An examination of the kinds of questions we ask ourselves provides a window through which to interpret our history and imagine our future. I suggest that there are three kinds of questions—large ones, small ones, and leaky ones. Those that are identified as large and small map onto the value structures we have created for ourselves in higher education. I call these structures caste systems in which some subdisciplines are valued over others, and theoreticians stand above both practitioners and skill teachers. Leaky questions are those that cross boundaries because they cannot be effectively answered by those residing in any one area or at any one level. I argue that leaky questions generate humility, mutual respect, and incentives for collaboration. I trace my own attempts to address all three kinds of questions as a sport philosopher and conclude that our brighter future in kinesiology, including our attempts to address the harms created by the caste system, requires us to see that most of the questions we find interesting are, in fact, leaky in nature.