As a recently retired academic leader—a former department chair, division head, dean, vice president, provost, and interim president—I have had time to reflect on the joys and woes of leadership at a small liberal arts college. What successes did I have? What failures? What could I have done differently that would have made my college a better institution? “Too soon old and too late smart,” an old saying goes. But there is some value in ex post facto assessments, yes?