30 Highlights from The Prince

Re-opened this iconic book for a read on this Fourth of July. I share my 30 highlights from the Prince below:

The Prince – Niccolo Machiavelli 

July 4, 2020 – Zac Upchurch Synthesis

1. Assimilation is made easier when two entities share common backgrounds/cultures (i.e., they speak the same language). Entities with shared cultures can be most easily assimilated by removing the previous leadership/ruler and by not creating great disruption in the acquired entity (i.e., change laws and taxes). 
2. It is more challenging to assimilate and maintain entities that do not share a common background/culture. Leadership/Ruler should be very present in the newly acquired entity to detect and manage early challenges before the challenge balloons. 
3. When a leader/ruler acts, it should be to pamper or to crush… for revenge is possible in minor actions. 
4. Weaker entities gravitate towards strong entities and leadership, but the leader/ruler must ensure that the weak entities do not yield too much strength or authority to later become a threat. 
5. A leader/ruler must look into the future, not only the present. A great leader/ruler looks around corners and solves not only for today, but for problems that may arise into the future. Conflict avoidance and/or not identify a small conflict today and letting the conflict balloon makes for a more challenging solution down the road. “One must never allow disorder to continue so as to escape a war.” 
6. An entity with a single ruler/leader is more challenging to conquer but once conquered, easier to maintain. An entity that is a composite of multiple rulers/leaders is easier to conquer (because allegiance can be more easily disunited) but more challenging to maintain (as keeping all rulers/leaders content is impossible). 
7. A leader/ruler, upon acquiring an entity, can: 1. Devastate the new entity; 2. Live in the new entity (see 2/); 3. Set up an oligarch but allow for the continued practice of existing laws. The more free a society, the more challenging 3. Is to maintain success as revenge is always on the mind. 
8. “It should be borne in mind that there is nothing more difficult to handle, more doubtful of success, and more dangerous to carry through than initiating changes in a state’s constitution.” If a leader/ruler undertakes this change, they must be able to stand alone and force the issue. Attempting to undertake this change through influence and persuasion will yield unsuccessful outcomes. If successful in the change, the leader/ruler will have little challenge maintaining the renewed entity. 
9. A leader/ruler can come to power through crime, but such a leader/ruler will never have glory. 
10. A leader/ruler must not hesitate but enact expedient actions. “Whoever acts otherwise, either through timidity or misjudgment, is always forced to have the knife ready in his hand and he can never depend on his subjects because they, suffering fresh and continuous violence, can never feel secure with regard to him. Violence must be inflicted once for all; people will then forget what it tastes like and so be less resentful. Benefits must be conferred gradually; and in that way they will taste better.” 
11. When a leader/ruler comes to power through the people (anointed by others in power or through the masses), the leader/ruler must gain the favor and the will of the people/masses. “… a wise prince must devise ways by which citizens are always and in all circumstances dependent on him and his authority…”
12. Create and hold a fortified base. Possessing a fortified base means that the opposition is less likely to attack your domain. Even in the event of attack, the fortifications should allow you to outlast attack through the simple attrition of time. A fortified base becomes a protector of the entire domain, even if the base does not encompass the entirety of the domain itself. 
13. Short tenures of leaders/rulers results in challenges to operationalizing leadership and rulership. 
14. Be skeptical of mercenary talent. Mercenary talent is either incompetent or misaligned with the leader/ruler interests. In either situation, power is undermined through mercenaries. 
15. Be skeptical of auxiliary talent. In defeat, you are on the hook and in victory, you left indebted to their power. 
16. “The first way to lose your state is to neglect the Art of war; the first way to win a state is to be skilled in the art of war.” 
17. Always be learning and asking questions. Pose “what if” scenarios to bolster your knowledge and increase likelihood of expecting the unexpected. 
18. Generosity is an often misunderstood concept. The most generous person is one who can “defend oneself against an aggressor and embark on campaigns without burdening the people.” It is better to be a person that in the short-term is characterized as a miser than a person that in the short-term is characterized as generous. 
19. To the common question, “Is it better to be feared or loved?” We answer both. In the absence of both, it is better to be feared. But most important of all, it is critical to not be hated. 
20. The five qualities a prince should display (though not necessarily live) include: 1. A man of compassion; 2. A man of good faith; 3. A man of integrity; 4. A kind man; 5. A religious man. 
21. The easiest pathway to being hated is to mess with the women or property of those under your leadership. And rule number one is to not be hated. Thus, don’t mess with women or property!!!!
22. There are two things a leader/ruler must fear: 1. internal subversion from their own; 2. External aggression by others. 
23. Wise leaders/rulers delegate the action of unpopular initiates and keep for themselves the action of popular initiatives. This further supports the number one rule – to not be hated by the masses. 
24. You cannot imitate what made others successful without consideration to the context that surrounded the success. Imitation without context and customization is a sure path to mediocrity or defeat. 
25. “The prince who is more afraid of his own people than of foreign interference should build fortresses; but the prince who fears foreign interference more than his own people should forget about them.” A fortress will not protect a hated leader/ruler. 
26. A leader/ruler is never neutral – they take a stand. However, when taking a stand, never align to a power that is stronger than your own (unless absolutely necessary) as you will always be subservient to the more powerful party. 
27. Throughout the year, engage with the populous through festivities/events/touch points. 
28. Shun flatterers. 
29. A leader/ruler never lacks advice, but advice should only be taken if asked for, not when others push advice absent your purpose. 
30. “The only sound, sure, and enduring methods of defense are those based on your own actions and prowess.”