Ryan Holiday
Writer · The Daily Stoic
Author of The Obstacle Is the Way, Ego Is the Enemy and The Daily Stoic. His Daily Stoic email has gone out every morning for close to nine years. He dropped out of college at 19 to apprentice under Robert Greene, ran marketing at American Apparel, then moved to a ranch outside Austin. Between the writing he raises cattle, donkeys and goats. Sixteen books in, the work still starts the same way: three notebooks and a walk. The research lives on index cards.
- Entries
- 25
- Does
- 17
- Recommends
- 8
- Discusses
- 0
Books
6 books in this stack
- BookRecommends$$$Cheap: Roughly under $50, or under $15/month.
Man's Search for Meaning
On his list of books to base your life on, for moving the question from what the meaning of life is to what your own actions answer. He points readers to Frankl's later book, Yes To Life, once they have finished it.
Source: RyanHoliday.net: Books To Base Your Life on (The Reading List)View item: Man's Search for MeaningOn record from 4 of 62 tracked people: 2 recommend it, 2 have discussed it - BookRecommends$$$Cheap: Roughly under $50, or under $15/month.
The Daily Stoic
Writing it put him in a daily rhythm he did not want to break, so he kept going once the manuscript was done. The Daily Stoic email came out of that.
Source: RyanHoliday.net: 34 Lessons From Writing Every Day for Two DecadesView item: The Daily StoicOn record from 4 of 62 tracked people: 3 recommend it, 1 has discussed it - BookRecommends$$$Cheap: Roughly under $50, or under $15/month.
Ego Is the Enemy
The second book in his Stoic series, on how ego threatens you whether you are chasing something, succeeding at it or picking yourself up afterwards. He opens on Cyril Connolly's line that ego sucks us down like the law of gravity.
Source: RyanHoliday.net: Books and CoursesView item: Ego Is the EnemyOn record from 2 of 62 tracked people: 2 recommend it - BookRecommends$$$Cheap: Roughly under $50, or under $15/month.
Meditations
Calls it one of the greatest books ever written and perhaps the only one of its kind, the private thoughts of the most powerful man in the world telling himself to be better. He is specific about the edition: read the Hays translation.
Source: RyanHoliday.net: Books To Base Your Life on (The Reading List)View item: MeditationsOn record from 1 of 62 tracked people: 1 recommends it - BookRecommends$$$Cheap: Roughly under $50, or under $15/month.
Stillness Is the Key
One of his own Stoic books. He planned its tour around cities with good pools, and wrote in it that few things settle you into the present moment like being in or around water.
Source: RyanHoliday.net: The Hobby That Changed My LifeView item: Stillness Is the KeyOn record from 1 of 62 tracked people: 1 recommends it - BookRecommends$$$Cheap: Roughly under $50, or under $15/month.
The Obstacle Is the Way
His first book on Stoicism. He describes the point as turning your thinking upside down, so an obstacle reads as a chance to persevere.
Source: RyanHoliday.net: Books and CoursesView item: The Obstacle Is the WayOn record from 1 of 62 tracked people: 1 recommends it
Supplements
1 supplement in this stack
- SupplementDoes it$$$Cheap: Roughly under $50, or under $15/month.
Caffeine
Sometimes takes a caffeine mint right before a run or a bike ride. He listed it, half joking, among the reasons he is glad to be alive.
Source: RyanHoliday.net: 37 (Or So) Lessons From A 37 Year OldView item: CaffeineOn record from 14 of 62 tracked people: 10 do it, 1 recommends it, 3 have discussed it
Protocols
9 entriesStructured routines and practices with a defined method.
Has added more weight training in recent years, though he lists it after swimming, running and riding. His line is that the form does not matter much, as long as there is one.
Source: RyanHoliday.net: You Need This Practice In Your LifeCranks the shower to cold every morning and says the research on immunity and metabolism is beside the point for him. He does it to settle who is in charge, quoting Seneca on treating the body rigorously so it stays obedient to the mind.
Source: RyanHoliday.net: You Actually Should Do Something That Scares You Every DayTook up more riding after an ankle injury and kept it alongside the running and swimming. He treats all three as versions of the same physical practice.
Source: RyanHoliday.net: You Need This Practice In Your LifeGuards his mornings for family first and then writing, and has told his assistant to schedule nothing before mid-morning. Early calls do not just take time, he says; they sap the energy the essential work needs.
Source: RyanHoliday.net: 34 Lessons From Writing Every Day for Two DecadesRuns the burned-out trails at Bastrop State Park or the seven and ten mile loops along Lady Bird Lake in Austin, lately in the mornings. His reasoning is that writing goes badly more often than it goes well, and a run almost always goes well.
Source: RyanHoliday.net: You Need This Practice In Your LifeSwims wherever he travels, to the point of planning a book tour around cities with good athletic club pools. What he likes is that no screen reaches him in the water, and he says he wrote a good chunk of Ego Is the Enemy doing laps.
Source: RyanHoliday.net: The Hobby That Changed My LifeLearned the method from Robert Greene while working as his research assistant and has run a messier version of it ever since. Passages move onto 4x6 cards a few weeks after he finishes a book, which he says is itself a form of editing: much of what he marked no longer looks worth keeping.
