Minority students from low-income families face challenges in their daily lives that continually interfere with their academic performance as well as their ability to prepare for college. Although the educational system is viewed as "the great equalizer" that gives everyone an opportunity for upward social mobility, sociological and educational research suggests otherwise. Most low-income minority students who overcome all the obstacles associated with their socioeconomic and racial backgrounds and achieve high levels of academic success do so as a result of a pivotal encounter with an educator who took the initiative to reach out to them and provide concrete academic guidance beyond their formal roles and responsibilities. Educators of students from low-income families have a special role to play in helping students be successful in life. The author's research and that of others suggest that when a relationship between an educator and a student becomes genuinely supportive, it can transform the student's path to postsecondary education. Thus, intentional academic interventions, or what the author calls educational "pivotal moments," are necessary for low-income and minority students to overcome the numerous disadvantages they face in society and in the educational system. Through academic interventions, educators can help any low-income minority student succeed academically and gain access to higher education. Principals in particular can play a unique role in creating a school community that recognizes the value of pivotal moments.