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David and Goliath by Malcolm Gladwell

Underdogs, Misfits, and the Art of Battling Giants

My Thoughts

This is my fourth time summarizing one of Malcolm Gladwell’s books. His writing makes me think and helps me to see how the world works from a different perspective and in ways that are often counterintuitive.

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My Favorite Quotes

• The act of facing overwhelming odds produces greatness and beauty
• What we think of as an advantage and a disadvantage is not always correct.
• One of the reasons we are so often confused about advantages and disadvantages is that we forget when we are operating in a U-shaped world.
• What is learned out of necessity is inevitably more powerful than the learning that comes easily.
• The powerful are not as powerful as they seem, nor the weak as weak.

Key Questions

• Why are we so shocked every time a David beats a Goliath?
• Why do we automatically assume that someone who is smaller, poor, or less skilled is necessarily at a disadvantage?
• What does it take to be that person who doesn’t accept the conventional order of things as a given?
• What if the relationship between the number of children in a classroom and academic performance is not linear? What if it’s an inverted U-shaped curve?

Table of Contents

• Introduction: Goliath
• Part 1: The Advantages of Disadvantages (and the Disadvantages of Advantages)
• Chapter 1: Vivek Ranadivé
• Chapter 2: Teresa Debrito
• Chapter 3: Caroline Sacks
• Part 2: The Theory of Desirable Difficulty
• Chapter 4: David Boies
• Chapter 5: Emil “Jay” Freireich
• Chapter 6: Wyatt Walker
• Part 3: The Limits of Power
• Chapter 7: Rosemary Lawlor
• Chapter 8: Wilma Derksen
• Chapter 9: André Trocmé

Introduction: Goliath

David and Goliath is a book about what happens when ordinary people confront giants. By giants, the author means powerful opponents of all types, from armies and mighty warriors to disability, misfortune, and oppression.

Each chapter tells the story of a different person who has faced an outsized challenge and been forced to respond.

Through these stories, Malcolm Gladwell wants to explore two ideas.

First idea: most of what we consider valuable arises from these kinds of lopsided conflicts. Because the act of facing overwhelming odds produces greatness and beauty.

Second idea: we consistently get these kinds of conflicts wrong, we misread them, we misinterpret them. Giants are not what we think they are, the same qualities that appear to give them strength are often the sources of great weakness. Being an underdog can change people in ways that we often fail to appreciate, it can make possible what might otherwise have seemed unthinkable.

We need a better guide to facing giants, and there is no better place to start that journey than with the epic confrontation between David and Goliath.

Goliath was expecting a warrior like himself to come forward for hand-to-hand combat. It never occurred to him that the battle would be fought on anything other than those terms.

The duel reveals the folly of our assumptions about power. The reason King Saul is skeptical of David’s chances is because David is small and Goliath is large. Saul thinks of power in terms of physical might. He doesn’t appreciate that power can come in other forms such as breaking rules, and substituting speed and surprise for strength.

A second deeper issue is that Saul and the Israelites think they know who Goliath is. They size him up and think they know what he is capable of, but they do not really see him.

The powerful and the strong are not always what they seem.

Part 1: The Advantages of Disadvantages (and the Disadvantages of Advantages)

Chapter 1: Vivek Ranadivé

This chapter is about Vivek Ranadivé and the story of how he coached his daughter’s 12-and-under girls’ basketball team despite, according to his own contention, never having touched a basketball until he reached his 40s.

What happens in wars between the strong and the weak when the weak side refuses to fight the way the bigger side wants to fight? The weaker party’s winning percentage climbs from 28.5% to 63.6%. Reference: How the Weak Win Wars: A Theory of Asymmetric Conflict by Ivan Arreguín-Toft.

We think of underdog victories as improbable events, but they aren’t, underdogs win all the time. Why are we so shocked every time a David beats a Goliath? Why do we automatically assume that someone who is smaller, poor, or less skilled is necessarily at a disadvantage?

There is a set of advantages that have to do with material resources, and there is a set of advantages that have to do with the absence of material resources. The reason underdogs win as often as do is that the latter are sometimes every bit the equal of the former.

We have a very rigid and limited definition of what an advantage is. We think of things as helpful that actually aren’t.

