This study investigates the personality differences of entrepreneurs who returned to business after bankruptcy and those who left their entrepreneurial careers. Failure narratives of 15 entrepreneurs helped explore enabling conditions that supported post-failure to either seek new business opportunities or abandon entrepreneurship. Analysis of the responses to shame from failure, coping strategies and personality traits revealed similar patterns of personality profile, shame processing and problem coping strategies for the restarter entrepreneurs who overcame their shame. Contrarily, non-restarters who could not cope with shame and depression exhibited distinctly different patterns of personality traits and coping approaches.