Jon Glatfelter
  • About
  • Top Books
  • Archives
  • Reading List
  • Contact

DAVID AND GOLIATH: UNDERDOGS, MISFITS, AND THE ART OF BATTLING GIANTS

5/17/2026

Comments

 
Picture
“Giants are not what we think they are. The same qualities that appear to give them strength are often the sources of great weakness.”
— Malcolm Gladwell
Paperback (6-8 hours) | Audible (7 hours)
My introduction to Malcolm Gladwell was nearly twenty years ago, when during a car ride I overheard my dad and another aerospace engineer colleague discussing The Beatles. I had just paused my iPod's Beatles playlist and caught some bits about the English rock band first getting started in Germany. 

Apparently in a book called Outliers, the rock legends' rise to fame can be attributed in large part due to their obsessive practicing, first in Liverpool and then as a band (minus Ringo) in Hamburg. After their two-year 'tour' abroad they returned home with three albums worth of polished and catchy songs plus a confidence in live performances. From the Beatles' example and many others, Gladwell popularized the 10,000 hour rule: it takes 10,000 hours of focused practice to achieve world-class mastery in any domain.

My dad and his colleague then rerouted the conversation back to aerospace topics, including how too few Allied bomber planes were returning safely during the early part of WWII. The Allied engineers had initially planned to reinforce the surviving planes' armor in the area with the most bullet holes. However, statistician Abraham Wald explained that this was a classic example of survivorship bias; it would be better to reinforce the planes' armor in the other parts, deducing that those areas were much more critical.

It took a while—and a worldwide pandemic—before I finally sat down with Gladwell's Outliers. After all, his books' ideas are almost memes in American culture (Outliers, David & Goliath, The Tipping Point); I felt that I basically understood his main points before even cracking the books open. But I didn't. And I don't think it's really possible to do so. Gladwell's books are deceptively complex.

Gladwell is a terrific writer; he concretizes his abstractions with rich, clear examples that show the same relationship in different times, places, and domains. For readers, this is an enjoyable read; it can feel all too easy to name, remember, and 'paint by colors' when trying to apply them to reality—or to wave the clear presentation off as an 'oversimplification' or 'narrative fallacy' or 'revisionism.' And while I don't always share Gladwell's framing of the examples, I do appreciate each of his books on the whole. They're rich with curious questions about everyday situations. 

From David & Goliath, what stayed with me most was not the author's thesis that disadvantages are secretly advantages. It was a deeper thread that stitches together his examples of paradigm-shifting ancient warfare, modern sports champions' psychology, and successful marketing tactics from 19th century French impressionists: that difficult conditions often force people to develop capacities they otherwise never would have discovered. And secondly, these capacities can be named, tried, and nurtured—capacities like courage, discipline, improvisation, and resilience.
​
20th CENTURY DESERT WARFARE
Gladwell compares David’s sling to guerrilla warfare and cites T. E. Lawrence's 20th century insurgency to defeat the larger, slower Turks through mobility and unpredictability. Lawrence wrote that, "Our largest available resource were the tribesmen…whose assets were movement, endurance, individual intelligence, knowledge of the country, and courage.”
​
SILCON-VALLEY GIRLS BASKETBALL
Vivek Ranadivé coached his daughter’s basketball team in a similar fashion. Instead of competing traditionally, the girls used relentless full-court pressure to exhaust stronger opponents. I liked Gladwell’s point that unconventional approaches often appear “unfair” simply because they reject accepted norms. Gladwell does acknowledges the cost of unconventional tactics briefly—constant pressure and high energy expenditure are exhausting—but over time the team found much more success when they played their own game. 
​
IVY LEAGUE SUCCESS
The chapters on American education and self-concept were some of the most convincing to me. Gladwell’s “Big Fish, Little Pond” idea argues that highly talented students can become demoralized when surrounded exclusively by even more elite peers. A strong predictor of graduation rate is actually students finding "Relative Success" in a pond where they can grow without overwhelming pressure; that is they need to find a desirable difficulty. 

