<p>For much of the twentieth century, and indeed before the establishment of the state, religious orders were central to establishing and managing second level schools in Ireland (Republic). As a result of ecclesial, societal and economic change dating from the 1960s, these Catholic second-level education providers began to question their specific role, unique identity and possible future. Issues such as a decline in vocations, changes in religious life, legislative developments, and the growing influence of Vatican II, contributed to this questioning. By the mid-1990s, this questioning led many religious congregations involved in second level education into a discernment process of planning for the future. The solution that emerged from the ensuing deliberations—the proposal to establish lay led Trusts—presents a major paradigm shift for Catholic education in Ireland. This paper explores the story behind this major paradigm shift. Employing the perspectives of those most closely involved, it explores the decision-making journey, the hopes for this new paradigm and the question of ‘where to from here’? Findings indicate that initial hurdles such as legal complexities and a distinct lack of enthusiasm gave way to a practical trusteeship model growing in confidence. They also indicate that highly effective characteristics of the journey such as collective discernment to plan for an uncertain future diminished once the Trusts were established. Whereas the findings are anchored in the Irish context, they are of interest to Catholic providers and policy makers worldwide engaged in planning for the future of Catholic education.</p>