Book Review: Gaddis' On Grand Strategy

Welcoming to the first issue of Profiles in Leadership.

*Edits made to reflect the change of focus from a general Bookstack to Profiles in Leadership.

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It wasn’t until reading The New York Times journalist Mike Isaac’s “The New Social Network Isn’t That New At All” when I realized that a newsletter could be the perfect remedy to my innate desire to socialize while distancing myself from Facebook.

As for its content, I decide to give you the greatest gift a friend could offer—the knowledge advantage—embedded in the reflections I extract from readings on great men and women.

In essence, Profiles in Leadership is a personal newsletter offering high-quality content on leadership and strategy anchored on books of history, literature, biographies, social sciences that achieved or might achieve the Lindy Effect.

Review: On Grand Strategy

John Lewis Gaddis’ book aims to train a new generation of leaders not with high-tech wizardry, theoretical frameworks, or ideologies. There are no 3-step formulae or life hacks promising you 10x success rate. Instead, it offers the kind of training that draws on principles extending across time and space, i.e. history, so a leader intuitively senses what has worked before or not and then re-apply the principles to the present situation at scale. A true modern classic. Full review here.

Should On Grand Strategy be summarized in one sentence, it would tether two simple tenets: great leaders must be both a hedgehog and a fox, comfortable in juggling combinations, contradictions, and contrasts; remember that your aspiration is limitless but your capabilities are constrained, so balance your ends and means.

Be 🦊 and 🦔 Simultaneously

Isaiah Berlin, a Latvian-born British philosopher, describes two categories of leaders in Aesopian term: “The fox knows many things, but the hedgehog knows one big thing.” A hedgehog relates everything to a central vision but a fox pursues many unrelated or contradictory ends. Political psychologist Philip E. Tetlock’s 15-year studies showed that foxes do better at predicting the future of world politics. But too fox-like also paralyzes a leader from uncertainties, who must appear to know what they do even when they don’t.

So the book opens with the Persian King Xerxes’ hedgehog vision to invade Greece and his fox-like uncle Artabanus’ hesitation to follow suit. The former suffered a humiliating defeat at the hands of Greeks, his defeat forever sealed in HerodotusThe Histories, the latter quickly forgotten by the world. The poignant lesson from Xerxes lies in the fact that both he and his uncle failed F. Scott Fitzgerald’s test of first-rate intelligence, that of “the ability to hold two opposed ideas in the mind at the same time, and still retain the ability to function.” The book is filled with such polar exemplars: the old Pericles, Julius Caesar, Augustine, Philip II, George III, Napoleon, Wilson, all hedgehogs trying to herd foxes; the younger Pericles, Augusutus, Machiavelli, Elizabeth I, Founding Fathers, Lincoln, Franklin D. Roosevelt, all foxes with compasses.

Leaders should to be both a fox and a hedgehog. Go with the flow, “[h]aving determined your destination, you set sails, motivate rowers, adjust for winds and currents, avoid shoals and rocks, allow for surprises, and expend finite energy efficiently.” For, quoting Spielberg’s film Lincoln, “[i]f in pursuit of your destination, you...achieve nothing more than to sink in a swamp...what’s the use of knowing true north?” Woodrow Wilson, the builder with a grand vision, disappointed his generation in the aftermath of WWI, but FDR, the “juggler”, surpassed his generation’s expectation during the depression and WWII. FDR once said: “I may be entirely inconsistent if it will help win the war.” According to some, FDR has “a second-class intellect”, but by Fitzgerald’s standard he definitely possessed a first-rate intelligence.

⚖️ Align Means with Ends

Gaddis also reminds leaders to match their aspirations with capabilities through time and space, adjusted for scale. Both Clausewitz and Tolstoy, two of Gaddis’ favorite authors in the book, understand that “ends, potentially infinite, can never be means, which are poignantly finite.” To go to Mars, you need to have the technology to build long-distance rockets. To build a billion-dollar smartphone app, phones and wifi must be widely adopted. Sounds simple, pretty much like common sense?

Unfortunately, Gaddis observes that common sense is like oxygen, the higher leaders climb, the less common sense they get. “Everything in war is very simple, but the simplest thing is difficult,” otherwise how could we explain the recurring military miscalculations overstretched by ambitious leaders? Xerxes’ grand army crossing into Greece, the Athenians sailed to fight in Sicily, the Romans marched into the Teutoburg forest, the Spanish Armada destroyed in the English Channel, the British struggle in the American revolution, and Napoleon on the river Niemen to invade Russia. What were they thinking? What had they forgotten? But history is easier read than made.

Clausewitz would suggest that they all failed to perceive “truth at every point”, which in these military instances meant climates, landscapes, logistics, their troops’ morale, and the enemies’ strategies. To see truth at every point, the leader must live among contradictions through what Machiavelli calls “sketching”, assessing the “knowns”, such as geography, climate, your own capabilities, the “probabilities”, as in the goals of adversaries, the reliability of allies, and your country’s capability to endure adversity, and finally “unknowns”, which lurk in the intersections of the first two. And so Napoleon lost his war by confusing aspirations with capabilities while Lincoln, a true master of common sense, preserved his Union by balancing ends with means.

