Building on career literature, we predict that an entrepreneur’s age at the time of re-entry has a unique and complex non-linear effect on the choice to become self-employed versus employed after an exit. Based on a database covering the whole Swedish population, we studied 79,356 entrepreneurs who experienced exit in a five year window (2000-2004) and we examined their career choice as self-employed versus employed. Our results show an inverted S-shaped curve which follows the career lifecycle stages (early, middle, and late). Also, we demonstrate that gender (man vs. woman) moderate the entrepreneur’s age/re-entry relationship.