Nationally, 30% of high school students do not graduate. Among this percentage, 50% are African-American. This study focused on at-promise African-American male classroom engagement where the researcher employed a mixed-methods methodology. Findings reveal that in order to engage and keep at-promise African-American males in high school, educators need to allow for self-guided learning. This kind of learning must translate into rewarding entrepreneurial type of experiences. The African-American males in this study perceive the construct of "school" as training and preparation to achieve their personal aspirations and goals. Teachers of such students are pedagogically strategic and have no problem with doing "whatever is necessary" to assure academic success for African-American males. Practitioners, both secondary and post-secondary must merge their curricular efforts for African-American males' successful matriculation into college, careers or self-authored livelihoods. Policy analysts who advocate for student-centered education should promote for more localized school governance. This kind of school oversight allows for more flexibility in terms of assuring that the educational experience benefits not just state and national economies but also the personal agendas of students. Truly, education in this light requires every educator who encounters students to not simply "touch their lives" but authentically know them. [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.]