Ancient Greek literature is filled with images of sailing the sea and all of the dangers attached to the enterprise. None of this was lost on Plato who arguably organizes his image of Socrates, who always seems to be grounded on land, around the idea of being engaged in the practice of philosophy as a way of being at sea; being at risk. The way of philosophizing Plato has Socrates practice appears to be intentionally risky and wrought with imminent danger. In this talk I appeal to the language of risk in Plato’s Phaedo with a view toward arguing that Plato’s understanding of philosophy calls us to a form of heroism informed by heroes like Achilles, Odysseus, and Theseus.