A photo was recently sent to me and it instantly took me back more than 30 years.
It’s my dad, and a family friend and me, water skiing, with my dad standing on our shoulders. It’s the kind of moment that feels almost unreal when you look at it now. Equal parts bold, chaotic, and somehow perfectly executed.
Even back then, I knew my dad and I were wired differently.
He was the showman. The spark. The one who could walk into any situation and raise the energy. The kind of person who would step out in a half Hartford Whalers, half badminton shorts outfit and say, “Let’s go skiing and I’ll stand on your shoulders.”
And me?
I was already the planner.
Before we even got near the water, my mind was racing with questions.
How long do the ropes need to be?
What speed do we need to go?
How are you going to climb up?
When are you going to climb up?
How are we going to brace?
Who’s on which side? (I’m left-handed, so that matters.)
Where he saw possibility, I saw variables.
But that’s exactly why it worked.
We did what great teams do, even if we didn’t realize it at the time. We slowed down just enough to think it through. We practiced the mechanics of the climb. We tested positioning. We made small adjustments before attempting something that, in hindsight, had no business working on the first try.
And then we went for it.
The stunt worked. Not just for a moment, but long enough to feel like we had actually pulled it off. We even managed a few loops at about 30 miles per hour.
Then came the question we hadn’t planned for.
My dad looked down and asked, “How do I get down?”
That pause is burned into my memory. Not because it went wrong, but because it highlighted something important. Planning gets you far, but it rarely covers everything.
I looked up and said, “We keep going and you jump.”
I still remember the look in his eyes.
It was a mix of trust, excitement, and maybe just a hint of realization that this part of the plan had been left to improvisation.
That moment has stayed with me ever since.
Not because everything went perfectly, but because of what it took to make it happen in the first place.
When I think about teams, leadership, and building something meaningful, I come back to that day more often than you might expect.
To do something remarkable, you need a mix of people and perspectives.
You need the creative spark. The person willing to say, “Why not?”
You need the promoter. The one who brings energy and pulls others in.
You need the planner. The one asking the hard questions before things get risky.
You need practice. Repetition. A willingness to test and adjust before going all in.
And you need adaptability. Because at some point, something won’t go according to plan.
The magic happens when those elements come together, not when one dominates the others.
If we had failed that day, I’m convinced I would still remember it just as clearly.
Because we would have tried again.
That’s the part that matters most. The willingness to attempt something ambitious, learn from it, and keep going until you get it right.
It’s easy to look at a snapshot and focus on the outcome. A perfect moment captured in time.
But behind every one of those moments is a blend of personalities, preparation, trust, and a bit of courage to figure things out as you go.
Some lessons stick with you for life.
This was one of them.
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