This quote highlights a profound observation about the consequences of overplanning, particularly in creative or uncertain ventures. It suggests that those who overplan may not necessarily avoid failure; instead, they may delay the inevitable realization that their plans are flawed. Overplanning can create a false sense of security, where time and resources are consumed in meticulous preparation, yet when things do go wrong, the psychological impact is more severe. The feeling of failure can be harder to digest because a greater emotional and intellectual investment was made in the plan's perceived certainty.

Reflecting on this, I see a tension between the desire for control and the acceptance of uncertainty that is central to creativity and innovation. Overplanning often stems from a fear of risks and mistakes, but ironically, it doesn't prevent failure—it prolongs the resistance to it and intensifies disappointment. Creativity, as suggested by Ed Catmull in "Creativity, Inc.", thrives in environments where experimentation and iteration are embraced, not stifled by rigid plans. Mistakes are part of the learning process.

Embracing uncertainty and accepting that failure is inevitable can foster resilience and lead to better outcomes in the long term. By not overinvesting in detailed predictions about the future, one can adapt more fluidly when changes occur. This quote is a reminder to balance preparation with flexibility, and to manage expectations so that setbacks are viewed as opportunities for growth rather than definitive failures. In essence, it's about cultivating a mindset that places courage and adaptation above rigid control.