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The first significant decision that Odysseus makes is his choice to decline Calypso's offer to become immortal and stay with her forever. This is significant because it demonstrates Odysseus' personality. He is a headstrong man and is quite loyal to his family, choosing to live and meet a mortal's death one day to return to his family rather than live forever with a goddess.
He makes a similar decision later on when he decides to leave Circe's island after having spent a year with her. This shows his love and consideratino for his men because they asked him to leave.
Another intelligent decision he makes is asking his crew to tie him to the mast of the ship when they pass the sirens' alluring song so that he could hear it yet not be allowed to give into it, which would surely lead to his death. He also had his men plug their ears so they would not give in to the sirens' song.
One of the bad decisions he makes is when he offends Poseidon by hurting the Cyclops, the son of Poseidon. The Cyclops asks his father to seek vengeance for him, throwing Odysseus off course yet again.
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