It’s honestly kind of funny that we use the word "Machiavellian" as a slur. You hear it and immediately think of some backstabbing office drone or a politician with a permanent smirk. But if you actually sit down and read The Prince by Niccolo Machiavelli, you realize the guy wasn't some cartoon villain. He was just tired of watching his home city, Florence, get kicked around by every superpower in Europe. He wrote this short, punchy manual in 1513, basically as a desperate job application to the Medici family. He wanted to show them he understood how the world actually worked, not how we wish it worked in Sunday school.
The book is tiny. You can finish it in an afternoon. But it has spent five centuries making people very, very uncomfortable.
Most people think it’s just a handbook for being a jerk. That’s a massive oversimplification. Machiavelli was obsessed with "lo stato"—the state. He believed that if a leader is too "good" in a traditional Christian sense, the state collapses, and then everyone gets killed or enslaved. So, is it "evil" to do something bad if it prevents a literal massacre? That’s the question he tosses in your lap. It’s a messy, gritty, and deeply honest look at power that most modern leadership gurus are too scared to touch.
The Most Misunderstood Advice in History
You’ve heard the line. "It is better to be feared than loved." People quote it like it’s a license to be a tyrant. But they usually leave out the second half of Machiavelli's thought. He said it’s best to be both, but since that’s basically impossible, fear is the safer bet. However, he was incredibly clear that being feared is NOT the same as being hated.
This is where most amateur dictators get it wrong.
Machiavelli warns that the moment a prince starts seizing property or messing with people's women, they start to hate him. And once the people hate you, you’re finished. Fear, in his mind, is about predictability and respect. It’s about people knowing there are consequences for breaking the law. If you’re just "loved," people will dump you the second things get inconvenient. But fear? Fear is held by a dread of punishment that never fails. It’s cold. It’s clinical. It’s pragmatic.
He uses Cesare Borgia as his primary case study. Borgia was a monster by most accounts, but Machiavelli admired how he cleaned up the Romagna region. It was a lawless mess of petty lords who spent their time robbing their subjects. Borgia put a guy named Remirro de Orco in charge—a man who was basically a human buzzsaw. De Orco used extreme violence to bring order. Once the order was established, Borgia knew the people would resent the cruelty. So, he had De Orco cut in half and left in the town square.
The message to the public? "Order is back, and the guy who was mean to you is dead. You’re welcome." It’s ruthless, but it worked.
📖 Related: The Betta Fish in Vase with Plant Setup: Why Your Fish Is Probably Miserable
Real Virtù vs. Being a Good Person
In The Prince by Niccolo Machiavelli, the word "virtue" doesn't mean what you think it means. He uses the Italian word virtù. It’s not about being kind or honest. It’s about prowess, energy, and the ability to adapt to "Fortuna"—luck or fate.
Think of it like this.
You’re a sailor. You can’t control the wind (Fortuna). But virtù is your ability to trim the sails, read the clouds, and keep the boat from flipping over. Machiavelli argues that a leader who is "good" all the time will inevitably be destroyed by the many who are not good. It’s a dark take. But if you look at history, or even modern corporate boardrooms, it’s hard to argue he’s 100% wrong. He suggests that a leader must learn how to not be good, and to use that knowledge—or not use it—depending on what the situation requires.
Why Honesty Isn't Always the Best Policy
Machiavelli has this famous bit about the Lion and the Fox. A leader needs to be both. The lion can’t defend himself against snares, and the fox can’t defend himself against wolves. So, you have to be a fox to recognize the traps and a lion to frighten the wolves.
- The Fox: This is the cunning part. If keeping a promise hurts you or the state, Machiavelli says you should break it.
- The Lion: This is the raw power. When the time for talking is over, you have to be able to crush the opposition so they can’t regroup.
He writes that if all men were good, this advice would be terrible. But since men are "ungrateful, fickle, pretenders, and deceivers," you’re a sucker if you play by the old rules while everyone else is cheating. It’s a cynical worldview, sure. But it’s built on his real-world experience as a diplomat watching kings and popes lie to each other’s faces for decades.
The Medici Rejection and the Irony of the Book
Here’s the part that most people miss. Machiavelli wrote this book for Lorenzo de' Medici, basically begging for a job. He had been tortured by the Medici's government (the "strappado"—look it up, it’s nasty) because they thought he was part of a conspiracy. He was living in exile on a farm, bored out of his mind, and drinking with local farmers.
He didn't get the job.