The story of Caroline Sacks struggling in chemistry at Brown U, despite being an exceptional student overall illustrates this clearly. I thought this section captured something true about comparison and confidence. People judge themselves locally, not globally. A student who would flourish elsewhere may interpret ordinary struggle at an elite institution as proof they do not belong. That said, I felt Gladwell leaned too heavily toward institutional explanations. The notes that interested me most were actually the counterarguments: resilience, growth mindset, and learning how to fail without collapsing emotionally. 

DSYLEXIC CREATIVITY
The chapter on dyslexia and entrepreneurship was compelling because it showed how weakness in one domain can create strengths elsewhere, like one's memory, negotiation tactics, trying creative solutions, developing persistence and a willingness to challenge norms. Emil “Jay” Freireich’s brutal upbringing shaped the aggressiveness that later allowed him to revolutionize leukemia treatment. I appreciated that Gladwell avoided claiming suffering is automatically noble. Still, I occasionally felt the book came close to romanticizing hardship by focusing heavily on successful survivors rather than the unknown and untold stories of many people broken by the same experiences. Definitely thought-provoking. [JG]
​
YOU MAY ALSO LIKE
Picture
OUTLIERS: THE STORY OF SUCCESS
Malcolm Gladwell
​

Picture
EXTREME OWNERSHIP: HOW NAVY SEALS LEAD AND WIN
Jocko Willink & Leif Babin
Picture
BOYD: THE FIGHTER PILOT WHO CHANGED THE ART OF WAR
Robert Coram
Picture
ONE MAN'S WILDERNESS: AN ALASKAN ODYSSEY
Richard Louis Proenneke
Comments
    Picture
    Picture
    Picture
    Picture
    Picture
    Picture
    Picture
    Picture
    SAVE OUR SOULS
    An Interview
    with artist Cyril Rolando
    ​

    Picture
    ANTHEM
    Ayn Rand

    Picture
    EXTREME OWNERSHIP
    Jocko Willink & Leif Babin
    ​

    Picture
    TOP BOOKS 2016
    My 10 favorite
    (re)reads of 2016
    ​

    Picture
    AN ILLUSTRATED BOOK OF BAD ARGUMENTS
    Ali Almossawi
    ​

    Picture
    BOOKS OF HUCKBERRY
    Summer 2016
    ​
    Picture
    Zorro: The Complete Pulp Adventures
    Johnston McCulley
    ​
    Picture
    MEDITATIONS
    Marcus Aurelius
    ​

    Picture
    DRAGON TEETH
    Michael Crichton
    ​

    Picture
    BRAVE NEW WORLD
    Aldous Huxley
    ​
    Picture
    NORTHANGER ABBEY
    Jane Austen
    ​
    Picture
    THE THREE MUSKETEERS
    Alexandre Dumas
    ​
    Picture
    THROUGH THE LOOKING GLASS
    Lewis Carroll
    ​
    Picture
    ROBINSON CRUSOE
    Daniel Defoe
    ​
    Picture
    THE BEST BOOKS OF 2024
    Growing gardens, Georgian knights, 'genius' foods, Bitcoin, Web3, and more...
    ​
    Picture
    FAUST
    Johann Wolfgang Von Goethe
    ​
    Picture
    ALICE IN WONDERLAND
    Lewis Carroll
    ​
    Picture
    TOP 10 BOOKS ABOUT ANIMALS
    Birds, elephants, octopus, tigers, bears, and more...
    ​
    Picture
    AWAKING BEAUTY
    The art of Eyvind Earle
    ​
    Picture
    TOP 10 ANIMAL STORIES
    Red deer, rabbits, roosters, dragons, mice, and more...
    ​
    Picture
    DR. NO
    Ian Fleming
    ​
    Picture
    JURASSIC PARK
    Michael Crichton
    ​
    Picture
    SALT
    Mark Kurlanksy
    ​
    Picture
    CHANTECLER
    Edmond Rostand
    ​

