Author Guide · Stoicism & Self-Improvement
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Ryan Holiday left the University of California, Riverside, at 19, became a research assistant to Robert Greene, and was soon director of marketing at American Apparel. In 2012, aged 25, he published Trust Me, I’m Lying, a book about how he had fed stories to blogs and watched them climb into the national press. Two years later he changed subject. The Obstacle Is the Way (2014) took its title from a line in Marcus Aurelius’s Meditations and was handed round the locker rooms of the New England Patriots and the Seattle Seahawks. Since then he has written mostly about the Stoics, and his books have sold more than 10 million copies in over forty languages. This guide covers his 13 key books, in order, and where to begin.
By Lisanne Swart · 13 key books · 2012–2025 · Updated October 2026
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Quick answer
Ryan Holiday’s best-known books are The Obstacle Is the Way (2014), Ego Is the Enemy (2016), The Daily Stoic (2016, with Stephen Hanselman) and Stillness Is the Key (2019), followed by the four-book Stoic Virtues series, from Courage Is Calling (2021) to Wisdom Takes Work (2025). Start with The Obstacle Is the Way. Below are his 13 key books in order, the series order, and the controversy over his early media work.
Where to Start with Ryan Holiday
If you want the book that made his name
→ The Obstacle Is the Way (2014) — Marcus Aurelius’s idea that the obstacle becomes the way.
If you want Stoicism one page a day
→ The Daily Stoic (2016) — 366 short readings, one for each day of the year.
If you want the Stoics’ own lives
→ Lives of the Stoics (2020) — 26 short biographies, from Zeno to Marcus Aurelius.
If you want a story rather than advice
→ Conspiracy (2018) — Peter Thiel, Hulk Hogan and the end of Gawker.
13 Ryan Holiday Books, in Order
Trust Me, I’m Lying
His first book, drawn from his work for clients including Tucker Max, Robert Greene and American Apparel’s Dov Charney. The first half argues that blogs, paid by the pageview, drive the news and can be manipulated, with a story passed from small sites to large ones; the second half looks at what that does to the media. Before publication he posed as an expert through the service Help a Reporter Out and was quoted by outlets including The New York Times and ABC. It entered The Wall Street Journal bestseller list.
The Obstacle Is the Way
The title comes from Marcus Aurelius: “The impediment to action advances action. What stands in the way becomes the way.” Holiday splits the response to an obstacle into three disciplines, perception, action and will, and illustrates each with short histories, from John D. Rockefeller to Amelia Earhart. Bill Belichick’s Patriots and Pete Carroll’s Seahawks passed it round their players. An expanded tenth-anniversary edition appeared in 2024.
Ego Is the Enemy
A book in three parts, Aspire, Success and Failure, about how ego gets in the way at each stage of a career. The examples run from Charles Darwin and Bill Belichick to Genghis Khan, Ulysses S. Grant and the Byzantine general Belisarius, whose victories went unrewarded. It forms an informal trilogy with The Obstacle Is the Way and Stillness Is the Key.
The Daily Stoic
Written with Stephen Hanselman: one page for each day of the year, each pairing a short passage from a Stoic such as Marcus Aurelius, Seneca or Epictetus with a commentary. It reached number two on The Wall Street Journal hardcover business list, and the name now covers his website, daily email and podcast. A tenth-anniversary edition came out in October 2026.
Perennial Seller
Why some books, films and albums keep selling for decades: The Shawshank Redemption, which flopped in cinemas, Greene’s The 48 Laws of Power, which sold more than a million copies without topping the bestseller lists, and Iron Maiden, still filling stadiums with little radio play. His argument is that lasting work comes from creators who do not separate the making from the marketing.
Conspiracy
In 2007 Gawker’s tech blog Valleywag outed the investor Peter Thiel as gay. Years later Thiel secretly paid for Hulk Hogan’s lawsuit over a sex tape Gawker had published, and in 2016 a Florida jury awarded Hogan 140 million dollars, which drove Gawker into bankruptcy. Holiday interviewed Thiel and Gawker’s founder Nick Denton on the record. The American Prospect praised his even-handed storytelling but faulted him for passing over the legal-ethics questions.
Stillness Is the Key
An argument for calm and focus, drawing on Stoic and Buddhist thinkers, from Confucius and Seneca to Thich Nhat Hanh and Nietzsche. The examples include the baseball player Sadaharu Oh, whose study of Zen informed his hitting, Fred Rogers, Anne Frank and her diary, and Winston Churchill at his country house, Chartwell.
