Retirement well-being expectations of incumbent family owned business CEOs is a critical precursor to successful succession events. The significant antecedents to retirement well-being expectation are family relationships, wealth management and transfer, leadership succession and development, and continuity and viability of the firm. Using data from a survey of 256 family firm CEOs we demonstrate those relationships and show a very strong connection between retirement well-being expectation and firm performance. Study results further our premise that antecedents to retirement well-being expectation are indirectly tied to the overall health and performance of the family firm