This study was undertaken to explore the critical factors influencing the self-concept of community college graduates in the development of their careers. Individuals with a positive self-concept are often associated with a good career choices and a well-panned career development path. Hence community college students should be girded with a positive self-concept to ensure success in their future careers. This qualitative research using multiple case study methods involved 15 community college graduates who have been relatively successful in their respective careers and were able to generate high incomes. Further data obtained were analysed using NVivo 8.0 to determine the relevant themes that emerged. The study observed the presence of five critical internal factors influencing self-concept: congruence, boldness in facing a challenge, vision, skills and experience.