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Identity and rational choice theories both view desistance from crime not just as a function of changing expectations about the risks, costs, and rewards of offending, but also due to changing preferences, tastes and desires (Giordano et al., 2002; Paternoster and Bushway, 2009). These two components of offending decisions are thought to jointly affect one’s actions, and to be differentially impacted by “turning points” and identity transformations. To date, however, the methods used to investigate identity theories of desistance have conflated expectations and preferences. In this paper, we develop a discrete choice random utility model as a means to estimate preferences and to, in turn, examine nuanced theoretical predictions. Specifically, using data from the Pathways to Desistance Study, we demonstrate how random utility models can allow for: 1) an assessment of the joint effects that perceived arrest risk (expectations) and risk tolerance (preferences) have on offending behavior; 2) the simultaneous estimation of how expectations and preferences change as individuals transition from adolescence to young adulthood and; 3) an examination of how life events and identity transformations differentially impact perceptions of risk and preferences for risk. We discuss theoretical and methodological implications of the method and findings for both life course criminology and sociological theory, more generally.