This paper investigates early employment influences on postsecondary expectations and enrolment for working men and women who have recently completed high school in the United States. We find that young workers still have very high expectations for postsecondary education, but that women are more likely to enrol. However, this difference is primarily due to high rates of female enrolment in less-than-four-year institutions. Job training from one's employer predicts higher odds of future postsecondary enrolment, but this relationship appears only for men. Recommendations are given for assisting young workers in realising postsecondary expectations and advancing social mobility, as well as how gender must be considered in these efforts.