J. S. Mill is typically thought of as a liberal utilitarian disciple of Jeremy Bentham, and in other readings as a modern Socratic or even a modern Epicurean. Mill and the Epicureans are alike in several respects: they theorize personal freedom and active character versus determinism and passivity, they oppose excessive love and praise friendship, and they are critical of traditional religiosity. In spite of these similarities, Mill and the Epicureans have a different conception of active character and citizenship, stemming from a difference in first principles. Mill's philosopher does not share the Epicurean aim of untroubledness (ataraxia), and Mill accepts the demanding task of educating and regenerating a mass democratic society. Below, I assess Mill's troubled hedonism, that is, his acceptance of often intense and long-term mental perturbations, justified by a decidedly non-Epicurean social reform project.