In the inaugural essay of his collection, Isaiah Berlin explores the evolving perspectives on history and their impact on society's understanding of progress and rationality. During the nineteenth century, there was a prevailing optimism about progress and belief in the power of rational solutions to societal and human problems. This optimism, however, began to crumble as the world transitioned into the twentieth century, marked by what Berlin describes as an intellectual chasm between the two eras regarding their worldview and historical interpretation.

The twentieth century ushered in a new consciousness, emphasizing the significance of unconscious and irrational forces in human behavior. Many came to prefer eliminating problems rather than engaging with them through rational discourse and argumentation. For instance, the challenges associated with human liberty—such as dissent, political extremism, or public demonstrations—were often addressed by suppressing the very desire for liberty among individuals. This strategy was infamously employed by regimes like Nazi Germany and the Soviet Union, which dismissed "bourgeois liberty" as both superficial and ineffective.

This approach threatened to establish a disturbingly "ideal society" where unsettling questions were never posed simply because they were inconceivable. This dystopian vision is vividly depicted in George Orwell's Nineteen Eighty-Four and, in a slightly altered form, in Aldous Huxley's Brave New World. According to Berlin, such a world is possible when people increasingly opt for security at the cost of personal liberty. To prevent this outcome, he advocates for a reduced reliance on rigid systems and a greater trust in human intelligence, nurtured in an environment of maximum freedom.