This paper is aimed at readers who are committed to new ways of designing supportive learning environments that individually adapt to how students want to learn. Its premise is supported by the need for society to acknowledge the diversity of the population and to shift the paradigm from school reform restricted by concrete structures to learning reform restricted only by the limiting internal structures of policy makers. The paper begins by describing the traditional model of education delivery to help build the case for personalized learning. This is followed by a description of influencing factors underlying the urgency for systemic reform in the delivery of education in America recognizing the influence of global forces which have transformed the way people work and live. It argues that "today's education system faces irrelevance unless we bridge the gap between how students live and how they learn" (Partnership for 21st Century Skills, 2006). That personalized learning, which includes the use of information and communications technology, individualized assessment for diagnosis, the planning of learning experiences for each student, and the provision of children's services to support the work of teachers as they endeavor to meet the needs of each learner (Caldwell, 2006), is the sought after transformational bridge. The paper identifies major barriers from which conflict is likely to emanate.