This chapter provides a blend of auto- and engaged ethnography in an attempt to push for understanding and knowing beyond the scientifically accepted and the emotionally taken-for-granted. By critically exploring and contemplating painful dilemmas and not-so-glorious solutions on their whiteness, the three authors meander along their professional trajectories and reflect on the contexts of their life histories. As white privileged scholars teaching at Vrije Universiteit Amsterdam and studying South African higher education transformation processes, we find ourselves often caught in the middle between engagement and uneasiness regarding spokespersonship about racism and related dimensions of exclusion. In three vignettes we account for this journey – in The Netherlands and in South Africa – and address the paradox of engagement from a compromised position.