This paper investigates the relationships of social structure and personality during a period of radical social change attendant on the early stages of the transformation of Ukraine from socialism to nascent capitalism. It does so by analyzing data secured from face-to-face interviews with a representative sample of urban Ukrainian men and women in 1992-93, together with a follow-up survey three to three and a half years later of all those respondents who at the time of the initial survey either were employed or were seeking paid employment.We found that the over-time correlations – the stabilities – of two underlying dimensions of personality – self-directedness of orientation and a sense of well-being or distress – were startlingly low, by comparison not only to the United States at a time of much greater social stability, but also to Poland at the same time as the Ukrainian study, albeit at a later stage of transition. The stability of a third fundamental dimension of personality – intellectual flexibility – was higher than those of self-directedness of orientation and distress, but considerably lower than past research had led us to expect. Still, despite massive changes in social and economic conditions and great instability of personality, the relationships of social structure with personality were remarkably consistent over time and, with the partial exception of those with the sense of wellbeing or distress, were quite similar to those of both socialist and advanced capitalist societies during times of apparent social stability. Our analyses suggest that consistency in the relationships between social structure and personality despite great change both in social structure and in personality results from the continued stability of proximate conditions of life that link position in the larger social structure to individual personality, and the continued strength of those linkages. Notable among these proximate conditions, for those people who were employed at the times of both the baseline and follow-up surveys, is the substantive complexity of their work.