At the core of liberalism, Trilling emphasized, was a “primal act of imagination.” Behind all the conceptual infrastructure that made up the liberal world was a visionary desire. Our laws and customs might be the forms of our freedom, but they could not account for its content, for the value we attach to it. The purpose of a liberal society was to free individuals to follow their dreams: the pursuit of happiness, unleashed. But what dreams? By definition, a liberal framework cannot say.

This, according to Trilling, was the paradox at the heart of liberalism—a paradox that, while not fatal in itself, posed a mortal danger to the life of liberal societies. As liberalism progresses, it erects political, economic and social structures with a view to rational improvement, affirming the human capacity to build a better world. But the more power it gains—the more effectively it reshapes the world in its image—the more it loses sight of what exactly this power is for. “In the very interest of affirming its confidence in the power of the mind,” Trilling wrote, liberalism “inclines to constrict and make mechanical its conception of the nature of the mind.” Imagining itself as a human creation, liberalism creates a society of machines.