This book takes a deep dive into the psychological underpinnings that motivate students to act in ways that subvert our intended curricular plans. The book classifies student subversions into two distinct categories: (i) obstructive subversions, which occur when the psychological needs of the student overwhelm or override the teacher’s intended goals, and (ii) constructive subversions, which occur when students perform unexpected acts that defy the educator’s implicit expectations but do so through actions that align in surprising ways with the educator’s intentions. Through a narrative style that highlights case studies from 25 years of classroom experience at the high school, university, and graduate level, the book aims to help educators understand and query the types of psychological foundations that give rise to unexpected, boundary-pushing attitudes and behaviors among students. The goal of Teaching in the Riptide is to embolden educators to deepen their understanding of the cultural roots and emotional forces that compel students to subvert. In the process, the book aims to enhance the educator’s own metacognitive awareness and capacities, so that they can act with more flexibility and compassion when working with students who challenge classroom norms. As we are living during a time of rapidly accelerating cultural change, innovation, and adversity, this book will serve as an invaluable tool for educators striving for personal authenticity and practical guidance to teach with greater effectiveness and serve the diverse needs of their students. Teaching in the Riptide will appeal to a broad spectrum of readers—students, researchers, teacher-educators, educators, pre-service teachers working in the fields of Classroom Management, Educational Psychology, Philosophy of Education, and Pedagogy. It will also serve as an invaluable companion to in-service teachers, policy makers and educational administrators, curriculum developers, and NGOs working in the field of education.