Quotes and big ideas from Niccolò Machiavelli’s “The Prince”

The Price was written by Niccolò Machiavelli in 1513 as a sort of instruction guide for new renaissance rulers. He wrote it in exile, hoping to use it to aid his return to a position of power he once held. It was to be a gift to gain favor with Lorenzo de Medici after he fell out of favor with him because he was accused of conspiracy, tortured, and exiled.

Machiavelli states in the book’s dedication that he would like to return to a position of authority and that he offers the advice contained in The Prince as the most precious gift he could offer.

Machiavelli himself was an Italian diplomat and political theorist we can assume from the text is well educated in the history, rise, and fall of various rules and kingdoms throughout history.

Throughout The Prince, he references everyone from Alexander the Great, to Pope Alexander the VI, to Cesare Borgia to make his case for a type of amoral, results-driven, course of action for new Princes to take. He draws on experiences as a diplomat to warn about the pitfalls of human nature and how to manipulate it to achieve your political goals.

He is particularly impressed and inspired by Cesare Borgia, saying of him:

“There was one man who showed glimpses of greatness, the kind of thing that made you think he was sent by God for the country’s redemption.”

Although it is relatively short, the book has made a great impression on popular culture and political philosophy. It’s responsible for bringing the word “Machiavellian” into usage as an insult to one’s character.

I’ve collected the big ideas and major quotes from Machiavelli’s classic treatise on political philosophy and political theory. I wouldn’t exactly call these inspirational quotes, but you will find a wealth of practical knowledge that will enable you to navigate and anticipate human nature to use to your advantage.

Big ideas and quotes from Niccolò Machiavelli’s The Prince

Machiavelli on maintaining power after victory

“True it is that when a State rebels and is again got under, it will not afterward be lost so easily.”

If you lose control of something you once had control over and are forced to take it back by force, then you’ve accomplished two things:

1. You’ve proven that you’re willing to fight to keep what’s yours. This is often a strong enough deterrent for most would-be usurpers, rebels, and thieves.
2. You’ve demonstrated that there is a cost to messing with you. Once people know that they will incur damage if they cross you, they’re less likely to do it.

“He, therefore, who acquires such a State, if he means to keep it, must see to two things; first, that the blood of the ancient line of Princes is destroyed; second, that no change be made in respect of laws or taxes; for in this way the newly acquired State speedily becomes incorporated with the hereditary.”

The first part of this is fairly obvious. You have to crush your enemies totally. Machiavelli mentions this idea several times throughout the Prince. The second idea is less transparent.

Machiavelli is telling you to not make any changes that would affect the way of life in the new state you command. At least not immediately. This means that you must acquire power and influence for other reasons than to change how things are done because making changes threatens the power you worked so hard to gain.

That’s because these changes generate the most kickback and potential for uprising and rebellion. As these things threaten your power, do not change them unless absolutely necessary. Think of this idea the next time you’re put in charge.

Consider the parts of the operation that are sacred to the people operating. Avoid making changes there unless necessary because the resistance will interfere with your ultimate goal.

**And let it here be noted that men are either to be kindly treated, or utterly crushed since they can revenge lighter injuries, but not graver. Wherefore the injury we do to a man should be of a sort to leave no fear of reprisals. **

If you can’t destroy someone completely, then leave them a way out to save face. Ideally, you give them a way to be your ally and friend instead.

Before you engage in a conflict, consider if you’re willing and capable to go all the way. If you aren’t, then don’t engage or do whatever you can to get them on your side.

**And let it be noted that there is no more delicate matter to take in hand, nor more dangerous to conduct, nor more doubtful in its success, than to set up as a leader in the introduction of changes. For he who innovates will have for his enemies all those who are well off under the existing order of things and only lukewarm supporters in those who might be better off under the new. **

Once again, we have another warning about making changes when you become the leader of an organization.

Change seems like a seductive slogan. In fact, it was the basis of Barrack Obama’s presidential campaign. However, most people don’t really want change—at least not in the way we typically think about it.

The people who are already doing well definitely don’t want things to change. The people who are moving up also don’t want things to change. The only people who want change are the ones suffering at the hands of the system in place.

If they and their sympathizers are the minority, then making changes will lead to a difficult rule. However, if there is a majority of supporters and beneficiaries of the new change, only then you should make it. Otherwise, leave things as they were.

