Ryan Holiday is a bestselling author known for bringing ancient Stoic philosophy into modern life through accessible, narrative-driven books. His works like The Obstacle Is the Way and Ego Is the Enemy have influenced millions seeking practical wisdom. He draws on historical figures and timeless principles to help readers navigate challenges and build better habits.
97 Books Recommended by Ryan Holiday
Ranked by popularity across all reading lists on this site
Looks at how we find purpose by dedicating ourselves to a cause, learning to love and finding a meaning to our suffering.
Looks at how we find purpose by dedicating ourselves to a cause, learning to love and finding a meaning to our suffering.
Also recommended by: Dustin Moskovitz, Ev Williams, Sam Altman, Aniela Gregorek, Bryan Johnson, Chelsea Handler, Chip Conley, Alastair Humphreys, Daniel Pink, Dave Elitch, David Blaine, Patrick Bet David, Emma Watson, Esther Perel, Fedor Holz, Jim Kwik, Jimmy Fallon, Jocko Willink, Jordan Peterson, Lex Fridman, Maria Popova, Mark Manson, Michael Gervais, Michael Hyatt, Pewdiepie, Phil Jackson, Robin Black, Shane Parrish, Simon Sinek, Steve Kerr, Terry Crews, Tom Bilyeu, Tony Robbins, Turia Pitt, Derek Sivers

Meditations
22 people recommendedThe private thoughts of the most powerful man in the world, admonishing himself on how to be better, more just, more immune to temptation, wiser.
Also recommended by: Naval Ravikant, Eric Jorgenson, Jack Dorsey, Sam Altman, Tobi Lutke, Adam Robinson, Anna Kendrick, Arianna Huffington, Chip Conley, Austen Allred, Patrick Bet David, James Clear, Jason Ferruggia, Joe Rogan, Lex Fridman, Mark Manson, Neil Strauss, Robin Sharma, Shane Parrish, Stewart Brand, Derek Sivers
The War of Art
16 people recommendedOne of Ryan Holiday's 2 answers to "what book are you most likely to give out as a gift?
Also recommended by: Aubrey Marcus, Brian Koppelman, Danny Miranda, Daniel Pink, Derek Sivers, James Clear, Jen Sincero, Jodie Cook, Joe Rogan, Lex Fridman, Marie Forleo, Michael Hyatt, Russell Moore, Seth Godin, Soman Chainani

Mastery
14 people recommendedrecommended 4xRead [this book] so that you can figure your lifeβs task and how to dedicate yourself to it.
Read [this book] so that you can figure your lifeβs task and how to dedicate yourself to it.
Read [this book] so that you can figure your lifeβs task and how to dedicate yourself to it.
Read [this book] so that you can figure your lifeβs task and how to dedicate yourself to it.
Also recommended by: Raj Shamani, Ev Williams, Aubrey Marcus, Patrick Bet David, Mark Hart, Maurice Ashley, Patrick Oshaughnessy, Robin Black, Robin Sharma, Rollo Tomassi, Terry Laughlin, Tom Bilyeu, Derek Sivers

Endurance
12 people recommendedThis book (and his life) were living proof of his family motto: 'Fortitudine vincimus' (By endurance we conquer).
Also recommended by: Sam Altman, Ray Dalio, Bryan Johnson, Andrew Klavan, Barry Ritholtz, Dominic Dagostino, Fred Wilson, Jason Fried, Jordan Peterson, Max Levchin, Scott Belsky
Bird by Bird
11 people recommendedOstensibly about the art of writing, but really it too is about life and how to tackle the problems, temptations and opportunities life throws at us.
Also recommended by: Brian Koppelman, Daniel Pink, Mark Bittman, Matt Haig, Matt Mullenweg, Mike Birbiglia, Ramit Sethi, Susan Cain, Tim Ferriss, Derek Sivers

The 48 Laws of Power
9 people recommendedrecommended 2xCritical for anyone trying to accomplish anything.
Critical for anyone trying to accomplish anything.
Also recommended by: Raj Shamani, Alice Little, Aubrey Marcus, Patrick Bet David, Dj Vlad, Neil Strauss, Rollo Tomassi, Derek Sivers

