Pin the Tail on the Donkey

Why Great Leaders Learn to Think in Paradox

June, 2026

It’s a childhood party game. The kind you played at birthday parties before liability waivers, excessive party bags, and curated experiences.

Each child gets blindfolded, handed a tail, spun around just enough to lose all sense of direction, and then released toward a wall with a picture of a donkey. The goal? Pin the tail in exactly the right spot.

Closest wins.

I tried very hard to win at this game.
I never did.
Which, in hindsight, may have been excellent preparation for leadership.

Because hidden inside this simple party game is a surprising lesson:
Get it right. Hit the exact spot. Win.

We carry that into adulthood. Into leadership.

We want the perfect decision, the precise strategy, the one move that proves we know what we’re doing. We’re still trying to pin the tail…only now the stakes are higher, and the donkey has a budget.

But here’s the problem: in real life, we’re still blindfolded.

Leadership is rarely about precision; it’s about navigation. And yet many of us have been trained into binary thinking: right or wrong, success or failure, nailed it or missed it. No wonder we feel the pressure.

Leadership doesn’t live in “either/or.” It lives in paradox.

A decision needs to be made. Waiting drains momentum.
But you don’t have all the information, and deep down, you know it.

Do you decide quickly or wait for clarity?

The paradox: you must act decisively, while staying humble enough to admit you might be wrong and change course when needed.

Try resolving that with a blindfold and a pin.

The best leaders don’t obsess over getting the tail in the exact spot. They remove the blindfold, slowly and imperfectly. They do that by asking better questions, inviting perspective, and resisting the urge for premature certainty.

They understand that wisdom isn’t about getting it right on the first try. It’s about seeing more clearly over time.

I’ve learned (often the hard way) that my quickest decisions are not always my best ones. But when I pause, sit in the tension, and allow for layered thinking, I get closer, not just to the right answer, but to the right understanding and better discernment.

Turns out, leadership isn’t about winning the game. It’s about realizing the game was flawed to begin with.

So, the next time you feel the pressure to get it exactly right, remember you might still be holding the tail, standing in the wrong direction.

And that’s not failure.
That’s leadership.

Todd Rutkowski

Read more reflections like “Pin the Tail on the Donkey " in my free ebook called “Lifelines.” Get Lifelines