Source: RyanHoliday.net: The Notecard SystemPuts sleep on his list of things to do every single day and has no patience for treating short nights as a badge of honor. Without the energy and clarity, he argues, none of the other habits on the list are worth much.
Source: RyanHoliday.net: 13 Life-Changing Habits To Try And Do Every Single DayTells readers to close out the day the way Seneca did, going back over what they did and said once the house has gone quiet. The questions he sets are narrow: did I follow the plan, was I prepared enough, what could I do better.
Source: RyanHoliday.net: 13 Life-Changing Habits To Try And Do Every Single Day
Habits
9 entriesRecurring behaviors recorded in public statements.
Reads hundreds of books a year and insists he reads slowly, on purpose. There is no trick, by his account: he carries a book everywhere and opens it in the gaps.
Source: RyanHoliday.net: Here's Some Stuff Worth Carrying With You EverywhereWalks the farm most mornings, then goes upstairs to the office and pulls out his notebooks.
Source: RyanHoliday.net: This Is The Most Important Thing You Can Do Each MorningThree notebooks every morning, in order: one sentence about the day just gone, two pages in a black Moleskine on yesterday's workout and work, then a prompt from his own Daily Stoic Journal. He puts the ritual at about fifteen minutes and says it leaves him calm and ready to write.
Source: RyanHoliday.net: This Is The Most Important Thing You Can Do Each MorningPart of the second notebook each morning is a few lines on what he is grateful for. He says he sometimes picks deliberately unpleasant subjects, a lost friendship or a big setback, and asks what he got out of them.
Source: RyanHoliday.net: This Is The Most Important Thing You Can Do Each MorningGets his quiet in the pool, swimming as often as he can partly because nothing can reach him there: no phone, no noise. He asks the reader how often they are truly unreachable, then answers that it is not often enough.
Source: RyanHoliday.net: 13 Life-Changing Habits To Try And Do Every Single DayTwenty years of writing almost every day, by his own count, plus a Stoic meditation emailed out every morning for close to nine years. He calls the daily email a forcing function: it gives him reps he would never get from publishing books alone.
Source: RyanHoliday.net: 34 Lessons From Writing Every Day for Two DecadesMarks passages, writes questions in the margin and folds the bottom corner of any page he wants to find again. He carries a pen for it, usually one taken from the last hotel, and says those marks are what he later transcribes onto cards.
Source: RyanHoliday.net: Here's Some Stuff Worth Carrying With You EverywhereCarries a coin reading Memento Mori in his left pocket and an Amor Fati coin in the right, both sold by his own Daily Stoic store. The thought of dying should shadow everything, he says, not as a downer but as a way to cut out nonsense.
Source: RyanHoliday.net: Here's Some Stuff Worth Carrying With You EverywhereNo alerts, no social media and no news on his phone; he keeps it for music, podcasts, calls and email. AirPods help it stay in his pocket, and he credits Cal Newport's digital minimalism for the framing.
Source: RyanHoliday.net: Here's Some Stuff Worth Carrying With You Everywhere
In their own words
Checked word for word against the linked source
“The whole ritual takes maybe 15 minutes and then it’s done. By the time I am finished, I am centered, I am calm and most importantly, I am primed to do the actual creative work by which I make my living.”
RyanHoliday.net: This Is The Most Important Thing You Can Do Each Morning (opens in a new tab) · 14 Nov 2017 On Journaling
“The reason I interrupt my warm showers by cranking the knob to the side is far more simple, in fact it’s nearly tautological. I do it to do it. It’s making a statement about who is in charge.”
RyanHoliday.net: You Actually Should Do Something That Scares You Every Day (opens in a new tab) · 16 Mar 2022 “What I love about swimming is that it’s one of the few places on Earth where screens can’t reach you. My phone doesn’t ring.”
RyanHoliday.net: The Hobby That Changed My Life (opens in a new tab) · 4 Sep 2024 On Swimming
“But I don’t want this to be easy. Writing them down by hand forces me to take my time and to go over everything again (taking notes on a Kindle is too easy and that’s the problem).”
RyanHoliday.net: The Notecard System (opens in a new tab) · 1 Apr 2014 “I have been writing almost every day for twenty years. How many millions of words is that? I don’t know.”
RyanHoliday.net: 34 Lessons From Writing Every Day for Two Decades (opens in a new tab) · 2 Jul 2025
Episodes from the feed
Show archive, The Daily Stoic (opens in a new tab)Last fetched . A title without a link is an episode the feed publishes no page of its own for.
- BONUS | 3 Life-Changing Lessons From Seneca in 3 Minutes (opens in a new tab) · 3m
- You’re in a Hurry and Don’t Know Why | A Hard Winter Training (opens in a new tab) · 8m
- The Moment Ryan’s Italy Trip Went Sideways (opens in a new tab) · 31m
- The Stoic Reminders Hiding All Over Rome (opens in a new tab) · 30m
- Don’t Let It Keep Slipping Away | The Philosopher's School Is A Hospital (opens in a new tab) · 6m
Stack notes are paraphrased. Anything in quotation marks is a short excerpt copied from the transcript it links to. Not medical advice. Not affiliated with, endorsed by, or reviewed by anyone listed. How this works.