Whether as parents, supervisors, or teachers, so many of us are in fact Jewish educators. I believe that at the very core of these roles, there is a tension between the responsibilities of transmission and transformation. Do we strive to raise children/followers (banim) or builders/innovators (bonim)? In my talk, I argue that the way we choose to engage with this enduring dynamic between the two paradigms has much less to do with ideology and more to do with personality and dispositions. I challenge listeners to use this lens to reflect thoughtfully on our choices and goals.