This narrative study investigated through storytelling the experiences of five students who attended a Montessori middle school and then transitioned to a public high school. The testimonies of the participants highlighted that, to help students make a successful transition to high school, it is useful to consider three elements: (a) developing academic and social-emotional skills, (b) fostering positive attitudes toward learning, and (c) creating opportunities to practice self-reliance, self-advocacy, and grit. The experience of these particular students accentuates the ability of a Montessori middle school to emphasize both academic rigor and the social-emotional skills that build the fortitude necessary for students to successfully transition to high school. This study suggests that Montessori middle school practices may foster the intellectual and emotional growth of students so that they can successfully transition to high school and are potentially buffered from many of the detrimental academic and emotional impacts of ninth grade.