Part one of David and Goliath is an attempt to explore the consequences of this error. Why do we automatically assume the battle is the giants to win? What does it take to be that person who doesn’t accept the conventional order of things as a given?

To play by David’s rules, you have to be desperate. You have to be so bad, that you have no choice.

We spend a lot of time thinking about the ways that prestige and resources and belonging to elite institutions make us better off. We don’t spend enough time thinking about the ways in which those material advantages limit our options.

Vivek Ranadivé coached a team of girls who had no talent, in a sport that he knew nothing about, and every one of those things turned out to be to his advantage.

Chapter 2: Teresa Debrito

What we think of as an advantage and a disadvantage is not always correct.

In this chapter and the next, the author wants to apply this idea to two seemingly simple questions about education.

The first question is: would you rather send your child to a school with crowded classrooms or small classrooms? Or put another way, what is the optimum class size?

People are ruined by challenged economic lives, but they are ruined by wealth as well. Because they lose their ambition, pride, and sense of self-worth. It is difficult at both ends of the spectrum.

There is an important principle that guides our thinking about the relationship between parenting and money. That principle is that more is not always better. It is hard to be a good parent if you have too little money. 

Nobody would ever say it is always true that the more money you have, the better parent you can be. The relationship between parenting and money is not linear. Money makes parenting easier until a certain point when it stops making much of a difference.

Scholars who research happiness suggest that more money stops making people happier at a family income of around $75,000 per year. After that, diminishing marginal returns set in. Reference: High Income Improves Evaluation of Life but Not Emotional Well-Being by Daniel Kahneman and Angus Deaton, from Proceedings of the National Academy of Sciences 107, no. 38 (August 2010).

This is an illustration of an an inverted-U curve demonstrating the proposed relationship between wealth and happiness, this is from the book and accompanying PDF attachment to the audiobook.

When the income of parents gets high enough, parenting starts to be harder again.

How do you teach “work hard, be independent, learn the meaning of money” to children who look around and realize they never have to work hard, be independent, or learn the meaning of money?

This dilemma drawn on a graph looks like a camel’s hump, this is called an inverted-U curve. U-shaped curves are hard to understand.

One of the reasons we are so often confused about advantages and disadvantages is that we forget when we are operating in a U-shaped world.

This brings us back to the puzzle of class size. What if the relationship between the number of children in a classroom and academic performance is not linear? What if it’s an inverted U-shaped curve?

Inverted U-shaped curves have 3 sides, and each side follows a different logic.

1. Left side: where doing more or having more makes things better.
2. Flat middle: where doing more doesn’t make much of a difference.
3. Right side: where doing more or having more makes things worse.

If you think about the class size puzzle this way, what seems baffling starts to make more sense.

A smaller classroom only translates to a better outcome if teachers change their teaching style when given a lower workload. The evidence suggests that teachers don’t do that, they only work less. This is a natural human response.

Can a class be too small? In the same way, a parent can make too much money.

A small class is potentially as difficult for a teacher to manage as a very large class.

On the question of class size, we have become obsessed with what is good about small classrooms, and oblivious of what can also be good about large classes.

Chapter 3: Caroline Sacks

French impressionist artists in the 1800s at the Café Guerbois wrestled with one crucial question about their careers, what should they do about the Salon des Refusés?

The Salon was the most important art exhibition in all of Europe. Acceptance by the Salon came with a cost: it required creating the kind of art they did not find meaningful. They risked being lost in the clutter of other artists’ work. Night after night they argued whether they should keep trying to get into the Salon or create their own art show for themselves.

Did they want to be a little fish in the big pond of the Salon, or a big fish in a little pond of their own choosing?

In the end, the impressionists chose to create their own show. This is one of the reasons their paintings now hang in every major art museum in the world.

The same dilemma comes up again and again in our lives, and often we do not choose so wisely.

The story of the inverted U curve reminds us that there is a point at which money and resources stop making our lives better and start making them worse. The story of the impressionists suggests a second parallel problem: we strive for the best and attach great importance to getting into the finest institutions we can. But rarely do we stop and consider, as the impressionists did, whether the most prestigious of institutions is always in our best interest.

One telling example is how we think about where to attend university.

The choice between the Salon or a solo show wasn’t a simple case of a best option and a second best option. It was a choice between two very different options, each with its own strengths and drawbacks.

