What were some of Odysseus' character flaws and mistakes in judgment?
Odysseus had undertaken so many acts which are worthy of praise, but there were some distinct moments where miscalculation were present. One of the faults of Odysseus is that it seems as if his irrepressible wit and cunning will lead him to be incapable of being content with returning home. Given the fact that the trials of war and the intensity of zeal and pain have defined his life, he does not demonstrate the capacity to simply return to Penelope and Telemachus and desist with his journeys and his conflicts on the battlefield. He professes his desire to return, but he revels so much in his voyage that one senses a bit of inauthenticity in his notion of simply "resting" upon his return. It seems like Odysseus' life is one where he is moving from one person to another, one island to another, and one state of existence to another. Perhaps, Homer is attempting to make a point that this is a uniquely human aspect of consciousness: A sense of definition which is constantly in flux, denying any permanence or sense of totality.
In terms of his actions, themselves, Odysseus does not act with the "fierce urgency of now," at several moments. This would lend an inauthentic spectre to his professed desire to simply want to return home. He wastes valuable time from his “nostos,” or journey home, on Calypso’s island where he indulges in sex, food and a basically hedonistic lifestyle. When he finally misses the excitement of activity and glory, he politely leaves for home. At the same time, he rejects Calypso's invitation to immortality, and in the process, demonstrates his self serving nature. Once he has become "bored" with his exploits with this woman, he rejects commitment to her and assumes his "piety" with having to return home. It is interesting to note that Penelope is designed to represent faithfulness and complete devotion to her husband, yet he does not do the same at several moments on his journey. He wants to colonize the Cyclops’ island. When he and his men are trapped and in severe danger of being eaten down to the last man, Odysseus thinks of a clever ruse to escape the monster. Just before he and his men are truly free of the beast, his appetite for fame makes him careless and he reveals his name. By doing this, he earns Poseidon’s wrath. In addition to this, there is a bit of in-authenticity in the relaying of this story. Odysseus makes it sound as if this were a moment in time where he was assuming a purely defensive position, but there were moments where Odysseus demonstrated a type of blood lust and engaged in reckless and cruel behavior that might lie outside the confines of traditional warfare.