    Picture
    EATERS OF THE DEAD
    Michael Crichton
    ​
    Picture
    THE BEST BOOKS OF 2016
    Houdini's How-To, American A-frames, Cyrano, ​and more...
    ​
    Picture
    TWICE TOLD TALES
    Nathaniel Hawthorne
    ​
    Picture
    THE HANDMAID'S TALE
    Margaret Atwood
    ​
    Picture
    THE SCARLET LETTER
    Nathaniel Hawthorne
    ​
    Picture
    NIGHT
    Elie Wiesel
    ​
    Picture
    TWELVE RULES FOR LIFE
    Jordan B. Peterson
    ​
    Picture
    THE ELEPHANT WHISPERER
    Lawrence Anthony
    ​
    Picture
    SPHERE
    Michael Crichton
    ​
    Picture
    CYRANO DE BERGERAC
    Edmond Rostand
    ​
    Picture
    THE MAN WHO LAUGHS
    Victor Hugo
    ​
    Picture
    PERENNIAL SELLER
    Ryan Holiday
    ​
    Picture
    FROM RUSSIA WITH LOVE
    Ian Fleming
    ​
    Picture
    PIRATE HUNTERS
    Robert Kurson
    ​
    Picture
    MEDITATIONS
    Marcus Aurelius
    ​
    Picture
    THE WAR OF ART
    Steven Pressfield
    ​
    Picture
    THE PICTURE OF DORIAN GRAY
    Oscar Wilde
    ​
    Picture
    ONE MAN'S WILDERNESS
    Richard Proenneke
    ​
    Picture
    SETTING THE TABLE
    Danny Meyer
    ​
    Picture
    SHANE
    Jack Shaefer
    ​
    Picture
    THE 33 STRATEGIES OF WAR
    Robert Greene
    ​
    Picture
    THE BEST BOOKS OF 2022
    Memoirs of a blind hero, magic lamps, Zarathustra speaking, and more...
    ​
    Picture
    THE BEST BOOKS OF 2021
    The Dwarf King, personality archetypes, creepy suburbs, Nietzsche, Taleb, and more...
    ​
    Picture
    THE BEST BOOKS OF 2020
    Bitcoin, climbing Kilimanjaro, practicing Roman virtues, a smart octopus, and more...
    ​
    Picture
    THE BEST BOOKS OF 2019
    Gothic tales, stoic stillness, an Alaskan odyssey, the war of art, and more...
    ​
    Picture
    OTHER MINDS
    Peter Godfrey Smith
    ​

