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24
BOOKS
you’ve never heard
of — but will

CHANGE

YOUR LIFE
{ RYAN HOLIDAY }

When you read
the same books as
everyone else, you don’t
learn anything new.
It’s skating to where
the puck was.

 by kraybon

{ RYAN HOLIDAY }

Reading is
about insight into
the human experience,
about understanding.
Don’t follow in
well-trod footsteps.
Carve a new path.
 by MarioMancuso

For the last five years,
I’ve tried to do just that
on my popular monthly
reading list email.

I’VE RECOMMENDED
HUNDREDS OF AMAZING,
LIFE-CHANGING BOOKS
TO TENS OF THOUSANDS
OF PEOPLE.
Subscribe to my Reading List

{ RYAN HOLIDAY }

Let’s explore some of
the unexpected, under-rated, and often

UNDISCOVERED FAVORITES

Cyropaedia The Moral Sayings of Publius Syrus: A Roman Slave Meditations The Man Without
a Country 12 Years A Slave Civil War Stories Forty Years a Gambler on the Mississippi Hunger
Letters from a Self-Made Merchant to His Son My Life and Battles
Company K Babbitt
Asylum: An Alcoholic Takes the Cure Ask the Dust Why Don’t We Learn from History? Strategy
The Crack Up On the Rock: Twenty Five Years in Alcatraz Death Be Not Proud The Harder They
Fall Losing the War The Measure of My Days The Power Tactics of Jesus Christ and Other Essays
The Tiger: A True Story of Vengeance and Survival Cyropaedia The Moral Sayings of Publius
Syrus: A Roman Slave Meditations The Man Without a Country 12 Years A Slave Civil War
Stories Forty Years a Gambler on the Mississippi Hunger Letters from a Self-Made Merchant to
His Son My Life and Battles Company K Babbitt Asylum: An Alcoholic Takes the Cure Ask
the Dust Why Don’t We Learn from History? Strategy The Crack Up On the Rock: Twenty Five
Years in Alcatraz Death Be Not Proud The Harder They Fall Losing the War The Measure of
My Days The Power Tactics of Jesus Christ and Other Essays The Tiger: A True Story of Vengeance
and Survival Cyropaedia The Moral Sayings of Publius Syrus: A Roman Slave Meditations The
Man Without a Country 12 Years A Slave Civil War Stories Forty Years a Gambler on the
Mississippi
Hunger
Letters from a Self-Made Merchant to His Son My Life and Battles
Company K Babbitt Asylum: An Alcoholic Takes the Cure Ask the Dust Why Don’t We Learn

24 BOOKS

1

Cyropaedia* 

by X E N O P H O N

X

enophon, like Plato, was a student of Socrates.
There are so many great lessons in here and
I wish more people would read it. Machiavelli
learned them, as this book inspired The Prince.
Buy the book on Amazon

* (a more accessible translation can be

found in Xenophon’s Cyrus The Great:
The Arts of Leadership and War)

{ RYAN HOLIDAY }

2

The Moral Sayings
of Publius Syrus: A Roman Slave 

by P U BL IU S SYR U S

T

he best philosophy comes from people who
were not “philosophers.” Syrus was a slave and
his moral maxims are far better than perhaps the
most famous book in this category, those of
Duc de la Rochefoucauld.
Buy the book on Amazon

{ RYAN HOLIDAY }

3

Meditations 

by M A R C U S AU R E L IU S
(Gregory Hays translation, do not read the others, they suck)

A

t some point around 170 AD, the single most
powerful man in the world sat down and
wrote a private book of lessons and admonishments
to himself for becoming a better, kinder and
humbler person. And this text survives and you
have access to it today.
Buy the book on Amazon

{ RYAN HOLIDAY }

4

The Lives of the Most Excellent
Painters, Sculptors, and Architects

by GIO R GIO V ASAR I

B

asically a friend and peer of Michelangelo,
Da Vinci, Raphael Titian and all the other
great minds of the Renaissance sat down in 1550
and wrote biographical sketches of the people he
knew or had influenced him. There are so many
great lessons about craft and psychology within this
book. The best part? It was written by someone
who actually knew what he was talking about, not
some art snob or critic, but an actual artist and
architect of equal stature to the people he was
documenting.
Buy the book on Amazon

{ RYAN HOLIDAY }

5

The Man Without A Country

by E D W AR D E . H AL E

P

atriotism is not a concept that gets a lot of
love today. But this essay/book makes you
think a little. Released in 1863 during the height
of the Civil War, the plot’s simple: an innocent man
caught up in Aaron Burr’s treasonous conspiracy
stands trial for his actions. For those with some
understanding of historical, you’ll enjoy the
meta-fiction of it, for those that haven’t it is still a
very good look into early America.
Buy the book on Amazon

