While paid work is a well-established predictor of health, several gaps in our knowledge about the relationship between adult work patterns and later health and mortality remain, including whether these benefits remain stable over long periods of time and whether they are dependent on job characteristics and experiences. In this paper we draw on more than three decades of data from the National Longitudinal Survey of Mature Women to assess how labor force participation over a period of twenty years during midlife affects mental and physical health and mortality over the following fourteen to twenty-three years. We find that persistent work earlier in life continues to predict improved health and longevity many years later as women pass retirement, even after accounting for many health-linked variations in this work experiences and the presence of later life work. These findings add to knowledge about the cumulative nature through which key adult social experiences shape health as individuals enter later life.