David & Goliath

Harry Cheslaw
8 min readJan 6, 2019

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By Malcolm Gladwell

The book focuses on the probability of improbable events occurring in situations where one outcome is greatly favoured over the other. The book contains many different stories of these underdogs who wind up beating the odds, the most famous being the story of David and Goliath.

Trying to play the Giant’s game rarely is successful. To win against the Giants, the Davids need to adopt different strategies. But most of the time underdogs don’t fight like Davids as they blindly accept the rules of the game as defined by the dominant players.

The Story Of David & Goliath

The book starts with the story of David & Goliath. Gladwell describes how the giant was expecting a traditional fight. “A warrior like himself to come forward for hand-to-hand combat. It never occurred to him hat the battle would be fought on anything other than those terms, and he prepared accordingly….He worse a heavy metal helmet..He had three separate weapons, all optimised for close combat.” However, David did not play by these rules and there was nothing that Goliath could do to stop his death.

“He was carrying over a hundred pounds of armour. He was prepared for a battle at close range, where he could stand…He watched David approach, first with scorn, then with surprise, and then with what can only have been horror-as it dawned on him that the battle he was expecting had suddenly changed.” At this time a typical sling could propel a rock at the equivalent speed of a fair-size modern handgun easily making itself deadly.

Gladwell posits that “the source that gave the giant his size was also the source of his greatest weakness…The powerful and strong are not always what thy seem…David game running toward Goliath, powered by courage and faith. Goliath was blind to his approach-and then was down, too big and slow and blurry-eyed to comprehend the way the tables had been turned.”

The Advantages Of Disadvantages (And The Disadvantage Of Advantages)

Suppose you were to total up all the wars over the past two hundred years that occurred between very large and very small countries. How often do you think the big side won?

“When the political scientist Ivan Arreguin-Tofu did the calculation a few years ago, what he came up with was 71.5%. Just under a third of the time the weaker country wins…What happens in wars between the strong and the weak when the weak side does what David did and refuses to fight the way the bigger side wants to fight, using unconventional methods…In those cases the weaker party’s winning percentage climbs from 28.5% to 63.6%.”

This idea was further explained in the story of Vivek Ranadive.

Vivek Ranadive coached Redwood City’s 12 year old girls in the US National Junior Basketball. In studying the game he was puzzled why the teams never seemed to play the full court (instead only defending only about 24 feet of the 94 feet court). He taught his girls to play a whole court pressing strategy. Because he came from Mumbai, he was not blinded by the way other American’s played.

On Rich Parents

Gladwell describes the psychologist James Grubman’s views on wealth and the issues of raising kids when you are wealthy. This illustrates that advantages can be disadvantages and vice-versa.

A parent has to set limits. But that’s one of the most difficult things for immigrants to wealth, because they don’t know what to say when having the excuse of ‘We can’t afford it’ is gone… ‘no we won’t’ is much harder. ‘No we can’t’ is simple’. Saying no when you have the money means justifying why you will not make the purchase based on your values. But then that requires that you have a set of values and know how to articulate them which is difficult for anyone to do, yet alone when you have a Ferrari in the driveway.

This example also illustrates the ‘n’ curve. Money makes parenting easier until a certain point — when it stops making much of a difference.

The ’n’ curve (or inverted ‘u’) — Giants are at a disadvantage in some areas as ‘more’ is not always better. The ’n’ curve suggests that benefits rise with numbers, but then plateaus before the benefits decline with increased numbers. Barry Schwartz and Adam Grant first termed it the inverted ‘u’, stating “All positive traits, states and experiences have costs that at high levels may begin to outweigh their benefits”. So a class size of 3 is just as bad as a class of say 40 (we assume the smaller the class size the better, but hundreds of studies of class size across 18 countries has concluded it has no effect on performance when within average limits).

A Big Fish In A Small Pond

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 suggest 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 hundred and fifty years ago, Paris was the center of art culture in France. Back then, every artist had one goal: get into the Salon, which was a gallery for all the greatest art within France.There was one problem, the Salon forced artists to conform to what the Salon believed was real art (i.e. young men at war and fair maidens under trees). The artists were forced to become the little fish in the big pond. It got to the point where some artists got sick of conforming and decided to create there own Salon with paintings that probably wouldn’t have made it into the Salon. This idea brought us to a more relatable, modern situation.

Caroline Sachs, an above-average high schooler, was trying to decide which college to attend, University of Maryland or Brown University. The challenge of picking which school she should go to was most difficult. The majority of students wouldn’t even think twice about it because attending the school with a better reputation would look better on a job application, right? No. The problem with the students who chose the better school is that they do not realise is they will be among other students who were valedictorians and 4.0 scholars, immediately making her a little fish in this big sea.

