The authors have a lot in common. They are white, cis women, former K-12 art teachers, and recent doctoral graduates. They both entered their first classrooms with good intentions to create lessons reflecting diverse students. Yet, after a few years of teaching, they developed a sinking feeling in the pit of their stomachs. They developed a sneaking suspicion that, despite their best intentions, the curriculum failed to be meaningfully inclusive, and was actually harmful. As they became university instructors in preservice programs, they wondered how they could chart new pathways with future art teachers, as caring mentors had done for them. To do this, they adopt five practices in their work: (1) building critical communities of care, (2) sharing our own mistakes, (3) fostering critical reflection, (4) learning from missteps, and (5) developing internal compasses. This work builds on critical frameworks like culturally sustaining pedagogies (Paris, 2021), and it is important to note that the practices the authors recommend are deeply rooted and informed by the communities in which they live and teach, as well as the scholars and mentors who have lit their paths. In the sections below, they outline the rationale for each approach and share snapshots of their own preservice teaching.