Trust Free Fall Leadership

What Skydiving Taught Me About Leadership.

We are often told that leadership is about being in the cockpit hands on the controls, eyes on the horizon, and responsible for every maneuver. But lately, I’ve been reflecting on a different kind of leadership: the kind that requires you to let go.

I call it the “Tandem Jump” approach to growth.

The Adrenaline of Letting Go
Years ago, I did a tandem skydiving jump. If you’ve ever been, you know the sensation: that moment at 10,000 feet where the door opens and you realise you are about to fall. It’s pure adrenaline, yet, strangely, I felt completely safe.

I wasn’t the one checking the altimeter.

I wasn’t the one worried about the parachute’s tension.

I was simply following instructions and going for the ride.

My instructor did the heavy lifting; he even filmed the experience while ensuring we stayed on course.

In that moment, I wasn’t the expert. I was the passenger in a massive lesson in trust.

Leadership is a Lesson in Surrender

In professional life, we often feel like we have to be the instructor. We feel the pressure to “film the moment,” “steer the chute,” and “stick the landing” all at once.

But true growth and true leadership often starts with the humility to be the one strapped to the expert.

Here is how “free falling” actually builds better leaders:

• Active Trust over Passive Control: Trusting a mentor [or in my case, God] isn’t “doing nothing.” It takes immense discipline to stay calm and follow instructions when the wind is rushing past you at 120 mph.
• The Power of Perspective: When you aren’t bogged down by the mechanics of the “drop,” you can actually look around. You see the world from a height that those on the ground can’t imagine.
• Learning Through Observation: By watching how an “instructor” handles the pressure, you internalize the skills you’ll eventually need when it’s your turn to lead others through their own free fall.

The Ride of a Lifetime

I see my journey now as that tandem jump. I am coming along for the ride, trusting that the “Instructor” [in my case, God] has the parachute handled. It turns the terrifying “free fall” of uncertainty into an exhilarating experience of safety.

Whether you are leading a team or navigating your own personal development, remember: you don’t always have to be the one pulling the ripcord. Sometimes, the most courageous thing a leader can do is trust the one who is looking after them from 10,000 feet.

What area of your life or work feels like a “free fall” right now, and how would it change if you shifted from “pilot” to “passenger”?

Roaming Chaplain