A rising number of students are pursuing graduate degrees while working and parenting young children. Gender differences in the experience of multiple roles are well-known, and graduate school and childbearing years tend to overlap. This study sought to discover how employed graduate student mothers (GSMs)---women fulfilling work, academic, and parenting roles---experience, perceive, and meet the demands of their multiple roles. Some of the work-family literature has explained the interface between the work and family domains using two contrasting perspectives (i.e. role conflict and role enrichment), and it is now known that role occupants can experience both conflict and enrichment throughout the course of meeting multiple role demands. The participants in the study were concurrently involved in the roles of parent of one or more preschool child(ren), graduate student (MA, EdD, or PsyD), and (full- or part-time) employee. Each woman completed a brief, structured demographic questionnaire and participated in a one-on-one, semi-structured, open-ended interview. A case-oriented, cross-case analysis using inductive and deductive methods was conducted. The findings indicated that employed GSMs experienced both challenges and benefits in the course of fulfilling student, family, and work role demands. However, an overall perspective of conflict or enrichment appeared to be related to the experience of role overload and certain student and family role factors, including the employed GSM's position in her graduate program, the role management technique she used, and the age(s) and number of her child(ren).