Books I Want My Kids to Read Someday: “David and Goliath” by Malcom Gladwell

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Sometimes, our greatest weaknesses are our greatest strengths. That’s the lesson from author Malcom Gladwell in David and Goliath: Underdogs, Misfits and the Art of Battling Giants. But Gladwell doesn’t rest on cliche. He’s known for his originality, surprising his readers with paradox after paradox.

Break the rules, Gladwell tells us, and he follows his own advice. His journalism has always done so supremely successfully.

Read this article collection because you want to experience perspective-shifting intellectual whiplash.

Key Takeaways

  • A common personality trait of successful underdogs is disagreeableness.
  • In the story of David and Goliath, David succeeded because he broke the rules–not because God intervened. He beat him because rock slinging was the most deadly form of fighting and Goliath wasn’t prepared. David wasn’t strong in the traditional way, so he found a way around the traditional way; he found strength in his weakness.
  • Basketball coach Vivek Ranadive succeeded because he broke the rules. He led a novice girls’ basketball team to the national championship for their division by playing full-press–something no other team did.
  • Teacher Teresa DeBrito succeeds because she breaks the rules. She actually prefers larger to smaller class sizes, and this perspective is backed by research. The lesson: often, things we see as good (like small class sizes) are bad after a certain point; there is a U-curve. For example, money makes parenting easier, until you have too much and it makes it harder again.
  • Caroline Sacks didn’t succeed in her major because she followed the rules. She made the decision to go to Brown instead of her second choice, a lesser-known school. This led her to quitting her preferred major, science, because of the difficulty she experienced at Brown. Had she gone to the second-tier school instead, she believes she would have stayed with it.
  • David Bois succeeded because of his weakness. His dyslexia made him an excellent listener and memorizer, and he ended up becoming a highly successful trial lawyer who could detect the slightest weakness in his opponent’s voice, though his mom thought he’d never even graduate high school.
  • Emil “Jay” Freireich succeeded because he wasn’t a people pleaser. His father died at a young age and his mom was also absent. He became a doctor who didn’t care what anyone thought, even ignoring orders at times, and pioneered a cure for leukemia.
  • Wyatt Walker succeed because he broke the rules. He worked with Martin Luther King, Jr. to incite cops to violence so the media would carry the story and the civil rights movement would gain momentum.
  • Rosemary Lawlor succeeded by questioning authority. She participated in a successful riot against unnecessary search, seizure and extended house arrest policies in Northern Ireland against the British army who had come to help keep peace during a civil war. The British army’s mistake: they didn’t establish legitimacy first.
  • In Brownsville, a NYC neighborhood, a police officer named Joanne Jaffe succeeded because she established legitimacy. She is leading an effort to help criminal kids turn around by first gaining their trust, bringing turkeys on Thanksgiving and gifts on Christmas and talking with the families.
  • Sometimes, reactions aren’t what we expect them to be. During the Blitz in London during WWII, everyone expected mass panic, but instead the remote misses created a sense of aliveness, exhilaration and invincibility.

About the Author

Malcolm Gladwell is a renowned author, journalist, and public intellectual widely recognized for his captivating storytelling and thought-provoking insights. With a unique ability to dissect complex ideas and phenomena, Gladwell has become a leading voice in contemporary nonfiction. His works, such as “The Tipping Point,” “Outliers,” and “Blink,” have garnered global acclaim, captivating audiences with their innovative perspectives on social sciences, psychology, and human behavior. Gladwell’s writing style seamlessly blends engaging narratives with rigorous research, making his books both accessible and intellectually stimulating. Through his distinctive approach, Gladwell has reshaped the way we perceive and understand the world around us, leaving a lasting impact on popular discourse and inspiring critical thinking.

Beyond his literary contributions, Gladwell’s influence extends to public speaking engagements and podcasting. He has delivered captivating talks at prestigious conferences and universities, captivating audiences with his ability to shed light on intricate social phenomena and challenge conventional wisdom. As the host of the popular podcast “Revisionist History,” Gladwell continues to explore hidden stories and reevaluate historical events, offering fresh perspectives and encouraging listeners to question established narratives. Through his multifaceted body of work, Malcolm Gladwell has emerged as a leading figure in contemporary intellectual discourse, captivating audiences with his unique blend of storytelling, rigorous research, and a deep understanding of human nature.


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