On Liberty opens by identifying the central question: not the freedom of the will in a philosophical sense, but civil and social liberty, meaning what power society may legitimately exercise over the individual. Mill traces how the struggle between liberty and authority has historically been fought against rulers, and then shows why the problem does not disappear when rulers become accountable to a democratic majority. A majority can still oppress, and the tyranny of prevailing opinion can be more penetrating than legal coercion.
The book's organising principle is the harm principle. The only legitimate basis for interference with any person's conduct, whether by law or by collective opinion, is self-protection, meaning the prevention of harm to others. Actions that concern only the person themselves fall outside the rightful jurisdiction of society, however foolish or degraded those actions may appear to others. Persuasion, remonstrance, and reasoning are always available; compulsion is not.
Chapter II makes the case for complete liberty of thought and discussion. Mill argues on two fronts. If the suppressed opinion is true, silencing it deprives humanity of the chance to exchange error for truth. If false, suppressing it loses the sharper perception of truth that comes from living collision with error. He also considers the case where a received doctrine contains partial truth on both sides, arguing that only free debate can combine them. The argument rests on the explicit claim that all silencing of discussion is an assumption of infallibility, and no individual or age is infallible.
Chapter III extends the argument from opinions to ways of living. Mill argues that different experiments in living are as valuable as different opinions, and that custom observed merely as custom develops none of the human faculties. Human nature is not a machine to be built after a model but a tree, which requires to grow and develop on all sides. A society that suppresses individuality loses the energy, originality, and character that only free development produces.
Chapter IV draws the boundary between individual and social authority. Each person is the most interested party in their own well-being and the one with most knowledge of their own circumstances; the interference of society rests on general presumptions that are as likely to be misapplied as not. Chapter V applies the two maxims (no compulsion for self-regarding conduct, accountability for conduct injurious to others) to trade, education, and government, and closes with the argument that a state which dwarfs its individuals in order to make them more docile instruments will find, in the end, that with small men no great thing can really be accomplished.