Organizations are built on interactions among leaders, members and the larger culture (Schein, 1990; Sessa & London, 2006). Beyond the people and communities of which they are a part, organizations carry history and face issues of both internal and external change. The combination of people, culture, organizational history and change set the stage for whether organizations can successfully learn and remain sustainable. Very little research has been done on a case study level regarding how organizations – specifically those that address higher education needs – begin, evolve, and adapt to change. This study seeks to fill that gap by looking at the specific case of Wakonse, a small teaching and learning conference held annually for the past 25 years. By focusing on a single case, we begin building the opportunity to make meaning of other organizations and why they persist (or not) and what strategies and key elements must be in place for organizations to remain viable.