This study aimed to closely examine what caregivers of children 9 years of age and younger perceive to be barriers affecting access to play. The current study is a lived inquiry (Dimitriadis, 2016) of my own experiences and of facilitated in-person conversations surrounding play, mostly with caregivers of children aged 9 years old and under. I also solicited hundreds of comments and submissions to a social media account surrounding this research. I used grounded theory methods to analyze the data, and founded a non-profit organization to aid in the application of some of the findings towards my own community. This study found that individuals can have great agency over the personal and systemic factors that appear to affect play. Awareness and prioritization of play is perceived to be the greatest catalyst to play and affects each of the following categories: The Cost of Play, Extracurricular Activities and Play, the Quality of Early Learning Environment, Mental Health and Play, and (Re)claiming a Playful Self. The participation in (re)claiming of a playful self, children’s play in early learning and school settings, community opportunities for whole wellness, and community opportunities for free play is a fundamental form of self and community compassion that lead to a greater sense of self and social justice. The current study adds to the study of play and accessibility through an autoethnographic, qualitative approach. It has also led to the creation of a website (Blaisdell, 2019) social media pages (Project Play YQR, n.d.), and some important community partnerships with other community-based organizations as a result of an action-orientation to the research. It also presents potential implications for community policy discussions and highlights the need for greater community education and awareness surrounding play.