The impressionists opened their first exhibition on April 15, 1874, and lasted one month. You can read more about it in this article: https://impressionistarts.com/first-impressionist-exhibition.

The second part of the Big Fish Little Pond bargain is that the option might be scorned by someone on the outside, but small ponds are welcoming places for those on the inside. They have all the support that comes from community and friendship, and they are places where individuality and innovation are not frowned upon.

There are times and places where it is better to be a big fish in a little pond than a little fish in a big pond. Where the apparent disadvantage of being an outsider in a marginal world turns out not to be a disadvantage at all.

The impressionists weighed prestige against visibility, selectivity against freedom, and decided the costs of the big pond were too great.

Relative deprivation is a term coined by Samuel Stouffer. He determined that we form our impressions, not globally by placing ourselves in the broadest possible context, but locally by comparing ourselves to people in the same situation as us. Our sense of how deprived we are is relative.

For example, if you are depressed in a place where most people are unhappy, you compare yourself to those around you and you don’t feel that bad. Can you imagine how difficult it is to be depressed in a country where everyone else is happy? Citizens of happy countries have higher suicide rates than citizens of unhappy countries.

The phenomenon of relative deprivation applied to education is called the Big-fish–little-pond effect. The more elite an educational institution is, the worse students feel about their own academic abilities. Students who would be at the top of their class in a good school can easily fall to the bottom of a really good school.

How you feel about your abilities, and your academic self-concept, in the context of your classroom shapes your willingness to tackle challenges and finish difficult tasks. It is a crucial element in your motivation and confidence.

More than half of all American students who start out in STEM programs drop out after their first year of school. What matters in determining the likelihood of getting a STEM degree is not just how smart you are, but how smart you feel relative to the other people in your classroom.

The smarter your peers, the dumber you feel. The dumber you feel, the more likely you are to drop out of science.

When hiring, should you consider a big fish in a little pond over a little fish from a big pond? A study on the topic found that the best students from mediocre schools are almost always a better bet than good students from the very best schools. Reference study: An Empirical Guide to Hiring Assistant Professors in Economics by John P. Conley and Ali Sina Önder.

We take it for granted that a big pond expands opportunities, just as we take it for granted that a smaller class is always a better class. This is not necessarily true. We have a definition in our heads of what an advantage is, and the definition isn’t right. 

What happens as a result? We make mistakes. We misread battles between underdogs and giants, we underestimate how much freedom there can be in what looks like a disadvantage.

Part 2: The Theory of Desirable Difficulty

Chapter 4: David Boies

What do we mean when we call something a disadvantage?

Conventional wisdom holds that a disadvantage is something that ought to be avoided, that it is a difficulty that leaves you worse off than you would be otherwise, but that is not always the case.

In the next few chapters, the author will explore the idea that there are such things as desirable difficulties.

The concept of desirable difficulties was coined by Elizabeth Bjork and Robert Bjork. Reference study: Making Things Hard on Yourself, But in a Good Way: Creating Desirable Difficulties to Enhance Learning. This study is also found in the book Psychology and the Real World.

The concept of desirable difficulties is a beautiful way of understanding how underdogs excel.

The world’s shortest intelligence test is the cognitive reflection test (CRT). It measures your ability to understand when something is more complex than it appears.

Do you know the easiest way to raise people’s scores on the CRT? Make it just a little bit harder. Making the test a little bit harder increased the average scores on the test. This is an example of desirable difficulty.

Adam Alter and Daniel Oppenheimer did an experiment on this called Overcoming Intuition: Metacognitive Difficulty Activates Analytic Reasoning.

They made the test more difficult by printing it in a font that was really hard to read. It forced the students to think more deeply and read the questions more carefully. If people have to overcome a hurdle, they will overcome it better when you force them to think a little harder.

Making the CRT more difficult in this way turned out to be desirable.

There are times and places where an obstacle that seems to cripple an underdog’s chances has the opposite effect and is actually a desirable difficulty.

Can dyslexia turn out to be a desirable difficulty?

Many of the most famous innovators of the past few decades have dyslexia. This includes Richard Branson, Charles Schwab, David Neeleman, John Chambers, and more.

