As a young lawyer and trader in Manhattan in the 1990s, I began to understand why so many become disillusioned after college. The world appears too big a place. Rather than fight the relentless indifference of the universe, many of my saner peers retreated to tending their small gardens. The higher one’s IQ, the more pessimistic one became about free-market politics — capitalism simply is not that popular with the crowd. Among the smartest conservatives, this pessimism often manifested in heroic drinking; the smartest libertarians, by contrast, had fewer hang-ups about positive law and escaped not only to alcohol but beyond it.
But I must confess that over the last two decades, I have changed radically on the question of how to achieve these goals. Most importantly, I no longer believe that freedom and democracy are compatible. By tracing out the development of my thinking, I hope to frame some of the challenges faced by all classical liberals today.