The title has a double meaning, because when it refers to “great expectations” it is talking about both Pip’s money and his plans for himself; neither worked out for him.
In many ways, Dickens is satirizing the role of money in determining one’s fate. Pip had one life in store for him before the money, and a different one after. Most people would agree that although a blacksmith’s life is not luxurious, having a trade you can be successful in and people who love you is preferable to being isolated in the city with people who pretend to be your friend only as long as you have money.
When Jaggers tells Joe and Pip that Pip has expectations, they gasp. They seem to understand exactly what he is saying.
“Now, I return to this young fellow. And the communication I have got to make is, that he has Great Expectations.” (ch 18)
He also comments that the expectations come with the money to support them. Pip is to be a gentleman. He will be set for life. Everything will be fine from now on.
Ironically, things don't go well for Pip. His life as a gentleman is lonely and full of conflict. He struggles, because he is not given guidance on what to do with the money. The other gentlemen that he associates with seem to mostly waste thiers.
When Pip learns that the money came from the convict, the whole illusion comes crashing down on him. He realizes that he is the same person he was, and he can go back to being that person. He had turned his back on those he loved, but seeing Magwitch sacrifice himself out of a paternal desire to see Pip was enough to return Pip to his simple lifestyle, and become much happier making his fortune, modest though it may be, on his own.