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This paper synthesizes learnings from our mixed-methods, longitudinal research with 141 educational leaders (2008–2021) about their most pressing challenges, how they address them, and their internal experiences of leading change. Here, we offer conceptual scaffolding to support leadership and leadership development for even more intentional stewardship and transformation within individuals, teams, organizations, and communities. In particular, we argue that—taken together—adaptive/technical, social emotional, and developmental lenses can help leaders engage in cathedral thinking—to build their own and others’ capacity over time to manage current and future ambiguities, complexities, uncertainties, and possibilities. Implications highlight vital needs for leadership preparation, curriculum, and workplace professional learning that links the outer world of action with the inner world of meaning making.