5 Lessons From Machiavelli

Niccolò Machiavelli (1469-1527) is probably the most misunderstood thinker within the Western canon. Associated with villainy, his name has even come to denote part of the “dark triad” personality traits. This reading of Machiavelli is partially understandable because so few are familiar with all of his works (or more likely they have never read The Prince and simply relied on trite essays concerning the book). Yet this “secretary par excellence” was one of the greatest thinkers and practitioners of security in Western history, a man absolutely devoted to his city who only sought to defend the Florentine republic against a litany of enemies.

Machiavelli served in government during a turbulent time. The Medici had successfully run Florence for about a century, bringing art, culture, and security to the city-state. Some mistakes by Piero the Unfortunate during the early 1490s led to a coup against the Medici, and a radical priest obsessed with the apocalypse named Girolamo Savonarola took control of the city in 1494 AD. Savonarola would die by execution because of his heresy, and this would bring to power Piero Soderini, which is when Machiavelli would come to government. He would serve in a number of important positions for more than a decade.

As second chancery, he became a critical government bureaucrat who produced relevant documents, and during this time he was also the secretary to the Dieci di Libertà e Pace (the council over war and diplomacy). As secretary for the Ten of War, Machiavelli would lead many important diplomatic missions, including to Pistoia to end conflict between factions, to the court of King Louis XII of France, to Cesare Borgia while he was trying to take over central Italy, and to the papacy multiple times. Importantly, his diplomatic missions would produce the basis for his most well-known work The Prince as several passages were lifted directly from his legations and notes on this work.

One of Machiavelli’s most brilliant actions as a government official was organizing a militia to support Florence’s security. Machiavelli did not trust mercenaries (condottiere) because many times they would abandon the military operation or even switch sides depending on payments. Like with other intellectual projects, Machiavelli dedicated prodigious efforts to the subject and created a successful militia that by 1506 was a capable fighting force. He even successfully led the militia to defeat Pisa in 1509. Machiavelli’s 27 Rules of War remain insightful, and he learned the important lessons from his work on militias.

Despite his brilliance and acumen, Machiavelli would precipitously fall from power with the return of the Medici in 1512. Because he had sided with Soderini, Machiavelli would be tortured with the strappado before being exiled to his estate. While in exile, Machiavelli would take on a second career as one of the most brilliant thinkers of the Western world, writing several critically acclaimed works of fiction, political science, military theory, poems, and history.

His magnum opus was Discourses on Livy, a text that provides a brilliant elucidation on the success of Rome, which Machiavelli attributes to its republican government. (A prime example of how Machiavelli is misunderstood as a thinker and historical figure.) Although this was a great contribution to political theory, Machiavelli was given the highest honor in Florence one could have by being commissioned by Giulio de' Medici (later Pope Clement VII) to write an official history. Florentine Histories was an eight-volume history of the republic that glorified the Medici, ending with Lorenzo the Magnificent's death in 1492. When it comes to his plays, Machiavelli was most famous for the satirical play La Mandragola about deception and love in the nobility. Two other well-received plays he wrote are Andria and Clizia. Interestingly, a common theme throughout his dramatist career was that of trickery, and Machiavelli would also expound on themes found in The Prince (except dealt with in a comedic manner).

Despite all of these works, the modern audience primarily (if not exclusively) knows Machiavelli for a work never published in his life: The Prince. Often described as a treatise or guidepost for autocrats, that is a gross misunderstanding of the work. What The Prince really offers readers is a detailed and objective analysis of how power works in reality rather than rose-colored, normative pablum that gives quixotic suggestions on effective governance. As translator W. K. Marriott noted, “But what invests The Prince with more than a merely artistic or historical interest is the incontrovertible truth that it deals with the great principles which still guide nations and rulers in their relationship with each other and their neighbours.”

Describing reality so well gave rise to the incorrect assessment that this was how Machiavelli wanted the world to be. Yet that same objectivity is what offers powerful lessons for those interested in governance and leadership. The five lessons given in this newsletter are derived from Machiavelli’s brilliance in The Prince.

5 Lessons from Machiavelli's The Prince

Lesson 1: Take decisive actions rather than half-measures

"If an injury has to be done to a man it should be so severe that his vengeance need not be feared." (Chapter III)

What Machiavelli means in this passage is that half-measures create more problems than they solve because an enemy will take the respite to regain their strength and attack you, a theme he continues in Chapter XXI. This issue is often seen in geopolitical problems, such as half-measures against terrorism and not neutralizing a threat actor. However, the broader principle is applicable for security professionals as well: act decisively. When approaching a problem, how often do organizations throw some money at the issue with little follow through? The product is invariably an unworkable chimera that inhibits security rather than improves it. Security professionals must act decisively and completely to mitigate problems or neutralize threats.

