In this paper I would like to present one of the essential aspects composing the theory of transformative learning. The concept of transformative learning was first introduced by Jack Mezirow in 1978 and his theory has been the leading theory in lifelong learning studies. Although Mezirow's theory of perspective transformation is the major theory of transformative learning, Robert D. Boyd has much influence on another perspective of transformative learning theory. In contrast to Mezirow who put emphasis on critical reflection and the work of rationality, Boyd emphasizes the work of collective unconsciousness, which is the key concept of analytical psychology pioneered by Carl G. Jung. While Mezirow sees the ego as playing the central role in the process of transformation, Boyd uses a framework that moves beyond the ego and empahsizes the totality of self. This paper shows the process of transformation of self according to Boyd's theory, focusing on the concept of discernment and the work of grieving. Also the role of fascilitators in transformative learning is sought. In the end I would like to present the practice of the Highlander Folk School, which effectively applied music, dance, literature etc., to work on the collective unconsciousness of the people.