Hiding things from a society that is always watching isn’t a very smart idea. It is also practically impossible to do, yet we always root for the people who try and break the crazy rules set up for them. Winston was heavily opposed to society throughout the novel 1984 and he was also opposing himself at some points. Winston was acting as any main character of a dystopian story would: he didn’t believe everything that society was trying to tell him and he didn’t want to follow the rules established for him. He knows that “Big brother is always watching,” but he thinks that just because he has a little hiding spot in his house that he can’t be seen from that he is an exception to that rule. He also relies on his instinct and less on reason
