My Thoughts On ‘The Prince’ by Machiavelli

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  • Post last modified:April 16, 2020
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Machiavelli’s “The Prince” is a true masterpiece. Written as a gesture in good faith to a new Prince, he outlines his own recommendations for acquiring a state, and how to keep it.

A beautifully written book on obtaining & maintaining power

There is enough discussion on whether ‘the ends justify the means’ so I refrained from that. Instead, I highlighted excerpts that stood out to me and have gone through and left a quick thought on each.

Admittedly, I’d started this book before the new year, but it’s a difficult read (given the language used), and I kind of slogged through it. When it was done, the blog post took just as long to write.

Thoughts and Excerpts from Machiavelli’s ‘The Prince’

It is in reference to Pope Julius that Machiavelli moralizes on the resemblance between Fortune and women, and concludes that it is the bold rather than the cautious man that will win and holds them both.


This is true in life, not just in love or women, or fortune as the author writes. It’s a motif so well-noted that it can be boiled down into numerous one-liners:

  • “Shooters take shots”
  • “You miss 100% of the shots you don’t take”
  • “The early bird gets the worm”
  • “Whoever ships, wins”
  • “He who hesitates is lost”
  • “He who laughs first, laughs last”

The Prince is bestrewn with truths that can beproved at every turn. Men are still the dupes of their simplicity and greed, as they were in the days of Alexander VI. The cloak of religion still conceals the vices which Machiavelli laid bare in the character of Ferdinand of Aragon. Men will not look at things at they really are, but as they wish them to be – and are ruined.


Forever optimists – we want the world to be the way we see it.

This can cause issues in life when the listener hear’s one thing, and interprets in in the way they wish to hear it.

Since we only live life in our own body, everything we’ve ever seen, heard, or known has passed through this selfish filter.

As business owner, I’ve dedicated decades of professional work to hone the skill of listening to what’s being said, finding the inaccuracies to what I’m saying or need, hearing what they’re actually saying, and bridging those gaps.

For, although one may be very strong in armed forces, yet in entering a province one has always need of the goodwill of the natives.

Chapter 3

This reminds me of when Jake (played by Ethan Hawke) leaves Alonzo (played by Denzel Washington) in the ‘hood at the end of Training Day.

“I’m the police. I run shit here… you just live here… Yeah that’s right you better walk away… you better walk away… ’cause I’ma burn this muthafucka down… King Kong ain’t got shit on me!”

The other and better course is to send colonies to one or two places, which may be as keys to that state, for it is necessary either to do this or else to keep there a great number of cavalry and infantry. A prince does not spend much on colonies, for with little or no expense he can send them out and keep them there, and he offends a minority only of the citizens from whom he takes lands and houses to give them to the new inhabitants; and those whom he offends, remaining poor and scattered, are never able to injure him; whilst the rest being uninjured are easily kept quiet, and at the same time are anxious not to err for fear it should happen to them as it has to those who have been despoiled. In conclusion, I say that these colonies are not costly, they are more faithful, they injure less, and the injured, as has been said, being poor and scattered, cannot hurt. Upon this, one has to remark that men ought either to be well treated or crushed, because they can avenge themselves of lighter injuries, of more serious ones they cannot; therefore the injury that is to be done to a man ought to be of such a kind that one does not stand in fear of revenge.

Chapter 3

Divide and conquer. Split them up so that the meek mind their own business and the aggressive act meek in fear of death. The part that really hit home was the brutal, but – in his mind – necessary advice: injury to the point you won’t fear revenge.

We’re seeing in modern day Mexican cartel murders.

From this a general rule is drawn which never or rarely fails: that he who is the cause of another becoming powerful is ruined; because that predominancy has been brought about either by astuteness or else by force, and both are distrusted by him who has been raised to power.

Chapter 3

This is the opposite of the old adage ‘don’t bite the hand that feeds you’ – as a hinge for success, you instantly become a target to those which you’ve hoisted into power.

Be careful when hoisting someone into power.

