Parents are central stakeholders within the youth sport context, yet their own health and well-being can be compromised due to the extensive commitment required to support their child’s sport development. Against a backdrop of transformative sport service research and eudaimonic well-being, the study presents an autoethnography of my experience as a parent attempting to subvert the traditional role of parent–spectator by engaging in “sideline” physical activity simultaneous to my child’s sport. A secondary purpose is to identify the program and facility design attributes within the community sport environment that facilitate or inhibit the well-being of parents via simultaneous participation. This study highlights how the lines between researcher and subject can be blurred to challenge taken-for-granted assumptions and strengthen well-being through mastery, autonomy, personal growth, interpersonal relations, and self-acceptance. Through lived experience and personal voice, I hope that my story will open new possibilities for transformative practices within community sport.