Mental Pivot

Notes and observations from a lifelong pursuit of learning.

Insights and interesting reads delivered straight to your inbox.
Sign up for the free Mental Pivot Newsletter.

Book Notes: “On Grand Strategy” by John Lewis Gaddis


On Grand Strategy by John Lewis Gaddis (2018) is a challenging meditation and wide-ranging history on the art of leadership and decision-making. Strategy, put simply, is the path to achieving a given objective in the face of limited means and constraints. When the stakes are particularly high—as in the case of war, politics and statecraft—the adjective “grand” is applied. As Gaddis notes, strategy carries an inherent conflict: ends exist in the imagination and are infinite (i.e., one can set any number of arbitrary goals), but means (i.e., capabilities, resources, skills) are finite. “Ends and means have to connect if anything is to happen” is the book’s leitmotif. This is the simple, frequently overlooked truth behind any successful strategy.

The majority of the book is devoted to a survey of historical figures spanning 2500 years: Xerxes, Pericles, Augustus Caesar, Augustine of Hippo, Machiavelli, Elizabeth I, Napoleon, Lincoln, Clausewitz, and Franklin Delano Roosevelt to name a few. Some figures profiled serve as cautionary lessons of strategic failure. Xerxes and Napoleon, for instance, sought ends that far exceeded their means; each was doomed, lacking the flexibility to deviate from their overly rigid world-views. Others, like Augustus Caesar, Elizabeth I, and Abraham Lincoln succeeded as grand strategists precisely because they wisely aligned aspirations with constraints.

The American writer, F. Scott Fitzgerald, defined a “first-rate intelligence” as “the ability to hold two opposed ideas in the mind at the same time, and still retain the ability to function.” Gaddis extends Fitzgerald’s idea to the realm of strategy, that is, first-rate leaders must simultaneously hold opposing ideas in their minds, be it ends vs. means, theory vs. practice, specialization vs. generalization, action vs. inaction, or any other number of conflicting polarities. This holistic approach to analysis and action is what separates the successful strategists from everyone else. This is not a complicated idea, but in practice it is exceedingly difficult to pull off. Moreover, without frequent reminders or periodic self-reflection, it is an idea that’s easy to overlook or forget.

In the first chapter, Gaddis invokes a famous but enigmatic proverb by the Greek poet Archilochus “The fox knows many things, but the hedgehog knows one big thing.” The metaphor of foxes and hedgehogs is often applied to different types of people, behaviors, and even strategies: hedgehogs are specialists and ideologues and foxes are generalists and pragmatists. Superficially, Gaddis appears inclined towards foxes; the biggest failures cited in the book are single-minded hedgehogs. Instead, with a nod to Fitzgerald’s quote on first-rate intelligence, Gaddis advocates for a union between the two: “We need to combine, within a single mind (our own), the hedgehog’s sense of direction and the fox’s sensitivity to surroundings.”

The examples in the book demonstrate that history’s greatest strategists were patient, calculating, and adept at taking small, deliberate steps toward their goals. Humility and self-awareness kept them from exceeding their grasp. When opportune, they could act quickly and decisively, but only insofar as they had created the necessary foundation from which to achieve their ends. Ultimately, the most successful strategists get the necessary sequencing right: they increase their means first and then attend to obtaining their ends. Unsuccessful strategies frequently exhibit the reverse. They lead from aspirations (ends) and fail to ever effectively manage their capabilities (means).

This was a strange but fascinating read for me. Strange because I was expecting something more instructional text on strategy, what I got instead an exploration of abstract theories and an eclectic (and, at times, excruciatingly detailed) set of historical case studies. The result is a bewildering and sometimes non-linear journey through the author’s wide-ranging thoughts on strategy. Unless the reader is particularly well-read, a subsequent re-reading would be necessary to grasp the full scope of Gaddis’ ideas and erudition. Alas, I am not up to the task, but I did enjoy the broad lessons and overall theme.

Pros: There’s a great deal of wisdom, history, and keen ideas to long ponder after reading this book.

Cons: Some historical accounts meander or delve into tangential territory. Connecting the specifics in the book back to the general themes is sometimes difficult.

Verdict: 7/10



  • The book was developed out of two experiences with grand strategy:

    • The author taught “Strategy and Policy” at the United States Naval War College from 1975 to 1977.
    • The author taught “Studies in Grand Strategy” at Yale from 2002 to the present.
  • The author draws on patterns across time, space, and scale. The author never explicitly defines these terms in the book, but here’s my rough understanding of them:

    • Time: Can mean history or simply the passage of time. For instance, in some cases when an opposing force must seize a quick victory, an effective strategy is to stretch the opponent’s commitment over a longer horizon.
    • Space: This can mean geography in some cases. In some cases it can refer to the more abstract domain or locale in which a person or group is interacting.
    • Scale: This refers different levels at which an idea operates (e.g., the individual, family, group, city, nation, world, universe, etc.).