See Julie Logan’s study of dyslexia among entrepreneurs Dyslexic Entrepreneurs: The Incidence; Their Coping Strategies and Their Business Skills.

Two possible explanations for the remarkable fact that many successful innovators and entrepreneurs are dyslexic.

1. They triumphed in spite of their disability. They are so smart and creative that nothing can stop them.
2. They succeeded, in part, because of their disorder. They learned something in their struggle that proved to be of enormous advantage.

The things David Boise learned to do because he could not read well turned out to be incredibly valuable.

Not being able to read a lot, and learning by listening and asking questions, means that he (Boise) needs to simplify issues to their basics. This is a powerful advantage because in trial cases, judges and juries have neither the time nor the ability to become experts in a case subject. One of his strengths is presenting a case that judges and juries can understand.

His opponents get bogged down in excessive details that can confuse the issues of a case.

Capitalization Learning vs Compensation Learning

Capitalization learning is getting good at something by building on strengths that we are naturally given. We do this continually by compounding learning in a virtuous circle.

Desirable difficulties have the opposite logic. They force people to compensate for something that is taken away from them. This is compensation learning.

Most of the learning we do is capitalization learning, it is easy and obvious. Compensation learning is really hard. It requires you to confront your limitations and overcome your insecurities.

Most people with a serious disability cannot master compensation learning, but those who can are better off than they would have been otherwise.

What is learned out of necessity is inevitably more powerful than the learning that comes easily.

It is striking how often successful dyslexics tell similar versions of the same compensation story.

Would Brian Grazer be one of the most successful movie producers in Hollywood if he wasn’t dyslexic?

Dyslexics are outsiders, they are forced to stand apart from everyone else at school because they can’t do the things that schools require them to do. 

Is it possible for that outsiderness to give them an advantage down the line? To answer that, it is worth thinking about the kind of personality that characterizes innovators and entrepreneurs. 

Psychologists measure personality through the Big Five inventory of personality traits.

• neuroticism (sensitive/nervous vs. resilient/confident)
• extraversion (outgoing/energetic vs. solitary/reserved)
• openness to experience (inventive/curious vs. consistent/cautious)
• conscientiousness (efficient/organized vs. extravagant/careless)
• agreeableness (friendly/compassionate vs. critical/rational)

Innovators and revolutionaries tend to have a very particular mix of openness, conscientiousness, and agreeableness traits.

Innovators have to be open, they have to be able to imagine things that others cannot and to be willing to challenge their own preconceptions. They also need to be conscientious. An innovator who has brilliant ideas but lacks the discipline and persistence to carry them out is just a dreamer.

Crucially, innovators also need to be disagreeable. Not obnoxious or unpleasant, but people who are willing to take social risks and do things that others might disapprove of.

A radical and transformative thought goes nowhere without the willingness to challenge convention. For example, if you have a new idea, and it’s disruptive, and you are agreeable, what are you going to do with that idea? If you worry about hurting people’s feelings and disturbing the social structure, you are not going to put your ideas forward.

“The reasonable man adapts himself to the world; the unreasonable one persists in trying to adapt the world to himself. Therefore, all progress depends on the unreasonable man.” -George Bernard Shaw

The most tantalizing possibility raised by dyslexia is that it might make it a little easier to be disagreeable.

One common trait of a lot of dyslexic people is they have a very highly developed ability to deal with failure. They look at most situations and see much more of the upside than the downside. The downside doesn’t phase them because they are so accustomed to the downside.

Dyslexia, in the best of cases, forces you to develop skills that might otherwise have lain dormant. It also forces you to do things that you might otherwise never have considered.

Chapter 5: Emil “Jay” Freireich

When a bomb falls, it divides the affected population into three groups.

1. The people killed. The most devastating for them.
2. The “near misses.” They feel the blast and see the destruction, perhaps they are wounded, but they survive deeply impressed. Leaves people traumatized.
3. Remote misses. The bomb hits down the street or the next block over. They survived. These people are left feeling invincible after surviving several remove misses.

The idea of desirable difficulties suggests that not all difficulties are negative. Being a poor reader is a real obstacle unless that obstacle turns you into an extraordinary listener like David Boies.

Traumatic experiences can have two completely different effects on people. The same event can be profoundly damaging to one group while leaving another group better off. There are two kinds of responses to something terrible and traumatic.

