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It is well documented that few offenders maintain a linear or constant trajectory in their criminal activities; instead, zigzag paths characterize most criminal trajectories. Understanding the dynamics of such intermittent cycles can contribute to reintegration efforts by identifying the factors that influence the interruption and resumption of criminal activity. One explanation of intermittency relies on the rational choice theory, which suggests that offenders weigh perceived outcomes (potential rewards) against the subjective probability of legal sanctions (risks) before deciding to commit a crime. The present study examines the effect of direct experience with the justice system (specific deterrence) and offender success in criminal ventures on the likelihood that offenders will interrupt and then restart their illegal activities. The study is based on detailed criminal career data from 172 offenders involved in lucrative forms of crime. Using the method of life history calendars, multi-level models based on month-to-month changes in the life circumstances of the offender were created. The results highlight the relevance of the rational choice perspective to understanding intermittent cycles, showing that its use makes it possible to demonstrate the direct influence and complementarity of sanctions and levels of criminal achievement.