All he ever seemed to get for all his choices and all his freedom was more miserable. And so he changes again. For Dewey, life presents not so much the paradox of choice as the fatalism of free will. Dewey is difficult, uptight, cruel, selfish, cold, driven, calculating, dissatisfied, empathetic, impossible, and inscrutable, and it is very easy to feel sympathy for him.
Dewey’s family and community discouraged him to explore the arts and to indulge in his own fleeting creative impulses – and encouraged him to worry about the social pressure to find productive employment. Yet Dewey defines himself by refusing not to partake in politics, art, and individual indulgence. His freedom frequently suggests that even he and our footloose society are rooted firmly in the past, with whole communities defined by choices made long ago. His assertions of individuality are struggles to define himself against his histories, family, and communities.
The die is cast, and he is locked in a generational dialectic. The meaning he yearns for is ultimately found only in his restless pursuits. Freedom today is the freedom to rebel, to fail, and to make mistakes – which, at the very least, are his own.”