Chapter 1: Crossing the Hellespont

  • Overview: A study in the contrasting approaches of Xerxes and his advisor Artabanus.

  • Author uses the proverb from the ancient Greek poet Archilochus as a thematic frame for the book:

    • “The fox knows many things, but the hedgehog knows one big thing.”

    • Isaiah Berlin (philosopher) wrote an essay on the topic:

      • Hedgehogs relate everything to a single central vision”
      • Foxes pursue many ends, often unrelated and even contradictory, connected, if at all, only in some de facto way.”
  • Story: Xerxes is on the cusp of crossing from Asia into Greek via the Hellespont (aka The Dardanelles) circa 480 BC.

    • Artabanus (Xerxes uncle and advisor) worries about the practical considerations of invading Greece.

    • Xerxes dismisses Artabanus: “If you were to take account of everything…you would never do anything. It is better to have a brave heart and endure one half of the terrors we dread than to [calculate] all of the terrors and suffer nothing at all…Big things are won by big dangers.”

    • Author sees Artabanus as a fox and Xerxes as a hedgehog.

      • “Artabanus stresses prices to be paid—in energy expended, in supplies stretched, in communications compromises, in morale weakened, in everything else that can go wrong—when seeking to move any large force across any body of land or water. Success requires taking on too much.”
      • “Xerxes…has a larger and longer view. If death is the price of life, why not pay the lesser prices that make lives memorable? Why be a forgettable King of Kings? Having tamed the Hellespont he can hardly stop.”
      • “Artabanus respects environments…Xerxes, in contrast, reshapes environments.”
    • Artabanus sees complexity and the immediate horizon. Artabansus is uncertain.

    • Xerxes sees the distant horizon and simplicity points the way. Xerxes is resolute.

  • Phil Tetlock’s (political psychologist) studies on forecasting. Demonstrated that “experts” were not the best predictors of the future.

    • Instead, Tetlock’s findings were that how a person engaged in truth-seeking was the most important predictor of forecasting skill.

    • Foxes were better predictors than hedgehogs of the future.

      • Foxes relied on diverse sources of information and constantly adjusting their worldview.
      • Hedgehogs “shunned self-deprecation and brushed aside criticism. Aggressively deploying big explanations, they displayed a ‘bristly impatience with those who do not get it.’” Hedgehogs would double-down in their beliefs.
    • Tetlock: “Self-critical thinkers are better at figuring out the contradictory dynamics of evolving situations, more circumspect about their forecasting prowess, more accurate in recalling mistakes, less prone to rationalize those mistakes, more likely to update their beliefs in a timely fashion, and—as a cumulative result of these advantages—better positioned to affix realistic probabilities in the next round of events.”

  • Xerxes failed invasion of Greece was an example of hedgehog behavior.

    • “Xerxes failed…to establish a proper relationship between his ends and his means.”

      • Ends exist in the imagination and are infinite.
      • Means are finite. (i.e., individual or societal capabilities)
      • “Ends and means have to connect if anything is to happen.”
      • The danger occurs when we fail to distinguish between the ends and means (people often conflate the two).
    • It is difficult to imagine the cumulative effects of small actions and unpredictable events.

  • F. Scott Fitzgerald’s definition of first-rate intelligence: “The ability to hold two opposed ideas in the mind at the same time, and still retain the ability to function.” (source: “The Crack-Up,” Esquire, Feb. 1936)

    • “It’s easy to see how two minds can reach opposite conclusions, but can opposites coexist peacefully within one?”
    • “The choices facing us are less often between stark alternatives—good versus evil, for instance—than between good things we can’t have simultaneously.”
  • “We need to combine, within a single mind (our own), the hedgehog’s sense of direction and the fox’s sensitivity to surroundings, while retaining the ability to function.”

  • Tetlock (Expert Political Judgement): “Foxes were better equipped to survive in rapidly changing environments in which those who abandoned bad ideas quickly held the advantage. Hedgehogs were better equipped to survive in static environments that rewarded persisting with tried-and-true formulas. Our species—Homo sapiens—is better off for having both temperaments.”

  • Grand strategy: The alignment of potentially unlimited aspirations with necessarily limited capabilities.

    • “Grand” refers to the stakes; specifically high stakes situations or outcomes.
    • If one seeks ends beyond their means, she must curb her ends (or increase the means) or risk failure.
    • If one increases their means, they can correspondingly increase their ends (within reason).
    • Strategy is the activity of connecting and aligning means and ends.
    • Note: We often conflate strategy with war. Military strategy is just one (very visible) aspect of strategy. Strategy as a concept goes far beyond war-making.
  • “A gap has opened between the study of history and the construction of theory, both of which are needed if ends are to be aligned with means.”

