This investigation of proactive personality focused on life satisfaction during a 10-year period in which people went from being full-time employees to being fully retired. The study contributes at the intersection of the literatures on proactive personality, careers, retirement, and life satisfaction. In a sample of 118 recent retirees across the U.S. workforce (mean age = 65), personality was correlated with assessments of life satisfaction over the prior 10-year period and a variety of control variables (individual, household, and previous job) were included so that we could examine the incremental and unique effects of proactive personality. Proactive people were more satisfied during this critical period of life. This was true whether differences in life satisfaction included or excluded differences in career satisfaction during that time. We discuss future research implications and potential practical implications for enhancing satisfaction during a life stage in which proactive behavior may be beneficial.