**Must not fail to remind the Prince who acquires a new State through the favor of its inhabitants, to weigh well what were the causes which led those who favored him to do so; and if it is seen that they have acted not from any natural affection for him, but merely out of discontent with the former government, that he will find the greatest difficulty in keeping them his friends since it will be impossible for him to content them. **

There’s a big difference between being someone’s choice out of desire and being someone’s choice out of desperation. In the former, they’ll do whatever it takes to keep you. In the latter, they’ll do just enough to not lose you.

From a political standpoint, we saw this play out in the 2020 American presidential election. Joe Biden is not a man with overwhelming charisma. Many of his opponents couldn’t imagine how he got the most votes in history. I thought it was quite obvious. His opponent, Donald Trump, was incredibly disliked. So much so that people who don’t usually vote, voted against him.

Even now, you don’t see people’s support of Biden. It borders on ambivalence and disappointment. But their hate for Trump is just as strong.

He will perceive that it is far easier to secure the friendship of those who being satisfied with things as they stood, were for that very reason his enemies than of those who sided with him and aided him in his usurpation only because they were discontented.

It’s easier to be friends with people who didn’t want things to change than those who did. This is only after you make the changes and stick with them. However, you’ll still face the initial friction, so this doesn’t contradict Machiavelli’s original advice.

The reason for this is that change threatens people. If you’re able to pull off your proposed changes without causing harm to their way of life, you will gain a new supporter.

For, in truth, there is no sure way of holding other than by destroying, and whoever becomes master of a city accustomed to living in freedom and does not destroy it, may reckon on being destroyed by it.

This piece of advice gives a dark message about the reality of taking ownership of something that was once someone else’s but not freely given to you. You either have to destroy everything it is and stands for or you will become just like its previous owner. This new direction may not align with your plans.

You see this when a company is taken over.

A lot of the old leadership is fired because the new owner has to put a new stamp on things. Even if the gesture is only symbolic and the underlying operating procedure and rules stay the same, the company is now under new leadership, and to make that clear, vital parts have to be built and restructured.

This reminds me of something Patrice O’Neil once said about being in a new relationship. He said that when he’s in a new relationship, he won’t do the stuff the girl’s old boyfriend did—even if she liked it—because she’s his girlfriend now.

A similar sentiment is echoed when it comes to why a man shouldn’t move into his girlfriend’s house and it’s much better to either have her move in with him or get a new place entirely.

Machiavelli on dealing with problems early

**When you are on the spot, disorders are detected in their beginnings and remedies can be readily applied; but when you are at a distance, they are not heard of until they have gathered strength and the case is past cure. **

An ounce of prevention is worth a pound of a cure. The earlier you solve a problem, the less likely it is that it will grow into a problem that you can’t solve.

**Hence we may learn the lesson that on seizing a state, the usurper should make haste to inflict what injuries he must, at a stroke, that he may not have to renew them daily but be enabled by their discontinuance to reassure men’s minds, and afterward win them over by benefits. **

This point is in the same vein as making sure that you destroy an enemy completely if you get into conflict with him. However, this is more of a preventative tone.

When you have to be a disciplinarian, any punishment or retribution you exert must be disproportionately severe enough to dissuade a further offense. A slap on the wrist is no punishment at all. Even a punishment that seems reasonable and appropriate will not suffice. It is important to make the punishment so great that the people you’re in charge of leading do not ever think of committing it again.

The importance of this can not be overstated in leadership. It is always easier to simply fire someone than it is to try to rehabilitate them and teach them a lesson. Most times, it’s not even worth it either.

**Nevertheless, the ruler is not truly wise who cannot discern evils before they develop themselves, and this is a faculty given to few. **

A good leader has to be a good strategist. Part of being a good strategist is seeing problems before they arise and dealing with them before they become too formidable.

**Wherefore, as has already been said, a Prince who is ignorant of military affairs, besides other disadvantages, can neither be respected by his soldiers nor can he trust them. A Prince, therefore, ought never to allow his attention to be diverted from warlike pursuits, and should occupy himself with them even more in peace than in war. This he can do in two ways, by practice or by study. **

So a general perspective to take here is that you should be wary of hiring people to do important things that you don’t know anything about. The more vital it is to your safety and success, the more important it is that you’re at least an intermediate.

This will keep you from being taken advantage of and being completely reliant on external forces that may not necessarily have your best interests

**A Prince should therefore disregard the reproach of being thought cruel where it enables him to keep his subjects united and obedient. For he who quells disorder by a very few signal examples will, in the end, be more merciful than he who from too great leniency permits things to take their course and so to result in rapine and bloodshed; for these hurt the whole State, whereas the severities of the Prince injure individuals only. **

Machiavelli is telling leaders to not worry about being viewed as cruel as long as the cruelty is practical for leadership. He provides simple reasoning for this course of action:

It’s easier when people think you’re harsh because they will be less likely to cross you. When they know that you’re lenient, they will take liberties and test your boundaries of leadership.

