How can we reconcile the fact that in order to act virtuously we appear to need to refer to the concept of a free will, while, at the same time, there are convincing philosophical arguments (aligned with a contemporary scientific understanding of natural causation) discrediting any viable notion of an unconstrained or uncaused will? Taking its cue from this important question, this chapter will proceed along the following lines. First, I aim to substantiate the link between contemporary character education and the concept of the free will so as to illustrate the interdependency between the two. Next, I will scrutinize the concept of a free will, raising some philosophical concerns about its validity in a contemporary educational context. This involves looking at the philosophical stakes involved in proposing a unique capacity to intervene with the causal order of nature. At this point, I will suggest that there is a way out of this conundrum, and I will continue by proposing a radically different understanding of the will, offered by the seventeenth century rationalist Spinoza. The chapter will close by looking at some of the practical consequences of grounding contemporary character education in a Spinozistic conception of the will.