The Great Gatsby
9 people recommendedrecommended 3xIβve read and re-read many times.
Iβve read and re-read many times.
Iβve read and re-read many times.
Also recommended by: Bill Gates, Ev Williams, Taylor Swift, Christopher Hitchens, Daniel Pink, Jim Carrey, Neil Degrasse Tyson, Ta Nehisi Coates
Even if youβve never watched a down of football, youβll get something out of this book.
Even if youβve never watched a down of football, youβll get something out of this book.
Even if youβve never watched a down of football, youβll get something out of this book.
Even if youβve never watched a down of football, youβll get something out of this book.
Also recommended by: Jack Dorsey, Ron Conway, Sam Altman, Vinod Khosla, Justin Kan, Keith Rabois, Noah Kagan
The Prince
8 people recommendedrecommended 3xRyan Holiday recommended this book on his blog.
Ryan Holiday recommended this book on his blog.
Ryan Holiday recommended this book on his blog.
Also recommended by: Patrick Bet David, Eric Ripert, Fred Wilson, Garry Tan, Neil Degrasse Tyson, Ryan Shea, Stewart Brand

The Road
8 people recommendedRead it when you have kids. When I finished this book, [I] walked into my son's room when he was asleep, sat on the floor, and I just wept.
Also recommended by: Oprah Winfrey, Aubrey Marcus, Charlize Theron, Jocko Willink, Joel Mchale, Lex Fridman, Sam Hinkie

Founders at Work
7 people recommendedInterviews with technology founders from one of the best investors of all time.
Also recommended by: Sam Ovens, Ev Williams, Ron Conway, Alexis Ohanian, Paul Graham, Derek Sivers

Titan
7 people recommendedrecommended 2xI found Rockefeller to be strangely stoic, incredibly resilient, and, despite his reputation as a robber baron, humble and compassionate.
I found Rockefeller to be strangely stoic, incredibly resilient, and, despite his reputation as a robber baron, humble and compassionate.
Also recommended by: Ray Dalio, Charlie Munger, Anthony Pompliano, Austen Allred, David Friedberg, Jason Calacanis

Range
7 people recommendedrecommended 2x[One of] the best books I read [in 2019].
[One of] the best books I read [in 2019].
Also recommended by: Bill Gates, Changpeng Zhao, Vinod Khosla, Daniel Pink, Keith Rabois, Michael Mauboussin
The Fish That Ate the Whale
6 people recommendedSucked me in completely. Everyone Iβve recommended it to loves it.
Also recommended by: Eric Jorgenson, Andrew Wilkinson, Jason Calacanis, Patrick Oshaughnessy, Trung Phan

The Book of Five Rings
6 people recommendedRyan Holiday recommended this book on his blog.
Also recommended by: Naval Ravikant, Jocko Willink, Joe Rogan, Lex Fridman, Pewdiepie
Ryan Holiday recommended this book on his blog.
Also recommended by: Brian Armstrong, Ev Williams, Derek Sivers, Keith Rabois, Patrick Oshaughnessy
The Autobiography of Malcolm X
6 people recommendedrecommended 3x[One] of the most inspiring men of the last 150 years.
[One] of the most inspiring men of the last 150 years.
[One] of the most inspiring men of the last 150 years.
Also recommended by: Brian Koppelman, Casey Neistat, Jason Calacanis, Jerrod Carmichael, Steve Aoki
Tiny Beautiful Things
5 people recommendedContains some of the most cogent insights on life, pain, loss, love, success, youth that I have ever seen.
Also recommended by: Emma Watson, Kathryn Minshew, Mark Manson, Shane Parrish

Lincoln
5 people recommended[One of] my three favorite books about [Lincoln].
Also recommended by: Jamie Dimon, Christopher Hitchens, David Sabatini, Tom Keene
Ryan Holiday recommended this book on his blog.
Also recommended by: Kevin Systrom, Austen Allred, Keith Rabois
The Power Broker
4 people recommendedOne of the most magnificent books Iβve ever read.
Also recommended by: Sam Hinkie, Shane Parrish, Trung Phan

