This paper is the result of joint work within the Laboratory 5 “Older People and Work”. It reflects on the challenges posed by population ageing in the workplace, emphasizing the importance of training and lifelong learning as essential tools for promoting individual and collective well-being. The transition towards an ‘ageing society’ requires a rethinking of professional skills, educational practices, and age management policies. By analysing experiences, research, and best practices – such as those promoted by INAPP, the Universities of Florence and Foggia, and the organizations from the Third Sector and civil society – the paper highlights innovative models of intergenerational learning, emerging professional roles in educational care within healthcare settings, and technological tools for health promotion. The aim is to support an integrated and inclusive approach to later-life work that values intergenerational relationships, prevents social exclusion, and promotes the dignity of older adults through care, education, and social and digital innovation in both living and working environments.