People have a tendency to assume that external success is an indication of internal satisfaction. Additionally, people often believe that if they see an individual as successful that he or she sees self in the same manner. This is not always true. The impostor phenomenon is a psychological construct that occurs in high achieving individuals who, despite their great success, feel fraudulent in certain areas of their lives. The purpose of this quantitative, descriptive, correlational study is to examine the relationship among feelings of fraud, self-esteem, and gender in high achieving African Americans. Specifically, a convenience sample from two mid-western university African American alumni associations was used in this study. A three-part Web-based survey was completed by the participants that included the Clance Impostor Phenomenon Scale, Rosenberg Self-Esteem Scale and a demographic survey. High achieving was defined by an annual income greater than the U.S median average and a profession. Statistically significant findings included the presence of impostor feelings in high achieving African Americans. Findings did not support a relationship among gender, self-esteem, and impostor scores. Recommendations included: differentiating between inner and outer self-esteem, examining motivation and family dynamics.