It is widely accepted that schools must adapt to meet the needs of our changing society and the 21stcentury learner. To effect real change and improvement in our schools - locally, nationally, and globally, we must question and rethink "school" - to develop a whole new vision for teaching, learning, and the student experience. Based on core values of innovation and individualization of the student experience, the NYC iSchool provides an example of how schools can and should redefine themselves. The iSchool model is successfully merging the pedagogical ideal of meaningful and relevant learning experiences that teach big ideas and valuable skills, with the realities of accountability, college preparation, and adolescent development. Most importantly, though, the iSchool model is rooted in a willingness to ask "why?" and "what if?" - to question what has always been, and to shift our focus from what's easiest and most efficient for adults or the system, to build an experience for each student that is personalized and that provides the range of experiences that will truly equip them with the academic foundation required for success in higher education and the critical 21st century skills required for success in life.