Readiness, often defined as the level at which students meet the qualifications to succeed in college and career, has long been a metric of the success of K-12 education in preparing students for post-secondary lives. In Oakland, California, the Oakland Unified School District (OUSD) has highlighted their top priority as “All students graduate college, career, and community ready.”, implementing different goals and actions throughout the years to achieve this priority. However, what does it mean to be ready for college, career, and community? How does the district measure readiness and support initiatives targeted at increasing student readiness? The aim of this study is to understand how school districts, focusing on OUSD, back up their goals of preparing students for the real world. Through a critical approach, this in-depth case study seeks to shed light on how metrics of readiness are understood and used by districts in supporting students. The implications of this study aims to problematize contemporary definitions of readiness, highlighting the ways school districts can improve standards and practices as it relates to college and career readiness to better serve its students. The findings indicate that there must be more transparency on the data behind how and why goals lead to readiness, and how specific actions align with the success of such goals. Better data practices can ensure that proposed actions to meet stated goals are met, as school districts place emphasis on readiness through meeting state standards, rather than preparing students for their post-secondary lives and beyond.