According to the New York State Education Department (NYSED), for the 2015-2016 school year about 25 percent of the total students enrolled in Long Island school districts were of Hispanic origin. For the same school year, NYSED also reports a total of 31 out of 641 (4.8 percent) building level administrators that identify as Hispanic or Latino, including males and females. On Long Island, the population rate of Latino students continues to grow at a much faster rate than the representation of Latinos as educational leaders. This qualitative study was designed to analyze the journeys of Latina or Hispanic female school administrators in Long Island school districts. Data was generated from semi-structured and opened interview questions, as well as responses to Angela Duckworth's Grit Scale. The interviews were intended to encourage the participants to voice their perspectives regarding the choices that led to a career in educational administration, the challenges they encountered along the way and the inspirations that gave them the necessary motivation to persevere. The ethnographic design allowed the researcher to focus on how culture and gender roles may have impacted a participant's pathway to their career. The information obtained was analyzed with the use of the NVIVO coding software and utilized to identify patterns and themes that emerged as a result of their responses. Much research has been done regarding the gender inequalities that exist between males and females in the similar positions. Very little research however, can be found specifically on the number of Latinas in administrative roles for education most likely because very few currently hold such positions. The purpose for this research was to contribute to the lack of literature on this topic. This information will assist in the implementation of effective support programs and appropriate interventions to facilitate the growth of Latinas in educational leadership roles. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]