    • “Historians, knowing that their field rewards specialized research, tend to avoid the generalizations upon which theories depend: they thereby deny complexity the simplicities that guide us through it.”
    • “Theorists, keen to be seen as social scientists, seek reproducibility in results: that replaces complexity with simplicity in the pursuit of predictability.”
    • “Both communities neglect relationships between the general and particular—between universal and local knowledge—that nurture strategic thinking.”

Chapter 2: Long Walls

  • Overview: A study in the contrasting strategies of Athens and Sparta in the 5th century BC and the Peloponnesian War.

  • Story: Athens builds a series of defensive walls around their port city circa 457 BC.

    • The Greeks, unlike the Persians, were faced with limited means. They only knew scarcity (from a geographic and resource standpoint).

    • Greece was divided into rival city-states. This resulted in a test-lab for varying strategies between rival cities.

    • Spartans developed a specialized strategy as a warrior culture.

    • Athens built a maritime culture that had a rich, interconnected network of trade with other Mediterranean cultures.

    • The Peloponnesian War (431-404 BC):

      • Conflict between Athens and Sparta.
      • War is the result of strategic decisions made many years earlier. For instance, when Athens sought to protect its interests with the wall.
    • The Athenians uses the wall to secure their base of operations and ensure unfettered lines of maritime commerce.

    • Sparta, having the strongest army in Greece, preferred to keep Greece wall-free.

    • “Each sought security but by different paths; neither could afford to be, simultaneously, tigers and sharks.”

  • Part of Athens long-term strategy was developing a strong culture. This culture gave Athenians something worth fighting for, cultural cohesion, and served as an inspiration to others.

    • Athenians democratized war by relying on walls, ships, and rowers. They had no “warrior elites” like the Spartans.
    • The democratic model gave citizens a stake in the future of Athens.
  • “The Greeks thought of culture as character. It was predictably across scale: the behavior of a city, a state, or a people in small things, big things, and those in between.”

  • “The abstractions of strategy and the emotions of strategists can never be separated: they can only be balanced.”

  • “Strategy requires a sense of the whole that reveals the significance of respective parts.”

Chapter 3: Teachers and Tethers

  • Overview: The lesson of Augustus Caesar along with the teachings of Sun Tzu.

  • Author revisits the theme of theory vs. practice/experience with two contrasting examples:

    • The Greek historians (e.g., Herodotus, Thucydides, etc.): Describe events and individuals and leave it to the reader to derive the lessons.

    • Sun Tzu: Sets for principles that are applicable in different contexts of time and space. Connects these principles to practices.

      • The Art of War…is neither history nor biography. It’s a compilation of precepts, procedures—and categorical claims.”
  • Once more the idea of connecting theory and practice is the critical piece in the puzzle of creating an effective strategy.

    • “History is full of borrowers and lenders who bought high but had to sell low. They disengaged their practices from their principles. They couldn’t resist proffered baits. What look like platitudes, in The Art of War, are in fact tethers, meant to prevent such separations.”
    • [Me: This is an important theme. Common sense is basic and simple, but it’s hard in the real-world given pressures and other considerations competing for our attention and emotion. Reminders are an underrated tool for keeping key principles top-of-mind.]
  • Reflection is a critical part of strategic thinking. Yet, how often is this aspect overlooked in lieu of objectives and plans?

  • Sun Tzu on the coexistence of simplicity and complexity:

The musical notes are only five in number, but their melodies are so numerous that one cannot hear them all. The primary colors are only five in number but their combinations are so infinite that one cannot visualize them all. The flavors are only five in number but their blends are so various that one cannot taste them all. In battle there are only the normal and extraordinary forces, but their combinations are limitless; none can comprehend them all.

* Per Gaddis, Sun Tzu tethers “principles, which are few, to practices, which are many.”
* “When simplicities mix, complexities become endless.”
  • Story: Augustus Caesar (Octavian) must navigate Roman politics and succession after Julius Caesar’s death. Julius Caesar named Octavian his heir and son (by adoption) in his will.

    • Octavian’s primary rival was Marc Antony.
    • Octavian made several shrewd initial moves to shore up his precarious position: he pledged his wealth to the Romans, he cultivated his relationship with Cicero (a crafty political actor) and enemy of Antony, he successfully staged Caesar’s funeral games.
    • “Octavian was less than half Antony’s age, but he was the far shrewder judge of character. He made himself a foil for the older man’s flaws: massive debts, sexual promiscuity, public drunkenness, explosive volatility.”
    • Octavian waited patiently to claim the consulship of Rome—once he had the loyalty of the army, support of Cicero and the senators, and when Antony threatened to march on Rome.
    • Instead of ruling alone, however, Octavian gave up his consulship and formed a triumvirate with Antony and Lepidus. This alliance allowed Octavian time to pick off both Antony and Lepidus and shore up his power.
    • Ultimately, Octavian waited for Antony and Lepidus to misstep, and when they did, he seized his advantage.
  • Octavian “seized opportunities while retaining objectives. He saw next steps where Antony stumbled. Octavian stuck to his compass heading while avoiding swamps: it’s almost as if Antony sought out swamps, sank into them, and then got bored with them.”

