This case describes a strategic planning process initiated by the division of student affairs at a small, private college. It presents several issues related to institutional identity, strategic planning initiative development, faculty and staff buy-in and stay-in, and the changing landscape of higher education. The case is designed for usage in educational leadership programs and is particularly pertinent to provoke discussions regarding leading from the middle, leadership for institutional change, and moral and ethical leadership. Students in educational leadership enrolled in student affairs leadership and administration courses, budgeting or strategic planning, or organizational theory courses can engage in discussion using multiple aspects of the case.