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This paper presents an in-depth multiple case study, which derives from our mixed-methods, longitudinal research with 141 school/district leaders (2008–2020) about their pressing leadership challenges. Here, we feature principals’ internal experiences to spotlight how they made sense of these challenges and how they helped others manage complexity and change. More specifically, we amplify the social-emotional and developmental capacities needed for leading change and how these capacities are inherent to how leaders successfully manage complexity and ambiguity. We discuss implications for leadership learning/preparation in our COVID19 world. Our research concludes that a holistic approach to leadership, which honors and unites the external world of action with inner world of reflection, better serves work-life balance and ultimately the performance of principals.