The decision to become an entrepreneur may be one adaptation strategy individuals enact when they experience low work-related wellbeing. To date we know that the interplay between work-related identification and work-related subjective wellbeing affects individuals work-related choices. However, we possess less knowledge about the nature of this relationship. Extant studies have linked work-related subjective wellbeing (SWB) to identification, yet conceptualization of work-related identification has, like SWB, typically been considered from a static state perspective rather than a dynamic process perspective. Further, researcher imposed definitions have been used rather than seeking individuals self-definitions. Our study seeks to complement existing work by showing that identification is a dynamic process where we explore the relationship between multiple identifications and wellbeing. We empirically investigate the interplaying processes of identification and work-related wellbeing in an in-depth, person-centered, life story approach to the entrepreneurial endeavor. Our sample was purposively selected to include individuals with a strong professional identification while enhancing the variability of challenges faced over time in the entrepreneurial identification process. Our novel sample and life story methodology contribute to illustrating the dynamics of wellbeing over time with a constant identification and dis-identification in moving between aspired and experienced wellbeing; as well as highlighting that wellbeing becomes the antecedent, means and result while entrepreneurship is the believed mechanism to come closer to experienced wellbeing.