This personal story chapter describes the journey undertaken by a transgender youth as she discovers her true gender identity. Told by a mother and daughter team, each individual shares her feelings and experiences from the time J is a toddler until the present, including preschool experiences, travel abroad anecdotes, school and social encounters, and family reactions and adjustments to J's transition and ongoing transformation. The chapter addresses the social, emotional, physical, academic, and economic factors that many transgender youth and adults face on a daily basis and suggests ways that schools and society can ease this complex process for individuals who are LGBTQ+.