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This study explores how school leaders in China interpret and enact holistic development (HD) under the Double Reduction Policy (DRP). As global education shifts toward whole-child development, China’s DRP attempts to reduce academic burden while fostering student well-being and multidimensional growth. Using constructivist grounded theory, we conducted interviews with 12 school leaders across diverse school contexts. Analysis yielded a five-domain conceptual model capturing the enactment of HD through relational, ethical, and context-responsive leadership. We introduce the metaphor of “rainy-day leadership” to describe adaptive strategies under conflicting policy signals. The study contributes to policy enactment theory by reframing school leadership as interpretive, moral, and situated work in complex reform environments.