Lesson 2: Objectivity in analysis is paramount

“There is such a gap between how one lives and how one should live that he who neglects what is being done for what should be done will learn his destruction rather than his preservation.” (Chapter XV)

Objectivity is incredibly difficult for analysts and security professionals. Due to ideology, personal experiences, and socialization, they bring a host of ideas and perceptions to a problem that distort the picture of what is happening. This is a notable issue for geopolitical risk analysts who usually are educated in a particular theoretical tradition for international relations rather than taking the world exactly as it is, which often defies theory. Other security professionals also have this problem as they cannot separate their personal experiences from a particular issue in which their experiences may or may not apply. Machiavelli teaches us to abandon those normative or experiential concepts when assessing a problem because it will almost always lead to incorrect or poor actions.

Lesson 3: The proper mindset is needed for different situations

"The lion cannot protect himself from traps, and the fox cannot defend himself from wolves. One must therefore be a fox to recognize traps, and a lion to frighten wolves." (Chapter XXVIII)

Everyone has heard the cliched aphorism, “If the only tool you have is a hammer, you tend to see every problem as a nail.” Security professionals and analysts must keep this in mind because not every problem is a nail. In fact, security professionals need to learn to take on different mindsets depending on the problem at hand. When there is a complicated problem that needs resolution, the security professional should take on the mindset of a fox. Study and analyze. However, not all problems can be dealt with through clever analysis. Sometimes security professionals need to act like a lion to scare off the wolves. Organizational problems typically arise when security professionals take on the wrong mindset. Be assiduously attuned to the situation and determine which mindset is requisite.

Lesson 4: Fortune does not control everything

"Not to extinguish our free will, I hold it to be true that Fortune is the arbiter of one-half of our actions, but that she still leaves us to direct the other half." (Chapter XXV)

One of the great contributions to political theory that Machiavelli added was the concept of virtù. While traditional theorists, often in the Christian tradition, connected the idea of virtue to the Aristotelian or Thomistic understanding, Machiavelli deviated from them by arguing virtù were those requisite qualities for leaders to confront the problems they faced. For Machiavelli, virtù encompassed courage, skills, and ruthlessness to do what is necessary. Virtù was critical because it is what would allow one to combat the oscillations of Fortuna (that is, the vicissitudes of fate beyond our control such as war, inclement weather, etc.). Security professionals face all kinds of external problems beyond their control, but virtù offers a tonic to those problems. Those who can muster the requisite courage, skills, and ruthlessness can perform their duties more effectively when Fortuna turns against them.

Lesson 5: Good leaders have honest advisers

“There is no other way of guarding oneself from flatterers except letting men understand that to tell you the truth does not offend you.” (Chapter XXIII)

A persistent problem in leadership is that advisers are unwilling to “speak truth to power” and state when obvious problems exist. Autocrats have especially had this problem, which is why their militaries tend to perform significantly worse than the militaries of democratic governments. Security leaders who keep “flatterers” around themselves instead of objective thinkers willing to call the leader out cause organizations to suffer tremendously. Programs will falter, and security becomes at best sclerotic and non-responsive. This means, though, that security leaders have to diligently create a culture that allows advisers and analysts to speak truth at all times, even when it is deeply uncomfortable or controversial. Flattering lies do more damage than painful truths.

July’s Cocktail: The Negroni

Like Florentine politics in the early 16th century, this is a sophisticated cocktail for those who enjoy an Italian aperitif. The Negroni is allegedly named after Count Camillo Negroni who decided to order an altered Americano with gin in lieu of soda some time in the 1910s at his favorite bar in Florence. This drink ingeniously combines herbal aromatics with a dry gin providing earthiness and vermouth giving sweetness. While in the US the drink is often served in a martini glass, the appropriate glass to use is a lowball (old fashioned glass).

Steps:

1.???Pre-chill the lowball glass (or fill with ice to be dumped out later).

2.???Fill a mixing glass with ice.

3.???Pour the following ingredients into the mixing glass over the ice: 1.25 ounce Tanqueray gin, .75 ounce Campari, 1 ounce sweet vermouth. Mix no more than 20 times.

a.???Note: If not Tanqueray than another gin with a juniper-heavy flavor.

b.???Note 2: The typical Negroni recipe calls for equal parts gin, sweet vermouth, and Campari, but the ratios provided will improve the flavoring.

4.???Cut a piece of orange peel (2 inches by .5 inches).

5.???Pour out the ice from the lowball glass.

6.???Rub the piece of orange peel around the glass and twist it to extract the oil. Leave in the glass.

7.???Place one large ice cube into the glass.

8.???Place the cocktail strainer over the mixing glass and pour into the lowball glass.

9.???Garnish with one orange slice.