This autobiographical-experimental documentary explores the backstory of Ben Duffy's first film, We Are Skateboarders, and the 15-year mental health journey that followed. At the time of making the original film, Ben was 19 years old and living with undiagnosed bipolar disorder. While We Are Skateboarders became the second most viewed skateboarding documentary after Dogtown and the Z Boys, it was not a commercial success. As the film gained momentum, Ben’s mental health challenges intensified, raising fundamental questions about how one defines success in both life and creative work. His path to healing began when he took a leap of faith into therapy, confronting years of trauma, shame, guilt, and complex PTSD triggered by the experience of making the film. The documentary captures Ben’s transformation, turning immense pain into catharsis, and portraying his journey toward self-love and compassion while living with undiagnosed bipolar disorder. It is a raw and inspiring exploration of resilience, creativity, and mental health.