{ RYAN HOLIDAY }

6

Twelve Years a Slave

by SO L O M O N N O R T H U P

I

f there is one book you read about slavery in
America, read this one. It’s the real story of a
born freedman in the North who, as a traveling
musician, was brought out of his home state on
false pretenses in order to be captured, kidnapped,
and transported South to be sold as a slave.
This book is just as good as Frederick Douglass’
memoir and I think illustrates the horrors of slavery
in a much more undeniable way.
Buy the book on Amazon

{ RYAN HOLIDAY }

7

Civil War Stories

by AMBR O SE BIE R C E

M

ark Twain, for all his bitterness and sarcasm,
was just more fun for average people to read
than Ambrose Bierce. But Bierce is the one who
truly captured the Civil War–a terrible and awful
conflict in which death and destruction and
stupidity were far more prevalent than strategy or
heroism.
Too many books about the Civil War are
inaccessible, with their flanking movements and
war vocabulary. This book is all people. Must read.
Buy the book on Amazon

{ RYAN HOLIDAY }

8

Forty Years a Gambler
on the Mississippi

by GE O R GE DE V O L

T

he memoir of a professional gambler, fighter
and criminal who rode the riverboats of the
Mississippi and Red Rivers. It’s a true and vibrant
snapshot of a period of American life that you can’t
get anywhere else. Gun fights, brawls, cons–it’s all
here. Fascinating, peculiar and very easy to read.
Buy the book on Amazon

{ RYAN HOLIDAY }

9

Hunger 

by K N U T H AM SU N

A

dark and moving first-person narrative, about
the conflicting drives for self-preservation and
self-immolation inside all of us. Hunger is about a
writer who is starving himself. He cannot write
because he is starving and cannot eat because
writing is how he makes his living. It’s a vicious
cycle and the book is a first-person descent into it.
Buy the book on Amazon

{ RYAN HOLIDAY }

10

Letters from a Self-Made
Merchant to His Son

by GE O R GE HO R AC E L O R IME R

T

his book is the preserved correspondence
between Old Gorgon Graham, a self-made
millionaire in Chicago, and his son who is coming
of age and entering the family business. The letters
date back to the 1890s but feel like they could
have been written in any era. Honest. Genuine.
Packed with good advice.
Buy the book on Amazon

{ RYAN HOLIDAY }

11

My Life and Battles 

by JAC K JO HNSO N

T

his is the lost and translated book that came
out of a series of pieces Johnson–perhaps the
greatest boxer who ever lived–wrote for a French
newspaper in 1911. It’s not very long but it is full of
really interesting strategies and anecdotes.
As Jack London put it after Johnson’s most
famous fight: “No one understands him, this man
who smiles. Well, the story of the fight is the story
of a smile. If ever a man won by nothing more
fatiguing than a smile, Johnson won today.”
Buy the book on Amazon

{ RYAN HOLIDAY }

12

Company K 

by WILLIAM MAR CH

F

ar and away the best book ever written about
WWI. But that’s the problem–WWI was
awful, perhaps the most awful thing of the 20th
century. And this book is forgotten precisely
because it portrays the war and its pointlessness too
realistically. We want to know, but we don’t really
want to know.
Buy the book on Amazon

{ RYAN HOLIDAY }

13

Babbitt 

by SIN C L AIR L E WIS

I

don’t think there was anyone in the 1920s who
would have believed that this book would be
completely forgotten.
Yet, here we are 80–90 years later: you’ve
probably never heard of the term or the book.
Perhaps it’s because the biting satire of American
suburban middle class life cuts deeper now than it
did then. It doesn’t matter if the book is old, it’s still
very funny and at its core, a critique of conformity
and what Thoreau called the “life of quiet
desperation.”
Buy the book on Amazon

{ RYAN HOLIDAY }

14

Asylum:
An Alcoholic Takes the Cure 

by WILLIAM SEABR OOK

I

n 1934, William Seabrook was one of the

most famous journalists in the world. He was also an
alcoholic. But there was no treatment for his disease. So he
checked himself into an insane asylum. There, from the
perspective of a travel writer, he described his own journey
through this strange and foreign place. Today, you can’t
read a page in the book without seeing him bump,
unknowingly, into the basic principles of 12-step groups
and then thwarted by well meaning doctors (like the one
who decides he’s cured and can start drinking again).
It breaks your heart to know that just a few years or decades
later, his options (and outcome) would have been so very
different (he eventually died of an opium overdose).
Buy the book on Amazon

