The best books about luck: winning, losing, and seeing opportunity

David Flusfeder Author Of Luck: A Personal Account of Fortune, Chance and Risk in Thirteen Investigations
By David Flusfeder

Who am I?

My father, when he consented to talk about all the moments in his life when the odds against his survival were so small as to make them statistically non-existent, would say, ‘I was lucky.’ Trying to understand what he meant got me started on this book. As well as being a novelist, I’m a poker player. Luck is a subject that every poker player has a relationship to; more importantly it’s a subject that every person has a relationship to. The combination of family history and intellectual curiosity and the gambler’s desire to win drove me on this quest.


I wrote...

Luck: A Personal Account of Fortune, Chance and Risk in Thirteen Investigations

By David Flusfeder,

Book cover of Luck: A Personal Account of Fortune, Chance and Risk in Thirteen Investigations

What is my book about?

What does it mean to be lucky? How might we mitigate bad luck and maximise good? Is there actually such a thing as ‘luck’—some force that intervenes between desire and its consummation?

This book is a quest, a battle against superstition, my own, as I search for a definition of luck from ancient times to modern, in the footsteps of some victors of luck and those who were defeated by it—and gambling along the way. Following the dictates of an online randomiser that decided the chapter order, we go to Siberia, Versailles and the Old Testament desert. The journey culminates in Las Vegas, where I make a final reckoning with superstition and courage and prudence and opportunity and truth.

The books I picked & why

Shepherd is reader supported. We may earn an affiliate commission when you buy through links on our website. This is how we fund this project for readers and authors (learn more).

The Gambler

By Fyodor Mikhailovich Dostoyevsky,

Book cover of The Gambler

Why this book?

This novel is the best account of the gambling psychology I know. It is a first-person narrative, ruthless in its depiction of the lies that addicts know they’re telling themselves. The story of a resentful compulsive gambler, the poor but superior tutor to a Russian family at “Roulettenburg,” it was itself the subject of a bet. Dostoevsky signed away his next decade’s worth of publishing profits unless he could deliver a new novel within a year. With six weeks to go he hadn’t written a word. He delivered the completed novel several hours before the deadline was going to pass. 

The Gambler

By Fyodor Mikhailovich Dostoyevsky,

Why should I read it?

2 authors picked The Gambler as one of their favorite books, and they share why you should read it.

What is this book about?

"The Gambler" is a gripping narrative of the dangers of an addiction to gambling. As was common with Dostoyevsky's writing he draws upon his own life in a semi-autobiographical way in "The Gambler". Dostoyevksy himself suffered from a compulsion to gambling and those first-hand experiences bring a depth of realism to "The Gambler" and to his portrayal of the main character, Alexis Ivanovitch, a young man addicted to gambling. "The Gambler" is an insightful look at the compulsive nature of the gambling addict and the tragic consequences of such an addiction.


Classical Probability in the Enlightenment

By Lorraine Daston,

Book cover of Classical Probability in the Enlightenment

Why this book?

Sadly, Games, Gods, and Gambling by FN David is out of print. This is the next best thing. Lorraine Daston has the supreme gift of making the complicated idea seem straightforward. This is an account of the frenzy for measuring that happened in the 18th century, and how it made the world we live in today, when the gambler’s eye for odds has become the algorithm of taming chance that guides all our decisions.

Classical Probability in the Enlightenment

By Lorraine Daston,

Why should I read it?

1 author picked Classical Probability in the Enlightenment as one of their favorite books, and they share why you should read it.

What is this book about?

What did it mean to be reasonable in the Age of Reason? Classical probabilists from Jakob Bernouli through Pierre Simon Laplace intended their theory as an answer to this question--as "nothing more at bottom than good sense reduced to a calculus," in Laplace's words. In terms that can be easily grasped by nonmathematicians, Lorraine Daston demonstrates how this view profoundly shaped the internal development of probability theory and defined its applications.


Hopscotch

By Julio Cortazar, Gregory Rabassa (translator),

Book cover of Hopscotch

Why this book?