Dyslexia is a classic example of this phenomenon. Many people with dyslexia don’t manage to compensate for their disability.

According to psychologist Dean Simonton, gifted children and child prodigies seem most likely to emerge in highly supportive family conditions. In contrast, geniuses have a perverse tendency to grow up in more adverse conditions.

Where did Freireich’s courage come from?

Courage is something acquired. We are all not merely liable to fear, we are prone to being afraid of being afraid. The conquering of fear produces exhilaration. When we conquer fear, the contrast between the previous apprehension and the present relief and feeling of security promotes self-confidence.

Courage is not something you already have that makes you brave when the tough times start. Courage is what you earn when you’ve been through tough times and you discover that they aren’t so tough after all.

If one remote miss brings exhilaration, we can only imagine what two bring.

What happens to children whose worst fear is realized, and then they discover that they are still standing? Many of them can gain a self-confidence that is the very father and mother of courage.

For every remote miss who becomes stronger, there are countless near misses who are crushed by what they have been through. There are times and places when all of us depend on people who have been hardened by their experiences.

Chapter 6: Wyatt Walker

This chapter is about Wyatt Walker, the executive director of the Southern Christian Leadership Conference and chief of staff for Martin Luther King Jr. He was heavily involved in the Birmingham campaign for Civil Rights.

David’s opportunities are the occasions in which difficulties happen to be desirable.

1. Dyslexics compensate for their disability by developing other skills, that at times can prove highly advantageous.
2. Being bombed or orphaned can be a near-miss experience and leave you devastated. Or it can be a remote miss and leave you stronger.
3. The lesson of the trickster tales is the third desirable difficulty. The unexpected freedom that comes from having nothing to lose. The trickster gets to break the rules.

Brian Grazer and Gary Cohn were two outsiders with learning disabilities. They played a trick and bluffed their way into professions that otherwise would have been closed to them.

David has nothing to lose, and because he has nothing to lose, he has the freedom to thumb his nose at the rules set by others. That’s how people with brains a little bit different from the rest of ours get jobs as options traders and Hollywood producers. That’s how a small band of protesters armed with nothing but their wits had a chance against Bull Connor.

Part 3: The Limits of Power

Chapter 7: Rosemary Lawlor

We often think of authority as a response to disobedience, but disobedience can also be a response to authority. If the teacher doesn’t do their job properly, a child will become disobedient out of boredom.

Disobedience is more often an engagement problem than a behavioral problem. If the teacher is doing something interesting, kids are quite capable of being engaged.

Instead of responding with a “let me control your behavior” mentality, teachers should be thinking “How can I do something interesting that will prevent you from misbehaving?”

Bad teachers can turn an eager and attentive student into someone doing cartwheels in the classroom.

When people in authority want the rest of us to behave it matters first and foremost how they behave. This is called the principle of legitimacy.

Legitimacy is based on three things:

1. People who are asked to obey authority need to feel like they have a voice, and if they speak up they will be heard.
2. The law has to be predictable. There has to be a reasonable expectation that the rules tomorrow will be roughly the same as the rules today.
3. The authority has to be fair. It can’t treat one group differently from another.

How you punish is as important as the act of punishing itself.

It is important for teachers to earn the respect of their students.

The powerful have to worry about how others think about them. Those who give orders are acutely vulnerable to the opinions of those they are ordering around.

When the law is applied in the absence of legitimacy, it does not produce obedience, it produces the opposite and leads to backlash.

What matters are the hundreds of small things that the powerful do, or don’t do, to establish legitimacy.

Chapter 8: Wilma Derksen

This chapter tells the story of Wilma Derksen and talks about the three strikes law and how it made crime worse in a lot of ways instead of better. I didn’t take many notes on this chapter.

What if, past a certain point, cracking down on crime stopped affecting criminals and maybe made crime worse?

There comes a point where the best-intentioned application of power and authority begins to backfire.

Chapter 9: André Trocmé

This chapter is about André Trocmé and the French town of Le Chambon-sur-Lignon.

Wiping out a town, a people, or a movement is never as simple as it looks.

The powerful are not as powerful as they seem, nor the weak as weak.

The beauty of the disagreeable is that they do not make calculations like the rest of us.

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