In a republic, the mission of higher education is to empower individuals to live fully in their time free from economic or public dependency. The mission endures, but times change. Because postsecondary education and training have become the most well-traveled pathways to middle class earnings, both students and the educators who serve them need to learn new rules of the college and career game. Students need to shop around for college because higher education is a student's first major investment in the transition from dependent adolescent to independent adult. Students deserve to know what they are paying for. The five rules presented in this report can help students navigate the college game in these uncertain times: (1) Education level still matters, and generally more education is better; (2) Education level matters, but program of study and majors matter even more; (3) While field of study is important, it does not control one's financial destiny--there is great variation in earnings within majors; (4) Less education can be worth more; and (5) Humanities and liberal arts majors never catch up with the highest earning majors.