    Picture
    WORKS AND DAYS
    Hesiod
    ​
    Picture
    NICHOMACHEAN ETHICS
    Aristotle
    ​
    Picture
    AMERICAN WOLF
    Nate Blakeslee
    ​
    Picture
    INFINITE JEST
    David Foster Wallace
    ​
    Picture
    PETER PAN
    J. M. Barrie
    ​
    Picture
    THE WIZARD OF OZ
    L. Frank Baum
    ​
    Picture
    THE NIGHT OF THE HUNTER
    Davis Grubb
    ​
    Picture
    THE ROMANTICS
    Edmond Rostand
    ​
    Picture
    FRANKENSTEIN
    Mary Shelley
    ​
    Picture
    SHOOTING AN ELEPHANT
    George Orwell
    ​
    Picture
    READ WRITE OWN
    Chris Dixon
    ​
    Picture
    THE MAN WHO WAS CYRANO
    Sue Lloyd
    ​
    Picture
    ANIMAL FARM
    George Orwell
    ​
    Picture
    CRIME AND PUNISHMENT
    Fyodor Dostoyevsky
    ​
    Picture
    DISCLOSURE 
    Michael Crichton
    ​
    Picture
    THE ELEPHANT WHISPERER 
    Lawrence Anthony
    ​
    Picture
    A TREE GROWS IN BROOKLYN 
    Betty Smith
    ​
    Picture
    THE BROWNING VERSION 
    Terence Rattigan
    ​
    Picture
    THE NOVEL OF THE CENTURY
    David Belos
    ​
    Picture
    THE UNPUBLISHED DAVID OGILVY
    David Ogilvy
    ​
    Picture
    ARMADA
    Ernest Cline
    ​
    Picture
    DRAGON TEETH
    Michael Crichton
    ​
    Picture
    THE HANDMAID'S TALE
    Margaret Atwood
    ​
    Picture
    SPHERE
    Michael Crichton
    ​
    Picture
    THE REPUBLIC OF IMAGINATION
    Azar Nafisi
    ​
    Picture
    ANNIHILATION
    Jerr VanderMeer
    ​
    Picture
    THE SCARLET LETTER
    Nathaniel Hawthorne
    ​
    Picture
    THE ADVENTURES OF HUCKLEBERRY FINN
    Mark Twain
    ​
    Picture
    SOME FANTASY NOVELS I LOVE
    A mini-round up
    ​
    Picture
    STATE OF FEAR
    Michael Crichton
    ​
    Picture
    THE HINGE OF THE WORLD
    Richard N. Goodwin
    ​
    Picture
    JURASSIC PARK
    Michael Crichton
    ​
    Picture
    THE ROMANTIC MANIFESTO
    Ayn Rand
    ​
    Picture
    THE MIRACLE WORKER
    William Gibson
    ​
    Picture
    BUG-JARGAL
    Victor Hugo
    ​
    Picture
    THE NEW PSYCHO-CYBERNETICS
    Dr. Maxwell Maltz
    ​
    Picture
    THE PRINCESS FAR AWAY
    Edmond Rostand
    ​
    Picture
    CONFESSIONS OF AN AD MAN
    David Ogilvy
    ​
    Picture
    SALT: A WORLD HISTORY
    Mark Kurlansky
    ​
    Picture
    THE EAGLET
    Edmond Rostand
    ​
    Picture
    THE BEST BOOKS OF 2017
    Charles Darwin, Idealistic Roosters, ​US Navy SEALS, Salt, and More...
    ​
    Picture
    THE WINSLOW BOY
    Terence Rattigan
    ​
    Picture
    THE LEAN STARTUP
    Eric Ries
    ​
    Picture
    TWELVE RULES FOR LIFE
    Jordan Peterson
    ​
    Picture
    WATERSHIP DOWN
    Richard Adams
    ​
    Picture
    THE 22 IMMUTABLE LAWS OF MARKETING
    Al Ries & Jack Trout
    ​
    Picture
    THE GENIUS OF BIRDS
    Jennifer Ackerman
    ​
    Picture
    FOR YOUR EYES ONLY
    Ian Fleming
    ​
    Picture
    NARRATIVE OF THE LIFE OF FREDERICK DOUGLASS
    Frederick Douglass
    ​
    Picture
    MONTESSORI: THE 1946 LECTURES
    Maria Montessori
    ​
    Picture
    DR. NO
    Ian Fleming
    ​
    Picture
    THE SWISS FAMILY ROBINSON
    Johann Wyss
    ​
    Picture
    SETTING THE TABLE
    Danny Meyer
    ​
    Picture
    SILAS MARNER: THE WEAVER OF RAVELOE
    Mary Ann Evans
    ​
    Picture
    WHITE FANG
    Jack London
    ​
    Picture
    OUTLIERS: THE STORY OF SUCCESS
    Malcolm Gladwell
    ​

    Picture
    PLAYING GOD IN YELLOWSTONE
    Alston Chase
    ​
    Picture
    MADE TO STICK
    Chip Heath & Dan Heath
    ​

    Picture
    TRUST ME I'M LYING
    Ryan Holiday
    ​

    Picture
Reading List
Top Books
Archives

I've been reading a book a week for 15+ years. On here, I share my favorites, fiction and nonfiction alike, as well as interviews with authors, artists, and entrepreneurs I admire. If you'd like to join a family of 5,000+ creatives, subscribe for the Reading List, a monthly email round-up for plenty of leads on your next read.