The topics that this paper discusses are dichotomous thinking, Chicanismo, and mental well-being. This paper explicitly analyzes how dichotomous thinking (a form of cognitive distortions) can harm the mental health of people with complex identities, such as the first-generation Mexican Americans (aka Chicanos). There is a common existential dilemma that the majority of first or second-generation Americans can relate to. It is the feeling of not being able to fully identify with the culture of one’s parents (usually a collectivist culture) nor being able to fully identify with the American culture (individualist culture). Dichotomous thinking is connected to this struggle because society pressures the Chicano to ‘pick a side’ culturally, despite the existence of the Chicano created by a mix of both contrasting cultures. This paper provides examples of what issues can manifest in the mental well-being of the Chicano relating to the pressure and restriction of identifying one’s complex identity to a binary categorization. The paper references psychological research studies related to this topic and population, as well as referencing examples of the contradictions that make up the Chicano identity, how dichotomous thinking delimits the freedom of authentic identity and generates unhealthy mental well-being.