Following an international popular theater festival that modeled theater as activism, two artist educators, one from Canada and one from India, cocreated a program for two groups of high school youth in the USA. The program aimed to engage activist pedagogies through theater. Inspired by Indian street theater forms and some epistemological approaches developed by Brazilian theater activist Augusto Boal, the program was launched, and after it concluded, a youth theater troupe formed, situating the youth as leaders, who used drama to engage audiences in critical dialogues. Rebecca worked with the youth during the initial program as well as the ensuing theater troupe. Ashok came to the USA to provide the initial training and served as a mentor throughout the lifecycle of the troupe. The troupe subverted traditional hierarchies by declaring itself directorless, producing original plays for 3 years. Students expressed their socio-political views and worked to raise individual and collective social awareness in processes similar to Paulo Freire’s conscientization, which involves active engagement with critical literacy, necessary for individual and collective agency and transformative action. When dealing with conflict, confronting issues through creative collective processes can serve to dismantle instances of groupthink that may lead to acts of bigotry. The plays explored many “isms” of students’ lived experiences. The plays became socio-political essays, creatively presented. After each performance, the youth engaged audiences in discussions about their plays, which served to extend conversations about the topics presented. The troupe’s lifecycle included touring nationally and internationally. As the two key adults guiding this project, we explore critical incidents using ongoing dialogue, to narratively review implications for antidiscriminatory education. The project was marked by bumps—personal and professional challenges. The directorless format replicated areas of privilege at times. These instances serve as reality checks of the complexities surrounding how identity and cultural norms interplay with power. Despite challenges that await educators who facilitate youth activism, we call for formalized spaces in schools to be dedicated to fostering activism for the development of antidiscriminatory education.