While it is true that ageing dramatically affects the sustainability of welfare systems, increasing life expectancy in most Western countries is also seen as an opportunity to live longer and better: The healthiest older people are also the most dynamic in terms of work activity and social and cultural capital. In this debate, media and communication technologies are often seen as tools to enable older people to age actively, thanks to their potential for inclusion. The empowerment of older people through the use of communication technologies is strongly influenced by the social and family context in which digital media are used and by the formal and informal contexts in which their use is learned. Starting from this context, this article investigates the relationship between career paths and the use of digital media among older people. We conducted 20 in-depth interviews and ethnographic sessions with Italian internet users aged over 65. The results show how their current condition (retired or employed) and the job previously held have a fundamental impact in both the processes of domestication of technologies and internet use, but also in the structuring of the home itself and the positioning and use of technologies in the domestic space of older people