Although mature males who make mid-career changes into elementary school teaching share some experiences with their female counterparts, there appear to be variations in their experiences which are specific to males. Data from a cross case analysis that focuses on the career transitions of 10 second career men who became elementary school teachers indicate that both men and women experienced stress related to their financial needs, the social image related to a career in teaching, and their relationships with their cooperating teachers. However, several issues appear to be specific to the male career changer, issues related to: the nature of gender socialization in our society, the schema of teachers and teaching held by male career changers at the time of their entry into the field, and life stage concerns that motivate men to make a career change into teaching. These issues have implications for the recruitment and education of male second career teachers at the elementary level. The bibliography includes 54 references. (IAH)