The character arc of Ryan Holiday
A life drawn by Character Arc from the public record
Born on 16 June 1987 in Sacramento County, California. Between then and now sit the University of California, Riverside left at nineteen, a marketing career, Trust Me I'm Lying in 2012, The Obstacle Is the Way in 2014, Ego Is the Enemy and The Daily Stoic in 2016, a podcast from 2018, and a book in almost every year since. The line below draws the story so far, in order.
Tap the line to pluck it. Hover or tap any mark for its card. Drawn from the public record of his life; the sources are at the foot of the page.
Who is Ryan Holiday?
He left at nineteen and never stopped writing.
He left the University of California, Riverside in his second year, at nineteen, to work instead. He went into marketing, and by his early twenties was director of marketing at American Apparel, which he left in October 2014. His first book, Trust Me, I'm Lying, came out in 2012 when he was twenty four, and was about how media manipulation actually works from the inside.
Then the line turns. The Obstacle Is the Way, published in 2014, took Marcus Aurelius and Stoicism and put them in front of a general audience, and it travelled first through sport: he visited NFL team headquarters and the book spread through locker rooms before it reached bookshops properly. Ego Is the Enemy and The Daily Stoic both came in 2016.
Since then the output has been relentless and steady: Conspiracy in 2018, Stillness Is the Key in 2019, Lives of the Stoics in 2020, Courage Is Calling in 2021, Discipline Is Destiny in 2022, The Daily Dad in 2023, Right Thing Right Now in 2024 and Wisdom Takes Work in 2025. He has hosted The Daily Stoic podcast since 2018, lives on a ranch near Austin, Texas and runs an independent bookshop there. A great many people encountered Stoicism because of him, which is not a small thing for a philosophy nearly two thousand years old.
The moments
Ryan Holiday's timeline.
The 2000s
He left at nineteen
Setback, and it changed everything. Nineteen, out of university, with no qualification and no plan anybody would have signed off.
The 2010s
Marketing at American Apparel
Milestone, and it changed his direction. A marketing directorship in his early twenties, which is where the first book came from.
Trust Me, I'm Lying
Milestone, and it changed everything. Twenty four years old, and a first book about how media manipulation works from the inside.
Growth Hacker Marketing
Milestone. A short second book, in the year between the first and the one that changed things.
Stay in marketing, or write
Crossroads, decided.
The paths laid out: write full time, taken, or stay in the job. He has published a book in almost every year since, and Stoicism is now read by millions who had never heard of it.
The Obstacle Is the Way
Milestone, and it changed everything. Stoicism, handed to a general audience. It travelled through locker rooms before it reached bookshops.
He left American Apparel
Setback, and it changed his direction. The salary gone, in the year the writing career actually started.
Ego, and The Daily Stoic
Milestone, and it changed everything. Two books in one year, one of them a page a day for a year.
The podcast begins
Milestone, and it changed his direction. A daily podcast on top of a book a year.
Stillness Is the Key
Milestone, and it changed his direction. The third of a trilogy, and then the biographies behind it.
The 2020s
The virtue series
Milestone, and it changed everything. Four cardinal virtues, one book each, delivered on time every year.
A bookshop, and a ranch
Milestone. A writer who opened a bookshop, which is either sentimental or exactly right.
The line reaches today still adding to itself, which is why it is drawn now rather than at the end. What it has set moving is an ancient philosophy back into general use, and a plainer demonstration besides: publishing something every year for more than a decade beats publishing a masterpiece you never finish.
What he wrote
Books by Ryan Holiday
- 2012
Trust Me, I'm Lying
His first book, on how media manipulation works, written from inside the trade that does it.
- 2014
The Obstacle Is the Way
Stoicism for a general audience. It spread through locker rooms before it reached bookshops properly.
- 2016
Ego Is the Enemy
The second of the trilogy, on the thing that undoes people after they succeed.
- 2016
The Daily Stoic
A page of Stoic philosophy for each day of the year, with Stephen Hanselman.
- 2019
Stillness Is the Key
The third of the trilogy, on doing less and thinking more clearly.
- 2021
Courage Is Calling
The first of four books, one for each cardinal virtue.
- 2022
Discipline Is Destiny
The second virtue, on self command as the foundation of everything else.
- 2025
Wisdom Takes Work
The fourth and final virtue in the series, published in 2025.
Your turn
Every line draws a unique story.
His left university at nineteen and shipped a book almost every year after. Yours is already further along than you think, and drawing it takes about five minutes.
Ryan Holiday: frequently asked questions
What people ask about his line.
What is Ryan Holiday's character arc?
What is The Obstacle Is the Way by Ryan Holiday?
Did Ryan Holiday go to university?
What is Ryan Holiday's virtue series?
What is The Daily Stoic by Ryan Holiday?
How many books has Ryan Holiday written?
Does Ryan Holiday own a bookshop?
Where does this timeline of Ryan Holiday's life come from?
More character arcs
Lives that rhyme with his.
Sources
- Ryan Holiday, English Wikipedia biography, filed under living people.
- Publisher records for The Obstacle Is the Way, Ego Is the Enemy, The Daily Stoic and the virtue series.