This study explicitly links processes of anticipatory socialization to social mobility and reproduction. An examination of the socializing messages exchanged between blue-collar parents (n = 41) and their children (n = 25) demonstrate that family-based messages about work and career seldom occur in straightforward, unambiguous ways. Instead, messages take several paths (direct, indirect, ambient, and omission). Further, the content of messages communicated along these paths often is contradictory. That is, sons and daughters receive messages that both encourage and discourage social mobility. Ultimately, these individuals must negotiate the meanings of family-based anticipatory socialization communicated to them through a mix of messages. (Contains 2 tables and 3 notes.)