The purpose of this study was to assess the relative influence of career, financial, personal, and legal factors on African American male engagement in postsecondary career and technical education and to determine whether the influence of these factors was moderated by the participants having graduated or not graduated high school and by their having or not having been previously incarcerated. Based a review of the literature, a twelve-item questionnaire was developed and subsequently examined by a panel of judges for the relevance and readability of its contents. After being mounted online, the questionnaire netted the responses of some 212 African American male students, all of whom were currently enrolled in a vocational program and most of whom had graduated from high school (62.3%) and had no previous history of incarceration (55.2%). To determine whether the hypothesized structure of the questionnaire could be empirically confirmed, a principal components analysis was conducted on participants' responses and yielded results similar but not wholly identical to the one premised on the literature review: specifically, a three- rather than four-factor structure that combined legal with personal items. A repeated measures comparison of the factor scores obtained from the empirically-derived structure pointed to significant differences in the importance that participants ascribed to the three factors: personal least, career most, and financial in-between. By high school graduation status, a Multivariate Analysis of Variance (MANOVA) pointed to no statistically significant differences in the subgroup ratings ascribed to the three factors. Apropos a second set of MANOVA outcomes, however, a statistically significant difference in the importance ascribed to the personal factor was observed by the respondent's incarceration history. [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.]