What skydiving taught be about bowling (and life) | Executive Coaching | Six and a Half Consulting
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What skydiving taught me about bowling (and life)

What skydiving taught me about bowling (and life)

Several years ago I formed a club called The Challenge Challenge.

The premise is simple: every 6 to 8 weeks, a group of friends and I get together to do 1) learn something new and 2) push us out of our comfort zones.  Every challenge rotates ownership and every challenge is held in complete secrecy by its organizer until the moment the other participants arrive. Every challenge, therefore, is a complete surprise.

In the past some of the challenges have included a double dutch jump rope class, tap dancing lessons, a virtual reality scavenger hunt, a unicycling course, a float house, and a Chinese medicine healing retreat.

The only rules at The Challenge Challenge are that each participant shouldn’t pay more than $100 per challenge and that organizers won’t put participant’s physical safety in risk.

Because my risk tolerance is on the higher side, recently I’ve been itching for a slightly more extreme activity. But, because rule #2 of The Challenge Challenge prohibits physical endangerment, I knew this time I would have to go it alone.

As a much younger man, I had bungee jumped over rocky canyons, paraglided over alpine forests, and once even scuba dived with sharks.  But I had never skydived. 

So, a few weeks ago, I made the decision to jump.

Immediately after I made my deposit, however, I froze in my tracks like I never have before.

Making the Jump

No longer the young, intrepid man I once was, the prospect of jumping out of a plane became an all consuming terror. And for the two weeks leading up to the jump, I watched myself spiral in a never ending loop of fear (there is no reason to risk my life for this) and shame (if I don’t jump, what would that make me?).

This loop was relentless.  On several occasions I woke up in the middle of the night in a panic.  “Why was I called to do this?  What a stupid idea!  I’ll just forfeit my deposit and quit” I would think to myself.  At the same time, polar thoughts like “you’ll be disappointed in yourself if you don’t jump” and “because you are so afraid, you must” appeared.

For 14 days I was entirely consumed with the idea of jumping out of a plane — and the risks of either going through with it or the consequences of not.  During meetings, driving my car, in conversations with anyone.  All I could think about was jumping out of a plane. 

On the day before my jump I found myself down yet another Google rabbit hole of “skydiving disasters” when I decided to go for a long walk by the ocean.  PJ, my business partner, often tells me that the ocean has the answers.  Like so many other times, she was right.

After an hour or so replaying the same conversation I had had with myself 1000 times for a fortnight, I sat down on a log and closed my eyes. 

No sooner than my eyelids touched, the word BOWL appeared on the backside of my eyes.



What’s the Lesson?

Lean into Love

In that instant I new that despite my paralyzing fear, I had to jump the next day.  And between now, then, and the ride back down to Earth, all I was supposed to do was BOWL.


For the next 24 hours, I can’t say that my fear subsided much.  And as I was yanked out of the plane by my tandem instructor it most certainly didn’t.

But the instant I began free falling and eaten alive by an indescribable fear, an incredible — arguably life altering —  thing happened as I practiced BOWLing.

Like a bolt of electric hot lightening, I observed that the underpinning of my fear was a desperate attempt to control my situation — an absolutely absurd attempt given the fact that I was strapped to the belly of someone else falling towards the ground at 120 mph.  For weeks, I saw how my fear of jumping was really being driven by a futile attempt to control something I had zero influence over. 

Indeed, the very lesson I was being demanded to learn was that I needed to let go.  And that the more I fought my own desperate attempt to control this situation — any situation — the more fear I’d have.

So, in that very second, I let go.  I released.  I surrendered to not knowing and to not having control.  I simply trusted the process, guided by love.

And the moment I did that, pummelling towards the ground with my cheeks flapping like a sail in the wind, I started laughing uncontrollably.   

And while my laughing has subsided in the weeks since my jump, the lesson hasn’t: underneath fear, when all attempt of control are relinquished, the world is actually a very, very funny place.

Casey Miller

Casey A. Miller, Co-Founder of Six and a Half Consulting, is on a mission: to use his big heart and gift of truth telling to help organizations, communities, and relationships thrive.

  • Scott Orth
    Posted at 19:48h, 09 April

    Great lessons learned. The beauty is that without having to jump out of a plane, I can learn vicariously from your experience (albeit in a much smaller way). And life is guaranteed to present me with my own versions of ‘jumping’ and my own opportunities to practice moving from fear and control, to love and acceptance. Thanks for sharing Casey!