More on this book
Community
Kindle Notes & Highlights
Xerxes listens patiently, but objects that “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.”
Lord Oxford had come across an intriguing line from the ancient Greek poet Archilochus of Paros. It was, as Berlin remembered it: “The fox knows many things, but the hedgehog knows one big thing.”
Hedgehogs, Berlin explained, “relate everything to a single central vision” through which “all that they say and do has significance.” Foxes, in contrast, “pursue many ends, often unrelated and even contradictory, connected, if at all, only in some de facto way.” The distinction was simple but not frivolous: it offered “a point of view from which to look and compare, a starting point for genuine investigation.” It might even reflect “one of the deepest differences which divide writers and thinkers, and, it may be, human beings in general.”
By way of an Oxford party, an Archilochus fragment, and Tolstoy’s epic, Berlin had stumbled upon two of the very best ways to become intellectually indelible. The first is to be Delphic, a trick known to oracles throughout time. The second is to be Aesopian: turn your ideas into animals, and they’ll achieve immortality.
foxes were far more proficient predictors than hedgehogs, whose record approximated that of a dart-throwing (and presumably computer-simulated) chimpanzee.
“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.”13 In short, foxes do it better.
But Xerxes failed, as is the habit of hedgehogs, to establish a proper relationship between his ends and his means. Because ends exist only in the imagination, they can be infinite: a throne on the moon, perhaps, with a great view. Means, though, are stubbornly finite: they’re boots on the ground, ships in the sea, and the bodies required to fill them. Ends and means have to connect if anything is to happen. They’re never, however, interchangeable.
he’d have seen that his armies and fleets could never have transported all that it would take just to invade Greece. Unless the king could induce those he was invading to supply his invasion (not easy), his own men (although probably not himself) would soon begin to get hungry (or thirsty, or tired). Resistance by a few, as at Thermopylae, would shake the confidence of many. And winter would be coming on.
Little things add up in unpredictably big ways—and yet, leaders can’t let uncertainties paralyze them. They must appear to know what they’re doing, even when they don’t.
The tragedy of Xerxes and Artabanus is that each lacked the other’s proficiency. The king, like Tetlock’s hedgehogs, commanded the attention of audiences but tended to dig himself into holes. The adviser, like Tetlock’s foxes, avoided the holes, but couldn’t retain audiences. Xerxes was right. If you try to anticipate everything, you’ll risk not accomplishing anything. But so was Artabanus. If you fail to prepare for all that might happen, you’ll ensure that some of it will.
F. Scott Fitzgerald’s test, from 1936, for a first-rate intelligence: “the ability to hold two opposed ideas in the mind at the same time, and still retain the ability to function.”21
immortal. The Delphic oracle would have been envious.23 One possible meaning for Fitzgerald’s opposites could be taking the best from contradictory approaches while rejecting the worst:
Ordinary experience, he pointed out, is filled with “ends equally ultimate . . . , the realization of some of which must inevitably involve the sacrifice of others.”
The choices facing us are less often between stark alternatives—good versus evil, for instance—than between good things we can’t have simultaneously.
to put it in terms any kid would understand: you can’t gobble all your treats on Halloween without throwing up.
We resolve these dilemmas by stretching them over time. We seek certain things now, put off others until later, and regard still others as unattainable. We select what fits where, and then decide which we can achieve when. The process can be difficult: Berlin emphasized the “necessity and agony of choice.” But if such choices were to disappear, he added, so too would “the freedom to choose,” and hence liberty itself.24
What, then, of Berlin’s claim, in his Tolstoy essay, that foxes and hedgehogs divide ...
This highlight has been truncated due to consecutive passage length restrictions.
“Some people are neither foxes nor hedgehogs, some people are both.”
for what choices would we have if stuck within categories, mimicking animals, that mandated predictability?26 If, as Fitzgerald argued, intelligence requires opposites—if freedom is choosing, as Berlin maintained—then priorities can’t be predetermined. They’d have to reflect who we are, but also
what we’re experiencing: the first we could know in advance, but not always the second. We’d 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.
[A] compass . . . [will] point you true north from where you’re standing, but it’s got no advice about the swamps and deserts and chasms that you’ll encounter along the way. If in pursuit of your destination, you plunge ahead, heedless of obstacles, and achieve nothing more than to sink in a swamp . . . , [then] what’s the use of knowing true north?28
“You see? Lincoln knows when to be a hedgehog (consulting the compass) and when a fox (skirting the swamp)!”
