Pharmacy administrators play a critical role in the success of health systems, yet pathways to pharmacy administration are incompletely understood. The purpose of this study was to explore and describe pathways to becoming a health-system pharmacy administrator, including challenges experienced and resources needed. Participants (N = 21) individually completed one or more journey maps detailing the pathway(s) to pharmacy administration and then engaged in small group discussion to identify common themes. A large group debrief was used to share and identify findings across small groups. Thematic analysis was utilized to identify common ideas shared. There was variation across the maps, illustrating many steps one might follow to become a pharmacy administrator. In the 23 maps completed, pathways most frequently began with pharmacy school (n = 9, 39.1%), high school (n = 6, 26.1%), or undergraduate training (n = 4, 17.4%). Most included residency training or dual master's of science in health-system pharmacy administration/residency training (n = 16, 69.6%). Common challenges included distractions, time constraints, grades/performance, financial constraints, and stress. Common resources needed included exposure to diverse career paths, pipeline and outreach support, mentoring, and leadership. Themes included debate about the definition of a pharmacy administrator, questions regarding the core competencies of the pharmacy administrator, discussion regarding ways to enter pharmacy administration, and reflection on the role of serendipity and networking. Understanding the pathways to pharmacy administration is critical to fostering a sustainable and competent workforce. Work must be done to identify strategies and develop processes for identifying, equipping, and retaining talented health-system pharmacy administrators and leaders.