The first part of the paper identifies a lack of clarity in the Nussbaum’s article entitled “Educacion para el lucro, educacion para la libertad” related to the connection between the concept of “freedom” and the “democratic skills” mentioned by the author. In order to make this connection clearer, this paper is concerned with the linkage that John Dewey establishes between “democracy” and “freedom”, which permits to discover that the connection depends on a conception of reality as something contingent, unfinished, and open to unexpected outcomes. This finding has some interesting pedagogic results which permit, in the second part of the paper, to formulate some ideas for teaching the “freedom” in the classroom. The last part of the paper -given the allegedly connection that some teachers establish between the concept of “freedom” and those of “happiness” and “autonomy”- posits some ideas about how to educate for being “free citizens”, through looking for a happy life, this being understood in the stoic sense of “peace of mind”.