After his first visit to Satis House where the owner, Miss Havisham, has asked for a boy to come and play with her adopted daughter, Estells, Pip's self-perception is altered irrevocably. As he examines his home, his "coarse" boots and hands, feeling inferior to the young lady who has scoffed at them, Pip yearns to become a gentleman.
Mysteriously, one night as Pip sits alongside Joe at the Blue Boar, a strangle gentleman sits at their table and informs Pip that he has "Great Expectations" with certain conditions attached to them. Of course, since Miss Havisham is the only rich person with whom he is acquainted, Pip assumes that she is his benefactor. In a few weeks, Pip sets out for London where he will be educated and become a gentleman. There Mr. Jaggers informs him that he is to receive a "liberal" stipend each month, but "you'll go wrong somehow, but that's no fault of mineResiding with the "pale young gentleman" who is Herbert Pocket, Pip and Herbert spend money lavishly; they purchase furniture, buy clothes, dine out, and Pip even hires a servant for his small apartment, a servant that he calls, "Avenger" as he takes from Pip what he does not have because of his spendthrift ways.
My lavish habits led his easy nature into expenses that he could not afford, corrupted the simplicity of his life, and disturbed his peace with anxieties and regrets.
Even when Pip and Herbert sit down to examine their affairs, they are unable to economize. But, after Pip receives a 500 pound annual allowance, he uses half of this and help from Miss Havisham to obtain a position for Herbert at Clarikker's bank. However, once Magwitch arrives in London, appearing at twenty-three-year-old Pip's apartment to reveal that he, in fact, is Pip's benefactor, Pip relinquishes his fortune entirely. Repulsed by the convict, Pip feels he cannot accept the money from Magwitch,
I got away from him, without knowing how I did it, and for an hour or more I remained too stunned to think. It was not until I began to think that I began fully to know how wrecked I was, and how the ship in which I had sailed was gone to pieces.
Soon thereafter, Pip goes to the office of Mr. Jaggers to ascertain the truth. Afterwards, however, Pip begins his moral regeneration as he chastises himself for his ill treatment of Joe, and he cares for Magwitch in his dying moments.
In Great Expectatiopns, Pip takes food to a convict as an act of kindness as a young boy. The convict, Magwitch, flees to New South Wales Australia and makes a fortune as a sheep farmer. He gives the money anonymously to Pip out of gratitude. That Magwitch, who is actually Estelle`s father, is the source of the money is revealed fairly late in the book. Pip spends his money to impress Estelle and a higher class of people that he wants to join. He also sets up a joint business venture with Herbert.