Like many regional institutions of higher education, Southern Oregon University (SOU) has been called to balance the imperatives entailed in delivering a relevant education to students, while also executing a financially sustainable enterprise model. In their struggle to balance the possible with the essential, SOU’s administration, faculty, and staff have pursued “creativity” as an important value, both strategically and tactically. The university has planned for creative learning at a strategic level, but has also witnessed and enabled vibrant creativity in curricular development and the creation of new academic programs. This chapter provides an inside account of SOU’s journey as an institution that emphasizes creative curricula and programs. The chapter also identifies relevant connections with the academic literature around creative learning and creativity studies.