James Miller describes one path through the history of ideas in his book Examined Lives: from Socrates to Nietzsche. However, as Edward Feser points out in his review in the June/July 2011 First Things, the book places more emphasis upon the steps of the path than on the path itself. Miller assumes, as do many others, a radical rupture between the ancient (represented by: Socrates, Plato, Diogenes, Aristotle, Seneca, Augustine) and the modern (represented by: Montaigne, Descartes, Rousseau, Kant, Emerson, Nietzsche).
If one instead assumes a literary hermeneutic of continuity, one might replace the six moderns as I have done in my booklist. First replace Montaigne with Shakespeare and then replace Nietzsche with O’Connor. Finally, to make the continuity clearer, backfill with Bonaventure and Dante on the one hand and Austen and James on the other.
In short, the real rupture that began during the Renaissance was poets, in a broad sense, regaining primacy regarding the examined life from the philosophers once advances in the sciences had restricted the domain of philosophy.