You see this play out in the opening scene of ‘The Dark Knight’ – by the end of the scene you know what’s coming.

A wise man ought always to follow the paths beaten by great men, and to imitate those who have been supreme, so that if his ability does not equal theirs, at least it will savour of it. Let him act like the clever archers who, designing to hit the mark which yet appears too far distant, and knowing the limits to which the strength of their bow attains, take aim much higher than the mark, not to reach by their strength or arrow to so great a height, but to be able with the aid of so high an aim to hit the mark they wish to reach.

Chapter 6

At first I interpreted this to mean “Follow the paths of those who walked before you; the land has already been walked, the wrinkles have been ironed out over time.” but after reading through it again, I realized the real message is:

Aim high. Higher. Higher still… higher… Go big!

Perhaps this is more accurately characterized in modern English by way of the common phrase, “Shoot for the moon; because even if you miss, you’ll land amongst the stars.”

Nevertheless, he who has relied least on fortune is established the strongest. 

Chapter 6

I found this one extremely interesting, because at first I thought it flew against a business adage I’ve long believed, “He who can spend the most money to acquire a customer, wins.” But now?

… I still believe that. It turns out they’re saying the same thing; the person who relies on their dollar the least, is able to spend most money.

Lesson? Don’t get to the top by way of cash. Or at least that, if you do, get there and diversify – spread your roots.

States that rise unexpectedly, then, like all other things in nature which are born and grow rapidly, cannot leave their foundations and correspondencies fixed in such a way that the first storm will not overthrow them

Chapter 7

Strengthening my notes from the last quote, here Machiavelli says if you come into power (or money) quickly, you must be prepared to spread your roots and focus on things which will make your power (or money) sturdy, solid, structurally sound.

There are two approaches to protect oneself from a storm.

  • The first is to build a solid structure – think rocks, cement, castles; and that of flexible structure
  • The second is to build a flexible structure – think rubber, bamboo, pole vaults, and those flappy-arm guys at used car dealerships

For men injure either from fear or hatred.

Chapter 7

Here, Machiavelli wastes no ink; in eight words he is able to distill the essence of violence. Beautiful.

He who believes that new benefits will cause great personages to forget old injuries is deceived.

Chapter 7

This could be chopped in many ways but at the very least, understand that on an emotional level, hand outs are not and will never be a sufficient reparation. To pay them is both naive as a solution, and as an expense. Find a better solution.

Yet it cannot be called talent to slay fellow-citizens, to deceive friends, to be without faith, without mercy, without religion; such methods may gain empire, but not glory.

Chapter 8

In Chapter 8, he talks a lot about power vs. reverence, or empire vs. glory. He admits that being kind and/or merciful, to be honest, to have faith (which can be read as following an honest path) are the only ways to get on top and stay on top.

And this is easily understood; as a caveman, it’s not in your best interest to murder your next door neighbours family. It’s anti social to the highest degree, everyone will perceive it as such, and makes it incredibly hard to build relationships with others.

For injuries ought to be done all at one time, so that, being tasted less, they offend less; benefits ought to be given little by little, so that the flavour of them may last longer.

Chapter 8

Just like my momma taught me: it’s better to rip the band-aid right off in one fell pull. Get it over with to avoid prolonging the pain.

And above all things, a prince ought to live amongst his people in such a way that no unexpected circumstances, whether of good or evil, shall make him change; because if the necessity for this comes in troubled times, you are too late for harsh measures; and mild ones will not help you, for they will be considered as forced from you, and no one will be under any obligation to you for them.

Chapter 8

Sounds like Machiavelli is saying that if you’re a nice guy, be a nice guy – and if you’re an authoritarian asshole, be one – for when you sail upon troubled waters, your natural character is your most precious ally, and likely your best chance at survival.

(Editors note: I should probably come back to this point at a later date, and/or read up on what exactly he meant about this part, though)

Because men, when they receive good from him of whom they were expecting evil, are bound more closely to their benefactor

Chapter 9

This is a passage that offers a ton of clarity. With regards to winning over former enemies, Machiavelli notes the ease of which you can win them over by being merciful when you have nothing to gain. In such cases, they themselves gain from your mercy, and are therefore sympathetic to you.

