Despite lifelong learning being on the European policy agenda since the 1970s, efforts to integrate learning throughout the life course have stalled. Using one hundred interviews with older workers in Germany, Poland, Sweden, and the United Kingdom, this study explores barriers to and facilitators of learning across the working life course at the individual level. While participation in lifelong learning is distributed over the life course in all four countries, learning is perceived as more important in the early and middle phases, with progression and job retention being key motivators. Gendered issues such as caring responsibilities and part-time work are more likely to affect women’s participation in learning, whereas ageism and age stereotypes increasingly act as barriers for all in all four countries. Given the European Extended Working Lives agenda, lifelong learning could be better integrated across the whole life course, including a life course approach to micro, meso, and macro Extended Working Lives policy.