**For of men it may generally be affirmed, that they are thankless, fickle, false studious to avoid danger, greedy of gain, devoted to you while you are able to confer benefits upon them, and ready, as I said before, while danger is distant, to shed their blood, and sacrifice their property, their lives, and their children for you; but in the hour of need, they turn against you. **

Generally speaking, people are friendly to you when it’s easy to be friendly. However, the moment that friendship requires real skin in the game and sacrifice, then many are nowhere to be found.

This isn’t to say that there is no such thing as a loyal friend. It’s only to say that a loyal friend who is by your side through thick and thin is a rare find.

**For a man may very well be feared and yet not hated, and this will be the case so long as he does not meddle with the property or with the women of his citizens and subjects. And if constrained to put any to death, he should do so only when there is a manifest cause or reasonable justification. But, above all, he must abstain from the property of others. For men will sooner forget the death of their father than the loss of their patrimony. **

Machiavelli notices that men can deal with all types of tyranny as long as the leaders don’t take his stuff or his women. Or put differently, the only thing that really matters to men is the ability to have a family and a place to raise it.

My experience (and I think many others) has been that men will go to war over with one another over women. I think Machiavelli overestimates the importance that the average person puts on things. Or rather, by ranking land with women, he’s either elevating land (in the modern sense, I’ve chosen to see this as “personal property”) to the level of women (or devaluing women to the level of land).

Dave Chapelle has a joke that sums this relationship up nicely:

“Men don’t need all that nice shit. That’s for women. A man would fuck a woman in a cardboard box if he could get away with it.”

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Be it known, then, that there are two ways of contending, one in accordance with the laws, the other by force; the first of which is proper to men, the second to beasts. But since the first method is often ineffectual, it becomes necessary to resort to the second.

“We can handle this like gentlemen or we can get into some gangster shit” is usually only said after it’s clear that things can’t be handled like gentlemen. The most effective way to solve problems with people isn’t always the most humane but it is the one that leaves the least doubt about the nature of the problem.

**But since a Prince should know how to use the beast’s nature wisely, he ought of beasts to choose both the lion and the fox; for the lion cannot guard himself against the toils, nor the fox from wolves. He must therefore be a fox to discern toils, and a lion to drive off wolves. **

To be an effective leader, you must be able to lead in a variety of ways. It’s not always diplomacy and it’s not always war. The ability to determine the best fit for the situation at hand determines your success.

Of this, however, I am well persuaded, that it is better to be impetuous than cautious. For Fortune is a woman who to be kept under must be beaten and roughly handled; and we see that she suffers herself to be more readily mastered by those who so treat her than by those who are more timid in their approaches. And always, like a woman, she favors the young, because they are less scrupulous and fiercer, and command her with greater audacity.

If you have to choose between “too cautious” and “too impetuous”, it is FAR better to be too impetuous. Opportunity is created expenditure of energy and effort. Not by conservation and prudence. If you don’t put yourself out there and take some risks, you’ll never see how beautiful your life can become.

Machiavelli on managing reputation

**The wish to acquire is no doubt a natural and common sentiment, and when men attempt things within their power, they will always be praised rather than blamed. But when they persist in attempts that are beyond their power, mishaps and blame ensue. **

There’s nothing wrong with an attempt. The problem is when you continue after it’s clear that it is beyond your ability or grasp. A lot of resources are wasted in trying to accomplish the unaccomplishable.

The challenge here is knowing the difference between formidable persistence and destructive denial. I don’t pretend to have a clear answer on how to determine the difference, but if your pursuit will endanger others or waste their time, then it’s worth having a hard conversation with yourself about your capabilities.

No one likes to admit that they can’t do something, but sometimes. that level of honesty is necessary.

**And here comes the question of whether it is better to be loved rather than feared, or feared rather than loved. It might perhaps be answered that we should wish to be both; but since love and fear can hardly exist together if we must choose between them, it is far safer to be feared than loved. **

I don’t believe that being loved and being feared are mutually exclusive. However, if you have to pick one, you’ll go a lot further if people fear you. This is because to do anything, you have to deal with other people. If they love you, they MIGHT be of assistance to you out of the kindness of their heart. If they fear you, then they’ll ALMOST CERTAINLY help you as a matter of survival.

