What is Winston's greatest pleasure in his life in 1984?
Winston's greatest pleasure in life is his work. His job at the Ministry of Truth is to rewrite history, doctoring documents so that they correspond with Big Brother's version of the truth. Most of Winston's work is
"tedious routine, but included in it there (are) also jobs so difficult and intricate that you could lose yourself in them as in the depths of a mathematical problem - delicate pieces of forgery in which you had nothing to guide you except your knowledge of the principles of Ingsoc and your estimate of what the Party wanted you to say".
Winston likes his job because he is good at it, and he looks upon it as a challenge and a diversion in his drab life. He is so skilled at what he does that he has even on occasion been entrusted to rectify the Times leading articles. Winston no longer thinks of what he does as forgery - the materials he works with have so little connection "to anything in the real world, that to him, it is "merely the substitution of one piece of nonsense for another" (Part I, Chapter 4).
Winston finds the greatest pleasure in life from his work. He works as a clerk at the Records Department in the Ministry of Truth, and his job description entails rewriting historical documents to match the current Party affairs and paint Big Brother in a perfect light. He dictates while a machine called speakwrite types. After it is finished, he destroys the documents containing the now obsolete information. Even though his job is somewhat monotonous, Winston enjoys it because it is complex and demands a great deal of mastery to accomplish the tasks. In fact, Winston appreciates the complexity of the job because he immerses himself in it to the point of forgetting about his bland life. He is so good at Newspeak that on several occasions he has been assigned to rectify articles for The Times.