Asking coaches about whether winning ever gets old always straddled a line for me. It felt like a cookie-cutter question, the kind of low-hanging fruit that led to some canned or cliche answer. I used to laugh at it because, at its face value, winning is what they're supposed to do. How could it, in any sense, ever feel bad?
Thinking about the question, though, changed my perception and understanding about what winning meant to a team. At every level, a coach or player is programmed to win to the degree that the negative of losing feels more intense, and I can't count the number of times I heard someone say, "Losing feels worse than winning feels good.