Past research has shown that valuing gender conformity is associated with both positive and negative consequences for self-esteem and positive affect. The current research (women, n= 226; men, n= 175) explored these conflicting findings by separating out investing in societal gender ideals from personally valuing one's gender identity ("private regard") and investigating the relationship to self-esteem, through either "autonomous" (behaviors that are freely chosen) or "pressured" (behaviors engaged in due to pressure from others or situation) motivation for gender-consistent behavior (communal behavior for women and agentic behavior for men). Confirming predictions, structural equation modeling revealed that investment in gender ideals predicted pressured but not autonomous motivation whereas private regard predicted autonomous but not pressured motivation. Additionally, autonomous motivation for gender-consistent behavior was positively associated with self-esteem whereas pressured motivation was negatively associated with self-esteem. Thus, investing or valuing one's gender identity was not shown to be costly for the self directly, but to instead influence self-esteem through motivation to enact gender-conforming behavior. Although the present research demonstrates a positive link between some aspects of gender conformity and self-esteem, we discuss how gender-conforming behavior can still have negative consequences (e.g., communal behavior in the context of male-sex-typed domains).