How do school leaders help students and parents, especially those from low-income families, understand the value of a college education? Engaging students and families early and often and using a continuum of strategies enables school leaders to close aspiration gaps, thus creating and sustaining a college-going culture for all students. Typically, college counseling initiatives begin in the middle of eleventh grade. Waiting until this late stage in a student's academic career guarantees missed opportunities. For students who do not see themselves in college, or who are unaware of the significance of their early academic work, the eve of senior year is simply too late. According to ACT (2008), "…the level of academic achievement that students attain by eighth grade has a larger impact on their college and career readiness by the time they graduate from high school than anything that happens academically in high school" (p. 2). In response to these conditions, school leaders in Oyster Bay and Westhampton Beach High Schools, (Long Island, New York), have created programs for students that jump-start college awareness beginning in eighth grade. In this article, the authors demonstrate how their schools used a continuum approach to close aspiration gaps, and in the process, close achievement gaps, thus create a college-going culture for all students.