Why Winning Is Overrated and What Actually Matters Instead
Series 4, Part 1 of Why Winning Is for Beginners
Estimated Reading Time: 2 mins
We’re taught to chase wins like they’re the whole point.
Gold stars in elementary school turn into six-figure launches. We think: If I win, I matter. If I win, I’m safe. But here’s what most high-achievers eventually realize:
The win feels good — until it doesn’t.
You hit the goal. But the inbox refills. The next demand arrives before you even catch your breath. The win that was supposed to change everything… just moves the target.
I remember one of my biggest wins: negotiating a long-term vendor contract at a price most people thought was impossible. The relationship became so valuable, the CEO flew us out to explore a deeper partnership the following year. He still jokes I got the best deal they’ve ever given.
But I’ll never forget a conversation we had months later. I told him, “You think the next level will feel better… but really, it’s just bigger challenges.”
He paused, then said: “Biggie said it best — mo’ money, mo’ problems.”
We laughed. But the truth hit hard.
The win didn’t save me. It just changed the game.
The Problem Isn’t You
It’s the game.
Most of us are playing finite games built to end in “win or lose.” But leadership, impact, and legacy aren’t like that.
They’re infinite games; the point isn’t to win. It’s to keep playing. To grow deeper, lead better, and shape a world that outlasts you.
And that changes the question:
How do I win faster? → How do I play well, for the long haul?
Here’s What I’m Learning
Winning is for beginners. Playing well is for legacy-builders.
This series is about shifting from short-term success to long-term significance — from the chase to the change. Before we go deeper:
Ask yourself — what game have I been playing? And has it truly been worth it?
Ready to Shift the Game?
If something in you has been questioning the hustle, the pressure, or the constant chase — you're not alone. You weren’t made to play someone else’s game. And you definitely weren’t made to burn out winning it.
Download “Game Changer: A Self-Audit for Purpose-Driven Leaders Who Want to Play Differently”
This guided reflection will help you get radically honest about:
The game you’ve been playing
What it’s been costing you
And how to realign with what actually matters
Because when you know your game, you can change how you play.
