In many ways, Pip's anticipation, or expectation, of events and acquisitions has been disappointing. Having been influenced by the reactions of his covetous Uncle Pumblechook and sister, Mrs. Joe, Pip comes to believe that somehow the wealthy are superior. For instance, when he is invited to go to the house of Miss Havisham, much ceremony in his home takes place and he is virtually baptized with water as his sister bathes him excessively at the pump. With ceremony his clothes are laid out and Uncle Pumblechook coaches him on his math before Pip makes his appearance at Satis House.
Of course, the contrast between what Pip has expected of this house and what he sees is marked. Satis House is in ruins, the interior is dark with no sunshine allowed to peep through the heavy curtains, the clocks have all been stopped at the same time, his escort is curt and impolite, ridiculing his appearance: "Why, he's a common laboring boy!" Rather than being received graciously as a guest, Pip is made to feel like a servant who must follow Estella and be the butt of her despairing remarks about his coarseness. Nevertheless, Pip is taken with Estella's beauty and, as for many, that which seems unattainable to him becomes most desirable. Thus, he leaves Satis House as the occupants are--dissastified. He is most disappointed in his expectations as he has been ridiculed for his coarse boots and common [meaning low-class] way of calling knaves in cards jacks. Pip's return home is miserable, but he dissembles to Pumblechook and Mrs. Joe because he knows that they have somehow elevated Miss Havisham to almost royalty, telling them of velvet coaches and games with flags as though he were, indeed, with a queen and a princess.
Pip's disappointment illustrates the theme of Appearance vs. Reality in Great Expectations, a theme that serves to elucidate the lesson that false values lead to falsity with oneself. For, later in the novel as Pip has pursued his false values, he berates himself:
All other swindlers upon earth are nothing to the self-swindlers, and with such pretenses did I cheat myself.
At the end of Chapter 19, it says, "This is the end of the first stage of Pip's expectations"--but Pip only achieves one thing--he has come into a lot of money. So, while he has the potential for some "great expectations" I don't think he really has achieved anything yet. All he has is the means by which to pursue it--cash. As we find out later, Pip's money does not make him into a man, but his hard work does because he loses the money, and as such, is forced to go to work with Herbert Pocket where, in the end, he does make a success of himself. The title of this novel is ironic because "expectations" does not mean the same thing as "achievement". Pip's plans were merely that -- "expectations"--and the achievement only came through hard work and diligence. Pip learns that the ones that love him the most in his life are Joe and Biddy. Joe is the one that comes to London and nurses Pip back to health. By the end of this chapter, Pip is only starting out, so the only thing he has really achieved is some money, a new suit, and big plans.