At the beginning of the novel, Winston harbors feelings of resentment and hatred towards the Party inside himself. Winston's only act of rebellion is simply writing "DOWN WITH BIG BROTHER" in his diary and contemplating the Party's oppressive hold on society. He fears being arrested by the Thought Police but does not initially try to undermine the government. As the novel progresses, Winston believes he has an ally in O'Brien and develops a relationship with Julia. Julia persuades Winston to exercise his individuality, and he begins to find respite during his brief interactions with her. Winston begins to act more rebellious by renting an apartment above Charrington's antique shop, carrying on an affair with Julia, and even attempting to join the Brotherhood by visiting O'Brien's home, where he receives "THE BOOK."

The more Winston engages in rebellious behavior, the closer he gets to being arrested by the Thought Police, which is something Winston accepts and anticipates. Eventually, Winston is arrested and taken to the Ministry of Love, where he is tortured by O'Brien. While he is being tortured, Winston tries his best to maintain his individuality by protecting his spirit. Unfortunately, Winston is taken to Room 101, where he eventually abandons hope and is brainwashed into becoming a loyal follower of Big Brother.

At the beginning, Winston realizes he can't hide from Big Brother since the ruling Party is everywhere. He feels claustrophobic with the posters of Big Brother in his apartment building, on the street, and everywhere he goes. His daily routine involves editing documents at the Records Department of the Ministry of Truth so they will reflect the Party's version of reality. Alienated from his colleagues and people in society, Winston feels a need to find his memories of the past that haven't been edited and his own individuality that defines who he is. His dreams provide an outlet to his search for the past, and he decides to risk everything by having an affair with Julia and trusting O'Brien, a member of the Inner Party. Winston feels betrayed by O'Brien when he exposes Winston and Julia, but at the same time, he respects him. After he's tortured and forced to love Big Brother again, Winston disappears mentally and physically while awaiting his execution.