The negative impact of unemployment on subjective well-being (SWB) is well known, but the role of age in this relationship remains unclear. We suggest that cumulative advantage (or disadvantage) associated with the duration of current employment status may produce an age-related divergence in SWB between employed and unemployed individuals. We used cross-sectional data on employed (n = 1382) and unemployed (n = 254) Germans (age 18-42) surveyed in 2005. We found that, among currently employed individuals, relatively older age predicted longer employment duration (tenure), which was related to higher SWB via higher income and higher perceived occupational security. Among currently unemployed individuals, age predicted longer unemployment duration, which was associated with lower SWB via lower perceived social support. Thus, age was indirectly related to higher SWB in employed individuals and to lower SWB in unemployed individuals. In this way, cumulative advantage of long-term employment and cumulative disadvantage of long-term unemployment contributed to the age-related divergence in SWB between employed and unemployed Germans already in the first half of working life.