  • “Most of the time…capabilities fall short—that was Octavian’s problem. Insufficiency demands indirection, and that, Sun Tzu insists, requires maneuver.”

    • Sun Tzu: “When capable, feign incapacity, when active, inactivity. When near, make it appear that you are far; when far away, that you are near. Offer an enemy a bait to lure him; feign disorder and strike him…When he concentrates, prepare against him; where he is strong, avoid him…Pretend inferiority and encourage his arrogance…Keep him under a strain and wear him down.”
  • “Victories must connect: otherwise they won’t lead anywhere.”

  • “Maneuvering, thus, requires planning, but also improvisation.”

  • “After Actium, Octavian began controlling events, rather than letting them control him.”

Chapter 4: Souls and States

  • Overview: The contrasting lessons of Augustine and Machiavelli—heaven vs. hell—and the reconciling of secular vs. spiritual jurisdictions.

  • Context: The rise of Christianity in the West alongside the apex of the Roman Empire presented a conundrum: “What did its [Christianity’s] subjects owe to Caesar and what to God?”

    • How could Christianity survive without state protection?
    • Could the state survive without the endorsement of Christianity?
    • Medieval and early modern thinkers grappled with the intersection between secular and spiritual worlds.
  • Augustine of Hippo (354-430 AD):

    • Emperor Constantine legalizes all religions in 313 AD. It is believed Constantine converts in 312, though it has been widely taught that he officially converted on his deathbed in 337.

    • “Augustine set out to reconcile faith with reason…”

    • The City of God (426) explores “overlapping terrestrial jurisdictions” of Heaven and earth.

      • “There is one God and there can be only one Caesar. Men owe allegiance to both while on earth.”
      • “Determining obligations to Caesar and God becomes, then, the grandest of strategic tasks, for it requires aligning limited human capabilities with an aspiration—an afterlife—that has no limits.”
      • “Man’s choices lie between the polarities, but no formulae reveal what those choices should be.”
      • “Augustine concluded that war, if necessary to save the state, could be a lesser evil than peace…” (in part, this is because the state, Rome in this case, allowed for the flourishing of Christianity).
    • Author frames Augustine’s pronouncements as “checklists” rather than commandments.

      • Example: Have you thought about this? Would it make sense to do X?
      • This represents a preference for persuasion over coercion and threats.
      • Checklists are more adaptable and flexible than commandments.
      • “Checklists pose common questions in situations that may surprise.” Considering these questions in advance covers more possibilities and sets you up for more contingencies.
    • “Alignment…implies interdependence. Justice is unattainable in the absence of order, peace may require the fighting of wars, Caesar must be propitiated—perhaps even, like Constantine, converted—if man is to reach God. Each capability brings an aspiration within reach…”

    • Proportionality: The means employed must be appropriate to the desired end.

  • Niccolo Machiavelli (1469-1527):

    • The Prince (1513): Exhibits a markedly different view of God and man from Augustine. Far more secular. Per Gaddis: “[Machiavelli fears God less than he does man.”
    • Machiavelli: “I judge that it might be true that fortune is arbiter of half our actions, but also that she leaves the other half, or close to it, for us to govern.”
    • “If governed badly, men’s rapacity will soon overwhelm them, whether through internal rebellion or external war. But if run with virtù—his untranslatable term for planning without praying—states can constrain, if not in all ways control, the workings of fortune, or chance.”
    • Key skills: imitation, adaptation, and approximation.
    • “Machiavelli embraces, then, a utilitarian morality: you proportion your actions to your objective…because some things have been shown to work and others haven’t.”
    • Machiavelli in The Discourses: “It is only in republics that the common good is looked to properly in that all that promotes it is carried out; and, however much this or that private person may be the loser on this account, there are so many who benefit thereby that the common good can be realized in spite of those few who suffer in consequence.”
  • “You proportion aspirations to capabilities. These are opposites—the first being free from limits and the second bound by them—but they must connect. That happens only when you hold both in mind simultaneously.”

    • “Augustine failed to show how God’s omnipotence could coexist with man’s freedom. Machiavelli solved that problem—God didn’t want to do everything—but created another by leaving God with little to do.”
    • Isaiah Berlin: We know but do not admit the truth that ideals cannot be attained. “Statecraft…can never balance realism against idealism: there are only competing realisms.”
  • Berlin: “It is on earth that we live, and it is here that we must believe and act.” (from “the Pursuit of the Ideal”)

Chapter 5: Princes as Pivots

  • Overview: The contrasting world-views of Philip II of Spain and Queen Elizabeth I.

