Using coping theory as an overarching theoretical framework, this paper investigates the effects of emotional and financial loss on re-entry into self-employment after firm failure and subsequent feelings of grief. I hypothesize that how firm failure is experienced influences the choice of coping strategies. In turn, the choice of coping strategies influences re-entry and feelings of grief. To test these hypotheses I developed a unique, longitudinal database of entrepreneurs who recently filed for firm bankruptcy. The findings largely support the hypothesized relationships. This paper shows that how entrepreneurs manage and cope with firm failure has implications for how they feel and whether they re-enter self-employment. Future research could investigate the relationship between entrepreneurial motivation and the use of adaptive coping strategies.