After five decades in nonprofit development, the author explores why donors openly discuss outright gifts but become secretive about planned giving. Key barriers include fear of mortality, financial insecurity, complexity, trust issues, family dynamics, and concerns about increased solicitation pressure. The $84.4 trillion wealth transfer opportunity is significant, yet fewer than 25% of donors with charitable estate plans notify organizations. Success requires building trust, simplifying processes, emphasizing confidentiality, creating legacy donor communities, and prioritizing family needs first before introducing charitable considerations.