Few individuals who embrace deviant trajectories maintain a constant level of deviance over time. Fluctuations, changes and transitions are commonplace in deviant lifestyles. A limited number of studies have examined these changes in a dynamic perspective. Drawing from the method of life history calendars and considering inter-and intra-individual changes, this study compares relapse episodes among gamblers (N=50) and offenders (N=107) trajectories. Results highlight the generalizability of the criminal career analytical framework. In particular, our findings emphasize the importance of considering both individual attributes and life circumstances. We also discover in this study that the effect of life circumstances is often conditional of certain individual characteristics.