Abstract: African American women are significantly underrepresented in corporate leadership positions and more of these women are making career shifts into self-employment. This qualitative study explores the variables that impacted 12 African American women's decisions to leave corporations and pursue self-employment. Particular emphasis is placed on participants' perception of and experience with the culture of their former workplace. Participants' primary motivation for becoming self-employed is highlighted by clarifying whether they felt pushed out of corporations due to glass ceiling barriers or pulled into self-employment. Data analysis consisted of analyzing units of meaning from transcribed interviews and finally refining categories into emergent themes. Results demonstrate that over half (7 out of 12) of the participants felt the pull or lure of self-employment was the main motivating factor in their decision to transition into self-employment. These participants also acknowledged that the organizational barriers they faced in their former workplaces also played a role in their choice to self-employ. Future research could explore more about organizational cultures left by high achieving African American women. The vision of work and social interaction of the organizational cultures the women left could be examined in order to determine whether it is constrained by gendered and other oppressive roles, images and relations.