Letters from a Stoic
4 people recommendedAfter Marcus Aurelius, this is one of my favorite books.
Also recommended by: Naval Ravikant, Jerzy Gregorek, Tim Ferriss

On War
4 people recommendedRyan Holiday recommended this book on his blog.
Also recommended by: Elon Musk, Dave Camarillo, Nelson Mandela

Parting the Waters
4 people recommendedrecommended 3xEpic.
Epic.
Epic.
Also recommended by: Barack Obama, Christopher Hitchens, Cory Booker
Invisible Man
4 people recommendedrecommended 3xOne of my favorite books.
One of my favorite books.
One of my favorite books.
Also recommended by: Dan Barreiro, Jacqueline Novogratz, Maya Angelou
Here Comes Everybody
3 people recommendedRyan Holiday recommended this book on his blog.
Also recommended by: Tyler Cowen, Derek Sivers
The River of Doubt
3 people recommendedrecommended 3xI thought I knew about Theodore Roosevelt.
I thought I knew about Theodore Roosevelt.
I thought I knew about Theodore Roosevelt.
Also recommended by: Patrick Oshaughnessy, Saagar Enjeti
History of the Peloponnesian War
3 people recommendedrecommended 3xAn obligation for every student of history.
An obligation for every student of history.
An obligation for every student of history.
Also recommended by: Matt Mullenweg, Steven Pressfield
A series of essays about Montaigne, who invented the essay.
A series of essays about Montaigne, who invented the essay.
A series of essays about Montaigne, who invented the essay.
Also recommended by: Marc Andreessen, Anthony Bourdain
A provocative book for the moment. Highly recommended.
A provocative book for the moment. Highly recommended.
Also recommended by: Marc Andreessen, Mike Rowe
Leadership: In Turbulent Times
3 people recommended[The author]'s masterwork.
Also recommended by: Lebron James, Scott Belsky
Status Anxiety
3 people recommendedEvery ambitious young person should read.
Also recommended by: Andrew Wilkinson, Garry Tan
The Tiger
2 people recommendedHoly shit, this book is good. Just holy shit.
Also recommended by: Patrick Oshaughnessy

Aeneid
2 people recommendedThereβs no other way to put: the story is AMAZING. Better than the Odyssey, better than Juvenalβs Satires. Inspiring, beautiful, exciting, and eminently readable, I loved this.
Also recommended by: Mark Zuckerberg
The Moviegoer
2 people recommendedrecommended 4xThe novel that every young kid stuck in their own head needs to read.
The novel that every young kid stuck in their own head needs to read.
The novel that every young kid stuck in their own head needs to read.
The novel that every young kid stuck in their own head needs to read.
Also recommended by: Walter Isaacson
The Moral Animal
2 people recommendedrecommended 2xThe definitive beginner text on evolutionary psychology and one of the easiest to get into.
The definitive beginner text on evolutionary psychology and one of the easiest to get into.
Also recommended by: Tom Bilyeu
What Makes Sammy Run?
2 people recommendedrecommended 2xAri Gold before Ari Gold existed
Ari Gold before Ari Gold existed
Also recommended by: Brian Koppelman
Essays
2 people recommendedrecommended 2xI strongly recommend [this book].
I strongly recommend [this book].
Also recommended by: Anthony Bourdain
Essays and Aphorisms
2 people recommendedrecommended 2xA brilliant composer of quick thoughts that will help us with our problems.
A brilliant composer of quick thoughts that will help us with our problems.
Also recommended by: Patrick Oshaughnessy