My thoughts on the price by machiavelli
We’re discussing ‘Il Principe‘ (The Prince) by Niccolo Machiavelli

For such a prince cannot rely upon what he observes in quiet times, when citizens have need of the state, because then every one agrees with him

Chapter 9

Just like my papa taught me: “Everyone’s your friend until the rent’s due.”

I’ve learned to never take stock during the good times, but instead to take stock during the tough times. It’s easy to trick people into thinking you’re a genius when things are going up; but much harder when things are crashing down.

For it is the nature of men to be bound by the benefits they confer as much as by those they receive.

Chapter 10

This is beautiful – you are bound by promises you make on both sides; as the leader and as the follower. My parents keep haunting me while reading this book: “If you say you’re going to do something, do it!”

We have seen above how necessary it is for a prince to have his foundations well laid, otherwise it follows of necessity he will go to ruin. The chief foundations of all states, new as well as old or composite, are good laws and good arms; and as there cannot be good laws where the state is not well armed, it follows that where they are well armed they have good laws.

Chapter 12

Good laws, and good arms. Rules, and weapons. Structure, and tools. It makes sense that these become the building blocks of Order, but I hadn’t put them together as inversely reliant on one another.

The fact is, they have no other attraction or reason for keeping the field than a trifle of stipend, which is not sufficient to make them willing to die for you. They are ready enough to be your soldiers whilst you do not make war, but if war comes they take themselves off or run from the foe; which I should have little trouble to prove, for the ruin of Italy has been caused by nothing else than by resting all her hopes for many years on mercenaries

Chapter 12 on hired soldiers.

On hired help and mercenaries – and if you’ve seen Game of Thrones, you’ll know this – Machiavelli notes they are there for money (not you!) so you understand that when push comes to shove, they are not willing to lay down on the tracks for you, they will run, or surrender.

A wise man once told me, “everyone’s your friend ’til the rent’s due.”

Therefore, if he who rules a principality cannot recognize evils until they are upon him, he is not truly wise; and this insight is given to few.

Chapter 13

I’m not sure on the last part – that it’s insight given to few, but perhaps few are able to devote the attention to detail needed to see things play out in the future.

Honing the skill of seeing a storm coming is something you can work at in business and in life. On an instinctual/surival level we’re a hop skip and a jump from the jungle; our DNA is tuned to sense when danger is near, we just need to pull that anxious, stressful, watchful third eye back out of our DNA and get it firing on all cylinders again, like the good ol’ days.

And it has always been the opinion and judgment of wise men that nothing can be so uncertain or unstable as fame or power not founded on its own strength.

Chapter 13

Every time I’ve seen someone rise to fame or celebrity based on circumstantial luck, or on a no-name husband or wife try to get famous, it’s been short lived so this part stuck with me.

The idea of getting to the top is nothing if you don’t have a mechanism to stay on top. In this light, it feels like the ‘aggressor’ archetype is truly the bottom rung on the ladder.

In contrast, the archetype who makes the place prosperous, who sows good in the community, who improves the livelihood of the people around them must be near the top of the ladder.

Nevertheless, liberality exercised in a way that does not bring you the reputation for it, injures you; for if one exercises it honestly and as it should be exercised, it may not become known, and you will not avoid the reproach of its opposite. 

Chapter 16

This is great. Yes, be liberal. Be open. Be friendly. Give. But let it be known you are being liberal, open, friendly, and giving.

To be this type of person in the world is a rare jewel, so you must avoid being that person and not receiving said praise.

An interesting take on selflessness, where a bit of selfishness increases the potency of the impact and strengthens the relationship between one’s self and others. 🤔

And there is nothing wastes so rapidly as liberality, for even whilst you exercise it you lose the power to do so, and so become either poor or despised, or else, in avoiding poverty, rapacious and hated.

