This chapter focuses on the impact of James Hillman's work, Pragmatism, on the development of Jung's Psychological Types. Through consideration of a change in his attitude to James's theory, the development of Jung's typology clarified. The year 1913 was very important in Jung's life, because at the beginning of the year he had terminated his relations with Sigmund Freud, with whom he had been an intimate associate since February 1907. In 1921, announcing the break of dawn, one of Jung's greatest works, Psychological Types, was published. The Red Book, as an exploration of individual experiences, and Psychological Types as a general theory, are quite different in their ways of expression and direction, but they are also combined inseparably within Jung himself. Pragmatism originated in the small town of Cambridge, Massachusetts, in the early 1870s. The theory of pragmatism was advocated for the first time in 1878 by the logician Charles Sanders Peirce.