Love is nice, but it doesn’t defend against the evil forces of the world that may be plotting against you. ​​​​​

**It is not essential, then, that a Prince should have all the good qualities which I have enumerated above, but it is most essential that he should seem to have them; I will even venture to affirm that if he has and invariably practices them all, they are hurtful, whereas the appearance of having them is useful. Thus, it is well to seem merciful, faithful, humane, religious, and upright, and also to be so; but the mind should remain so balanced that were it needful not to be so, you should be able and know how to change to the contrary. **

Machiavelli warns us that there is a danger in practicing all the good qualities that you espouse. A certain level of hypocrisy keeps you alive because you must be able to react to your challengers and deal with them properly.

I interpret this passage because it’s better to practice mercy but not be merciful. If you practice merci, you can stop practicing mercy. If you are merciful, it is now a personality trait that you may find difficult to shed when the time calls for a more aggressive stance.

For if he well consider the whole matter, he will find that there may be a line of conduct having the appearance of virtue, to follow which would be his ruin and that there may be another course having the appearance of vice, by following which his safety and well-being are secured.

Returning to the question of being loved or feared, I sum up by saying, that since his being loved depends upon his subjects, while his being feared depends upon himself, a wise Prince should build on what is his own, and not on what rests with others. Only, as I have said, he must do his utmost to escape hatred.

This is the best argument for choosing to be feared over being loved. It’s impossible to *make* someone love you. You can inspire it, but it’s ultimately their choice. Fear, on the other hand, requires an active effort to not experience it and furthermore, to act courageously in the face of that feeling.

Most men are not built to resist fear. They must be trained. And even then, they have a breaking point.

**Moreover, men are less careful about how they offend he who makes himself loved than he who makes himself feared. For love is held by the tie of obligation, which, because men are a sorry breed, is broken on every whisper of private interest; but fear is bound by the apprehension of punishment which never relaxes its grasp. Nevertheless, a Prince should inspire fear in such a fashion that if he does not win love he may escape hate. **

When a person fears your retribution, they are much less likely to betray you. Love is a powerful motivation to stay loyal, but fear is even better.

People will do more to avoid pain than experience pleasure.

**And there is no quality so self-destructive as liberality; for while you practice it you lose the means whereby it can be practiced, and become poor and despised, or else, to avoid poverty, you become rapacious and hated. For liberality leads to one or other of these two results, against which, beyond all others, a Prince should guard. **

The problem with generosity is that if that’s the quality that you are known for, it will attract people with schemes to bleed you dry. And even if you think that’s too pessimistic, consider this: even the people around you with good intentions may take advantage of you—not because they’re evil people, but because your help enables them.

And once you decide to change your method of interaction with people—that is, to stop being so generous—they will then view you with contempt because you are cutting them off.

This is the problem found when you lead with generosity. You lock yourself into an invisible contract: we’ll be kind and compliant as long as you give. They no longer have any reason to respect you when you stop.

This isn’t to say that one should lead through fear and violence, but leading through kindness and generosity establishes a condition that you can not always meet and do your job effectively.

Machiavelli on paying for help

**Mercenaries and auxiliaries are at once useless and dangerous, and he who holds his State by means of mercenary troops can never be solidly or securely seated. For such troops are disunited, ambitious, insubordinate, treacherous, insolent among friends, cowardly before foes, and without fear of God or faith with man. Whenever they are attacked defeat follows; so that in peace you are plundered by them, in war by your enemies. And this is because they have no tie or motive to keep them in the field beyond their paltry pay, in return for which it would be too much to expect them to give their lives. **

Mercenaries are loyal to the pay they receive. This means that it’s possible that your opponent can buy them from you. Most of us will never be able to apply this advice to a war environment, but it becomes even more potent when applied to our daily lives.

Employers continue to learn that they will lose their employees if they don’t pay them well. Old ideas of company loyalty have flown out the window. Now people with skills are going to the highest bidder. If companies don’t adjust, then they’ll be left in the dust.

There is a word about auxiliaries as well, which (in Machiavelli’s context) are troops brought in from allied countries or kingdoms to fight on your behalf. These are better than mercenaries, but they come with their own problems. Mainly, if they won’t fight as hard and they become aware of your weaknesses in case they decide to make conquer you.

Analogously to the real world, auxiliaries are like partnerships. Be careful if you team up with someone to sell online or launch a product. If they’ve got significantly more market share than you, you may find your intellectual property heavily borrowed—if not outright stolen.

