It’s about stepping into the unknown.

It’s about testing yourself, breaking your routine, and risking a little comfort for a shot at growth, meaning, and magic.

The men who become warriors, leaders, and badasses?

They say yes more often than they say no.

They face the dragon not because they’re fearless, but because they know the real danger is staying in the cave.

The 3 Enemies of Adventure:
Comfort, Comparison, and Cowardice

There are three forces that quietly kill the adventurous spirit in men.

1. Comfort – You build a life that feels “safe” but isn’t satisfying. You know the routine. Same job. Same habits. Same conversations. No risk, no stretch. And eventually—no spark.
2. Comparison – You look at others on social media or in your peer group and think, “Well, they’re doing better, so who am I to want more?” Or worse: “It’s too late for me.”
3. Cowardice – You fear failure. Rejection. Embarrassment. So you lower your standards and pretend you’re content. You choose certainty over curiosity. Safety over self-discovery.

Let me say this clearly:

Adventure as a Leadership Strategy

You want to lead?

You want to become someone worth following?

Then go live.

Adventure is a crucible.

• It strips away pretense.
• It exposes your weaknesses.
• It reveals what you’re made of.

And it gives you stories—real stories—not ones you repost or regurgitate, but stories you earned.

Think about it.

Who do you trust more:

• The guy who read about danger in a book
• Or the guy who’s been in the fire and came back with scars and wisdom?

Your future tribe—whether that’s your family, your friends, your business team—they want you to go on that adventure.

They want a leader who’s lived.

When you venture out—whether it’s to start something, end something, or explore something—you develop what every warrior-leader must have:

• Initiative
• Resilience
• Resourcefulness
• Presence

These aren’t taught in classrooms.

They’re forged in the field.

Adventure is the classroom of life.

How to Start Living the Adventure Today

You don’t need a cruise ticket.

You need a decision.

Here are 5 simple ways to say yes to the adventure, starting now:

1. Pick one thing that scares you—and do it this week. Call someone you’ve been avoiding. Apply for that job. Take the class. Book the ticket.
2. Break one comfort pattern. Eat somewhere new. Change your routine. Take a different route home. Shock your system out of autopilot.
3. Initiate a meaningful conversation. With your dad. Your brother. A friend. Ask a real question. Go deeper. Lead with honesty.
4. Write down your 3 big “someday” dreams. Now pick one. Circle it. And make it today’s plan.
5. Remind yourself: you’re not getting out of this life alive. Every day you wait is a day you lose.

Your future self is watching.

And he’s begging you:

Don’t play it safe. Play it real.

Putting It On the Mat

Your Call to Action

As the ship glides into the Baltic Sea, I find myself sitting in one of the upper-deck cafés.

I’m sipping a cappuccino, reading, and looking out over the endless blue.

But I’m not really here for the views.

I’m here for the feeling.

That feeling you get when you finally do the thing you promised yourself you'd do.

And the strange thing is—once you’re in it, it doesn’t feel like escape.

It feels like home.

Adventure isn’t about leaving your life.

It’s about returning to it.

I think about Birgit.

I wonder if she ever felt the same way sitting in a Paris café in the 60s, talking to struggling artists and philosophers.

I imagine her as a young woman, stepping into the unknown, leaving behind the safety of “normal,” and creating a life of elegance, depth, and beauty.

That’s what I want for you.

Not the café. Not the cruise.

The courage to live.

The courage to leave behind the hollow pursuit of “shoulds” and build a life of musts.

If you’re reading this, you might be at your own version of that Westwood Borders café—searching, hoping, waiting for a sign.

Let this be it.

Your life isn’t going to begin “someday.”

It starts when you stop watching and start walking.

• Start booking.
• Start risking.
• Start leading.

Because no one’s coming to rescue you from the ordinary.

And no one can live your adventure but you.

👊 Now It's Your Turn: Action Steps for the Week

1. Write down one adventure you’ve been putting off. Big or small. Then pick a date. Commit.
2. Message a friend or mentor who inspires you. Tell them what you’re planning. Invite accountability.
3. Every day this week, do one thing outside your norm. Shake up your world. Find the magic hiding behind routine.
4. Journal the question: “If I died one year from now, what would I regret not doing?” Then go do it.
5. Reply to this email. Tell me your adventure. I’ll read it. I might even write you back.

You don’t need to be fearless.

You just need to be in motion.

Life’s too short to sit it out.

Live the adventure.

Die with stories, not regrets.

And never forget—

The map is not the territory.
But the mat is always the truth.

—Chuck
Co-Founder, The Leader’s Dojo​

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