Pip doesn't manage money very well. He is quite lazy about following it. Pip describes his life at Bernard's Inn with Herbert: "We spent as much money as we could, and got as little for it as people could make up their minds to give us. We were always more or less miserable and most of our acquaintances were in the same condition... our case was in the last aspect a common one."
They "check their affairs" by shuffling papers and bills and realize that, though they are in far in debt both, are quite unsure just how far in debt they have gone. After one evening of "checking their affairs," a letter comes for Pip announcing the death of Mrs. Joe Gargery.
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