David and Goliath

David and Goliath

Underdogs, Misfits & the Art of Battling Giants

Malcolm Gladwell

Summary in 100 words or less

Strengths and weaknesses, advantages and disadvantages, blessings and misfortune aren't always what they turn out to be at face value. What we think of as misfortune is the best thing that can happen to us, and what we think as an advantage can lead to the worst outcome.

Commentary

My Highlights

What we consider valuable in our world arises out of these kinds of lopsided conflicts, because the act of facing overwhelming odds produces greatness and beauty.

Giants are not what we think they are. The same qualities that appear to give them strength are often the sources of great weakness. And the fact of being an underdog can change people in ways that we often fail to appreciate.

Having lots of resources is an advantage. But it makes you immobile and puts you on the defensive. Meanwhile, movement, endurance, individual intelligence, knowledge, and courage allowed underdogs to do the impossible.

The willingness to try harder than anyone else set winner and losers apart.

Underdog strategies are hard. To play by David’s rules you have to be desperate. You have to be so bad that you have no choice.

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

Any fool can spend money. But to earn it and save it and defer gratification – then you learn to value it differently.

Like any parent, he – a self-made successful person – wanted to provide for their children, to them more than he had. But he had created a giant contradiction, and he knew it. He was successful because he had learned the long and hard way about the value of money and the meaning of work and the joy and fulfillment that come from making your own way in the world. But because his success, it would be difficult for his children to learn those same lessons.

People are ruined by challenged economic lives. But they’ve ruined by wealth as well because they lose their ambition and they lose their pride and they lose their sense of self-worth.

Money makes parenting easier until a certain point – when it stops making much of a difference.

Wealth contains the seeds of its own destruction.

Many people have simply fallen into the trap that wealthy people and wealthy institutions and wealthy countries – all Goliaths – too often fall into: the school assumes that the kinds of things that wealth can buy always translate into real-world advantages.

We all assume that being bigger and stronger and richer is always in our best interest, but it isn’t.

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 Big Fish-Little Pond option might be scorned by some on the outside, but Small Ponds are welcoming places for those on the inside.

There are times and places when 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.

When you are a little fish in one of the deepest and most competitive pond, the experience of comparing yourself to all the other brilliant fishes will eventually shatter your confidence. It makes you feel stupid, even though you aren’t stupid at all.

We form our impressions not globally, by placing ourselves in the broadest possible context, but locally – by comparing ourselves to people “in the same boat as ourselves.” Our sense of how deprived we are is relative.

Citizens of happy countries have higher suicide rates than citizens of unhappy countries, because they look at the smiling faces around them and the contrast is too great.

How you feel about your abilities in the context of your surrounding shapes your willingness to tackle challenges and finish difficult tasks. It’s a crucial element in your motivation and confidence.

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

Normally we think that we are better at solving problems when they are presented clearly and simply but the opposite happened. Making the questions “disfluent” causes people to think more deeply about whatever they come They’ll use more resources on it. They’ll process more deeply or think more carefully about what’s going on. If they have to overcome a hurdle, they’ll overcome it better when you force them to think a little harder. And that’s what we called the desirable difficulty.

An extraordinarily high number of successful entrepreneurs are dyslexic.

The opposite of desirable difficulty is “capitalization learning”: we get good at something by building on the strengths that we are naturally given.

As human beings, we are hardwired to seek the approval of those around us. Yet a radical and transformative thought goes nowhere without the willingness to challenge convention.

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 one trait in a lot of dyslexic people is that by the time they got out of college, their ability to deal with failure was very highly developed. And so they look at most situations and see much more of the upside than the downside.

Learning how to deal with the possibility of failure is really good preparation for a career in the business world.

The idea of desirable difficulty suggests that not all difficulties are negative.

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

There are things that either build you up or put you down.

The weak could compete in even the most lopsided of contests if they were willing to use their wits.

The occasions in which difficulties, paradoxically, turn out to be desirable when the unexpected freedom that comes from having nothing to lose.

We need to remember that our definition of what is right is, as often as not, simply the way that people in positions of privilege close the door on those on the outside. David has nothing to lose, and because of that, he has the freedom to thumb his nose at the rules set by others.

When you are in the position of David, you got to use what you got.

It has been said that most revolutions are not caused by revolutionaries in the first place, but by the stupidity and brutality of governments. – Sean MacStiofain

We often think of authority as a response to disobedience, however, disobedience can also be a response to authority.

When people in authority want the rest of us to behave, it matters – first and foremost – how they behave.

The principle of legitimacy is based on three things. First, the people who are asked to obey authority have to feel like they have the voice – that if they speak up, they will be heard. Second, the law has to be predictable. There has to a reasonable expectation that the rules tomorrow are going to be roughly the same as the rules today. And third, the authority has to be fair. It can’t treat one group differently from another.

Power has an important limitation. It has to be seen as legitimate, or else its use has the opposite of its intended effect.

The inverted-U curve is all about limits. They illustrate the fact that “more” is not always better; there comes a point, in fact, when the extra resources that the powerful think of as their greatest advantage only serve to make things worse.

The human psyche follows the course of least resistance. The course of least resistance is what’s easy.

This final lesson about the limits of power is not easy to learn. It requires that those in positions of authority accept that their greatest advantage has real constraints.

The excessive use of force creates legitimacy problems, and force without legitimacy leads to defiance, not submission.

There are real limits to what evil and misfortune can accomplish. If you take away the gift of reading, you create the gift of listening. If you bomb a city, you leave behind death and destruction. But at the same time, you create a community of remote misses. If you take away a mother or a father, you cause suffering and despair, But one time in then, out of that despair rises an indomitable force.

More book notes

Principles
How Will You Measure Your Life
The Almanack of Naval Ravikant
Think and Grow Rich
The 48 Laws of Power

Get my email delivered to your inbox once in a while

Three to five things I learned—that will help you work less, earn more, and live a better life. (Also get notified of new posts and masterclasses)

Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.

👆 Join 3,100+ leaders, creatives, and knowledge workers today.

Dean is a strong voice in the self-mastery space. His newsletter consistently delivers insightful ideas on how to become a better version of yourself and is the only newsletter that I always read.

Sebastian Kade

Head of product and engineering