On Grand Strategy
By John Lewis Gaddis
Penguin, 2018

How do you make the most of possibilities? How can you best accomplish your goals? You do it by abiding to what Gaddis calls a “grand strategy”: “the alignment of potentially unlimited aspirations with necessarily limited capabilities.”

That is, you can’t do everything – there isn’t enough time or resources. You must choose wisely. But what exactly does that entail? Answering this question is this book’s focus.

There are two ways of being in the world. One entails being driven by a central vision – an ideal of how things are or should be. This could be a religion or political stance. Such an idea informs choices: what one does is in service to bending reality to comport to that idea.

The other way is more responsive. Instead of being driven by a central vision, one adapts to conditions on the ground. This might lead to actions that appear contradictory, but ultimately effective (if possibly misdirected) – Fitzgerald’s assertion that the mark of a first rate intelligence is the ability to function while holding two opposed ideas in mind.

These two ways of being in the world map to Isaiah Berlin’s distinction between hedgehogs and foxes. (“The fox knows many things, but the hedgehog knows one big thing.”) On Grand Strategy argues that you want to land somewhere in the middle.

Why? Because a hedgehog mindset provides direction and focus while a fox mindset provides cunning and resourcefulness. Combining them allows you to move forward in a particular direction while effectively responding to conditions on the ground.

As Machiavelli knew, you can’t attain ideals. But you can work towards them. This is a hard swallow for many people who deem unacceptable situations that deviate from their ideals. But effectiveness requires a pragmatic approach to things-as-they-are – maintaining “lightness of being,” which Gaddis describes as

the ability, if not to find the good in bad things, then at least to remain afloat among them, perhaps to swim or to sail through them, possibly even to take precautions that can keep you dry.

The book illustrates the interplay between the two approaches through comparative case studies from history, including Xerxes, Pericles, Augustus Caesar, Elizabeth I, Philip II, Napoleon, The American Founders, Abraham Lincoln, FDR, and Stalin. Gaddis weaves in commentary from a range of classic thinkers on the relationship between ideals and facts, including St. Augustine, Machiavelli, Sun Tzu, Tolstoy, Clausewitz, and Berlin himself.

The lesson: effective leadership entails knowing where you’re going but also responding to conditions you find on the way. That is, you must balance ambition and capabilities. Idealism compromises your ability to see clearly. As Feynman put it, “The first principle is that you must not fool yourself and you are the easiest person to fool.” Don’t eschew ideals, but hold them lightly.

On Grand Strategy by John Lewis Gaddis