Career opportunities for women were limited until the 1970s. Teaching is a profession women have long pursued. The purpose of the study was to determine if differences exist in Kentucky women teachers’ demographic characteristics and career choice outcomes by age cohort/era. The population consisted of women who lived in the state of Kentucky and the teacher sample consisted of 110 females, ranging in age from 25-74. Findings from this study were examined through the Social Cognitive Career Theory’s (SCCT) three constructs: self-efficacy, outcome expectations, and personal goals. Five key influences were reviewed from literature: age, resources, educational attainment, teaching responsibilities, and motherhood. The educational level of all women in this sample consisted of respondents earning a bachelor’s degree or higher, with the majority having obtained a master’s degree. It was found that the teacher sample of the Kentucky Women’s Educational Attainment Study was highly influenced by their educational and occupational decisions. They were influenced by their personal values and family in their marriage and parenting decisions. Personal goals, outcome expectations, and self-efficacy were being met for these teachers by accomplishing their education and career goals while balancing their parenting choices.