This study sought to understand the perceptions of nine Latinas of Puerto Rican descent from an urban district in New York State about their career paths in the field of educational administration. Story narratives developed through semi-structured autobiographical interviews comprised the main data source. The findings indicated that interactions between cultural and family values in the internal/personal world and perceptions in society-at-large define, for the most part, the messages the women received and believed and later altered through their personal governing values upon adulthood. The elements of cultural accommodation and governing values were the filters these women used to examine new challenges and decide their career movement and leadership style. This filter was constantly modified by each situation, especially new ones. Social perceptions of Hispanic women in both the society-at-large and the workplace culture imposed major barriers to career advancement. Family and friends constituted the main support system for these Hispanic women in leadership positions. Career planning and the acquisition of a mentor might enhance the presence of Hispanic women in key leadership positions in education. [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.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]