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This paper critiques a qualitative strand of inquiry conducted within a statewide study of college readiness strategies using historical consciousness as a framework. Using interview data from 39 staff members across six ostensibly exemplary schools, we found common practices. Interviewees emphasized rigorous coursework, a college-going culture, counselor support, career and technical education (CTE) pathways, and writing skills. We contextualize these findings using historical examples to show weaknesses of these efforts that practitioners may not realize. Historically, students of color and those from rural and low-income backgrounds had fewer opportunities than others to access high-level coursework, counselors, and colleges. Moreover, practices marginalized those same students to training for service work. Such historical reflections illuminate potential problems with common college readiness strategies.