In this article, the authors highlight Indigenous helper Vicky Boldo/kisêwâtisiwinyôtin:iskwew’s (Gentle Wind Woman) approach to healing knowledges. kisêwâtisiwinyôtin:iskwew’s background of Cree, Coast Salish and Métis ancestry, in addition to living a scarring experience as a trans-racial adoptee, created a ground of insight and self-care that sparked her awareness and reliance on Mother Earth as part of her survival. This chapter documents kisêwâtisiwinyôtin:iskwew’s insights into the sacred and inseparable relationship to Earth and all beings as crucial to overall wellbeing. The authors discuss kisêwâtisiwinyôtin:iskwew’s teachings about connection, embodiment and utilizing inner resources to move through the pain and trauma of separation from the self and sacred. Ultimately, kisêwâtisiwinyôtin:iskwew exemplifies the need to centre the ways in which people respond to hurt assisted by positive social environments that challenge and stop structures of abuse. This understanding gained as a “wounded healer” in turn creates spaces for individual learnings extending into intergenerational teachings on healing and dignity.