Edison
2 people recommendedrecommended 2xA really good biography.
A really good biography.
Also recommended by: Marc Andreessen
Plutarch’s Lives Volume 1
2 people recommendedI strongly recommend [this book].
Also recommended by: Mark Twain
Shadow Divers
2 people recommendedrecommended 3xA work of art.
A work of art.
A work of art.
Also recommended by: Patrick Oshaughnessy
Candide
2 people recommendedrecommended 3xA light hearted satire that pokes fun at optimism, philosophy, politics, and power.
A light hearted satire that pokes fun at optimism, philosophy, politics, and power.
A light hearted satire that pokes fun at optimism, philosophy, politics, and power.
Also recommended by: James Clear
Plutarch’s Lives Volume 2
2 people recommendedrecommended 3xI strongly recommend [this book].
I strongly recommend [this book].
I strongly recommend [this book].
Also recommended by: Mark Twain
The Epic of Gilgamesh
2 people recommendedrecommended 4xI read this on my honeymoon (probably the only person on the beach reading it, if I had to guess).
I read this on my honeymoon (probably the only person on the beach reading it, if I had to guess).
I read this on my honeymoon (probably the only person on the beach reading it, if I had to guess).
I read this on my honeymoon (probably the only person on the beach reading it, if I had to guess).
Also recommended by: Stewart Brand
The 33 Strategies of War
2 people recommendedrecommended 4xRyan Holiday recommended this book on his blog.
Ryan Holiday recommended this book on his blog.
Ryan Holiday recommended this book on his blog.
Ryan Holiday recommended this book on his blog.
Also recommended by: Patrick Bet David
Boyd
2 people recommendedrecommended 3xProbably the greatest post-WWII military strategist; he developed the F-15 and F-16, revolutionized ground tactics in war and covertly designed the US battle plans for the Gulf War.
Probably the greatest post-WWII military strategist; he developed the F-15 and F-16, revolutionized ground tactics in war and covertly designed the US battle plans for the Gulf War.
Probably the greatest post-WWII military strategist; he developed the F-15 and F-16, revolutionized ground tactics in war and covertly designed the US battle plans for the Gulf War.
Also recommended by: Patrick Oshaughnessy

Hamlet
2 people recommendedPhilosophy runs through this play.
Also recommended by: Naval Ravikant
Fahrenheit 451
2 people recommendedrecommended 3xRyan Holiday mentioned this book on Twitter.
Ryan Holiday mentioned this book on Twitter.
Ryan Holiday mentioned this book on Twitter.
Also recommended by: Tim Ferriss

The Rise of Theodore Roosevelt
2 people recommendedrecommended 2xSpectacular. Heβs my favorite president.
Spectacular. Heβs my favorite president.
Also recommended by: Jamie Dimon
Wikinomics
2 people recommendedrecommended 2xRyan Holiday recommended this book on his blog.
Ryan Holiday recommended this book on his blog.
Also recommended by: Tyler Cowen
Pillar of Fire
2 people recommendedIncredible.
Also recommended by: Christopher Hitchens
The Second Mountain
2 people recommended[One of] the best books I read [in 2019].
Also recommended by: Hugh Jackman
Xenophon’s Cyrus the Great
2 people recommendedrecommended 4xEvery ambitious young person should read.
Every ambitious young person should read.
Every ambitious young person should read.
Every ambitious young person should read.
Also recommended by: Patrick Bet David
The Library Book
2 people recommendedrecommended 3x[One of] the best books I read [in 2019].
[One of] the best books I read [in 2019].
[One of] the best books I read [in 2019].
Also recommended by: Celeste Ng

