Three longitudinal studies examine a fundamental question regarding adjustment of personal values to self-chosen life transitions: Do values fit the new life setting already at its onset implying value-based self-selection? Or do values change to better fit the appropriate and desirable values in the setting, implying value socialization? As people are likely to choose a life transition partly based on their values, their values may fit the new life situation already at its onset, leaving little need for value socialization. However, we propose that this may vary as a function of the extent of change the life transition entails, with greater change requiring more value socialization. To enable generalization, we used three longitudinal studies spanning three different life transitions and different extents of life changes: Vocational training (of new police recruits), education (psychology vs. business students) and migration (from Poland to Britain). Although each life transition involved different key values and different populations, across all three studies we found value-fit to the life situation already early in the transition. Value socialization became more evident the more aspects of life changed as part of the transition, i.e., in the migration transition. The discussion focuses on the implications of these findings for research on values and personality change, as well as limitations and future directions for research.