Many African Americans are leaving high school prior to graduation and are entering college for the first time beyond the age of 30 years, a phenomenon that has an effect on school systems, the community, and society as a whole. The research problem addressed was the need to understand the experience of an increasing number of African Americans who previously dropped out of high school and are entering college as nontraditional students. Research shows that postsecondary degree completion rate for nontraditional students is lower than for traditional students. The purpose of this phenomenological study was to better understand barriers encountered in high school and later motivations for pursuing degree completion and higher education choices later in life. The research questions addressed understanding more clearly factors concerning why students drop out of high school and why they decided to enter college later in life. Transcribed semi-structured interviews and field observation notes of 10 participants were coded and analyzed following an iterative and recursive approach suggested by Miles & Huberman using ATLAS.ti software. Six themes emerged from the research interviews: (a) teen pregnancy, (b) parental involvement, (c) school experience, (d) academic performance, (e) home life and, (f) self-improvement. These themes were integrated to describe a lived experience where self-efficacy, environment, psychosocial development and gender specific circumstance played a role in leaving high school without a diploma. The desire to attend college was prompted by a need for self-improvement. The study contributes to social change by informing the specific content for comprehensive retention programs that sufficiently address the challenges faced by African American high school students. [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/en-US/products/dissertations/individuals.shtml.]