Feelings of being misaligned with one's environment are pervasive in work and non-work environments, and can lead to decreased overall well-being. In this qualitative study, we explore the relationship between idealized professional identities and professionals' perceptions of misalignment with their environments. We use data from 58 semi-structured interviews with (ex-)entrepreneurs to develop a model of internal and external identity misalignment, which depicts the potential detrimental effect of a tolerated idealized professional identity - i.e., increased sensitivity to perceived misalignment, and the conditions under which this relationship exists. We contribute to identity literature by introducing the concept of internal identity misalignment and showing how it and other factors may moderate the relationship between idealized professional identities and perceived misalignment. We also contribute to entrepreneurship literature by highlighting the dangers of idealizing the identity of the "entrepreneur", as well as emphasizing entrepreneurs' need to be acknowledged for the value they create for society.