  • Pivots: The point on which something rests or turns.

    • Augustine and Machiavelli are pivots in Western thought (theoretical pivots).
    • Philip and Elizabeth are pivots of history. Two different approaches that influenced subsequent global and societal developments.
    • One cannot pivot if they are pinned down. One can only pivot if they are free by keeping ends within their means.
  • “Philip rushes from crisis to crisis…never fully in control…Elizabeth, in contrast, refuses to hurry…she sets times and places. She resists unnecessary expenditures of resources, energy, reputation, and unusually in a monarch—virginity.”

    • Philip is Augustinian—attempting to connect the City of Man with the City of God.
    • Elizabeth is Machiavellian.
  • Elizabeth (1533-1603):

    • “Elizabeth sought not to abolish English Catholicism, but to nationalize it by denying papal authority over the state she ruled.”
    • Learned to delegate authority and lean on experts in other fields.
    • Garrett Mattingly (historian): Elizabeth’s strategy “was to arrange the courtiers and counselors around her, the diplomats and envoys, the kings and powers of the Continent in an elaborate interlocked design so cunningly and delicately balanced that each part should counteract another and she herself should always be free.”
    • She was determined to be governed by no one and remain truly sovereign.
    • “Blessed with an island, not Philip’s scattered provinces, Elizabeth could avoid the costs of a standing army, adapt her navy for protection or provocation, and align her state as necessary—never permanently—with the continental enemies of her enemies.”
  • Philip II (1527-5798):

    • Inherited a sprawling global empire from his father—along with a financial mess.
    • Was a micromanager. Saw the interests of the state inextricably tied to God and, as the executor of God’s will, saw decision-making as his sole responsibility. He saw delegation as “religious dereliction.”
    • “How could Philip have no superior but be paralyzed by constraints?…[he] ruled and depended on revenues from a patchwork of peoples owing him little loyalty. Noncontiguous boundaries compounded the problem, as did the king’s dislike of delegating authority.”
    • Philip was at war for 42 1/2 of his 43 years as king.
    • “What Philip wanted was loyalty from his subjects, prosperity within his provinces, credibility among his competitors, a return to orthodoxy…He failed to see incompatibles, and hence the need to pursue certain objectives at the expense of others.”
    • “Philip placed his plan within a larger revival of Catholic crusading, aimed this time at liberating Canterbury, not Jerusalem. The Augustinian obligation to serve the state had evolved into a papal obligation to serve the church…by killing European Christians who’d rejected Rome’s authority.”
    • Philip on invading England: “I am so attached to [the invasion] in my heart, and I am so convinced that God our Savior must embrace it as His own cause, that I cannot be dissuaded. Nor can I accept or believe the contrary.”
  • Machiavelli: Circumstances change and rulers must not be reliant on old promises in new situations.

  • Elizabeth could not match the Spanish Armada in a head-to-head confrontation:

    • She had her fleet track Spanish ships and pick off individual vessels opportunistically.
    • “The English didn’t defeat the Armada, but they wore it down, which amounted to the same thing.”
    • The Armada was poorly organized and the invasion poorly planned which lent further advantage to Elizabeth.
    • “When warned that his objectives [Philip’s] exceeded his capabilities, the king would claim that those doing the warning themselves lacked faith: God would close the gap.”

Chapter 6: New Worlds

  • Overview: The birth of the United States as a result of England’s bottoms-up approach to colonization (compared to Spain’s top-down approach) and the subsequent evolution of the American Republic.

  • Overview: The contrasting world-views of Philip II of Spain and Queen Elizabeth.

  • Geoffrey Parker (historian): “The failure of the Spanish Armada laid the American continent open to invasion and colonization by northern Europeans, and thus made possible the creation of the United States.”

  • The English overseas expansion strategy:

    • Elizabeth let merchants and settlers risk their ships and resources. She minimized the exposure of her navy and treasury.
    • “She sought self-sufficiency in overseas enterprises.”
  • “Spanish America, by the 1750s, had six times the population and many more times the size and wealth of its northern counterpart…”

  • Spain fostered a uniform approach to colonization and rule. England fostered a more diverse approach where a mosaic of self-sufficient communities developed.

  • “British America was a society whose political and administrative institutions were more likely to evolve from below than to be imposed from above. That made it a hodgepodge, but also a complex adaptive system.”

  • “Controlled environments encourage complacency, making it hard to cope when controls break down, as they sooner or later must.”

  • The “light touch” approach used by England ultimately led to the American perspective on freedom, liberty, and self-determination.

