Following the 2016 general election, yoga practitioner, instructor, and scholar Cara Hagan felt listless and disconnected from a yoga community that seemed to perpetuate the same violence of erasure and othering of marginalized people she observed in American society. As she distanced herself from that community, Hagan also found herself distanced from her yoga practice. This work follows the author’s journey back to her practice and toward a more liberatory way of life through the cultivation of her “Five Essential Questions” – touchstones on the path of self-study (svadhyaya) and collective freedom. Explored through a variety of settings, this piece and the questions therein demonstrate the need for people-of-color-only healing and contemplative spaces spaces, a heightened sense of awareness around systems of oppression among yoga communities, and the ability for everyone to drastically reimagine the roles they play in their relationships to oppression. Offered to the reader as an extended letter, Five Essential Questions for Inner and Outer Liberation affirms the experiences of other BIPOC, while providing opportunity for ongoing introspection and actionable steps for us all.