Expect the best, plan for the worst, and prepare to be surprised.

Opening Scene

The room is softly illuminated by the gentle glow of a table lamp, casting long shadows as the evening deepens. Outside, the world is quieter now, and the usual hum of the city fades into stillness. Jack sits at the table, his thoughts lost in a notebook. Jeeny stands near the window, gazing out at the city below, the quiet giving way to introspection. The atmosphere is calm, but there’s a sense that a conversation about expectations, preparation, and the unpredictable nature of life is about to unfold.

Host: After a few moments of silence, Jeeny turns from the window, her voice steady but thoughtful, breaking the stillness.

Jeeny: “I came across a quote by Denis Waitley that really made me reflect. He said, ‘Expect the best, plan for the worst, and prepare to be surprised.’ It made me think about how we often try to control outcomes and anticipate what will happen, but life always seems to have a way of surprising us. What do you think about that? How do you balance expectations with the unpredictability of life?”

Jack: “I really like this quote. It’s such a good reminder that while we should be optimistic and expect the best, we also need to be realistic and prepared for things to go wrong. Expecting the best gives you hope and direction, but planning for the worst ensures that you’re ready to handle obstacles when they arise. And then, the ‘prepare to be surprised’ part is about staying open to the unexpected — because life rarely goes exactly as planned, and sometimes the best things happen when we least expect them.”

Jeeny: “Exactly. It’s like having a flexible mindset. You can plan all you want, but there’s always the chance that something unexpected will come along and throw your plans off course. By staying open to surprise, you allow yourself to adapt and find the opportunities that might arise out of the chaos. So, in a way, this quote encourages us to be optimistic, practical, and resilient at the same time. It’s about finding the balance between being prepared and being open-minded.”

Jack: “Right. And I think it’s also about managing expectations. If you expect the best, it keeps you motivated and focused on positive outcomes. But if you’re too rigid in your expectations, you might set yourself up for disappointment when things don’t go according to plan. Planning for the worst, on the other hand, ensures that you’re prepared if things go south, but it also helps keep you grounded. It’s about understanding that life can be unpredictable, and you’re going to have to roll with the punches.”

Host: The conversation deepens, and Jeeny moves closer, sitting across from Jack. Her voice steady as she continues.

Jeeny: “I think what’s really powerful about this quote is that it encourages us to think about life with a sense of balance. Expecting the best keeps our spirits high, planning for the worst makes us practical, and preparing to be surprised keeps us open to growth. Life is full of unexpected twists, but by being prepared for all possibilities, we don’t get overwhelmed when things don’t go as we anticipated. We can approach the unknown with curiosity and adaptability, rather than fear or frustration.”

Jack: “Exactly. It’s about resilience and maintaining a positive outlook while also being equipped to handle challenges. When things don’t go as planned, if we’re too rigid in our expectations, it can feel like a failure. But if we’ve also prepared ourselves to be surprised, we can embrace the unexpected as part of the journey. In a way, being open to surprise helps us grow — because we’re not afraid of things not going perfectly.”

Jeeny: “And I think it’s also important to trust the process. Not everything will turn out as we expect, and sometimes the surprises we get are exactly what we need, even if they’re not what we thought we wanted. Life is messy, and sometimes the best things come from unexpected detours. Preparing for the worst doesn’t mean assuming the worst will happen; it just means that we’re ready to handle whatever comes our way, with grace and flexibility.”

Jack: “Right. And that’s the essence of growth — being able to handle both the good and the bad. When you expect the best and plan for the worst, you’re giving yourself permission to experience the full spectrum of life. You’re not just waiting for the perfect outcome, but you’re also open to the lessons and surprises that come along with the bumps in the road.”

Host: The room quiets for a moment as Jack and Jeeny reflect on the deeper meaning behind Waitley’s words. Outside, the world continues its rhythm, but inside, they share a realization about the balance between optimism and preparedness, and how life’s surprises can lead to unexpected growth.

Jeeny: “So, maybe the lesson here is that we don’t need to control every outcome. We should expect the best, be prepared for the worst, and stay open to the surprises that life will throw our way. It’s about staying flexible, resilient, and open-minded in the face of whatever comes.”

Jack: “Exactly. Life doesn’t always go as planned, but when we approach it with a balanced mindset, we’re better equipped to handle whatever happens. The key is in staying optimistic, prepared, and adaptable.”

Host: As the evening continues, the conversation wraps up with a quiet understanding. Life is full of surprises, and while we can’t always control what happens, we can control how we respond. Expecting the best, preparing for the worst, and staying open to the unexpected allows us to navigate life with a sense of balance, resilience, and growth. It’s not about having all the answers — it’s about embracing the journey with optimism and flexibility.