Researchers and economists have argued that the economic and social stagnation of African Americans is the result of their lack of self-confidence, initiative, and commitment toward their own advancement. This qualitative study examined whether historical conditioning and personal experiences have created a hypersensitivity in this population to events triggering behaviors that mirror the success fearing personality when seeking social, economic, and political advancement. It used Zuckerman and Allison's fear of success scale to identify the range of success fearing in 30 African American men and women aged 35 years or more; this group was also interviewed regarding their lived experiences when pursuing advancements in the United States workforce. The interview questions were formulated using Cohen's fear of success factors; responses were inductively coded and organized using ATLAS.ti 7 software program. Regardless of their fear of success scale (FOSS) scores, the participants' interview responses revealed that even in the absence of explicit or implicit discrimination, there was an unconscious expectation of racism, and that strong family, religious, and educational influences aided in preserving these expectations. The participants were also found to be hypersensitive to events that triggered behaviors mirroring the characteristics of success fearing personality. The findings of this study can have far-reaching implications for the overall social and psychological betterment of African Americans in organizations, educational institutes, and political/civic action groups. It should be used to begin an alternative conversation of personal and social reconciliation, emotional healing, and pride, which participants asserted was the cornerstone of African American progress in the 1960s.