Over the 2019-2020 school year, trust and race were explored with High Tech High Media Arts staff in iterative research cycles. Through individual structured conversations with White colleagues and professional development with all staff, trust was measured through a participants’ ability to authentically share their views and opinions with other staff members. Key findings included the following: affinity spaces increase the capacity to engage authentically, courageously, and critically; time, structure, and trust are necessary resources in building racial literacy; racial literacy work is hopeful and divisive; and relational trust is cultivated through targeted structures. In the pursuit of authentic relationships amongst staff, self-work must be a priority, this work must be supported and shared amongst staff, and racial literacy must be at its core.