This article reports on a critical qualitative study of a whiteness workshop series to understand the past experiences, contexts, and relationships that motivate White people and people of colour to participate in an in-depth anti-racism workshop, and what participants learn through engaging in this workshop series. First, most participants, White and of colour, are motivated to do racial justice work due to a marginalisation experience based on race, ethnicity, class, gender identity, sexual orientation, and/or religion in childhood. Second, the series introduces a self-reflexive communication process that is new to many participants. Third, participating in the workshop series prompts some towards activism, while others limit themselves to self-reflection. I argue that two factors create this divergence in post-workshop activism: (1) the level of experience with anti-racism work with which participants entered the workshop; and (2) the focus of the workshop on individual attitudes and skills over systemic racism.