Graduating high school and entering college, the workforce, or the military may all be understood as examples of major life transitions. Such transitions may be experienced in different ways, may be easy or difficult, and may or may not be successful. One life transition infrequently studied is the military-to-civilian transition that service members experience. The current study focused on the transition period service members experience upon reentry to civilian life after they have separated from the service. A successful transition was assessed in two ways: the ease to which the service member adjusted to civilian life and their satisfaction with life immediately after discharge from the military. This study incorporates both positive and negative effects of serving on the service members’ perception of the ease and success of their transition to civilian life and their satisfaction with life. Personality traits were assessed to determine if individual differences also predicted success during the transition period and satisfaction with life. Participants were 595 United States military service members who had separated from the service less than 10 years prior to the time of data collection. The results of the current study indicate that positively experienced deployments, positive discharge training experience, more frequent contact with other veterans, the kind (positive or negative) of situation returned to, and post-traumatic stress symptoms significantly predicted service members perceived ease of adjustment to and satisfaction with civilian life. Extraversion and negative emotionality similarly predicted these same outcomes. No significant gender differences were observed. These findings suggest a potential avenue future researchers and policy makers might take to better help service members adjust to civilian life. One avenue may be to create an intervention of a standardized discharge training experience all service members receive when separating from the service. This training should treat adjustment back into civilian life as multifaceted and involve the service member and those individuals who make up their social support system.