Chapter 16

As a continuation to the above, he remarks on how quickly liberality drains your resources, and leads to one of poor or hated.

At this level, it’s clear as day that a big part of giving, and helping others is letting it be known that they’re being helped; letting others know you’ve helped is part of your path to virtue among society.

Upon this a question arises: whether it be better to be loved than feared or feared than loved? It may be answered that one should wish to be both, but, because it is difficult to unite them in one person, it is much safer to be feared than loved, when, of the two, either must be dispensed with.

Chapter 17

I loved that he didn’t devalue the concept of chosing to be loved; an honest understanding that there will be both types of people in the world.

Instead he choses only to say that fear is safer. Anyone who’s chosen love knows there’s nothing safe about it.

Nevertheless a prince ought to inspire fear in such a way that, if he does not win love, he avoids hatred; because he can endure very well being feared whilst he is not hated, which will always be as long as he abstains from the property of his citizens and subjects and from their women.

Chapter 17

Just because they don’t like you doesn’t mean they have to hate you.

Should you choose fear, realize that unbridled violence won’t keep you at the top. Walk the line between fear and hatred; avoid the latter and your estate remains strong.

Machiavelli's human archetypes for the Lion and the Fox
Machiavelli’s human archetypes for the Lion and the Fox

A prince, therefore, being compelled knowingly to adopt the beast, ought to choose the fox and the lion; because the lion cannot defend himself against snares and the fox cannot defend himself against wolves. Therefore, it is necessary to be a fox to discover the snares and a lion to terrify the wolves.

Chapter 18

Machiavelli spends quite some time discussing the intricacies of the Fox and the Lion archetypes, settling on a recommendation to be both, for each of their respective strengths.

Therefore it is unnecessary for a prince to have all the good qualities I have enumerated, but it is very necessary to appear to have them.

Chapter 18

Similarly to what was mentioned before, being sly like a Fox and fierce like a Lion won’t help if your enemy doesn’t know it. Your reputation should precede you so that enemies have reason to give pause.

That pause can make all the difference; as we all know, he who hesitates is lost.

It makes him hated above all things, as I have said, to be rapacious, and to be a violator of the property and women of his subjects, from both of which he must abstain. And when neither their property nor their honor is touched, the majority of men live content, and he has only to contend with the ambition of a few, whom he can curb with ease in many ways.

Chapter 19

As can be imagined, the book is chalk full of morose opinion, as in the above where he suggests a man’s pride can be beaten and bruised, but not severed entirely.

Most people are happy if you just don’t fuck with them. Leave their property and honour intact and never the twane shall meet.

Reading between the lines, we hit on a sullen, lonely undertone here in the negative space Machiavelli leaves hanging – with property and honour off the table, there’s still plenty left to be a rapacious violator.

And one of the most efficacious remedies that a prince can have against conspiracies is not to be hated and despised by the people, for he who conspires against a prince always expects to please them by his removal; but when the conspirator can only look forward to offending them, he will not have the courage to take such a course, for the difficulties that confront a conspirator are infinite.

Chapter 19

Just by avoiding being hated by the people gives you an edge over someone looking to attack or overthrow.

What a simple concept: avoid being hated. Easy enough, and gives you a semi-permanent leg up on the competition.

And here it should be noted that hatred is acquired as much by good works as by bad ones, therefore, as I said before, a prince wishing to keep his state is very often forced to do evil

Chapter 19

I wonder here if he’s talking more of, “you need to crack some eggs to make an omelette,” or, “how the sausage is being made”? I assume he’s discussing the latter – the kind of evil deeds people hear rumours of but can never substantiate, and those which people secretly applaud behind closed doors.

This may have been well enough in those times when Italy was in a way balanced, but I do not believe that it can be accepted as a precept for to-day, because I do not believe that factions can ever be of use; rather it is certain that when the enemy comes upon you in divided cities you are quickly lost, because the weakest party will always assist the outside forces and the other will not be able to resist.

