The purpose of this qualitative study is to better understand how urban high schools prepare their students of color (SoC) for “college and career readiness” through asking the following: What does educating for “college and career readiness” look like? How are students being educated for “college and career readiness”, and How do students learn about and interpret “college and career readiness?” With these central questions and responses from two Greenwood City School District (GCSD)* principals and nine GCSD students, we learn the focus within the “college and career readiness” paradigm is largely dedicated to student’s college preparation and occupational exposure, but not much in the way of introducing challenging aspects of tomorrow’s occupational landscape including neoliberalism, globalization, automation, and workplace discrimination. This study concludes with recommendations that education practitioners critically deconstruct the language used to imply sufficiency of the college degree in yielding reliable, secure employment for students of color, as well as encourage more transparency with students pertaining to what likely lies ahead in the workplace of tomorrow.