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Curiosity #87 - Running Toward the Edge

Jun 03, 2026
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🎤 Quotable quotes: “This feels like a terrible idea."

— Nick, approximately three seconds after running off a mountain in Lake Como

 

This week, I found myself standing on the side of a mountain overlooking Lake Como.

About to go paragliding.

Now, if you know me, you know this should not have happened.

I don't love heights.

Let's just say the Grand Canyon and I have a complicated relationship. Standing near the edge makes my stomach do gymnastics that would earn high scores from Olympic judges.

And yet there I was.

Strapped to a paraglider.

Preparing to run off a mountain.

Voluntarily.


🏟 Why This Matters for You

Here's the strange part.

I wasn't afraid.

Or at least not nearly as afraid as I should have been.

A few steps later, we were airborne, floating nearly a mile above Lake Como.

And somewhere between the takeoff and the landing, I realized something.

The difference wasn't courage but trust.

At the Grand Canyon, the thing that made me nervous wasn't the height.

It was me - and my balance, footing, confidence.

Paragliding was different.  I wasn't alone.  I was attached to a professional who had done this hundreds, maybe thousands, of times.

I trusted him.

And that trust changed everything.  The risk didn't disappear.  My relationship to the risk did.


🪂 Ted Lasso Knew This

One of Ted's greatest gifts wasn't making people braver.

It was making them feel supported enough to try.

Roy didn't become a coach because coaching suddenly felt safe.

Jamie didn't change because growth became easy.

Rebecca didn't take risks because uncertainty disappeared.

They moved forward because they trusted the people around them.

Trust doesn't remove the possibility of failure.

It makes the possibility of success feel worth pursuing.


🤝 What This Means for You

I've always considered myself fairly risk averse.

Which is why, looking back, one thing still surprises me.

I don't think I ever had it in me to start a company by myself.

I was happy being employee number five. Employee number eight. Employee number three.

Founder?

That felt different.

Too risky.

Too uncertain.

Too many cliffs.

And yet Marnie and I started a company together.

Then scaled it.

Then sold it three years later.

Not because I suddenly became a risk taker.

Because I trusted my co-founder.

Trust didn't eliminate the risk.

It gave me the confidence to face it.

That's a lesson that extends far beyond entrepreneurship.

Sometimes the biggest opportunities in life sit on the other side of a leap you're not ready to take alone.

The question isn't always:

"Am I brave enough?"

Sometimes the better question is:

"Who do I trust enough to take this leap with?"


🏁 Final Thought

As we floated over Lake Como, I kept thinking about how strange it was that I felt calmer thousands of feet in the air than standing at the edge of the Grand Canyon.

Then it hit me.

Fear often shrinks when trust grows.

Ted Lasso never taught people to be fearless.

He taught them to believe in each other.

And sometimes that's enough to get you running toward the edge.


— Nick & Marnie
Your tea sipping, risk calculating, occasionally mountain-jumping friends

 

More leadership musings


🍪 Biscuits with the Boss: 

Icebreaker time:

What's something you've done that surprised you because it seemed too risky beforehand?

Now the tougher question:

Was it courage that got you there?

Or was it trust?


🌎 This week in Here - There - Every F’ing where 

Scroll back up and check out Lake Como again! That's where you could find Nick this week. Amazing!

As school starts to wrap up for the year, Marnie met with Talbot County's superintendents advisory board. It was a great day where she met some very cool people :)

Believe! 

Nick & Marnie

 


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