Popular conceptions of college and career readiness are growing beyond strictly academic competencies such as literacy and numeracy. New thinking on the many dimensions of preparedness has produced volumes of research and scores of new products, making the process for educators and employers to focus on the readiness paradigms that suit their needs very difficult. This paper attempts to clarify the readiness landscape. Three readiness paradigms are introduced—the college readiness index for middle school students, the Conley Readiness Index, and GRIT (Growth, Resilience, Instinct, and Tenacity)—and their goals, theoretical foundations, and empirical support are reviewed. This paper dedicates particular focus to strands of convergence and divergence between these three approaches. The paper concludes with a short set of recommendations focused on how new approaches to college and career readiness can be used to support smarter and earlier interventions and open college and career pathways to all learners.