Lives of the Stoics
Written with Stephen Hanselman: 26 short biographies in roughly chronological order, from Zeno, the merchant who founded the school in Athens, to the emperor Marcus Aurelius. Each chapter gives its subject a nickname, such as “Cato the Younger, Rome’s Iron Man”. It includes one woman, Porcia Cato, and the honorary non-Stoic Cicero. The Stoic writer Donald Robertson praised it as material “not easily obtainable elsewhere”.
Courage Is Calling
The first of four books on the Stoic cardinal virtues, in three parts: fear, courage and heroism. Its examples include Charles de Gaulle, Florence Nightingale, Martin Luther King Jr., Frederick Douglass, the Roman senator Helvidius Priscus, who defied the emperor Vespasian, and Frank Serpico, the New York detective who exposed police corruption.
Discipline Is Destiny
The second Stoic Virtues book, on temperance, or self-discipline. Its models include Lou Gehrig, Queen Elizabeth II, the boxer Floyd Patterson, Marcus Aurelius and Toni Morrison; its cautionary tales are Napoleon, F. Scott Fitzgerald and Babe Ruth.
The Daily Dad
The format of The Daily Stoic applied to fatherhood: a short reading on parenting for each day of the year. Holiday wrote it as the father of two young sons.
Right Thing, Right Now
The third Stoic Virtues book, on justice, which Holiday treats as the virtue the others serve: doing what is right even when it costs something. Its figures include Marcus Aurelius, Florence Nightingale, Jimmy Carter, Gandhi and Frederick Douglass.
Wisdom Takes Work
The final Stoic Virtues book, published in October 2025, argues that wisdom is the virtue the other three depend on. Drawing on Montaigne, Seneca, Joan Didion and Abraham Lincoln, it covers learning through reading and experience, listening more than talking, and questioning one’s own beliefs, and warns that power and intelligence are dangerous without wisdom.
In What Order to Read Ryan Holiday
Most of Holiday’s books stand alone, and each one is built from short chapters that can be read separately. The Obstacle Is the Way (2014), Ego Is the Enemy (2016) and Stillness Is the Key (2019) are often read as a loose trilogy; Penguin sells them together as The Way, the Enemy, and the Key. The Daily Stoic and The Daily Dad are meant to be read one page a day, starting on any date.
The Stoic Virtues series follows the four cardinal virtues and is best read in order: Courage Is Calling (2021, courage), Discipline Is Destiny (2022, temperance), Right Thing, Right Now (2024, justice) and Wisdom Takes Work (2025, wisdom). Trust Me, I’m Lying, Perennial Seller and Conspiracy are about media and marketing, and can be read at any point.
A reading path
1. The Obstacle Is the Way (2014)
2. Ego Is the Enemy (2016)
3. The Daily Stoic (2016)
4. Lives of the Stoics (2020)
5. Courage Is Calling (2021)
6. Conspiracy (2018)
Everything Else Ryan Holiday Published
Beyond the 13 key books: 3 more, grouped by kind.
Open a group with the + to see every book in it.
Other books
3
3 books · 2013–2025
- 2013Growth Hacker Marketinga short book on start-up marketing; a paperback edition followed in 2014
- 2017The Daily Stoic Journala companion journal to The Daily Stoic, one prompt for each day
- 2025What You’re Made Forlessons from the life of the basketball coach George Raveling
The years · 1987–2025
Quick facts about Ryan Holiday
- Known for
- Popular books on Stoic philosophy, written as short, story-led lessons for everyday life, after an early career exposing how he manipulated the media.
- 1987
- Born in Sacramento County, California
- 2025
- Wisdom Takes Work completes the series
- Born
- 16 June 1987, Sacramento County, California
- Education
- University of California, Riverside; left at 19
- Worked
- Research assistant to Robert Greene; director of marketing at American Apparel until 2014; runs the marketing agency Brass Check
- Married
- Samantha Hoover, in 2015; they have two sons
- Bookshop
- The Painted Porch, on Main Street in Bastrop, Texas
- Sales
- More than 10 million copies, in over forty languages
The red mark is 2014: The Obstacle Is the Way, the first of his books on Stoic philosophy.
How Ryan Holiday Writes: A Story, Then a Lesson
Holiday writes in short chapters, each built round one idea and one or two stories from history: a general, an athlete, an emperor, a writer. The philosophy usually comes as a quotation from Marcus Aurelius, Seneca or Epictetus, followed by a story that shows it in practice and a plain conclusion for the reader. He mixes ancient and modern freely, so that Belisarius and Bill Belichick can appear in the same book.
His research runs on index cards, a method he learned from Robert Greene while working as his research assistant. He reads with notes in the margins, waits a few weeks, then copies what still matters onto 4-by-6 cards, one thought per card, filed by theme in boxes; for The Obstacle Is the Way, he has written, he filled thousands of them. The cards are later sorted into chapters.
