You must prepare to step into a different age when reading Machiavelli. An age where reading itself is a rarity. Where elaborate games with the written word abound. Where the word good is actually Good. The Good. Not only does a supreme being rule over everyone, but He has granted them a natural law through which right and wrong are known. Before His revelation, elements of that law were brought forth by the pagan philosophers. Because of them, because of Providence, you live at the pinnacle of human history. All prior happenings point to your time. You live in the Good Place. Why is it miserable?
There are merchants and guilds but capitalism, properly speaking, does not exist. People will fight and die for republics, but modern democracy is not yet visible. Mathematicians, scientists, and Renaissance men abound, but dedication to sustained scientific inquiry or educational institutions is a shadow of what it is now.
Still, it is vital to understand the devotion and sacrifice that went into promoting certain ideas. The just and productive parts of our world come from some of them. Machiavelli himself was tortured after the secular republic he served was overthrown. We might assume the ideas they fought for are not fully realized or coherent. I would caution that we should not underestimate their vision.
An example of that vision, ironically enough, resides in a notion of politics Machiavelli rejected. Aristotle discussed political rule as being able to rule and be ruled in turn. This beautiful proposition about politics stemmed from a beautiful one about community. "[A]ll communities aim at some good, and... the community that is most authoritative of all the others does so particularly, and aims at the most authoritative good of all." The polis, the city, aims at the "good of all."
Why did Machiavelli reject these ideas about politics and community? I could tell you "they didn't work," and while that's a reasonable answer, it is also a shallow one. If something does not work in building a safer world, a world where everyone can thrive, then that something is liable to be harmful. It isn't just that ancient rhetoric about virtue and reason was corrupted. It was corruptible to begin with.
Before we step into the "Letter to Vettori," it is worth looking at excerpts from the most famous part of The Prince. In chapter 17, "Of cruelty and pity and whether it is better to be loved than feared, or rather feared than loved," Machiavelli lays out the logic of property rights, the foundation for modern constitutionalism and capitalism. 17 itself is a symbolic number: I'd guess 10 (commandments) + 7 (perfection) = the perfect law. The title is about the disposition of authority. Should it punish cruelly or engender sympathy? By implication, should the law be loved or feared?
Machiavelli will speak of "the prince," but the prince for a variety of reasons might as well be the law. He says "it is safer to be feared" than loved and highlights how little loyalty one has from the people you govern. The deemphasis on love is a blow against Christian and classical ideas about politics. If the law is from God, if you are a true citizen, should you not love the law? This sounds alien to us because we're so used to the law being a demonstration of power meant to inspire fear. But what if we lived in a world where most people believed that strict obedience to the law bought immortality? What if that were preached incessantly?
Machiavelli goes further. A prince should be feared but not hated. He should show respect for the property of his citizens as he will inspire a revolt otherwise. Gone are ideas about duty, say, to one's feudal lord. You have a "duty" inasmuch as you can obtain and maintain what is yours. More radically, the logic behind constitutionalism and capitalism entails a dismissal of the familial: "above all things he must keep his hands off people’s property, because a man will forget the death of his father sooner than he would forget the loss of the property his father left to him." Machiavelli isn't just saying some of us value what we own more than the lives of those we love. He's establishing this as a political constant, the one thing you can depend on.
What do we do with a letter which encourages no less than the Ambassador to the Vatican (Vettori) to "quiet quit?" Consider the passage below:
...I am extremely pleased to see how methodically and calmly you fulfill your public duties. I exhort you to continue in this manner, because whoever forgoes his own interests for those of others sacrifices his own and gets no gratitude from them.
Do your public duties "methodically and calmly," Machiavelli says, but keep your own interests at the forefront. If you don't, you by default sacrifice for others, and they will certainly be ungrateful.
Honestly, this career advice hits like a truck. It undeniably creates a bridge between the 16th century and the 21st. All the people who won't read or prevent others from doing so have no clue what they're missing. Someone from 500 years ago is telling his friend not to forget his own goals in an environment where exciting projects emerge all the time. For example, the Pope might want to conquer various Mediterranean islands in order to counter Venetian influence. If you offer help in order to win favor with His Holiness, you must make sure you get something concrete in return. The Pope, in other words, had better pay.
I'm evaluating my own projects in light of this advice. I need to write more often. I certainly should be heard more than, say, the vast numbers of neo-Nazis who have not so recently crawled out of the woodwork (and who, unfortunately, have their own ideas about Machiavelli & Nietzsche). I also need a larger network, i.e. more people I can aid and who can support what I do. --Yeah, I know, Machiavelli said not a prince should be careful with depending on the loyalty of others, but I know some people want to help. It's worth trying to find more of them.--
In general, the "Letter to Vettori" is extremely relatable. Much more than, say, the executives at Ticketmaster and their hatred-generating business model. Machiavelli details what seems to be a depressive episode (catching birds with his hands for a month), fighting with a friend over a few dollars, being taken advantage of by those who want cheap firewood, and getting into more fights during stupid card games.
When you have an artifact that's relatable, a time capsule which immerses you in the world of another person, the discontinuities are moments of revelation. Machiavelli might be one of a handful of people who walked this earth who understood that.
The most famous passage from the Letter is steroidal LARPing. Machiavelli describes changing his outfit completely before reading ancient history, rhetoric, philosophy, and literature. He dresses in the "garments of court and palace," the clothes he had when he was formally an Ambassador. He reads as if everything depends on his efforts:
I nourish myself on that food that alone is mine and for which I was born; where I am unashamed to converse with them and to question them about the motives for their actions, and they, out of their human kindness, answer me.
On the one hand, the tone is delusional and arrogant. "That food that alone is mine?" No one else is capable of reading and thinking through serious matters? On the other, I've witnessed a number of people in my life show they were unserious. I thought better of them. I thought they could be trusted to show regard for others, demonstrate restraint, not just blindly insist they were right or stop caring entirely. I've realized very few are called to leadership. Many want power or the ability to punch down; it will take a lifetime, in a number of cases, for them to show sensitivity or gather answers that matter.
I believe that's why I can take Machiavelli's most grandiloquent sentence seriously: "And for four hours at a time I feel no boredom, I forget all my troubles, I do not dread poverty, and I am not terrified by death." Part of me wants to scream. I read plenty of philosophy myself. I get bored and anxious! And I certainly know that if I don't have a job lined up, homelessness is a very possibility! Don't even get me started on dying alone! But this sentence isn't about a reader like me. Machiavelli invokes the symbolism of medieval numerology. Four is the number for completeness, e.g. the four horsemen of the apocalypse. He places himself alongside others who have not feared death, most notably Jesus and Socrates. He believes he has something to say which, if taken seriously, will change everything for generations to come.
I don't even know how I'm writing. Machiavelli's statements in the Letter feel blinding. He has an ambition which is hard to conceive, let alone articulate. I think most of us would like to discover one good idea. We'd be happy with that. Or maybe aid in popularizing one. But to commit to the notion that we could teach rule, that the world could have fewer tyrants if we were fearful of the right things--yeah, you would have to set yourself up as a prophet, a prophet unlike any other.
What is so remarkable about Machiavelli is how careful he is with words. He's fully conscious of the logic entailed in each idea of his. In the case of teaching a political science, he does not just hearken to the classical teaching that true rulers share proximity with divinity. He understands the full implication of giving humankind a way to a stable, safe world where, for once, we can be free.