Career and College Readiness (CCR) generates higher levels of persistence, grit, motivation, and competencies in performing work- or school-related tasks among learners during post-secondary life. One primary limitation defining the present scholarship on CCR is the authentic analysis of the on the ground or field practices high schools perform to increase learners’ CCR competencies. The inadequate research on actual CCR practices in high schools motivated this study. To learn more about how high schools prepare students for post-secondary life, 16 principals from high schools provided detailed narratives on CCR practices in their institutions. Principals completed interviews of one to two hours using Microsoft Teams, supplying the researcher with specific information and examples of how their institutions equip students for future careers and higher education. Manual qualitative thematic analysis of the entire transcript guided the organization and interpretation of the findings, allowing the presentation of meaningful themes supported by a plethora of illustrations. Six themes representing 18 distinct CCR practices emerged, and the themes were rigorous curriculum, content knowledge, key academic behaviors, key cognitive strategies, multiculturalism, and citizenship development. Results partially supported the pervasive CCR model based on Conley’s readiness index. Increasingly, diversity and citizenship learning have defined high schools’ CCR work in preparing learners to become effective local and global citizens. The current investigation paves the way for future observational and field research uncovering whether schools truly prepare students or not, and such preparation varies across community, country, and institutional characteristics.