Attaining a post-secondary credential has become increasingly important for securing opportunities to get high-return jobs in the United States in the 21st century. Students from low-income families are underrepresented at every milestone in the educational pipeline, limiting their ability to attain post-secondary credentials and break the intergenerational transmission of poverty. This study seeks to identify educational pathways to high-paying careers that may improve social mobility. The authors assess the extent to which successful transit of these pathways is contingent upon students' educational preparation and performance. This study uses comprehensive data on the high school, postsecondary, and workforce experiences of every public school student in the state of Florida belonging to a cohort of 144,545 students in the 9th grade in 1996. Florida has one of the lowest high school graduation rates in the country, and thus faces particular challenges to increasing the educational attainment of its students. Key findings are summarized in three sections: (1) Effect of Education on Earnings; (2) Postsecondary Outcomes; (3) Differences in Earnings and Postsecondary Outcomes by Family Income. Findings lead the authors to believe that low-cost informational services would be highly effective in increasing course completion, credential attainment and earnings, thereby boosting the earnings of low-income students. Four appendixes are included: (1) Abbreviations and Definitions; (2) Methodology for Regression Models; (3) Descriptive Statistics; and (4) Results for Regression Models. (Contains 19 footnotes, 30 figures and 7 tables.)