This chapter explores the dual constructs of Winnicott’s notion of holding environment and Altvatar et al.’s notion of “stepping up and stepping back” into leadership roles. The merging of the two constructs provides a double lens through which to analyze the Truth and Reconciliation Commission (TRC) process in post-apartheid South Africa in the mid-1990s. Reporting from that era provides first-hand recollections and transcripts of the process. In addition, the political moment of transition and healing via TRCs serves as an arena in which to consider the importance of a holding environment when undertaking social justice missions in which leadership and followership are ineluctably entwined. While the outcome of South Africa’s TRCs is considered imperfect, I suggest that the establishment of similar such holding environments would further dialogue and efforts toward peace and reconciliation in the United States around issues of race.

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