The sustainability of the student affairs profession continues to be questioned, as is the conditions influencing attrition and "burnout" of those working in the student affairs profession over time. Therefore, understanding the workplace conditions of midlevel student affairs administrators continues to be an important area of inquiry in both higher education and human resources research. This generic qualitative study explores factors that influence workplace satisfaction of midlevel student affairs administrators working in either the United States or Canada. Data includes narrative based on individual, one hour interviews and is analyzed using the lens of positive organizational scholarship and a workplace satisfaction framework. Findings present factors ultimately influencing participants' workplace satisfaction, with implications for practice for midlevel student affairs administrators, human resources divisions, and senior leaders working on university and college campuses.