Rebel Talk: Hole Punch

There are moments in life when a single, simple action holds deep meaning.

A handshake. A signature. A first step.

Or in this case—a hole punch.

Two Fridays ago, I sat across from a DPE (Designated Pilot Examiner), exhausted from nine months of relentless learning, flying, studying, and grinding. When he smiled, reached for my temporary student pilot certificate, and punched a hole through it—marking me, officially, as a Private Pilot—I nearly felt my heart burst.

That tiny hole was the closing of one chapter, and the opening of another I had dreamed about since I was a little boy.

The Dream Deferred

I can’t remember when it started. Maybe it was sitting at air shows as a kid, eyes glued to the sky, watching those planes carve up the clouds like paintbrushes on a canvas. Maybe it was family trips, when I’d stare out the window and wonder what it felt like to be up front—hands on the yoke, master of the sky.

But the dream of becoming a pilot always felt like one of those “someday” things. Life has a way of crowding out dreams, doesn’t it?

Work.
Businesses.
Marriage.
Kids.
Responsibilities.

The to-do list gets longer. The days get shorter. And “someday” slips further and further away.

I’ve lived a lot of life. Built companies. Watched them fall. Rebuilt again. Navigated marriage. Endured divorce. Raised kids. Fought battles. Won some. Lost others. Life never handed me “down time.”

But one day, not long ago—in my 40’s, staring that “someday” in the face—I asked myself the hard question:

“If not now… when?”

The answer was simple: there was no perfect time. There would never be a perfect time. And I was tired of waiting for a window that wasn’t going to open itself.

I thought about that saying I’ve always loved:

“A year from now, you’ll wish you had started today.”

So I said it out loud—“F*ck it. Today is someday.”

The Climb

What followed was one of the most challenging and rewarding chapters of my life.

I didn’t just have to learn how to fly a plane—I had to become:

✈️ A weatherman — able to read the skies like a seasoned forecaster.
✈️ An engineer — understanding the inner workings of every part of my aircraft.
✈️ A mechanic — knowing what could go wrong and how to troubleshoot it.
✈️ A physicist — comprehending aerodynamics and forces most people never think about.
✈️ A pilot — mastering control, navigation, and decision-making under pressure.

And I had to do it while juggling:

✅ Running multiple businesses.
✅ Raising kids with busy sports and school schedules.
✅ Showing up in my relationships.
✅ Honoring my other passions and hobbies.

There were nights when I was dead tired, but still opened up the books.
There were early mornings spent preflighting a plane in cold wind while others were still in bed.

There were weekends sacrificed for long flights and lessons.

But through it all, I had an incredible partner cheering me on. That support mattered more than I can say.

The Punch

Then came the day. Checkride day. The written was passed. The oral was completed. The flight was flown.

And then… the hole punch.

It hit me harder than I expected. That tiny click of the punch was the sound of decades of dreaming finally being realized.

I can now climb into a plane—my plane—and see the world from the sky. Not as a passenger. As a pilot.

Why I’m Telling You This

Look—I didn’t write this to boast.

I wrote this because I know there’s someone out there right now—maybe YOU—who has a dream that feels “too big.”

You think:
“I don’t have time.”
“It’s too late.”
“Life is too busy.”

I used to think that too.

But here’s the truth: You will never have enough time. There will never be a perfect moment. You either choose to start, or you keep pushing it off until the window closes for good.

The lesson?

Start.
Take the first step.
Turn ‘someday’ into today.

If you do, nine months—or a year—or two years from now, you’ll be standing on the other side of your own “hole punch” moment.

And trust me—it will be worth every ounce of sacrifice and struggle it took to get there.

Be relentless. Be bold. Be the one who flies.

Now go punch your own damn hole.

Stay Relentless,

Ryan