In this article we use data from the Longitudinal Study of American Youth to examine the influence of parent education on pathways to science, technology, engineering, mathematics, and medicine (STEMM) professions. Building on a general model of factors related to STEMM education and employment, we employ a two-group structural equation model to examine the factors that predict enrollment in a postsecondary STEMM program and employment as a STEMM professional. The results of this analysis indicate that most of the variables in the two models function in a similar manner, but the levels of parental encouragement, help, and direction vary significantly between college-educated and non-college-educated families. The children of non-college-educated parents were less likely to take algebra in Grade 8, take calculus in high school, and take calculus in college than were the children of college-educated parents. Young adults that grew up in noncollege families were less likely to enter postsecondary education; more likely to begin postsecondary education at a community college; less likely to earn a baccalaureate, graduate, or professional degree; and less likely to become a STEMM professional. The analysis reveals a clear pattern of cumulative advantage and cumulative disadvantage, and the final section of this article discusses the need for educational and public policy leaders to develop strategies and programs to address the substantial differential associated with parent education. (Contains 5 tables and 2 figures.)