It would exacerbate the tragedy of the current economic situation if no lessons were learned from it which would contribute to future growth and prosperity. That applies equally to the business sector and to the education sector. This is not to imply that many current, effective superintendents do not ask the very questions posed in this essay; Routinely, they do! However, teachers have long cherished the "teachable moment" in their classrooms, where reality creates a unique opportunity for true learning. Hopefully, the unfortunate reality of today's economic milieu can provide a "teachable moment" for prospective superintendents in university preparation programs to engage in ongoing reflection upon, and examination of, the schools and districts they aspire to lead.