Last night, I played Monopoly with my eight-year-old son. As I won and he landed on one of my properties, unable to pay the rent, his frustration was clear. "If you win, I lose," he said. "That’s a competition, not just a game."
It made me realize that he wasn't just reacting to the game; he saw it as a contest with clear winners and losers. In his mind, losing wasn’t just part of the game, it was a failure.
This mindset is something I often see in business leaders. Many view every project, pitch, or decision as a win or lose competition. Whether it’s landing a client, meeting a target, or outshining the competition, business owners can get caught up in the pressure of winning. But when they only focus on the outcome, they miss the bigger picture.
In both business and life, it’s not just about winning. The most successful leaders understand that setbacks aren’t failures, they’re opportunities to learn, adapt, and improve. Winning is just one part of the process, but it’s the lessons learned from losing that lead to true growth.
When I explained this to my son, I said, "The game isn’t about always winning. Every time you play, you get better." But he wasn’t convinced. He wanted to win, and he wanted it now.
What struck me was his determination. The next morning, he set the game back on the table, ready to try again. "This time, I’m going to win," he said.
That determination is something all business leaders can learn from. Success isn’t about avoiding failure. It’s about showing up, learning from each experience, and evolving. The most successful leaders don’t shy away from losing, they embrace the lessons that come with it, refine their strategies, and keep going.
Whether in business or a board game, the game isn’t over until you decide to stop playing. The key to success lies in persistence, learning, and courage to face both the wins and the losses.
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