Whereas present theories of transformative learning tend to focus on the rational and reflective actor, in this article it is suggested that spontaneous action may play a decisive role in transformative learning too. In the spontaneity of action, novelty finds its way into life, gains momentum, is respected by others and reflected by the actor. Such transformation processes are investigated both with the means of theoretical reflection and of empirical inquiry. Based on nine narrative interviews typical phases of transformative learning processes are identified. Owing to the comparative nature of the study, it was also possible to develop an age-related typology that overlaps certain phases of the transformation process. These empirical findings constitute the background against which the nexus of spontaneous action and transformative learning is reflected theoretically. Theories drawn upon include John Dewey's Pragmatism and George Herbert Mead's Social Pragmatism. Both scholars provide rich theoretical concepts for reflecting on the nature of that what so often eludes from the control of both educators and learners: the spontaneity of the beginning.