Fitzgerald’s linkage of intelligence, opposing ideas, and the ability to function:
I mean, by common sense, the ease with which most of us manage, most of the time. We generally know where we’re going, but we’re constantly adjusting our route to avoid the unexpected, including obstructions others place in our path while on their way to wherever they’re going.
The psychologist Daniel Kahneman attributes this proficiency to an unconscious reliance on two kinds of thinking. “Fast” thinking is intuitive, impulsive, and often emotional. It produces, when needed, instant action: it’s what you do to keep from running into things, or to keep them from running into you. “Slow” thinking is deliberate, focused, and usually logical. It needn’t result in action at all: it’s how you learn in order to know.
Which is what grand strategy is meant to prevent. I’ll define that term, for the purposes of this book, as the alignment of potentially unlimited aspirations with necessarily limited capabilities.
If you seek ends beyond your means, then sooner or later you’ll have to scale back your ends to fit your means.
ends can be infinite and means c...
This highlight has been truncated due to consecutive passage length restrictions.
You won’t have a strategy until you’ve connected these dots—dissimilar though they are—within the situation in which you’re operating.
Alignments are necessary across time, space, and scale.
what is “training,” as Clausewitz understands it? It’s being able to draw upon principles extending across time and space, so that you’ll have a sense of what’s worked before and what hasn’t. You then apply these to the situation at hand: that’s the role of scale. The result is a plan, informed by the past, linked to the present, for achieving some future goal.
The engagement, however, won’t in all respects follow the plan.
Not only will its outcome depend on what the other side does—t...
This highlight has been truncated due to consecutive passage length restrictions.
but it will also reflect “unknown unknowns,” which are all the things that can go wrong before you’ve even encountered an adversary. Together, these constitute what Clausewitz called “friction,” the collision of theory with reality
As authority increases, however, so does self-consciousness. With more people watching, practice becomes performance. Reputations now matter, narrowing the freedom to be flexible. Leaders who’ve reached the top—like Xerxes, or Tetlock’s experts—can become prisoners of their own preeminence: they lock themselves into roles from which they can’t escape.
grand strategies—alignments of means with ends—become
the past prepares us for the future only when, however imperfectly, it transfers. Just as capabilities restrict aspirations to what circumstances will allow.
He does so within time and space but also across scale:
No one can anticipate everything that might happen. Sensing possibilities, though, is better than having no sense at all of what to expect. Sun Tzu seeks sense—even common sense—by tethering principles, which are few, to practices, which are many. He fits the mix to the moment, as if setting sound levels on a synthesizer, or color combinations on a computer screen. He leaves enough options to satisfy any fox, while retaining the purposefulness of a hedgehog. He keeps opposing ideas in his mind by projecting them across time, space, and scale.
Leadership in The Art of War, then, is seeing simplicities in complexity.
Octavian was fortunate, of course, to have survived his own illnesses and the many risks he ran, but he was also more careful than Alexander in deploying strengths and in compensating for weaknesses. “He who knows the art of the direct and the indirect approach will be victorious,” Sun Tzu writes, appearing as usual to cover all possibilities. But then he tethers: “Such is the art of maneuvering.”
Direct approaches work, Master Sun suggests, only when capabilities approximate aspirations. Abundance allows all you want: there’s little need for maneuver.
Most of the time, though, capabilities fall short—that was Octavian’s problem. Insufficiency demands indirection, and that, Sun Tzu insists, requires maneuver:
Why would the most powerful man in the world sit still for instruction, at such length, on the rotation of crops, the nurturing of vines, the breeding of cattle, and the keeping of bees? John Buchan, an earlier biographer, suggested that Octavian was ready to slow down, to look around, and to think about how to use power now that he had no rivals. He was shifting from navigation to cultivation.54
The rising Octavian had spent a decade and a half fending off, buying out, circumventing, eliminating, or capitalizing on threats
After Actium, Octavian began controlling events, rather than letting them control him.
Pivoting requires gyroscopes, and Elizabeth’s were the best of her era. She balanced purposefulness with imagination, guile, humor, timing, and an economy in movement that, however extravagant her display, kept her steady on the tightrope she walked.
Assuming stability is one of the ways ruins get made. Resilience accommodates the unexpected.
British America “was a society whose political and administrative institutions were more likely to evolve from below than to be imposed from above.”10 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.

