In Bradbury's Fahrenheit 451, when and how does Montag realize he can no longer be a fireman? 

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Montag is radicalized into rejecting his profession in a series of slow realizations, in which he begins to connect the dots of his life and how unhappy he is. Clarisse is the catalyst that starts him on the journey; her appearance in his life is quickly followed by Mildred's suicide attempt. He starts to come alive emotionally and to question his society's values, which he realizes have left him empty and unsatisfied.

The turning point comes as he participates in a book burning in which the owner of the books, an older woman, commits suicide by burning herself up rather than living without her books. Montag comes home stunned and changed:

His hands were ravenous. And his eyes were beginning to feel hunger, as if they must look at something, anything, everything.

He has a book he has stolen from the woman's house in his hands. At this point, he no longer wants to go to work. He no longer enjoys book burning. He asks Millie to call Beatty and tell him that he (Montag) is sick. All of this is part of his metamorphosis into a new person. He tries very hard to explain his reasoning and his experience to Mildred, but she is completely conventional in her thinking:

"Mildred, how would it be if, well, maybe, I quit my job awhile?"

"You want to give up everything? After all these years of working, because, one night, some woman and her books—"

"You should have seen her, Millie! "

"She's nothing to me; she shouldn't have had books. It was her responsibility, she should have thought of that. I hate her. She's got you going and next thing you know we'll be out, no house, no job, nothing."

"You weren't there, you didn't see," he said. "There must be something in books, things we can't imagine, to make a woman stay in a burning house; there must be something there. You don't stay for nothing."

It is the fact that the woman was willing to die for her books that has such a profound impact on Montag. He realizes there must be something of great value in books.

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The self-immolation of the older woman provides the catalyst for Montag's disillusionment with his role as a fireman. That someone should be prepared to die for the right to read books makes him realize the importance of what it is that he and his fellow firemen are destroying on a regular basis. There must be something in these books that people find so special, so precious, and so enduring that they're willing to commit suicide if they must lose it altogether.

Montag now starts to realize that, contrary to what Captain Beatty has always told him, books are not simply the repository of trivia—they are so much more valuable than Beatty would have him believe. It won't be until Montag begins his regular discussions with Professor Faber that he fully comprehends the importance of books as transmitters of cultural value. But for now at least, he's taken his first faltering steps on the road toward wisdom and understanding.

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Montag considers quitting his job as a fireman after a woman commits suicide by burning herself with her books. This event shakes Montag to his core because he doesn't understand why people would kill themselves over books. He decides to stay home sick the day after the woman dies so he can sort the situation out in his mind. He talks to his wife about not going back to work as a fireman, but it isn't until Montag speaks with Professor Faber that he finally decides he doesn't want that job anymore. Montag describes his frustrations with society to Faber by saying,

Nobody listens any more. I can't talk to the walls because they're yelling at me. I can't talk to my wife; she listens to the walls. I just want someone to hear what I have to say. And maybe if I talk long enough, it'll make sense. And I want you to teach me to understand what I read (82).

Faber teaches Montag about how people in their society don't care about reading, intellectual thinking, or overthrowing the government. If Montag doesn't like the way things are, he will have to do something about it on his own. Faber suggests, however, that the firemen would have to be taken out of the equation before they could convince the populace to support reintroducing books into their society. This talk interests Montag. It gives him a purpose in life because he admits the following to Faber:

This afternoon I thought that if it turned out that books were worthwhile, we might get a press and print some extra copies (85).

The fact that Montag wants to start printing books illegally shows he is not aligned with the philosophy behind his job as a fireman. Once Faber is willing to print more books as long as the firemen aren't a threat anymore, then the plan to frame firemen by planting books in their homes surfaces. When Montag and Faber both commit to this scheme, he officially stops being a fireman. Therefore, Montag realizes he can't be a fireman anymore once he commits to a life of sabotage in order to bring the government down.

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