This qualitative, multiple case study explored what women working in student affairs reported as influences on their career choices and the impact that the type and level of student interaction has on their careers. Data from semi-structured interviews and journal entries were obtained from ten women working in student affairs at private, four-year institutions of higher education in the Midwest. The "Stage Model of the Careers of Successful Women" (White, Cox, & Cooper, 1992) provided the theoretical framework and the basis for selecting women for the study. Two women at each of the five stages of White, Cox, and Cooper's model participated in the study. A within-case analysis was conducted for each woman at each stage and revealed themes that she felt influenced her career choices. A cross-case analysis was conducted for the two women in each stage and revealed what these women shared as influences on their career choices. Interaction with students influenced the career choices of seven of the ten women studied. The sharing of stories about their careers by women can be just as beneficial for the women sharing as for the women listening, an unexpected finding that confirmed the work of Belenky, Clinchy, Goldberger and Tarule (1986). Additional themes and stories that emerged from the data are described. Based on the findings of the study, White, Cox, and Cooper's (1992) model of career development for women was found to be insufficient for explaining their career choices throughout the lifespan. A new model was developed to better represent the career development of the women studied. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]