This chapter examines how inequality which builds up over an entire lifetime from disparities in the length of life, employment rates, earnings and pensions evolves across birth cohorts. It shows that great strides in longevity have been a common phenomenon across countries and genders, but also that marked gaps in the length of life between educational groups and genders exist in all countries for which data are available. It then turns to education- and gender-related gaps in total-career labour earnings by showing how the diverse trends in employment rates, hourly wages and annual hours worked shape their evolution from one generation to the next. The chapter subsequently investigates how inequality during the working life and gaps in life expectancy translate into differences in pension benefits. A pilot dynamic micro-simulation model finally simulates for a limited number of countries the impact of higher life expectancies on the share of healthy life years and on the length of working lives. It also estimates the effect of raising the retirement age on the career length and pension entitlements across socio- economic groups of the late 1960s cohort.