The purpose of this study was to discover how ethnicity, gender, and mentoring influenced the career experiences of Jamaican administrators in Sunshine County Public Schools (SCPS), a pseudonym that was used for a large public school district in Florida. This qualitative, phenomenological study focused on the career experiences of eight Jamaican administrators in SCPS. Seven of the participants were all native-born Jamaicans and one was a first generation Jamaican, born in England to Jamaican parents and raised in Jamaica until the age of 14. The researcher gained this understanding by interviewing participants in-depth about how their Jamaican ethnicity, gender, and personal mentoring experiences impacted their personal and professional journey as administrators in SCPS. Findings and conclusions will inform mentoring and educational leadership literature on strategies for success geared toward this understudied population. / by Denise P. Barrett-Johnson. / Thesis (Ph.D.)--Florida Atlantic University, 2012. / Includes bibliography. / Mode of access: World Wide Web. / System requirements: Adobe Reader.