Non-profit organizations that promote gender equity are central and yet understudied actors in reconciliation work in so-called "Canada." Building on Epps' 'settler problem' (2003, 2013), the research study explores the interconnected nature between Western feminism and settler colonialism and how this contributes to what I term the "settler feminist problem (SFP)," a problem that might be resisted within the non-profit sector. A critical feminist ethnographic methodology and relational theoretical frame was engaged, in conversation with Indigenous Storywork, to make meaning from the resistances, tensions, and breakthroughs I observed in settler staffs collective learning as they took part in mandated Truth and Reconciliation Workshops (TRW) and voluntary Truth Telling circles (TTC). In dialogue with settler participant stories, I share vignettes crafted from my personal journal entries, meeting notes, and audio-recordings that represent what I see as "radical shifts" in my learning while engaging with Indigenous methodologies and mentors. Ultimately, drawing from Indigenous pedagogies and futurisms, I offer a speculative "three-dimensional settler feminist theory" that aspires to go beyond the SFP and shallow reconciliatory narratives and instead supports feminist non-profit agencies to build more meaningful relationships with Indigenous clients, families, children, and the wider community.