Modern Machiavelli: How to be a 21st century prince without selling your soul

Is it better to be feared or loved? Do the ends justify the means? Is all fair in business and politics? Machiavelli says, “Yes.”

You may have heard of the book The Prince, Niccolò Machiavelli’s infamous sixteenth-century manifesto on politics, power, and ruling a kingdom. If you’re like me, you may have wondered what The Prince is all about, and if it has any implications for modern times.

Before I go on about some of the pragmatic leadership lessons from the book, let me start by saying that this is an evil text. Old Nick recommends such practices as lying, ruining, destroying, and murdering, as long as these practices extend a prince’s rule and lead to stability in the realm. For example, on multiple occasions Machiavelli endorses throwing a big party for all of your enemies and then surprising them with a big murder-feast like a Game of Throwns red wedding.

Using all of The Prince as a step-by-step twenty-first century how-to management book will get you fired, jailed, and probably executed.

That being said, I did find a lot of truth about how leadership and politics work, but there is a slippery slope here. Skillful princes have to learn the difference between the fake-world of work and the real-world of life, and they have to trust their conscience. This isn’t MGT101 stuff here, this is the advanced course which includes quite a bit of the dark side/black magic.

Ok, enough with the warnings. Here’s what I think we can take away from the evil genius without damning our eternal souls:

Never be Hated

Never oppress your subjects and never mess with people’s property and family. These are sure-fire ways to break Machiavelli’s number one rule of ruling: Never be hated. Once your people hate you, you’re as good as gone.

A prince can never secure himself against a hostile people… The worst a prince may expect from a hostile people is to be abandoned by them; [and] from hostile nobles he has not only to fear abandonment, but also that they will rise against him.

Is it Better to Be Feared or Loved?

Machiavelli’s answer to this is, “Both, with fear being slightly better if things ever get really bad.” Now, I don’t advocate for a culture of fear in any workplace. I do believe that it’s probably not a bad thing to be known as someone others shouldn’t try to pull any shenanigans on. Fear aside, Machiavelli says a prince’s rule is only as strong as the foundation it sits on, and that foundation has to built on the support of the people.

One who becomes prince through the favor of the people ought to keep them friendly, and this he can easily do seeing they only ask not to be oppressed by him.


When you find good ministers (direct reports), be loyal to them by protecting them and showering them with honors, praises, and treasure. You have to be your people’s best option, or they will go find the better ruler. It also helps to be loyal to those who are higher up the chain, being careful to never make enemies with people who are more powerful than you.

Those who so bind themselves [to your fortune] ought to be honored and loved…To keep his servant honest the prince ought to study him, honoring him, enriching him, doing him kindness, sharing with him the honors and cares.

Beware of Flatterers

They’re up to no good. And you really need people who an give you honest feedback and advice. Yes-men will blind you with your own hubris.

[There is] a danger from which princes are with difficulty preserved, flatterers, of whom courts are full. Because men are so self-complacent in their own affairs, and in a way so deceived in them, that they are preserved with difficulty from this pest. There is no other way of guarding oneself from flatterers except letting men understand that to tell you the truth does not offend you.

Come out of the Fortress and Support Individual Endeavors

Machiavelli advocates for coming out of the high walls of your office and supporting the small endeavors of the people. He recommends attending as many events as possible, and support the modern day equivalents of people going back to school, finding new hobbies, or taking on side ventures.

[A prince] should encourage citizens to practice their callings peaceably… so that one should not be deterred from improving his possessions; but a prince ought to offer rewards to whoever wishes to do these things and designs in any way to honor his city or state.

Ruin or Weaken Enemies

Machiavelli recommends crushing your competitors through any means available. Rival firms are competing for your livelihood, and they won’t hold back from trying to ruin you. When it comes to competition, unleash the beast the lies within.

Achilles and many other princes of old were given to the Centaur Chiron… which means they had for a teacher one who was half beast and half man, so it is necessary for a prince to know how to make use of both natures, and that one without the other is not durable.

Afterword: It’s worth noting that there are terms like “servants” above, and that the article is written only from the masculine perspective. I’m just communicating the spirit of the book, which was written 500 years ago. Obviously the views are a bit outdated at this point, and no one should think of coworkers, direct reports or otherwise, as servants.