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While there are many good reasons for seeking a college education, college as the ultimate goal of a secondary school experience has been called into question as a remedy for the persistent outcome disparities between youth growing up in poverty and their more privileged peers. In this paper, we draw on qualitative data gathered from 161 secondary school educators in seven schools to explore how participants make sense of their role in preparing students for life after high school. We specifically examine these educators’ shifting views towards postsecondary education and how their views shape the way they formulate goals for their students after graduation and what they emphasize in their teaching.