👉Read the full review here.

Thin Slices

Reply to this email and recommend your funny thin slices for the next issue!

My favorite line of the month:

For sweetest things turn sourest by their deeds,

Lilies that fester smell far worse than weeds.

Shakespeare, Sonnet 94

The funniest anecdote of the month:

A memorable victim [of Queen Elizabeth] was the Earl of Oxford, who, one day while bowing respectfully, farted loudly. Elizabeth said nothing and seemed not to notice, but Oxford, humiliated, went into exile for seven years. At last he reappeared, bowed again, this time silently, and waited anxiously. “My lord,” the queen responded (I like to think after a slight pause), “I had forgot the fart.

John Lewis Gaddis, On Grand Strategy, page 134


Reply to this email and recommend your news articles for the next issue!


  • Do you desire greatness and often feel disappointed when life turns out to be ordinary? You’re not alone. Avram Alpert offers an alternative attitude: Pursuing the good-enough life . However, good enough is not easy to achieve. (The New York Times)

  • “When he was a child, books were gifts. For his daughters, he made sure they were a given…Some people love books reverently…so tenderly did she treat their spines. My father, by contrast, loved books ravenously. His always had a devoured look to them.” A heartfelt personal story about Kathryn Schulz’s relationship with books and her father. (The New Yorker)

  • “I thought, This is it. My time is up; I’ve cheated death twice and now he’s coming to claim me,” reflects Emilia Clarke, better known as Daenerys in the TV series Game of Thrones, in her personal struggle against aneurysm. (The New Yorker)

  • Looking for some short fictions? Check out this piece from Sally Rooney, my favorite millennial author. (The New Yorker)


  • #ThankGodIt’sMonday!? “Don’t stop when you’re tired, stop when you’re done!” The hustle culture is on the rise. Who’s benefiting from the hustle culture? Why is our generation enamoured with it? Erin Griffith has some ugly truth and sensible opinions to share with you. (The New York Times)

  • A new entrepreneur lobbying firm is named after the stoic sympathizer Cicero. Why is the Silicon Valley so obsessed with Stoicism now? My intellectual history professor Ada Palmer is quoted in this article! (The New York Times)


  • Growing cows is bad for the environment. You’ve probably also heard of or tasted Beyond Meat? Read this Technology Review article to get a glimpse of the heated race to make the juiciest lab-grown meat. (Technology Review)

  • After the Internet, are you wondering what the next big tech platform will be? So is Kevin Kelly. In this long-form essay, Kelly explores a mirrorworld powered by AR, in which each element in our world will have a digital twin. (Wired)

  • “What’s Crispr?” It’s a new class of molecular tools that scientists can use to edit any kind of genetic material. Crispr systems are the fastest, easiest, and cheapest methods available of all time for manipulating the code of life in any organism on Earth, humans included. It is certainly news worthy of your attention. (Wired)

  • Huawei and 5G internet. Well, that’s not all. Beneath the ocean, a “secret” battle on building undersea cables for the control of the Internet has started, featuring also Huawei. Attacks on undersea cables could have “the same effect as used to be achieved in, say, World War II by bombing the London docks or taking out a power station.” Perhaps we should care. (The Wall Street Journal)


  • Europe, not the home to most billion-dollar startups, but definitely the land of regulations that curb billion-dollar enterprises. Europe believes consumers own their data and competition must not be locked out by firms. The Economist explains the pros and cons of Europe’s tech regulations. (The Economist)

  • Reflecting on a British Airways ad devoid of internationalism, Sam Byers laments the state of Brexit with indignation and a sense of dark humor. “We are, in almost every sense, on a plane to nowhere, and because we have nowhere to go, we have to convince ourselves that nowhere is exactly where we wish to be.” “Nowhere man.” (New York Times)


Below are the books that I have either started or wish to start reading in April, including SPQR: A History of Ancient Rome, Alexander Hamilton, The Histories, War and Peace, His Excellency, and Unlocking the Customer Value Chain.

My Bookstack

Check below for the books I’ve read this year (the ratings will adjust in every issue, the only not so Lindy section in this newsletter).


  • Crime and Punishment, Fyodor Dostoevsky (Literature)

  • The English Patient, Michael Ondaatje (Literature)

  • The Buried Giant, Kazuo Ishiguro (Literature)

  • For Whom the Bell Tolls, Ernest Hemingway (Literature)

  • On Grand Strategy, John Lewis Gaddis (History)


  • Warlight, Michael Ondaatje (Literature)

  • The Cat’s Table, Michael Ondaatje (Literature)

  • Purity, Jonathan Franzen (Literature)

  • Conversations with Friends, Sally Rooney (Literature)

  • Why We Sleep, Matthew Walker (Psychology, Neuroscience)


  • The Fifth Risk, Michael Lewis (Politics)

  • Blooms of Darkness, Aharon Appelfeld (Literature)

  • The Secret Lives of Baba Segi's Wives, Lola Shoneyin (Literature)


  • Contagious: How to Build Word of Mouth in the Digital Age, Jonah Berger (Marketing)

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