{ RYAN HOLIDAY }

15

Ask the Dust

by JO HN F ANT E

T

his is the west coast’s Great Gatsby. Fante has

benefited from some recognition—mostly thanks
to Bukowski championing him in his later years—but
because the book is about Los Angeles and not New York
City, it is mostly forgotten.
Bandini, the subject of the series, is a wonderful
example of someone whose actual life is ruined by the
fantasies in his head–every second he spends stuck up there
is one he wastes and spoils in real life. He’s too caught up and
delusional to see that his problems are his fault, that he’s
vicious because he can’t live up to the impossible expectations they create, and that he could have everything he
wants if he calmed down and lived in reality for a second.
Buy the book on Amazon

{ RYAN HOLIDAY }

16

Strategy and
Why Don’t We Learn from History? 

by B.H. L IDDE L L HAR T

T

hese are two very short books but will help you
understand the topics more than thousands of
pages on the same topic by countless other writers.
In my view, Hart is unquestionably the best writer
on military strategy and history.
His theories on the indirect approach is life
changing, whether you’re struggling with a business
or just office politics. I can’t say much more than
read these books. It’s a must.
Buy Strategy and Why Don’t We Learn from History? on Amazon

{ RYAN HOLIDAY }

17

The Crack Up 

by F . SC O T T F I T Z G E R A L D

I

f you like Asylum, read The Crack Up, a book
put together by Fitzgerald’s friend Edmund
Wilson after his death. It is such an honest and
self-aware compilation of someone hell-bent on
their own destruction. At the same time,
Fitzgerald’s notes and story ideas within the book
make it undeniably clear what a genius he truly was.
It’s a sad and moving but necessary read.
Buy the book on Amazon

{ RYAN HOLIDAY }

18

On the Rock:
Twenty Five Years in Alcatraz 

by AL V IN K AR P IS

J

ohn Dillinger was played by Johnny Depp.
Most people know who he was—mostly
because he died in a hail of bullets. But they forget
that the other Public Enemy #1 at the time was
Alvin Karpis and he didn’t die. In fact, he lived up
until the 1980s. Just enough time to do a couple
decades at Alcatraz with guys like Al Capone.
During a temporary transfer to an alternate prison,
Karpis met a young weirdo named Charlie Manson
and taught him how to play guitar.
Buy the book on Amazon

{ RYAN HOLIDAY }

19

Death Be Not Proud 

by JO HN GU NT HE R

W

ritten in 1949 by the famous journalist
John Gunther about his death of his son—
a genius—at 17 from a brain tumor, this book is
deeply moving and profound. Every young person
will be awed by this young boy who knows he will
die too soon and struggles to do it with dignity
and purpose.
Buy the book on Amazon

{ RYAN HOLIDAY }

20

The Harder They Fall 

by BU DD SC HU L BE R G

B

udd Schulberg’s (who wrote On the Waterfront)
whole trilogy is amazing and each captures a
different historical era. All you need to know about
Schulberg’s writing is captured in this quote from
his obituary: “It’s the writer’s responsibility to
stand up against that power. The writers are really
almost the only ones, except for very honest
politicians, who can make any dent on that
system. I tried to do that. And that’s affected me
my whole life.”
Buy the book on Amazon

{ RYAN HOLIDAY }

21

Losing the War  

by L E E SAN D L IN

T

his is an essay, not a book, but if you
have to read one thing about WWII, this
is it. Sandlin is a master and the essay is free,
read it.
Read the essay here

{ RYAN HOLIDAY }

22

The Measure of My Days 

by F L O R I D A SC O T T M A X W E L L

T

he daily notes of a strong but dying woman
(born 1883, written in 1968) watching her life
slowly leave her and wind to a close. The wisdom in
this thing is amazing and the fact that most people
have no idea exists–and basically wait until the end
of their life to start thinking about all this is very
sad to me.
Buy the book on Amazon

{ RYAN HOLIDAY }

23

The Power Tactics of Jesus Christ
and Other Essays  

by JAY HAL E Y

T

he title essay in this book is peerless and
amazing. The rest of the essays, which talk
about Haley’s unusual approach to psychotherapy
are also quite good. If you’ve gone to therapy, are
thinking about going to therapy, or know someone
going to therapy, this book is a must-read.
Buy the book on Amazon

{ RYAN HOLIDAY }

24

The Tiger: A True Story
of Vengeance and Survival  

by JO HN V AIL L ANT

I

’ll end with this book because it’s the most
recent. The (true) story is simple: man in Siberia
wounds tiger while hunting to feed his family.
Tiger goes on killing spree while hunting the man
down, and is stopped only when the Russian
government dispatches a special SWAT team to
track and kill it. This is probably the single best
piece of nonfiction journalism I’ve ever read.
Buy the book on Amazon

{ RYAN HOLIDAY }

N

o one is saying you should
skip your high school
reading list.
The problem is thinking that
that’s enough. In order to work
for “everyone,” those books had
to be safe. Don’t read safe.

READ DANGEROUSLY.
{ RYAN HOLIDAY }

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recommendations
like this:

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