Hesitation Kills More Dreams Than Failure
Journal

Hesitation Kills More Dreams Than Failure

How three long-term projects collided into one chaotic two-week stretch, and what it taught me about timing, trust, and never hesitating.

 

“I firmly believe that any man’s finest hour—his greatest fulfillment to all he holds dear—is that moment when he has worked his heart out in a good cause and lies exhausted on the field of battle—victorious.”  - Vince Lombardi

To read this is to know me a little better.

Most days I wake up, get after it, and chip away at projects. I write notes, I apply them, I plan the next day—knowing full well no day ever goes as planned.

But the week of September 23rd was, to put it mildly, different. And it changed me, I suspect, forever.

Two businesses I started almost four years ago (one being this one) and a film I first began 18 years ago—relaunched four years back—all collided at once. International travel, new launches, public speaking. A week where everything I’d been building for decades demanded my full attention in a single moment.

Entrepreneurship, as in life, is a funny game. Man makes plans—God laughs. Still, the echo of my long-time friend and business partner rings in my ear each morning: just say yes. Say yes until it doesn’t make sense anymore, or until it no longer lights you up.

So I’ve built my framework around a simple truth: hesitation kills more dreams than failure ever will. It means I often dive in headfirst.

Four years ago was a strange time in the world—pandemic, panic, politics, and uncertainty. Alongside that, I wasn’t sure whether I had washed up on the shore of my own life or if I was catching the perfect wave into calm waters. Maybe somewhere in between.

It set the stage.

Back then I drafted a five-year plan: a movie, a TV show, and a business. It was ambitious, but with strategy and segmented execution, I believed I could block and tackle my way through.

Filming 24 hours in Amman for Naked Revival 

 

Instead, each project sputtered to life in fits and bursts. None ever seemed to gain real momentum. Not because they bled each other dry—but because life intervened. Partners had challenges. Money ebbed and flowed. The market shifted under our feet.

Holding on to each dream felt like clutching smoke.

Darkness descended on me more than once. Then something shifted. No explanation, just stubborn persistence. Bang your head against the prison wall long enough and eventually, something cracks. A venture capitalist once told me that, though admittedly, I did lose his money.

In my twenties I told myself those years were for chasing the dream. In my thirties I often feared I was wasting them—wandering in the dark corners of an artist’s and entrepreneur’s moon while my peers built “proper” lives. I carried their quizzical glances, my wife’s patient questions, and my own gnawing doubts like weights.

Still, Annie Dillard wrote: “If you stay still, earth buries you. Like it or not.”


Finding Nowhere in Kitimat 

 

So I kept moving. Writing. Filming. Building. Hoping to offer inspiration by actually accomplishing something I hoped would be worth sharing.

And then, all at once, it happened.

I had just wrapped filming Episode 2 of Finding Nowhere in Kitimat.

I boarded a plane to Amman, Jordan, to speak at the GX Summit about Raising Global Citizens, the film I began nearly two decades ago.

And in the middle of it all, we signed the merger agreement to take Naked Revival public on the Toronto Stock Exchange—and finally, I might add—gave the market a first live look at our early product mix and our evolving brand.

Three long-term projects. All colliding.

Theory and practice. Hesitation and abandonment. Abundance and scarcity. They’re in constant conversation with each other, like rival voices echoing across the same canyon. Which road will we choose to traverse—the one paved with a veneer of security, or the one that demands faith? In entrepreneurship, as in life, it’s never clean. You’re always negotiating between holding back and leaping forward, between retreat and risk. But the truth is, every meaningful path is carved by those who choose abundance over abandonment, action over hesitation.

My first thought: Holy shit. A TV show, a global stage, and a merger—all in the same week.

My second thought: How the hell am I going to hold this together?

That’s the lesson: you don’t control timing. You just ride the wave.

As a kid, I was always moving. Projects, goals, adventures stacked on top of each other. Breaking things just to see how they worked. The world was wide open.

But adulthood narrows the aperture. Safety nets and fear creep in. We lose the impulse to leap. I get it—I have a family to feed too. And there were plenty of dinners where I wondered how I’d put food on the table the next day.

Ideas are like storms—you don’t control them. Sometimes they rage. Sometimes they leave you stranded in the desert. They can be your muse, your lover, or your heartbreak.

And now here I was, caught between fear of failure and fear of success. Whispering to myself: Don’t fuck this up.

The Greeks judged if a life was well-lived if a man lived with eudaemonia (a "good spirit" in a holistic sense). I like to call it passion. 

To say yes—to anything, to everything—is certainly one way to live with passion. To say yes unlocks the great mysteries of life or more accurately, your life. It’s why hesitation is the true killer.

And so you keep going. Through the chaos, through the doubt, through the years of nothing happening—until suddenly, everything happens at once.

When timelines collide, they don’t just stack—they smash together with atomic energy, creating something entirely new.

That week in September, I realized: all those years, all those late nights, all those doubts—they were never wasted. They were leading here.

And when you rise from the rubble of it all, you find yourself changed. Stronger. Someone capable of holding their own dream in both hands.

Again, hesitation kills more dreams than failure ever will. 

Timing? You’ll never control it. But you can keep showing up. Keep building. Keep putting yourself in the stream where chance, faith, and convergence might meet.

That’s where I live now. In the collision.

Entrepreneurship lives in the space between theory and practice—the elegant plan and the messy execution. You can map the route all day long, but until you take the first step, it’s just ink on paper.

Abstraction. Impulses that cascade into an asymmetry I can’t quite name—one that seems to connect the dots across businesses, adding value to each. Do the projects create it, or has it always existed between them? By dint of persistence—or maybe providence—I trust more in God than in my own grasp of control. Because the courage to grow and pursue your dreams is also the courage to let go. To name the cost. To stop bargaining with yourself. To resist horse-trading on the things that matter most.

You ascend. You adapt. You grow—into someone capable not just of dreaming, but of holding the dream.

Previous
A Simple Guide to Men's Skin Care - Naked Revival and The American Boxer