The assisted living industry is predicted to experience considerable growth due to the simultaneous aging of the baby boom generation and their subsequent need for long-term care. This study investigates individuals’ pathways to administration in assisted living and the ways in which assisted living administrators define and carry out their roles. The study contributes to the understanding of the knowledge, skills, and personal traits needed by those who assume these vital leadership roles in an industry poised to care for the bourgeoning population of older adults. The sample for this study is 44 administrators who work in a random sample of 45 assisted living facilities in Georgia. Qualitative methods were used to analyze the data. The data revealed that multiple multi-level factors not only facilitate an administrator’s pathway to AL administration, but these factors also help to shape how an administrator experiences his or her role within an ALF.