This chapter talks about lessons that from a year-long program entitled the Leadership and Racism Program (LRP). The LRP program is designed with a two-day retreat and four additional full days of follow-up sessions. The follow-up sessions, though not neglecting the personal journeys of participants, take a more active focus upon issues of strategy. There is no doubt that a conversation about oppressions and in particular racism is seldom one in which folks seek to engage. Compassion is defined as a feeling of deep empathy and respect for another who is stricken by misfortune and the strong desire to actively do something about it. No doubt the word racist carries as much baggage for White people as does the 'n' word for People of Color. Helping White people to move away from the immediate need to distance themselves from the term racist and, instead, inviting a conversation to examine racism appears to keep people in the conversation.