American Caesar
2 people recommendedrecommended 3x[One of] the best books I read [in 2019].
[One of] the best books I read [in 2019].
[One of] the best books I read [in 2019].
Also recommended by: Elon Musk
Letters to His Son on the Art of Becoming a Man of the World and a Gentleman
[The author] wrote his letters to his illegitimate son, tutoring him on how to learn, how to think, how to act, how to deal with important people. I donβt agree with all his advice but most of it is great.
The Lives of the Most Excellent Painters, Sculptors, and Architects
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.
Sex on the Brain
One of the better books on evolutionary biology that focuses almost entirely on the biological and psychological differences between men and women.
Sherman
This was someone I knew little about before I read the book, and by the end of it found myself referencing and thinking of him constantly.
Selected Epigrams
Hilarious. I have one hanging on the gate in front of my house.
Fight Club
recommended 4xIβm amazed how many young people havenβt read this book. Truly life-changing.
Iβm amazed how many young people havenβt read this book. Truly life-changing.
Iβm amazed how many young people havenβt read this book. Truly life-changing.
Iβm amazed how many young people havenβt read this book. Truly life-changing.
Letters from a Self-Made Merchant to His Son
recommended 4xThe (supposedly) 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 (supposedly) 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 (supposedly) 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 (supposedly) 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.
Rules for Radicals
recommended 4xThis is the '48 Laws of Power' written in more of an idealist, activist tone.
This is the '48 Laws of Power' written in more of an idealist, activist tone.
This is the '48 Laws of Power' written in more of an idealist, activist tone.
This is the '48 Laws of Power' written in more of an idealist, activist tone.
The Harder They Fall
recommended 4xAbout boxing and loosely based on the Primo Carnera scandal.
About boxing and loosely based on the Primo Carnera scandal.
About boxing and loosely based on the Primo Carnera scandal.
About boxing and loosely based on the Primo Carnera scandal.
Brave New War
recommended 3xRyan Holiday recommended this book on his blog.
Ryan Holiday recommended this book on his blog.
Ryan Holiday recommended this book on his blog.
Fragments
A bit poetic. But those beautiful lines are really the same direct advice and timeless, perspective-changing observations.
The Pirate’s Dilemma
recommended 2xRyan Holiday recommended this book on his blog.
Ryan Holiday recommended this book on his blog.
The Net Delusion
recommended 2xRyan Holiday recommended this book on his blog.
Ryan Holiday recommended this book on his blog.
The Moral Sayings Of Publius Syrus
recommended 3xA Syrian slave in the first century BC, Publius Syrus is a fountain of quick, helpful wisdom that you cannot help but recall and apply to your life.
A Syrian slave in the first century BC, Publius Syrus is a fountain of quick, helpful wisdom that you cannot help but recall and apply to your life.
A Syrian slave in the first century BC, Publius Syrus is a fountain of quick, helpful wisdom that you cannot help but recall and apply to your life.
Tough Jews
recommended 4xAmazing book [...] about Jewish gangsters.
Amazing book [...] about Jewish gangsters.
Amazing book [...] about Jewish gangsters.
Amazing book [...] about Jewish gangsters.
Ulysses S. Grant
recommended 4xI loved [this book] a lot.
I loved [this book] a lot.
I loved [this book] a lot.
I loved [this book] a lot.
The Cathedral & the Bazaar
recommended 3xRyan Holiday recommended this book on his blog.
Ryan Holiday recommended this book on his blog.
Ryan Holiday recommended this book on his blog.
Average Is Over
Changes how you see the future and help explain real pain points in our new economyβboth good and bad.
The Strategy Paradox
recommended 4xRyan Holiday recommended this book on his blog.
Ryan Holiday recommended this book on his blog.
Ryan Holiday recommended this book on his blog.
Ryan Holiday recommended this book on his blog.
On Sparta
recommended 3xA collection of biographies (and aphorisms) from the famous Spartans.
A collection of biographies (and aphorisms) from the famous Spartans.
A collection of biographies (and aphorisms) from the famous Spartans.
Totto-Chan
Has sold something like 5 million copies in Japan alone (an insane number). Totto-Chan is a special figure in modern Japanese cultureβshe is a celebrity on par with Oprah or Ellen.
Reveille for Radicals
recommended 2xThis is the '48 Laws of Power' written in more of an idealist, activist tone.
This is the '48 Laws of Power' written in more of an idealist, activist tone.
Sixteen Satires
recommended 2xBitter, sarcastic attacks on Rome.
Bitter, sarcastic attacks on Rome.
Up from Slavery
recommended 2xRyan Holiday recommended this book on his blog.
Ryan Holiday recommended this book on his blog.
President Lincoln
recommended 3x[One of] my three favorite books about [Lincoln].
[One of] my three favorite books about [Lincoln].
[One of] my three favorite books about [Lincoln].
The Woman’s Hour
recommended 4x[One of] the best books I read [in 2019].
[One of] the best books I read [in 2019].
[One of] the best books I read [in 2019].
[One of] the best books I read [in 2019].
Lone Star
recommended 3x[One of] the best books I read [in 2019].
[One of] the best books I read [in 2019].
[One of] the best books I read [in 2019].