The most pressing challenges facing American Catholic educational leaders today are funding, Catholic identity, and leadership. Funding is the most pressing issue and it involves recruiting and retaining teachers, balancing affordability with quality, and justifying the worth of Catholic schools. Catholic identity issues include reconciling the tensions between Catholic school vision and 21st century reality. Leadership issues center on the overwhelming job description, lack of system support and collaboration, and inadequate preparation and succession. To meet modern challenges, the author recommends that Catholic schools act more like a system, innovate, fight for government funding and enlarge private bequests, become more international in focus and flavor, and be more intentional about leadership succession.