As the COVID-19 pandemic moves into its next phase, academic leaders are facing a new set of organizational challenges. A return to pre-pandemic programs, structures, and processes is unlikely at best. A changed environment is confronting an old institutional model. Students are expressing a preference for a more flexible college experience, one more individualized and supportive. The world of work is evolving, inviting a closer tie between college and career. After the past three semesters, faculty and staff have found different work styles challenging yet inviting. A new fiscal environment presents both opportunities and changed priorities for both students and colleges.