This paper explores Nietzsche's account of the free spirit's genesis, as primarily given in the 1886 prefaces written for the works of his ?free spirit trilogy?. In particular, it will focus on how what will be argued is the free spirit's distinguishing capacity for radical questioning is created out of the process described there. That is, it will examine how what Nietzsche calls, ?the experience of sickness?, in enabling the free spirit's liberation, helps forge a mode of philosophical awareness which (...) is not otherwise attainable. However, the second half of this paper goes on to explore how the success of this process is endangered by a certain psychological tendency to which free spirits are susceptible. In other words, the free spirit's chance of enduring those painful depths of sickness necessary for liberation is threatened by the appeal of ?romantic pessimism?; a perspective which offers consolation by idealizing the sufferer's state. As such, then, in our final section, we will examine Nietzsche's efforts to combat this phenomenon. In particular, we will look at his advocacy of a specific kind of asceticism for this purpose, and with it his attempt to show how a true liberation of the spirit can be achieved. (shrink)