This paper investigates how cumulative disadvantages of non-employment and non-standard work are affecting careers and subjective well-being of older Europeans from 13 countries. In previous research, unemployment, labour market inactivity and part-time work had negative effects, however they were seldom addressed in a common study and over the whole career. In two complementary analyses, first, the employment history of older Europeans is analysed with sequence analysis methods to show how non-employment and part-time work shape careers and to illustrate gender differences. In a second step, adverse career components are used to exemplify cumulative disadvantages on subjective well-being in old age. Data from the Survey of Health, Aging and Retirement in Europe (SHARE) is used for the analyses. After optimal matching and clustering of the retrospective employment history, the results indicate that women experience more turbulent careers with more periods of nonemployment and part-time employment. The analyses of subjective well-being show that labour market inactivity and unemployment have negative effects in old age for men, but less for women. Part-time employment has a differentiated effect for women, however not for men.