Going to college is a familiar first step towards fulfilling the American dream for graduating high school students and their families. Yet for many in this country, the reality of their everyday lives is increasingly riddled with obstacles and tough choices about their future educational and career pathways. In light of these challenges, many school, community, and state education leaders, as well as various public and private agencies have pressed on with aggressive campaigns to build a more robust college-going and college-readiness culture within their local schools and communities. College readiness is an especially salient goal in South Texas, where educational attainment rates hover among the lowest in the country (Texas State Data Center, 2007). But what does college readiness mean within this educational context, especially from the perspective of school and community leaders charged with promoting and realizing this goal? This brief highlights some key findings from a study that examined the role leaders assume in promoting the goal of college readiness in the Rio Grande Valley of South Texas. Using focus group data gathered as part of a larger initiative focused on college readiness efforts within this region, the study investigated how school and community leaders decode the goal of college readiness and self-examine their respective roles in promoting a college-going culture. To further understand the educational context of this region, it is first necessary, however, to review the higher education infrastructure and opportunities that currently exist.