👉 See also: Why the Siege of Vienna 1683 Still Echoes in European History Today
Lorenzo supposedly liked a pair of hunting dogs he received as a gift better than the manuscript of The Prince. Machiavelli died a few years later, never knowing his "little book" would become the foundation of modern political science. Some scholars, like Jean-Jacques Rousseau, actually argued the book was a satire. They thought Machiavelli was secretly a republican who wrote it to "expose" the tactics of tyrants to the public. While most modern historians don’t buy that, it adds a layer of mystery to the text. Was he a teacher of evil, or a whistleblower?
Why You Should Still Read It in 2026
We live in an era of "authentic leadership" and "radical transparency." These are nice words. They look great on LinkedIn. But The Prince by Niccolo Machiavelli asks the questions we don't want to answer in public.
Is it better for a CEO to be liked and the company to go bankrupt, or for a CEO to be a "hard-ass" and save 5,000 jobs?
Machiavelli pushes you away from the "what should be" and forces you to look at the "what is." He hates "imagined republics." He has no patience for people who spend their time dreaming of utopias while their actual neighbors are suffering. For him, the highest moral act is the preservation of the community, even if the leader has to soil their hands to make it happen.
He also gives great advice on surrounding yourself with the right people. He says there are three types of brains:
- Those who understand things by themselves.
- Those who understand what others explain to them.
- Those who understand neither.
If you’re a leader, you need the first or at least the second. He also warns about flatterers. He says the only way to guard yourself against flattery is by making people understand that telling you the truth does not offend you. But—and there's always a "but" with Niccolo—if everyone can tell you the truth, they stop respecting you. So, you should only pick a few wise men and give them the liberty to speak the truth, and only when you ask for it.
Practical Insights for the Modern Reader
If you're going to apply Machiavelli today, don't go out and start cutting people in half in the town square. That’s a fast track to prison. Instead, look at the underlying logic of his power dynamics.
✨ Don't miss: Why the Blue Jordan 13 Retro Still Dominates the Streets
1. Assess your "Fortuna" vs. "Virtù"
Identify which parts of your current situation are pure luck and which parts you actually control. Machiavelli says luck is like a raging river. You can't stop the flood, but you can build dikes and dams during the dry season so the damage is minimized. Are you building your dams right now?
2. Avoid the Middle Ground
One of Machiavelli’s biggest gripes was "half-measures." He believed that if you have to hurt someone, you should do it so severely that you don't have to fear their revenge. If you just give them a "slap on the wrist," they’ll spend the rest of their lives trying to ruin you. In a modern sense, this means if you're going to make a hard decision—like a firing or a pivot—do it decisively. Don't linger in the "awkward middle" where everyone is miserable and nothing is resolved.
3. Be Present
He argued that a prince who lives in a newly conquered territory can spot trouble as it arises. If you stay far away, you only hear about the disaster when it's too late to fix. In leadership, this means "Management by Walking Around." You can't lead from a spreadsheet. You have to be where the work is happening.
4. The End Doesn't Always Justify the Means
This is the most famous misquote. Machiavelli never actually wrote "the end justifies the means" (il fine giustifica i mezzi). He wrote that in the actions of men, and especially of princes, one looks at the final result. If a leader succeeds in keeping the state safe and prosperous, the "means" will always be judged honorable by the public. It’s a subtle difference. He’s not saying "do whatever you want." He’s saying "if you win, the history books will be kind to you."
5. Study History, Not Just Theory
Machiavelli was a nerd for the Romans. He spent his nights "dressing up" in royal robes to read the classics. He believed that human nature never changes. The same mistakes made by ancient Greek generals were being made by 16th-century Italians. The same mistakes are being made in 2026. If you want to know what’s going to happen next, stop looking at "trends" and start looking at historical patterns.
The Prince by Niccolo Machiavelli isn't a book about being "bad." It’s a book about being effective. It strips away the varnish of polite society and shows the gears of the world grinding away. It’s uncomfortable, it’s cynical, and it’s occasionally horrifying. But it’s also undeniably real. Whether you’re running a country, a company, or just trying to navigate a difficult social circle, Machiavelli offers a lens that is as sharp today as it was when he was sitting in his farmhouse five hundred years ago.
Next Steps for Deepening Your Knowledge:
- Read the source text: Look for the Harvey C. Mansfield translation; it’s widely considered the most accurate to Machiavelli's original, rugged prose.
- Contrast with "The Discourses": To see Machiavelli’s true personal politics, read Discourses on Livy, where he argues passionately for a republic rather than a principality.
- Contextualize the history: Research the life of Cesare Borgia and the fall of the Florentine Republic (1512) to understand the chaos that fueled Machiavelli’s urgency.