What Skydiving Taught Me About Leadership

Posted 2 days ago - Nov 1, 2026

From: JJ Simmons
What Skydiving Taught Me About Leadership

A few years ago, for my 41st birthday, I decided to jump out of a perfectly good airplane.

Some of you are thinking, “That sounds amazing!” Others are wondering why a birthday cake wasn’t good enough! I wanted an adventure, and skydiving seemed like a good idea. At least while I was still on the ground.

My friends Devon and Danielle picked me up in a car filled with balloons, with a birthday soundtrack playing. They made me feel so loved. They were also very clear about their role: moral support. They had absolutely no intention of jumping with me!

Then I met Eren, my instructor. She helped me get ready, walked me through what would happen, and listened to my concerns.

But when we reached 14,000 feet and it was time to jump, I suddenly had questions.

What am I trying to prove here? Is this a midlife crisis? And why does Eren have a helmet and I don’t?

We jumped anyway.

I had one job…pull the handle when it was time to open the parachute.

Y’all. I forgot.

I was so focused on the videographer in front of me that I completely missed what I was supposed to do. Eren tapped my hand, trying to get my attention. Then she pulled the handle herself, and we began floating. It was beautiful.

After we landed, I realized what had happened and I was so disappointed in myself. Eren reassured me: “That’s what I’m here for.”

My friends were cheering, and I left feeling like I could do anything. But think about how much help went into that moment. People encouraged me, prepared me, and stepped in when I needed them.

Maybe you’ve been offered a leadership role and wonder whether you’re ready. Maybe you’re starting over, returning to school, or feeling drawn to serve in a new way. You can see the next step, but you also have a whole list of questions.

What if I get it wrong? What if I’m not good at this? What if everyone finds out I’m scared?

Psalm 56:3 gives us a simple prayer for moments like those: “When I am afraid, I put my trust in you.” (NIV)

There is room in that verse for fear. We can bring our questions to God while choosing to trust Him. You don’t have to wait until your stomach settles or your voice stops shaking to pray, “Lord, help me take the next step.”

And pay attention to the people who can help you along the way. Mentors…friends that can pray with you… Asking for help is part of growing into what God has placed before you.

That matters when you’re used to being the person everyone else depends on. You need encouragement and guidance, too. Give someone the opportunity to show up for YOU!

Make the phone call. Ask someone to mentor you. Find out what that class requires. Let yourself be a beginner who still has things to learn.

Following Jesus involves trusting Him with outcomes we cannot control. We can prepare thoughtfully, listen to wise counsel, and move forward knowing His presence goes with us, even when the road is difficult.

So what is one step you’ve been putting off because you’re afraid?

Write it down. Pray about it. Tell someone who will encourage you and help you prepare.

Take the leap!

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