According to Department of Education reports on public high school dropout rates for 2009, a national average of 44.3% of dropouts left their secondary school education in the 11th and 12th grades. The majority of school dropouts attributed the reason for dropping out of school to boredom. High social and economic costs associated with dropping out of school such as poverty, high unemployment rates, low earnings, and incarceration create a burden for tax payers and jeopardize the competitive advantage of a nation. The purpose of this qualitative phenomenological study was to explore and describe students' experiences with career mentoring and its influence on reducing the high school dropout rate. Subjects were 24 high school seniors at South Dade Senior High School in Miami Dade County Public Schools. An empirical phenomenological method, with its goal of presenting themes of meaning through lived experience, was used to provide the guidelines for data collection, processing, and analysis. Two main themes (experience with career mentoring and the effects of career mentoring) and 10 sub-themes (qualities of a career mentor, social experience, influence of career mentors, perception of career mentoring, perception of career mentors, vicarious learning, positive reinforcement, attitude towards dropping out of school, improved performance, and self-efficacy) emerged as the essence of students' explorations into the structure of the human lifeworld, the lived world as experienced in everyday situations, and relations with career mentoring. Evidence of learning through observation, imitation, social persuasion, and intentionality of mentors reflected on the tenets of social learning theory. The results as analyzed through students' narratives revealed self-efficacy, improved academic performance, and social and workplace skills were positive outcomes of career mentoring. Evidence of transformation in students and intentionality on the part of students to succeed because of their experiences with career mentoring substantiated the proposed use of career mentoring as a dropout prevention strategy. Social significance included collaboration between schools, individuals, and organizations within a community for work-based initiatives to promote positive youth engagement. Recommendations for future research included a longitudinal study to explore the long-term results of career mentoring on students' future professional and personal lives. [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.]