  • Thomas Paine’s Common Sense (1776): “Paine’s pamphlet was the literary equivalent of Elizabeth’s fireships: an incendiary device meant to unnerve an enemy, rally a defense, and make history pivot.”

  • The process of American independence was gradual. The first step was to proclaim it and then work organically towards realizing it.

  • “Americans were unsure, in 1776, what kind [of government] they wanted. So they settled for governments ground in the interests of each state, linked loosely by the Articles of Confederation.”

  • The “second American revolution” follows the Revolutionary War. In this instance, the goal was to correct the failures of governance resulting from the first and implement an effective Federal government and constitution.

  • The Federalist Papers and the Constitution sought to align incompatible aspirations with limited capabilities.

    • How to create a Union without overwhelming the constituent parts (States).
    • How to prevent an empire from succumbing to tyranny.
    • How to prevent an overbearing majority from overwhelming the minority.
  • James Madison solves the problem through scale. The proposed constitution “forms a happy combination in this respect; the great and aggregate interests being referred to the national, the local and particular to the State legislatures.”

  • By the 1820s, the United States was assured in its position to assert the Monroe Doctrine: this is the policy that the United States would not tolerate further colonization or puppet monarchs in their hemisphere.

  • In contrast, the Spanish New World colonies did not achieve the level of independence and stability of the United States.

    • Simon Bolivar argued that South America was in a state of “permanent infancy.”
    • “Once the world’s greatest empire, Spain was now too weak to prevail, but had trained no one to take its place.”
    • Smaller authoritarian nations emerged. But by nature, these leaders resisted greater cooperation with their neighbors and lacked the foresight to create a unified nation.
    • The result was that a comparable United States of South America could not form.

Chapter 7: The Grandest Strategist

  • Overview: A look at the 19th centuries ideas of Carl von Clausewitz and Leo Tolstoy and their similar approaches to “grand strategy” vis a vis the Napoleonic Wars.

    • On War by Clausewitz (1831)
    • War and Peace by Tolstoy (1867)
  • “Not only do Tolstoy and Clausewitz see the practice of war similarly: they also construct theories, drawn from their own military experiences, about the limitations of theory itself.”

  • “Common sense is indeed like oxygen: the higher you go, the thinner it gets. As each triumph topped its antecedent, Napoleon’s grammar became his logic. Like Caesar, he rose so far above fundamentals as to lose sight of them altogether.”

  • Clausewitz: “War is…and act of force to compel our enemy to do our will….Force—that is, physical force, for moral force has no existence save as expressed in the state and the law—is thus the means of war; to impose our will on the enemy is its object.”

    • If war reflects politics, it must be subordinate to politics and therefore policy. The absence of guiding policy renders war as senseless violence.
    • Clausewitz: “The political object is the goal, war is the means of reaching it, and means can never be considered in isolation from their purpose.”
  • Napoleon’s goal when invading Russia: Alexander’s compliance in France’s blockade of Great Britain (aka “The Continental System”).

    • Napoleon sought a quick war whereby Russia immediately capitulated.
    • Alexander counteracted Napoleon by retreating into the vast Russian hinterland: he scorched the earth (it wasn’t in short supply) and extended the time and distance required for Napoleon’s campaign. Effectively, Napoleon was overextended and then suffered from famine and frost.
  • Coup d’oeil (aka an “inward eye”): Clausewitz’s emphasis on the importance of reflection, perception, and linking strategy to imagination.

    • It is related to Machiavelli’s concept of sketching: “conveying complexity usably.”
    • Planning can be used to anticipate surprises.
    • Example form Clausewitz: “Imagine a traveler who late in the day decides to cover two more stages before nightfall. Only four or five hours more, on a paved highway with relays of horses: it should be an easy trip. But at the next station he finds no fresh horses, or only poor ones; the country grows hilly, the road bad, night falls, and finally after many difficulties he is only too glad to reach a resting place with any kind of primitive accommodation. It is much the same in war.”
  • Friction: “Once conditions become difficult, as they must when much is at stake, things no longer run like a well-oiled machine.”

    • Murphy’s Law: anything that can go wrong, will go wrong.
    • An enemy’s retreat can create tremendous friction for the attacking party as evidenced in the examples of Xerxes and Napoleon.
    • One must consider the many points of failure: landscape, logistics, climate, morale, your opponent’s strategies, etc.
  • Clausewitz: “What sort of mind is likely to display…military genius, experience and observation will both tell us that it is the inquiring rather than the creative mind, the comprehensive rather than the specialized approach…”

  • Clausewitz on theory: “Theory exists so that one need not start afresh each time sorting out the material and plowing through it, but will find it ready to hand and in good order. It is meant to educate the mind of the future commander, or, more accurately, to guide him in his self-education, not to accompany him to the battlefield…”

  • “The modern term for sketching is net assessment, an evocation…of the elements, in environments, most likely to determine outcomes. If done well it will include ‘knowns’—geography, topography, climate, your own capabilities, the objectives you’re seeking; ‘probabilities’—the goals of adversaries, the reliability of allies, the constraints of cultures, your country’s capacity to endure adversity; and, finally, a respectful acknowledgement of the ‘unknowns’ that will lurk in the intersections of the first two.”

