While this book did not make my Top Ten list, it was referenced multiple times by the authors within that list. So, I just had to see for myself.

While I don’t think everything is applicable today (like killing all of the family members of your freshly conquered enemies), I think a lot of the principles about business and politics apply to today. Below is a list of some of the quotes from the book and my brief insight into its application..

On taking on a new leadership role…

• 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.
  • Lesson: You cannot rule with brute force, even if that is how you got your role.
• He who has annexed them, if he wishes to hold them, has only to bear in mind two considerations: the one, that the family of their former lord is extinguished; the other, that neither their laws nor their taxes are altered, so that in a very short time they will become entirely one body with the old principality.
  • Lesson: If you walk into a new leadership situation, don’t start making changes. Observe how things are working and let them play out before making small improvements.
• Whenever those states which have been acquired as stated have been accustomed to live under their own laws and in freedom, there are three courses for those who wish to hold them: the first is to ruin them, the next is to reside there in person, the third is to permit them to live under their own laws, drawing a tribute, and establishing within it an oligarchy which will keep it friendly to you.
  • Lesson: As a leader you need to reside with your team. Hopefully the other two options are off the table in a business scenario…
• And it ought to be remembered that there is nothing more difficult to take in hand, more perilous to conduct, or more uncertain in its success, than to take the lead in the introduction of a new order of things, because the innovator has for enemies all those who have done well under the old conditions, and lukewarm defenders in those who may do well under the new.

Good Advice

• 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.
  • Lesson: Learn from others who have done great things. Reject the advice and criticism of people you do not want to be like.
• 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.
  • Lesson: Rolling layoffs are Constant restructuring is stupid and Machiavelli knew that in 1513…
• Nevertheless he ought to be slow to believe and to act, nor should he himself show fear, but proceed in a temperate manner with prudence and humanity, so that too much confidence may not make him incautious and too much distrust render him intolerable.
• Because the Romans did in these instances what all prudent princes ought to do, who have to regard not only present troubles, but also future ones, for which they must prepare with every energy, because, when foreseen, it is easy to remedy them; but if you wait until they approach, the medicine is no longer in time because the malady has become incurable; for it happens in this, as the physicians say it happens in hectic fever, that in the beginning of the malady it is easy to cure but difficult to detect, but in the course of time, not having been either detected or treated in the beginning, it becomes easy to detect but difficult to cure.
  • Lesson: Early detection is vital.
  • Lesson: Contingency planning is vital.
• And the first opinion which one forms of a prince, and of his understanding, is by observing the men he has around him; 
  • Lesson: Don’t hang out with losers.

Okay…just the fun quotes

• 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.
• 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.

Modern Day Politics?

Oh look, not much has changed since 1513…

• Some princes, so as to hold securely the state, have disarmed their subjects; others have kept their subject towns distracted by factions; others have fostered enmities against themselves;
• He who obtains sovereignty by the assistance of the nobles maintains himself with more difficulty than he who comes to it by the aid of the people, because the former finds himself with many around him who consider themselves his equals, and because of this he can neither rule nor manage them to his liking.
• because then every one agrees with him; they all promise, and when death is far distant they all wish to die for him; but in troubled times, when the state has need of its citizens, then he finds but few. And so much the more is this experiment dangerous, inasmuch as it can only be tried once. Therefore a wise prince ought to adopt such a course that his citizens will always in every sort and kind of circumstance have need of the state and of him, and then he will always find them faithful.
• And that prince who, relying entirely on their promises, has neglected other precautions, is ruined; because friendships that are obtained by payments, and not by greatness or nobility of mind, may indeed be earned, but they are not secured, and in time of need cannot be relied upon; 
• Every one sees what you appear to be, few really know what you are, and those few dare not oppose themselves to the opinion of the many, who have the majesty of the state to defend them;
• But when you disarm them, you at once offend them by showing that you distrust them, either for cowardice or for want of loyalty, and either of these opinions breeds hatred against you.