The speaker visits Machiavelli’s place of exile in Tuscany, where Machiavelli wrote The Prince and other works, and reflects on a famous private letter Machiavelli wrote to a friend describing his daily life in exile. The letter reveals a striking combination of deep seriousness and childlike levity in Machiavelli’s character, and contains a beloved passage about how Machiavelli would shed his muddy work clothes, dress in his finest garments, and spend four hours in his study reading the ancient thinkers as if they were dear friends, feeding on philosophy as food. The speaker unpacks four reasons why this passage is so meaningful, drawing connections to aesthetics, friendship with the dead, philosophy as nourishment, and learning through reconstruction.
Machiavelli’s Day in Exile
Machiavelli’s letter describes a humble, even impoverished daily routine in exile:
He wakes up and tends to his wood-cutting business, haggling with people for money.
He goes to the local inn (whose outer walls are still preserved) for food and drink.
He plays cards with friends, arguing loudly over small stakes, swearing and joking in a crude, vulgar manner.
Despite this lowly daily life, he was simultaneously writing The Prince as an ambitious, world-historic work aimed at securing eternal glory and a return to political relevance.
This combination of gravity and levity is rare among great political thinkers. The speaker notes that Machiavelli also wrote self-satirical comedies (such as The Mandragora, performed for the Medici), something no other major modern political theorist—not Hobbes, not Hegel—is known for doing well. Rousseau is perhaps the closest comparison.
The Beloved Passage: Entering the Study
The speaker’s favorite passage from Machiavelli describes his evening ritual in the very study still standing at the exile house:
At evening, Machiavelli returns home and enters his study.
At the door, he removes his muddy, mire-covered work clothes and puts on his “regal and courtly garments.”
Dressed finely, he enters “the ancient courts of ancient men,” where he is received lovingly.
He “feeds on the food that alone is mine and that I was born for.”
He is not ashamed to speak with the ancients and ask them the reasons for their actions, and “they in their humanity reply.”
For four hours, he feels no boredom, forgets every pain, does not fear poverty, and is unafraid of death.
He composes The Prince from what he has gathered, reflecting deeply on what a principality is, how it is acquired, maintained, and lost.
Four Reasons the Passage Resonates
1. Dressing with Dignity, Even Alone
Machiavelli changes into his finest clothes before reading, even though he is completely alone. The speaker sees this as honoring the subject matter—letting the gravity of the aesthetics mirror the gravity of the ideas.
This reflects an ancient (especially Platonic) view that beauty and the good are not competing but unified: beauty is striking in a way that abstract virtues like justice are not, and that striking quality can serve as a ladder up to higher goods.
Modernity often treats aesthetics and substance as opposites (assuming beautiful surfaces hide shallow content), but Machiavelli’s ritual suggests the outer form can elevate and support the inner work.
2. The Great Books as Living Friends
Machiavelli dresses as if to meet good friends because he genuinely treats the ancient thinkers as friends. The speaker relates this to his own experience reading Augustine during the difficult period of building his second company:
Reading Peter Brown’s biography of Augustine of Hippo felt like talking to a friend who understood his struggles—Augustine, at a similar age, had felt the same pull between career and contemplation, eventually giving up his career, which led to his conversion.
For Machiavelli, who had lost everything and had nearly been executed, the ancients offered a safe harbor where he could be his true self.
This is a counter-Platonic idea: in the Phaedrus, Socrates criticizes writing because it cannot adapt its speech to different readers, unlike live conversation. The speaker disagrees, arguing that the great works seem to speak differently each time one returns to them with more maturity, and that close reading allows one to “ask” ancient thinkers questions about modern problems (e.g., asking Nietzsche about incels or Plato about technology).
3. Philosophy as Food
Machiavelli describes the books as “the food that alone is mine and that I was born for.” This gastronomical metaphor appears elsewhere in his work, notably in the Discourses, where he criticizes moderns who collect antiquities (vases) without truly “tasting” the ancients.
The analogy works because food is digested and becomes part of you, just as philosophy must be imitated and integrated, not merely known.
Philosophy is not a science aimed at abstract truth claims; it is aimed at truths that nourish a life. Having correct propositions is useless if they are not internalized—just as a feast on a table benefits no one if it cannot be touched and eaten.
Machiavelli’s ambition shows even in the food analogy: he calls it “the food that is mine alone,” suggesting a possessive, personal claim on this nourishment.
4. Learning Through Reconstruction and Reproduction
Machiavelli says that because Dante taught that “to have understood without retaining does not make knowledge,” he notes down what he has gathered from the ancients and composes a work from it—The Prince itself.
The speaker identifies this as his own core learning strategy, drawn from his math background where understanding comes from reconstructing proofs:
The “great books project” (interviewing scholars, preparing lectures, giving condensed summaries, and memorizing the material) is not primarily altruistic teaching but a selfish learning strategy—a way to digest and absorb the material by reconstructing it in his own words.
Reading Machiavelli’s letter while standing in the very house where it was written felt like being “literally and figuratively invited into the ancient court of a good friend.”
