This is arguably one of Socrates' most famous quotes, and in fact, living the examined life was the main cause of him sippin' on a killer cocktail. But, what does he mean? Why does he think that death is favorable option to living an unexamined life? What does the examined (or conversely, the unexamined) life look like? Another way to think about this is "Why does Socrates so willingly accept his fate?". Just food for thought.
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"On one hand, he denies having any kind of specialized knowledge, and on the other hand, he makes assertions"
The assumptions of rationality are not knowledge.
Rationality might assume "an unexamined life is not worth living" although we have no knowledge what "life" really is.