But let’s think about Caroline’s decision in the same way the Impressionits thought about the Salon. What the Impressionist’s understood was that the choice between the Salon and 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 very things that made the Salon so attractive-how selective and prestigious it was-also made it problematic. The Salon was the Big Pond. But it was very hard to be anything at the Salon but a little fish.

By choosing this, Caroline becomes an average student, which was a completely new concept for her. In the end, the decision she made ended up causing her to drop her intended major because it was too difficult and pick up a new one. This major was less appealing to her, and was not her passion. Now don’t you wonder what would have happened if she would have chose to be a big fish in a little pond? So does she.

The academic Michell Change founded out that all things being equal, the likelihood of someone completing a STEM degree rises by 2 percentage points for every 10-point decrease in the university’s average SAT score. As the better class you are in, the dumber you feel; the more likely you are to drop out.

Relative Deprivation

Caroline was experiencing what is called “relative deprivation” a term coined by the sociologist Samuel Stouffer during the Second World War who was commissioned by the U.S. Army to examine the attitudes and moral of American soldiers. Stouffer discovered that “we form our impressions not globally but locally-by comparing ourselves to people “in the same boat”…Our sense of how deprived we are is relative”. This explains why countries in which people declare themselves as happy also have the highest suicide rates.

The Theory Of Desired Difficulty

Cognitive Reflection Test

This is the world’s shortest intelligence test invested by the Yale Professor Shane Fredetick. It involves such questions as “A bat and a ball cost $1.10 in total. The bat costs $1.00 more than the ball. How much does the ball cost?”.

“The CRT is really hard. But here’s the strange thing. Do you know the easiest way to raise people’s scores on the test? Make it just a little bit harder such as printing out the test questions in a font that is really hard to read.”

Therefore the difficulty turned out to be desirable as the students were forced to think look/think about the question harder.

A good example of this is dyslexia. “Dyslexia are outsiders as well…Is it possible for that “outsiderness” to give them some kind of advantage down the line”

Gladwell describes how Psychologists measure personality using the “Big Five” model which assesses personality based on:

  • Neuroticism
  • Extraversion
  • Openness
  • Conscientiousness
  • Agreeableness.

“The psychologist Jordan Peterson argues that innovates and revolutionaries tend to have a very particular mix of these traits — particularly the last three: openness, conscientiousness and agreeableness…Innovators need to be disagreeable…They are people willing to take social risks-to do things that others might disapprove off. As humans beings we are hardwired to seek the approval of those around is. Yet a radical and transformative thought goes nowhere without the willingness to challenge convention”.

The Case Of Gary Cohen

Gary David Cohn (born August 27, 1960) is an American investment banker who served as the 11th Director of the National Economic Council and was the chief economic advisor to President Donald Trump from 2017 to 2018.He was the president and chief operating officer of Goldman Sachs from 2006 to 2017.

He suffers with severe dyslexia. He started his career selling aluminium siding and window frames for U.S. Steel in Cleveland. He wanted to get into trading but there was no way he could get it through the official route so had to find another way.

He went down to wall street and was watching the traders work from the viewing room when he saw someone yell to the Clerk ‘I’ve got to go, I’m running to LaGuardia’. He immediately goes to the Taxi Rank and says to the man ‘I hear your going to LaGuardia, can we share a cab?’. The stranger turned out to be very high up in one of Wall Street’s brokerage houses and just that week the brokerage had opened a business buying and selling options. Cohen lied to him the entire way there telling him that he knew all about options. The man gave Cohen his number and scheduled an interview. Before the interview Cohen memorised the book ‘Options as a Strategic Investment’ and started the job a week later. Cohen states that he was able to do this due to his dyslexia.

My upbringing allowed me to be comfortable with failure. The one trait in a lot of dyslexic people I know is that by the time we got out of college, our ability to deal with failure was very highly developed. Dyslexia forces you to develop skills that might otherwise have laid dormant. — Gary Cohen

Positives From Negative Events

Gladwell describes how in fact even traumatic experiences can be beneficial.

He describes the Psychiatrist MacCurdy’s analysis on why the Blitz did not decrease morale describing how there are three types of case:

  • Those Killed
  • Near Misses (those whose houses have been destroyed)
  • Remote Misses (people who have not been affected but perhaps there neighbours have).

He describes that people can experience post traumatic growth.

Post-traumatic growth (PTG) or benefit finding is positive psychological change experienced as a result of adversity and other challenges in order to rise to a higher level of functioning.

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