The auxiliaries know how your operation works because you had to reveal it to them to work together. But if they have a significantly greater reach than you, be careful. This analogy in mind as you read the rest of Machiavelli’s quotes about dealing with mercenaries and auxiliaries.

**Captains of mercenaries are either able men or they are not. If they are, you cannot trust them, since they will always seek their own aggrandizement, either by overthrowing you who are their master or by the overthrow of others contrary to your desire. On the other hand, if your captain is not an able man the chances are you will be ruined. **

**For the gains resulting from mercenary arms are slow, late, and inconsiderable, but the losses are sudden and astounding. **

**In short, with mercenaries, your greatest danger is from their inertness and cowardice, with auxiliaries from their valor. Wise Princes, therefore, have always eschewed these arms, and trusted rather to their own, and have preferred defeat with the latter to victory with the former, counting that as no true victory which is gained by foreign aid. **

**For the friendships which we buy with a price, and do not gain by greatness and nobility of character, though they are fairly earned are not made good, but fail us when we have occasion to use them. **

Machiavellian tactics in modern politics

You ought never to suffer your designs to be crossed in order to avoid war, since war is not so to be avoided, but is only deferred to your disadvantage.

Wherefore, a wise Prince should devise means whereby his subjects may at all times, whether favorable or adverse, feel the need of the State and of him, and then they will always be faithful to him.

To govern more securely some Princes have disarmed their subjects, others have kept the towns subject to them divided by factions; some have fostered hostility against themselves.

For I do not believe that divisions purposely caused can ever lead to good; on the contrary, when an enemy approaches, divided cities are lost at once, for the weaker faction will always side with the invader, and the other will not be able to stand alone.

Machiavelli on managing people

Add to this, that a Prince can never secure himself against a disaffected people, their number being too great, while he may against a disaffected nobility, since their number is small. The worst that a Prince need fear from a disaffected people is, that they may desert him, whereas when the nobles are his enemies he has to fear not only that they may desert him, but also that they may turn against him; because, as they have greater craft and foresight, they always choose their time to suit their safety, and seek favor with the side they think will win. Again, a Prince must always live with the same people, but need not always live with the same nobles, being able to make and unmake these from day to day, and give and take away their authority at his pleasure.

Men are always averse to enterprises that are attended to with difficulty, and it is impossible not to foresee difficulties in attacking a Prince whose town is strongly fortified and who is not hated by his subjects.

A Prince, therefore, who has a strong city, and who does not make himself hated, can not be attacked, or should he be so, his assailant will come badly off; since human affairs are so variable that it is almost impossible for anyone to keep an army posted in leaguer for a whole year without interruption of some sort.

Not to be hated or despised by the body of his subjects, is one of the surest safeguards that a Prince can have against conspiracy. For he who conspires always reckons on pleasing the people by putting the Prince to death; but when he sees that instead of pleasing he will offend them, he cannot summon the courage to carry out his design.

To be brief, a Prince has little to fear from conspiracies when his subjects are well disposed towards him; but when they are hostile and hold him in detestation, he has then reason to fear everything and everyone.

So that, on the whole, the best fortress you can have, is in not being hated by your subjects. If they hate you no fortress will save you; for when once the people take up arms, foreigners are never wanting to assist them.

And it will always happen that he who is not your friend will invite you to neutrality, while he who is your friend will call on you to declare yourself openly in arms.

And here let it be noted that a Prince should be careful never to join with one stronger than himself in attacking others, unless, as already said, he be driven to it by necessity. For if he whom you join prevails, you are at his mercy.

For there is no way to guard against flattery but by letting it be seen that you take no offense in hearing the truth.

Men will always grow rogues on your hands unless they find themselves under a necessity to be honest.

Machiavelli on opportunity and luck

But while it was their opportunities that made these men fortunate, it was their own merit that enabled them to recognize these opportunities and turn them to account, to the glory and prosperity of their country. They who come to the Princedom, as these did, by virtuous paths, acquire with difficulty, but keep with ease.

A Prince who rests wholly on Fortune is ruined when she changes.

For no man is found so prudent as to know how to adapt himself to these changes, both because he cannot deviate from the course to which nature inclines him, and because, having always prospered while adhering to one path, he cannot be persuaded that it would be well for him to forsake it. And so when occasion requires the cautious man to act impetuously, he cannot do so and is undone: whereas, had he changed his nature with time and circumstances, his fortune would have been unchanged.

To be brief, I say that since Fortune changes and men stand fixed in their old ways, they are prosperous so long as there is congruity between them, and the reverse when there is not.