In 2010, three women from the University of the Pacific came together for a panel presentation at the annual National Association of Student Personnel Administrators (NASPA) conference to discuss their diverse experiences in student affairs. All recognized leaders in NASPA, these women reflected the rich history and promising future of student affairs. The initial stories they shared were later supplemented by additional conversations and narratives from two other women in student affairs at the university. Together, these five women, from senior student affairs officers to up-and-coming new professionals, represent different generations, ethnicities, and cultures. The stories shared in this article represent the experiences of women from different generations, providing insight into common ground and emerging perspectives on leadership.