Through qualitative inquiry, this study identifies and analyzes the factors that support or undermine the achievement of Black males completing IT degrees and entering the workforce. This paper presents the findings of a study examining the underrepresentation of Black male participation in IT guided by the Individual Differences Theory of Gender and IT. Throughout this paper there are common themes related to individual identity, coping mechanisms and environmental influences. This chapter portrays my experience and interactions with these Black men in regards to obstacles, roadblocks, diversions and ultimately success in pursuing and staying on an IT career path. The research centered around three district research questions. The first research question was how do Black male Individual Identity Characteristics influence IT degree pursuit and attainment? The second research question was in which ways do societal characteristics encountered by Black males influence IT degree pursuit and attainment? The final research question was how do Institutional Characteristics encountered by Black males influence IT degree pursuit and attainment? The findings could lead to a better understanding of how the factors that influence Black male participation could be used to recruit and retain Black males.