  • Overstretch: A resulting weakening that comes from conflating ends and means.

    • An opponent can can effectively apply leverage in these situations: “small maneuvers that have big consequences.”

Chapter 8: The Greatest President

  • Overview: John Quincy Adams, Abraham Lincoln, abolition and the Civil War.

  • Adams overreached in his first annual message to Congress (1825).

    • He lacked a mandate but sought a sweeping set of reforms and ambitious agenda: a national university, federal infrastructure projects, a stronger navy, global commerce, and a diplomatic program to bolster the Monroe Doctrine.
    • He failed to connect aspirations to abilities and was a one-term President.
  • Adams post-Presidential career:

    • Adams ran as a Congressional Representative and served in Congress for 15 years (the only former President to do so).
    • Adams served on the Supreme Court of the United States.
    • “More than any other American before Lincoln…it was Adams who placed the Constitution within the frame of the Declaration—all men were created equal—where he knew that the Constitution, as it then stood, couldn’t comfortably sit.”
  • Abraham Lincoln (1809-1865):

    • Lincoln, recognizing the limitations of his looks, determined that his best strategy, on the interpersonal front, was to be liked.
    • Rival Stephen Douglas supported the self-determination on the question of slavery for the Kansas-Nebraska territory. Douglas had hoped that this would favor abolition. In reality, it did not as grass-roots groups and transplants aimed to swing the balance in favor of slavery.
    • During the celebrated Lincoln-Douglas debates (1858), Lincoln effectively connected principles with practices in decrying the moral bankruptcy and hypocrisy of slavery.
  • Confederate attack on Fort Sumter in Charleston harbor begins the American Civil War in 1861.

    • Lincoln had waited patiently for this and had assumed the moral high-ground on behalf of the Republic: “You can have no conflict, without being yourselves the aggressors. You have no oath registered in Heaven to destroy the government, while I shall have the most solemn one to ‘preserve, protect, and defend’ it.”
  • Lincoln’s unwavering objective in the Civil War: the preservation and restoration of the Union.

    • Slavery had to be abolished, but this could not be accomplished without first securing the Union.
  • Lincoln’s general strategy for the war: Use the greater numbers of the Union to counteract the Confederacy’s superior concentration (owing to geography) with simultaneous points of attack.

    • Lincoln’s approach violated American conventional wisdom of the time: occupation, fortification and defense of fixed positions.
    • Eventually, Lincoln found Ulysses S. Grant who would prosecute the war in the Lincoln’s manner.
  • Lincoln overtly pursues abolition to win the war.

    • Had he done so too early, he might have lost the war (example: the Union retained four slave states whose slaves were not emancipated at the beginning of hostilities).
    • Lincoln ordered the formation of Black regiments which gave the Union additional manpower (it also made it harder for the Union to prevent Black veterans their freedom).
  • Lincoln was criticized by abolitionists for not embracing emancipation early enough or forcefully enough. But Lincoln was a pragmatist and grand strategist—balancing goals and capabilities. Lincoln stated in 1862:

My paramount objective in this struggle is to save the Union, and is not either to save or destroy slavery. If I could save the Union without freeing any slave I would do it, and if I could save it by freeing all the slaves I would do it; and if I could do it by freeing some and leaving others alone I would also do that. … I shall do less whenever I shall believe what I am doing hurts the cause, and I shall do more whenever I shall believe doing more will help the cause. I shall try to correct errors when shown to be errors; and I shall adopt new views so fast as they shall appear to be true views.

  • Following Antietam (1862), Lincoln delivers the Emancipation Proclamation.
  • Lincoln succeeded because he didn’t succumb to overreach: “No expectations lured Lincoln apart from those he set for himself: he started small, rose slowly, and only when ready reached for the top. His ambitions grew as his opportunities expanded, but he kept both within his circumstances.”

Chapter 9: Last Best Hope

  • Overview: Franklin Delano Roosevelt and World War II (alongside a brief comparison with Woodrow Wilson and World War I).

  • In the early 1900s: “Railroads…had made Europe and Asia a single continent…Britain, over the next half century, might lose control of the sea; and that from these patterns of rise and fall a new struggle for the world could emerge…”

  • Early 20th century British thinkers Mackinder (geographer) and Crowe (diplomat) explored new ways of adapting British power under changing political structures.

