The Prince, Niccolo Machiavelli

Finished: September 3, 2023

Rating: 4 out of 5.

Why I read this

No I don’t want to take over the world, and no I don’t want to learn how to use deception to install myself in a position of power (and then hold it through all means necessary). I did however reflect a lot on a comment my fiancée made to me a while back regarding a family friend who runs a relatively large company. She said that at that level you have to be a shark, and although he seems nice he definitely is a shark. So, in my recent books I’ve read a lot about the good side of behavioral psychology and human nature (think Humankind that I reference frequently), but here I wanted to read something that showed a bit of the other side, do we really need an inner “shark”? Or lion and fox as Machiavelli would suggest? Regardless, any book that survives 500 years should be at least somewhat interesting right?

What I learned

First and foremost I was expecting the suggestions of the famous Machiavelli to be significantly darker and more sinister than what I found in this read. Ultimately, I found that many of the suggestions made for how a Prince might take or hold power were often well advised, such as suggestions that a Princedom won through merit is more easily held than through fortune, or that a good rule of thumb is for any prince to avoid the hatred of his people. Therefore, I wanted to share some lessons that I found insightful that I thought could apply to modern leaders and leave out the relatively few more sinister suggestions.

If a leader wants to hold onto leadership of a new territory he is best served by being physically present in this new territory. So if you acquire a business, physical presence of leadership is important. 

No matter how strong your army is, when you enter a new area the good will of the people is necessary. If you want to enter a new market good relationships with the clients there are essential.

Treat others well or utterly crush them (maybe not so kind, but possibly pretty good advice, interesting as a concept in Ender’s Game as well)

If you earn your position by qualities of merit it will be difficult to fall from that position, but if you are installed via luck or nepotism you can fall easily and quickly. Working your way up in a company versus switching around for various roles will secure your position for the future. 

A good way to win favor with someone is to do them service. 

Sometimes being capable of negative qualities, cruelty, or cheapness, or frightening, can be a good thing because we don’t live in a perfect world where only those with excellent qualities always succeed. A real leader should not have to act this way, but it is possible they will need to and when that happens a good leader is prepared. 

“For I do not believe that divisions purposely caused can ever lead to good”. Solidarity is always a value to stand strongly against others. 

“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.” Basically do your best not to be hated by your groups. 

Although a bit condescending about how a Prince should only take advice at times of his choosing, Machiavelli goes on to encourage Princes to ask for advice often and to be a “patient hearer of the truth, and even if displeased should he perceive that any one, from whatever motive, keep it back.” To be open to hear even hard truths from your staff or teams and to discourage those who do not readily share the truth feels like a good value.

To end this section I wanted to discuss a remark that Machiavelli makes regarding whether or not to build your foundation on the trust of the people “and the risk of the experiment is the greater in that it can only be made once”. It is true and interesting how it relates to the psychology of Nudge that many major decisions in life we don’t get to do more than a few times so it is a challenge for people who have never done it before to make good decisions (think getting married, buying a house, moving to a new city, etc.). So regardless if the advice above is correct or not, regarding leadership it is always best to think wisely because you may not ever get another chance.

What I didn’t like

It feels a bit strange to critique a book written hundreds of years ago and that has managed to stay in print all this time. Clearly it has been interesting to various actors over time. Moreover, I’m not in agreement with all the points made, but the thought provoking nature of these points is at least interesting.

However, I did have a few small critiques of the publishing of the book. Clearly the publisher took just the original text, printed it as cheaply as possible and sent it out the door. Some minor additions could really have taken this start and made it significantly better, such as a foreword/introduction explaining the context of the book. Thoughts by influential people on how the main points apply to modern day. Even something simple like an index/glossary for all the archaic names or a quality map showing the regions of Italy at the time would have made some of the points more pungent for the reader unfamiliar with fifteenth and sixteenth century Italian geography (I venture to say most of the readers fall into this category).

Questions I asked

How can we relate a Princedom to a company? In modern society there are few true autocratically led governments and war is frowned upon, but companies are still often lead by one or few and non-violent business wars among major corporations still happen. 

Why does Machiavelli have such a reputation for treachery and deceit when his teachings are outdated, but often benign?

What are some modern examples of Princes that have established leadership and can we do a case study of how their success relates to Machiavelli’s teachings?

My Favorite Quote

“and the risk of the experiment is the greater in that it can only be made once”

Niccolo Machiavelli

Books I liked like this one

The Personal MBA: Josh Kaufman (for straightforward (although more modern and moral) ways to run a business)

Ender’s Game: Orson Scott Card (For the question if the ends justify the means)


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