When everyday life becomes ever more permeated by digital technologies, many older people join ICT trainings to improve their digital skills. Given that digital skills include more than the command of technology (for instance, changing social practices) teaching ICT to people who grew up long before internet and social media can be challenging. The purpose of this article is to propose a theoretical account of a key element for how teaching digital skills to older people can be made successful. Drawing on qualitative interview data with 26 ICT instructors as well as concepts from sociological theory (lifeworld, role-taking) and cognitive science (dual process model), we argue that ICT training needs to take into account the lifeworlds of older participants. In order to be successful, ICT trainings have to appeal to the current lifeworlds of older people while at the same time overcome mismatching lifeworlds. By connecting content and pedagogics to the older adults’ needs, values, and desires, instructors can successfully help integrate new skills into the lifeworld of the older participants.