Argentinians in 1950s Paris argue about art and philosophy. They fall in and out of love to a jazz soundtrack. The novel itself is in love with the modern city and the secret patterns of chance. Prefacing it is a ‘table of instructions’ in which the author writes that "this book consists of many books, but two books above all. The first can be read in a normal fashion and it ends with Chapter 56... The second should be read by beginning with Chapter 73 and then following the sequence indicated at the end of each chapter."

There’s an exhilaration of structure, a deadpan formal playfulness that still thrills. It’s the book that taught me the most about reading. And, not entirely coincidentally, it’s the book that made me realise I was going to become a writer.

Hopscotch

By Julio Cortazar, Gregory Rabassa (translator),

Why should I read it?

1 author picked Hopscotch as one of their favorite books, and they share why you should read it.

What is this book about?

"Cortazar's masterpiece ... The first great novel of Spanish America" (The Times Literary Supplement) • Winner of the National Book Award for Translation in 1967, translated by Gregory Rabassa

Horacio Oliveira is an Argentinian writer who lives in Paris with his mistress, La Maga, surrounded by a loose-knit circle of bohemian friends who call themselves "the Club." A child's death and La Maga's disappearance put an end to his life of empty pleasures and intellectual acrobatics, and prompt Oliveira to return to Buenos Aires, where he works by turns as a salesman, a keeper of a circus cat which can…


The Wild Ass's Skin

By Honoré de Balzac, Helen Constantine (translator),

Book cover of The Wild Ass's Skin

Why this book?

A young man loses all his money in a Paris casino and goes off to drown himself in the Seine. Before he can do so, he wanders into an antiquarian’s shop of treasures and is offered the skin of the title, a magical pelt that will grant its possessor any wish, but shrink each time, diminishing the possessor’s life force in the process. It’s a moral tale of wish fulfillment and identity, but most of all, it’s a thrilling glittering dark tale of ambition and excess. 

The Wild Ass's Skin

By Honoré de Balzac, Helen Constantine (translator),

Why should I read it?

1 author picked The Wild Ass's Skin as one of their favorite books, and they share why you should read it.

What is this book about?

'Who possesses me will possess all things,
But his life will belong to me...'

Raphael de Valentin, a young aristocrat, has lost all his money in the gaming parlours of the Palais Royal in Paris, and contemplates ending his life by throwing himself into the Seine. He is distracted by the bizarre array of objects in a chaotic antique shop, among them a strange animal skin, a piece of shagreen with magical properties. It will grant its possessor his every wish, but each time a wish is bestowed the skin shrinks, hastening its owner's death. Around this fantastic premise
Balzac…


The Courtiers Manual Oracle: or the Art of Prudence

By Baltasar Gracián,

Book cover of The Courtiers Manual Oracle: or the Art of Prudence

Why this book?

When I was researching Luck, I came across many books that claimed to teach the willing acolyte how to seize opportunity and how to maximise reward while minimising risk. This is the one that’s worth paying attention to. The Oracle is a collection of three hundred maxims for practical success, in condensed, often paradoxical form, written by a seventeenth-century Jesuit. Nietzsche said of it that "Europe has never produced anything finer or more complicated in matters of moral subtlety" and who’s going to argue with Nietzsche?

The Courtiers Manual Oracle: or the Art of Prudence

By Baltasar Gracián,

Why should I read it?

1 author picked The Courtiers Manual Oracle as one of their favorite books, and they share why you should read it.

What is this book about?

This is a reproduction of a classic text optimised for kindle devices. We have endeavoured to create this version as close to the original artefact as possible. Although occasionally there may be certain imperfections with these old texts, we believe they deserve to be made available for future generations to enjoy.


5 book lists we think you will like!

Interested in gambling, Buenos Aires, and science?

7,000+ authors have recommended their favorite books and what they love about them. Browse their picks for the best books about gambling, Buenos Aires, and science.

Gambling Explore 33 books about gambling
Buenos Aires Explore 11 books about Buenos Aires
Science Explore 152 books about science

And, 3 books we think you will enjoy!

We think you will like Ask the Dust, A Fan's Notes, and Cassidy's Girl if you like this list.