George Orwell's 1984 depicts a dystopian future society ruled by a totalitarian one-party state. Everything about Winston's daily life -- from his job, to the food he eats, even to what he watches on TV -- is tightly controlled and monitored by the state. Despite this invasive tyranny, Winston manages to think, to doubt, and finally, to risk autonomy.
Winston's character development demonstrates individualism because the character becomes progressively more autonomous and less restrained by the authoritarian system designed to govern his every action and thought. Moreover, his character demonstrates the inherent risk of individualism. The possibility of capture and torture are never far behind Winston; this danger is what makes his actions so meaningful and significant. Indeed, the latter half of the novel consists mainly of Winston fleeing the authorities who would have him detained and "re-educated."
Winston's character depicts individualism as a radical political act, the necessary antidote to totalitarian rule. Thus, the character helps us to understand what's at stake when we are confronted with a choice between individualism and agency on the one hand, and blind or fear-based obedience to authority on the other.
At the beginning of George Orwell's novel, 1984, we find Winston as an unhappy party member, afraid of committing some unfaithful act under the watchful eye of Big Brother. Although he occasionally attempts to skirt the everpresent cameras and microphones for a little private thought--and for some risky annotations in his private, written diary--he doesn't break out of his shell until he discovers that fellow party member Julia is interested in him. Her own acts of disobedience further encourages Winston's actions. Winston's foolhardy acts of individualism--renting a room above an antique shop for elicit meetings with Julia and rendezvousing with her in other places--eventually gets him arrested. He is tortured relentlessly under the watchful eye of his hero, O'Brien, yet Winston holds out far longer than is expected. Although he eventually gives in to the torture, he is completely broken.