Chapter 20

Allegiance can not to be trusted; the weaker side will always assist the enemy when you’re not there to protect them. Build your own moats.

For this reason many consider that a wise prince, when he has the opportunity, ought with craft to foster some animosity against himself, so that, having crushed it, his renown may rise higher.

Chapter 20

This part was interesting as it doesn’t seem to matter who you bait into attacking you, so much as it matters that the fight is easily won and you crush them. The rumour will take it from there.

Thus it will always happen that he who is not your friend will demand your neutrality, whilst he who is your friend will entreat you to declare yourself with arms.

Chapter 21

It’s better to stand and fight than to die on the side lines. I spent some time looking into this quote further, as I wasn’t sure if he was saying:

  • Non-friends demand neutrality, and
  • Friends allow you to arm yourself

Or if he was saying (as I now believe):

  • Non-friends demand neutrality, and
  • Friends owe you and respect you for having fought with/for them

Because there are three classes of intellects: one which comprehends by itself; another which appreciates what others comprehended; and a third which neither comprehends by itself nor by the showing of others; the first is the most excellent, the second is good, the third is useless.

Chapter 22

Simple enough. Choose one of:

  1. Be smart (The Imp)
  2. Surround yourself with smart people (Daenerys), or…
  3. You’re screwed (Joffrey)

* Game of Throne characters listed for clarity.

Because there is no other way of guarding oneself from flatterers except letting men understand that to tell you the truth does not offend you; but when every one may tell you the truth, respect for you abates.

Chapter 23

Rising to the top and finding oneself surrounded by yes men, before losing sight of what it was that got you there (ie. forgetting one’s roots) resulting in a sharp decline in stature is one of the oldest tropes in the book.

The solution, as outlined above, is far simpler than it is easy: Simply show people (with actions) that the truth does not offend you.

But if a prince who is not inexperienced should take counsel from more than one he will never get united counsels, nor will he know how to unite them. Each of the counsellors will think of his own interests, and the prince will not know how to control them or to see through them. And they are not to found otherwise, because men will always prove untrue to you unless they are kept honest by constraint.

Chapter 23

This is why offices need timesheets, and why clients need progress reports. You simply cannot trust others to remain honest if there aren’t scrutinized often.

Therefore, do not let our princes accuse fortune for the loss of their principalities after so many years’ possession, but rather their own sloth, because in quiet times they never thought there could be a change (it is a common defect in man not to make any provision in the calm against the tempest), and when afterwards the bad times came they thought of flight and not of defending themselves, and they hoped that the people, disgusted with the insolence of the conquerors, would recall them.

Chapter 24

We see this every time a recession hits. When the tide goes out, it’s easy to see who’s been swimming naked. 🏊🏻‍♂️ 🩲

This is why a strong estate or business will have months of rations, provisions for rainy days built in. When they’re needed, they’re rarely the only aspect of one’s life that’s being pressured.

They’re not there to save you, they’re there to be one last thing to worry about when it comes to time to save yourself.

But a man is not often found sufficiently circumspect to know how to accommodate himself to the change, both because he cannot deviate from what nature inclines him to do, and also because, having always prospered by acting in one way, he cannot be persuaded that it is well to leave it; and, therefore, the cautious man, when it is time to turn adventurous, does not know how to do it, hence he is ruined; but had he changed his conduct with the times fortune would not have changed.

Chapter 25

This reminded me of Kelly Starrett’s seminal fitness book, Becoming a Supple Leopard where he talks about wanting your body not to be ‘durable like cement’, but ‘durable like bamboo’.

Machiavelli implies a similar idea here: one must be sensitive to change and open minded enough to see it when confronted with it. Seems easy enough in a vacuum, but gets substantially more difficult when you add in the two factors mentioned:

  • One’s personality feels engrained in their nature. Asking them to deviate from said personality is an attack on him/her the person
  • Until now, he or she has always succeeded by acting how they are which silently coaxes them to ignore advice

Another case where – as Ryan Holiday aptly pointed out – ego is the enemy.

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