His marketing background shows. Trust Me, I’m Lying, Growth Hacker Marketing and Perennial Seller are about getting work noticed and keeping it in print, and he has built the Stoic books into a wider operation: the Daily Stoic email and podcast, and a bookshop in Bastrop, Texas. Critics argue this makes his Stoicism more practical than philosophical; his readers tend to see that as the point.
Watch
Ryan Holiday in Conversation with Rich Roll
In this two-hour interview from 2021, Rich Roll talks with Holiday about fear and courage, the subject of Courage Is Calling, the first book in his Stoic Virtues series.
Frequently asked questions about Ryan Holiday’s books
How many books has Ryan Holiday written?
This page lists 16 books: the 13 key books above, plus Growth Hacker Marketing (2013), The Daily Stoic Journal (2017) and What You’re Made For (2025), written with the basketball coach George Raveling. Three of the 16 were written with Stephen Hanselman: The Daily Stoic, The Daily Stoic Journal and Lives of the Stoics.
What are Ryan Holiday’s books in order?
His key books in order: Trust Me, I’m Lying (2012), The Obstacle Is the Way (2014), Ego Is the Enemy (2016), The Daily Stoic (2016), Perennial Seller (2017), Conspiracy (2018), Stillness Is the Key (2019), Lives of the Stoics (2020), Courage Is Calling (2021), Discipline Is Destiny (2022), The Daily Dad (2023), Right Thing, Right Now (2024) and Wisdom Takes Work (2025).
What is the Stoic Virtues series order?
Four books, one for each Stoic cardinal virtue: Courage Is Calling (2021), Discipline Is Destiny (2022), Right Thing, Right Now (2024) and Wisdom Takes Work (2025). They cover courage, temperance, justice and wisdom. A boxed set of all four came out in May 2026.
Where should I start with Ryan Holiday?
The Obstacle Is the Way is the usual start: short, story-led chapters built on one idea from Marcus Aurelius. If you would rather read the Stoics in small doses, start with The Daily Stoic, one page a day.
What is Ryan Holiday’s most famous book?
The Obstacle Is the Way (2014), which NFL coaches including Bill Belichick and Pete Carroll gave to their players, is probably his best known, alongside Ego Is the Enemy (2016) and The Daily Stoic (2016).
Is Ryan Holiday controversial?
Partly, for his early career. In Trust Me, I’m Lying (2012) he described tactics he had used for clients such as American Apparel and the author Tucker Max, including leaking documents, creating fake social media accounts and buying traffic for stories. Before the book came out he posed as an expert through the service Help a Reporter Out and was quoted by The New York Times, MSNBC and ABC. Later, some critics, including the philosopher Massimo Pigliucci and the New York Times reporter Alexandra Alter, questioned how far his books reflect Stoic philosophy; Alter called his approach “more entrepreneurial than philosophic”.
Did Ryan Holiday work for Robert Greene?
Yes. He was Greene’s research assistant in his early twenties, and Greene was later one of the clients described in Trust Me, I’m Lying. Holiday took over Greene’s index-card research method, which he still uses.
What is the Daily Stoic?
First a book: The Daily Stoic (2016), written with Stephen Hanselman, with one Stoic passage and a short commentary for each day of the year. The name now also covers Holiday’s website, daily email and, since 2018, the Daily Stoic podcast. A tenth-anniversary edition of the book came out in October 2026.
Does Ryan Holiday own a bookshop?
Yes. In January 2020 he and his wife bought a 140-year-old building on Main Street in Bastrop, Texas, outside Austin, and opened it during the pandemic as The Painted Porch bookshop.
How old is Ryan Holiday?
He was born on 16 June 1987, in Sacramento County, California, and lives outside Austin, Texas, with his wife and two sons. He is still publishing: Wisdom Takes Work came out in October 2025, and a tenth-anniversary edition of The Daily Stoic in October 2026.
Footnotes
- Ryan Holiday — Wikipedia
- Trust Me, I’m Lying — Wikipedia
- The Obstacle Is the Way — Wikipedia
- Ryan Holiday — Penguin Random House
- The Notecard System — RyanHoliday.net, 2014
- Review of Conspiracy — The American Prospect, 2018
Bibliography last verified 9 October 2026. Where sources give different first-publication years, this page uses the year in library catalogues or the publisher’s own record.
This list was not put together by a machine.
The notes are all mine,
and the books are all his.
Lisanne x
Written by Lisanne Swart, who has curated reading lists and author guides at lisanneswart.com since 2021.
See more on her personal bookshelf.
“Ego is the enemy of what you want and of what you have.”
— Ryan Holiday, Ego Is the Enemy (2016)
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