This study describes a researcher-educator collaborative intervention that aimed to promote identity exploration among 9th-grade students in a literature lesson. The intervention focused on an introductory lesson about a poem from the curriculum, and involved designing educational activities anticipated to trigger identity exploration, promote a sense of safety, and scaffold exploratory action among students. Analysis of observation of the lesson, students' products, and post-lesson focus groups suggested that the lesson was successful in eliciting engagement in identity exploration among many, albeit not all, students. The analysis also suggested that exploration-promoting activities contributed to students' adaptive motivation and engagement in literature and in writing. The findings highlight the complex, dynamic, non-determined, and inherently contextualized nature of identity exploration. The study emphasizes the need for interventions that employ theoretical principles as well as contextual knowledge in the design of educational activities, and the application of continuous design-evaluation cycles, for the successful promotion of identity exploration in educational settings.