    • “Maritime supremacy, then, demanded not just the balancing of power on continents that Makinder had emphasized, but also the reassurance of states bordering seas that the single dominant power at sea respected their interests, as well as its own.”
    • “The British had accomplished this, Crowe argued, by promoting ‘the right of free intercourse and trade in the world’s markets.’”
    • Nations would prefer a free-trade friendly naval power like Britain to the alternative.
  • Henry Kissinger on The Great War:

    • “They seemed oblivious to the huge casualties of the still relatively recent American Civil War, and expected a short, decisive conflict. It never occurred to them that the failure to make their alliances correspond to rational political objectives would lead to the destruction of civilization as they knew it…Instead, the Great Powers managed to construct a diplomatic doomsday machine, though they were unaware of what they had done.”
  • Woodrow Wilson’s strategic failure in the aftermath of World War I:

    • The United States lacked expertise in international diplomacy at this time.
    • Wilson’s “Fourteen Points” were high on theory and low on practical application.
    • Paul Cambon (French diplomat): “Unversed in European politics…[Wilson devoted himself] to the pursuit of theories which had little relation to the emergencies of the hour.”
    • In trying to make the world safe for democracy, Wilson was destabilizing the world unwittingly.
  • “The United States was, in one sense, more powerful than ever: its industrial output now exceeded that of Britain, Germany, France, Russia, Italy, and Japan combined. But the distrust of power written into its Constitution deprived its leaders of the authority—at least in peacetime—to deploy that power.”

  • Post-World War I power dynamics:

    • Germany and Hitler aimed to secure space and resources to compete and prevail in the new world order.
    • The USSR and Stalin sought to counteract Capitalism and liberal democracy.
  • Franklin Delano Roosevelt (FDR) comes to power in 1932 on the heels of an economic depression and rising totalitarianism in Europe and Asia.

    • Like Lincoln, FDR must shore up the domestic front before he can expand his aspirations.
    • In 1933, he extends diplomatic recognition to the Soviets. He is criticized for the move, but it carries the potential of future alignment against Germany and Japan.
    • FDR upgrades the US Navy as one of his first acts and frames it as a public works project.
    • FDR cannot impose his will or ideology on the Republic. He can improvise and edge forward slowly and persistently. “Nothing would succeed without widespread continuing public support.”
  • “Capabilities might, at some point, catch up with interests: that couldn’t happen, though, until Americans again perceived dangers, revived their economy, and regained faith in themselves.”

  • Lend-Lease Act (1941) authorized military assistance to any country deemed of national interest by the president. Most presumed that Great Britain would be the beneficiary, but should Germany turn on the Soviets, it could be used to aid Stalin once allied.

  • On Roosevelt’s patience regarding entering World War II: Roosevelt was waiting for three things, 1) American rearmament; 2) Soviet survival and viability (as they were a critical continental ally); and 3) A “Fort Sumter” moment which would give America the moral high-ground and public support—Pearl Harbor provided this along with Hitler’s declaration of war.

  • America emerged from World War II at a comparatively low cost of American lives, half the world’s manufacturing capacity, 2/3 the world’s gold reserves, 3/4 of its invested capital, the largest navy and air force, and the world’s only atomic weapons (for a time).

Chapter 10: Isaiah

  • Overview: Conclusion and a return to the ideas of Isaiah Berlin.

  • FDR: “I am a juggler and never let my right hand know what my left hand does.”

  • FDR: “I may be entirely inconsistent if it will help win the war.”

  • “Consistency in grand strategy, then, was less a matter of logic than of scale: what made no sense to subordinates could make perfect sense to him. For he saw better than anyone relationships of everything to everything else—while sharing what he saw with no one.”

  • Oliver Wendell Holmes (Supreme Court justice) on FDR: “A second-class intellect. But a first-class temperament!”

  • Clausewitz: “Any complex activity if it is to be carried on with any degree of virtuosity, calls for appropriate gifts of intellect and temperament.”

  • “Temperament…it’s not a compass—that’s intellect. But it is a gyroscope, an inner ear complementing Clausewitz’s ‘inward eye.’ Like poles on tightropes, temperament makes the difference between slips and safe arrivals.”

  • Tetlock’s view of good judgement: A balancing act that requires rethinking core assumptions while preserving our existing worldview.

  • Berlin’s two inequivalent concepts of liberty:

    • Positive liberty: The freedom from the need to make choices by yielding them to some higher authority (e.g., a collective, party, state, ideology, theory). Contradictions are removed by silencing them. This approach can drift towards tyranny.

      • “Hedgehogs trying to herd foxes.”
    • Negative liberty: The freedom to make choices. This approach cultivates cacophonies and can drift towards anarchy.

      • “Foxes with compasses.”
  • Learning to live within the condition of complexity, uncertainty, and contradictions requires a great deal of adaptability.

Get weekly email updates and additional content: Sign up for the free Mental Pivot Newsletter.