Current cultural, social, and economic trends challenge traditional concepts of learning and lifelong learning. This paper draws on the twofold nature of learning in a knowledge society and explores options for technological support. The concept of Second-Order Learning Objects is introduced as a potential means to foster generative learning. Generative learning goes beyond what is already known and extends or transforms the socially shared knowledge including its artefacts and practices. According to the notion of individual and social learning as a process of reflective action, the role of strategies and media for reflection and inquiry is stressed. This paper outlines the use of schematically represented strategies for learning and reflection and sketches important features of a pursuant modelling approach.