This essay reflects on the changing valences of character, especially in the context of the ``rise`` of the novel, the genre that more than any other casts itself as the study of ``real life.`` Earlier Theophrastan characteristic writing is increasingly perceived to be ``flat`` and contrary to the ``round`` characters with depth and uniqueness, who alone represent ``true life`` in commentaries that have become standard. In The Rise of the Novel, Ian Watt inherits Forster`s and Woolf`s standards of what constitutes ``real life`` in literature, hence his painful discomfort with the preponderance of the flat character and type names in Fielding`s novels. I try to chart how the novel has come to be "un-characteristic" writing. I argue that the deep and private self, the unique and the equal self, the changeable and characterless self, indeed the modern ideal of the ``real`` self can be illuminated by the sociological and philosophical analysis of money by the early German sociologist, Georg Simmel. According to Simmel, money, so often vilified as the source of all human evil, gives birth to the private, isolated self. The reverse of this freedom is the inconsolable loneliness but also what can best be explained as a "spiritual" experience of "an island of subjectivity, a secret, closed-off sphere of privacy." The new-found depth of the inner, private self―largely unknowable by the other―becomes a general experience only within the economy of the cash nexus. Simmel`s analysis of this secret, private self, perhaps the supreme value in modern Western thought, complicates prior understandings of character, virtue, and ``real life`` itself.