Public policies encourage later retirement, but they often do not account for discrepancies in the capacity for extending working lives. This paper studies trends and inequalities in extending working lives between 1990 and 2019 from gender and education perspectives in seven countries (Australia, Germany, Russia, South Korea, Switzerland, United Kingdom, and United States). The three-decade-long data provide insights into the societal transition toward extended employment that began in the mid-1990s. Using latent class growth analysis, we identify five universal trajectories representing late-life employment in all countries: Early, Standard and Late Exit patterns, and stable Nonemployment and Late Employment patterns. Regression analyses show that Non-Employment dominated the 1990s, but it significantly declined, giving space to Late Employment as one of the major employment pathways. Gender and educational differences are considerable and stable and constitute important stratification markers of late careers. Progress toward later employment affects all analyzed countries but in different ways, suggesting the simple generalizations of one-country findings can be risky. We discuss the risks of universal progress toward extending employment that can bring unequal results and negative consequences for vulnerable groups. This study also contributes methodologically by exploring the trajectory-oriented perspective on late careers.