This chapter explores the foundational question of “why” engage in mission leadership, arguing that understanding the purpose empowers leaders to navigate the many “hows.” Drawing from the wisdom of experienced Catholic educators, the chapter posits that the “why” of leadership is enacting Christ’s vision within the distinctive mission of the Catholic school and its unique identity within a multiplicity and variable learning environments. This mission is situated within a context of rapid change, necessitating a paradigm of leadership that fosters continuous learning, expansive thinking, and collective aspiration. The chapter outlines three key motivations for the work: the privilege of personal growth, the call to authenticity and alignment with vocation, and the challenge of integrating scholarship with organisational and community expectations. It emphasises that mission leadership is not an abstract phenomenon but deeply connected to the identity, relationships, and practices of the Catholic school community. The significance of the challenge is made clear: “One must recognise that, more than ever before, a Catholic school’sCatholic school job is infinitely more difficult, more complex, since this is a time when Christianity demands to be clothed in new garments, when all manner of changes have been introduced in the Church and secular life, and particularly, when a pluralist mentality dominates and the Christian GospelGospel is increasingly pushed to the side-lines” (Congregation for Catholic Education [CCE], 1977, para. 60).