This article provides a retrospective account of 25 years of qualitative and quantitative inquiry into the psychological characteristics, leadership strategies, and attributes that education deans bring to their positions and the contextual factors that contribute to their staying power. Over multiple, mixed-methods studies, some 423 education deans shared their views through interviews, vignette responses, situational self-analyses, and surveys. The main results indicated that a mature ego is at the centerpiece of effective leadership, allowing deans to invoke different dimensions of their leadership to adapt proficiently to their professional environment. Their professional identities, attributes, and capacities, stemming from their mature ego, contributed to job satisfaction and longevity. Relevant professional development arose as worth considering.