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This qualitative study explores how trans and nonbinary (TNB) K–12 students and their caregivers envision affirming, inclusive environments in and outside of school. Using interviews, artwork and focus groups, this paper analyzes gender journeys and ideal educational environments using transformative, trans-inclusion, and trans development frameworks. Preliminary findings show participants envision schools that eliminate binary gender norms, celebrate queer and trans identities, and honor individual autonomy over gender and sexuality. These imaginings align with Horton and Carlile’s (2020) trans-emancipatory model and challenge genital-based sex assignment, advocating for gender-inclusive education, spaces, and policies. The study offers school leaders concrete insights for creating affirming environments where TNB students are not only safe—but free to thrive, imagine, and define themselves on their own terms.