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This is an interesting question. I think that Orwell concludes two different points on this. On one hand, there is what Orwell would like to see in humanity, but there is also what Orwell does see in humanity. I sense a definite tension between what is and what should be in Orwell's work. I do see Orwell as hoping that individuals possess freedom no matter what, and if happiness is elusive, one can chalk it up to individual freedom. That fact that Winston never is able to experience freedom, in its purest of senses, because of Big Brother and the configuration of Oceania is testament to this. Orwell would argue that the government of Oceania is quite content when individuals are "happy" and willing to sacrifice their freedom as it substantiates the state and emboldens the government. This is why Orwell would probably wish humans to have freedom and strive for happiness, for in this condition, the state does not possess all encompassing power. At the time of writing, Orwell believed that neither superpower was really willing to be happy with freedom of the individual and that both sought to control the individual and the freedom within he/ she. In the end, it is this condition, suggesting that one validates freedom over happiness that Orwell might like to see in the individual as it decreases the power from the state.
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