Utilizing data from the 20-year record of the Longitudinal Study of American Youth (LSAY), this analysis uses a set of variables to predict employment in engineering for a national sample of adults aged 34 to 37. The LSAY is one of the longest longitudinal studies of the impact of secondary education and postsecondary education conducted in the United States. A structural equation model found that mathematics is a primary gateway to an engineering career, beginning with algebra track placement in Grades 7 and 8 and continuing through high school and college calculus courses. Home and family factors such as parent education and parent encouragement of science and mathematics during secondary school also enhanced the likelihood of a young adult becoming a professional engineer. In addition, young men were substantially more likely to become professional engineers than young women. Considering each of these factors, this article seeks to understand the varied pathways available to students interested in engineering careers.