Never change a winning game; always change a losing one.

Host: The room feels thoughtful, with the soft light of evening casting a warm glow across the space. Outside, the world continues at its usual pace, but inside, the conversation feels like it’s about to touch on the importance of adaptation and strategy in life and work. Jeeny sits at the table, her fingers lightly tracing the rim of her cup, her expression reflective. Jack stands near the window, arms crossed, watching the street below.

Jeeny: (her voice gentle, yet filled with curiosity) “You ever think about how sometimes, the key to success isn’t just in sticking with what’s working, but knowing when to change what isn’t? How the real challenge is in recognizing when a strategy is no longer effective and having the courage to pivot?”

Jack: (glancing over at her, his voice dry, but intrigued) “Adapting and knowing when to change? Yeah, it’s interesting how we often think that consistency is the key to success, but sometimes, the real challenge is in being willing to change when things aren’t working. What made you think about it?”

Jeeny: (nodding slowly, a small smile forming as she shares her thought) “I was thinking about something Bill Tilden said: ‘Never change a winning game; always change a losing one.’ It made me reflect on how crucial it is to recognize when things are working and when they’re not, and then having the wisdom to either stick with what’s working or adjust what isn’t.”

Jack: (pauses, considering her words carefully) “So, he’s saying that when things are going well, don’t mess with it, but when things are falling apart, that’s when you need to be willing to make a change? That the key to success is understanding when to make adjustments and when to stay the course?”

Jeeny: (smiling more deeply now, her eyes steady as she explains further) “Exactly. Tilden’s point is about strategy and timing. Success doesn’t come from being stubborn—it comes from being able to assess the situation and understand what’s working and what’s not. If something is winning, don’t disrupt it. But if something is losing, don’t be afraid to change it, to adapt, and to try a new approach.”

Host: Jeeny’s words seem to settle in the room, creating a shift in the conversation about adaptation, strategy, and knowing when to change. Jack stands still, his expression softening as he processes the deeper message behind Tilden’s statement. The world outside continues its rhythm, but inside, the conversation feels rooted in a more profound understanding of how success is often about knowing when to adjust.

Jack: (his voice quieter now, almost reflective) “I see what he means. It’s about being aware of what’s working and what’s not and having the flexibility to change course when things aren’t going well. Success is about being responsive, not rigid—knowing when to push forward and when to pivot.”

Jeeny: (nodding, her voice calm, yet filled with quiet strength) “Exactly. Sticking with what’s working is important, but being adaptable and willing to make changes when something isn’t working is just as crucial. The best strategies are the ones that evolve and adjust to circumstances.”

Jack: (pauses, a small smile forming on his face as the idea settles in) “It’s liberating, isn’t it? To realize that success doesn’t come from stubbornly holding on to one thing—it’s about being smart enough to know when to change, when to adjust, and when to trust that something new might be the key to progress.”

Jeeny: (smiling warmly, her voice gentle, yet filled with wisdom) “Exactly. Growth and success come from flexibility—being able to adjust when things aren’t going as planned and having the confidence to make those changes. It’s not about failure; it’s about learning and moving forward with a new strategy.”

Host: The room feels lighter now, as though the conversation has shifted into a deeper understanding of strategy, adaptability, and growth. Jack turns from the window, his posture more relaxed, his thoughts clearly reflecting on the importance of knowing when to change. Jeeny watches him, content in the realization that success doesn’t come from never changing, but from knowing when change is necessary to keep moving forward. The world outside continues its rhythm, but inside, there’s a shared understanding that the key to lasting success lies in being willing to change what isn’t working and stick with what is.