Skydiving, Serendipity, and the Boxes We Build for Ourselves

In 2013, a few days before my birthday, I was running errands—the usual grind. I remember sitting in the parking lot of a bank, weighed down by a nagging thought: How should I celebrate?

Suddenly, I remembered something I’d always wanted to do: skydive.

My first reaction was the same as always: Someday I’ll do that.

But then I caught myself. When is “someday”? It’s not on any calendar I’ve ever owned.

At that moment, I realized I had no real excuse. I lived in a major metro area, certainly big enough to support a skydiving operation or two. I had disposable income from my work as a software architect and my nights and weekends gigging as a magician.

Why not today?

That thought—someday could be today—ended up being the genesis of a kind of rebirth. The day I discovered the difference between existing and living.

The First Jump

A quick web search led me to Skydive Spaceland, and I booked a tandem jump for the following weekend.

The days leading up to the jump, I was full of bravado. On the day itself, I was joined by friends and family—a few courageous enough to jump with me.

We signed waivers, sat through instructional videos (and disclaimers), met our tandem instructors, were geared up, and crammed into the plane.

At altitude, my bravado began to evaporate. Conversation wasn’t possible over the roar of the engines, and without a phone to distract me, I sat silently with my thoughts. Watching the world shrink beneath the window was sobering.

At around 6,500 feet, the plane throttled back and a red light came on above the door. One man—someone I assumed was staff—crouched by the open door, checked the light, and then… woooosh. He was gone.

Not staff. Not a tandem student. Just a guy jumping for fun.

It was horrifying. But the plane climbed on.

Fear, Then Flight

By the time it was my turn at the door, I was convinced this was the worst idea of my life. I braced for terror, told myself, “a minute is nothing.”

And then—

We weren’t falling. We were flying.

There’s really no other way to describe it. Zero terror. Zero rollercoaster drop. Just play, in the sky.

For once, my brain—the one that never shuts up—was silent. I was 100% present, completely in the moment.

Under Canopy

Once the parachute deployed, it was a whole new experience.

It’s silent. Peaceful. A 360° panorama. Clouds at arm’s reach. I tugged on the controls, playing with turns and spirals, before my tandem instructor guided us to a precision landing in front of the waiting cameraman.

Afterward, they tried to upsell me on another tandem jump. Savvy move—who wouldn’t want to do it again?

But I had seen something else: the fun jumper.

Not staff. Not a one-off thrill-seeker. Just someone who played in the sky because he wanted to.

And I realized: that could be me.

Beyond “One More Ride”

Instead of buying another ticket, I signed up for the license program. A week later I made my first solo jump. A few weeks after that, I had my license.

Skydiving taught me three important lessons that go far beyond the drop zone:

1. “Someday” isn’t on the calendar. If you want to make it happen, make it happen. A goal is a dream with a deadline.
2. We put ourselves in boxes of our own construction. There are more possibilities than the ones we assume.
3. Everything cool is on the other side of fear.

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Postscript: Being New Again

I was a below-average canopy pilot, and I botched most of my first 80 landings. I couldn’t control my fall rate very well.

I had forgotten what it was like to be new at something. That’s an important skill to (re)learn, because as we get older, we tend to give up too quickly.

Skydiving reminded me that stumbling through the awkward phase is how we grow—whether in the sky or anywhere else.