This study investigated the influences of retirement transition, age, and gender on aspects of daily experiences in adults (aged 50-75 years) who stayed working (n=138) and who transitioned into retirement (n=72). Data derived from the first and second waves of the Daily Diary Study of the National Survey of Midlife in the United States. Participants completed telephone interviews about their experiences across eight consecutive days. Findings showed a significant interaction effect of retirement transition and age on daily stressors. Gender did not significantly moderate the associations between retirement transition and daily experiences. These findings suggest that retirement transition must be considered in the context of life course influences, especially age, to better determine the quality of daily experiences of midlife and older adults, and these life course influences should be considered in programs and services aimed to help adults navigate the retirement experiences.