Ryan Holiday

Prominent writer on strategy and business.

Ryan Holiday is a media strategist and prominent writer on strategy and business. After dropping out of college at nineteen to apprentice under Robert Greene, author of The 48 Laws of Power, he went on to advise many bestselling authors and multiplatinum musicians. He served as director of marketing at American Apparel for many years, where his campaigns have been used as case studies by Twitter, YouTube, and Google and written about in AdAge, the New York Times, and Fast Company. His first book, Trust Me I’m Lying—which the Financial Times called an “astonishing, disturbing book”—was a debut bestseller and is taught in colleges around the world. He is the author of two other books and is now published in 16 languages. He currently lives in Austin, Texas with his rebellious puppy, Hanno and pet goats

PhilosophersNotes on Ryan Holiday's Books All PhilosophersNotes

The Daily Stoic

366 Meditations on Wisdom, Perseverance, and the Art of Living

by Ryan Holiday, Stephen Hanselman

This book combines two of my favorite things: Stoicism + Ryan Holiday’s wisdom. Stoicism was one of the most influential philosophy of the Roman world and has continued to influence many of history’s greatest minds. As Ryan says: It’s time to bring it back as a powerful tool “in the pursuit of self-mastery, perseverance, and wisdom.” This is one of the my favorite books ever. Big Ideas we explore: the #1 thing to know about Stoicism, how to create tranquility, a good answer to “What’s the latest and greatest?!,” the 2 essential tasks in life and the art of acquiescence (aka amor fati).

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Antifragility & Modern Hērō & Stoicism

Ego Is the Enemy

by Ryan Holiday

Meet the enemy: Your ego. Our guide, Ryan Holiday, wrote one of my favorite books of 2015: The Obstacle Is the Way. Ego Is the Enemy is now one of my favorite books of 2016. It’s fantastic. Big Ideas we explore include: defining ego, becoming more than a flash in the pan, finally answering the question of whether it takes 10,000 or 20,000 hours to attain mastery, the virtue and value of staying true to your own path and making it rather than faking it.

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Leadership & Stoicism

Ego Mastery Modern Classic soul Spirit Top 101 Wisdom

The Obstacle Is the Way

The Timeless Art of Turning Trials into Triumph

by Ryan Holiday

Ryan Holiday is brilliant. So is this book. The ancient Stoics taught us how to not only accept challenges but to thrive on them. Ryan brings their wisdom to life with compelling stories of great peeps who have rocked it in the face of adversity. In the Note we'll take a quick look at the three keys to making obstacles work for us: Perception + Action + Will.

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Antifragility & Stoicism

mental training Mind Modern Classic Philosophy Top 101

+1s Inspired by Ryan Holiday All +1s

How to High Five Your Inner Daimon
#3

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My Philosophy in One Word

To the extent that there’s a gap between who you’re capable of being in any given moment and who are actually being in that moment, you will experience a level of discontent. Regret. Anxiety. Depression. As per our last +1, a bad-daimon. aka:

+1 inspired by Note: Ego Is the Enemy

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Masterpiece Days & Optimal Living

Actualization Areté disconnected Eudaimonia Excellence flourish micro-moment soul Spirit Virtue

The Obstacle Is the Way
#61

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Plus: The Paradox of Fire

Marcus Aurelius once wrote to himself in the journal he never intended to publish that we now know as Meditations that “The impediment to action advances the action. What stands in the way becomes the way.”

+1 inspired by Note: The Obstacle Is the Way

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Antifragility & Stoicism

Acceptance challenges courage Growth mental training Mind omms Philosophy success

Euthymia
#100

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How to Live with Energized Tranquility

First: Welcome to our 100th +1. It’s a special milestone. Kinda excited about it. 😃 Let’s celebrate it with one of my favorite words ever: euthymia. Seneca talks about the power of euthymia in his classic essays. He tells us that euthymia is all about kn...

+1 inspired by Note: Ego Is the Enemy

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Purpose & Stoicism

Actualization Authenticity Dharma flourish Philosophy priorities self-awareness self-mastery soul Spirit unmotivated

The Serenity Prayer
#133

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Serenity + Courage + Wisdom = A Winning Combo

In our last +1 we talked about Byron Katie’s idea that you can be in one of three businesses: someone else’s business, God’s business or YOUR business. Quick recap: We want to stay out of other people’s business and we want to stay out of God’s business as w...

+1 inspired by Note: The Daily Stoic

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Conquering Anxiety & Stoicism

Mind Power self-awareness success

The 5 (Greek) Keys to Optimizing
#200

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Areté + Eudaimonia + en*theos + Hērōs + Euthymia

We’re hitting another exciting milestone in our +1 series today: #200. Let’s celebrate in style. We celebrated #100 with one of my favorite Greek words: euthymia. You may recall that euthymia is a word ...

+1 inspired by Note: Ego Is the Enemy

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Hero Training & Optimal Living

Areté en-theos Eudaimonia euthymia hero-training Optimal Living soul Spirit Wisdom

You, a Farmer and His Horse
#375

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A Zen Fable on Good and Bad Luck

Once upon a time in a land far away, there was an old farmer. This man had a horse. Then, one day, his horse ran away. All the neighbors said, “Gah!! That’s such a bummer. What bad luck.” The man said, “Maybe. It is what is.” Then, one day, the horse return...

+1 inspired by Note: The Daily Stoic

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Antifragility & Stoicism

Growth Mind self-awareness Wisdom

How to Reclaim Lost Time, Energy + Brainpower
#557

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Pro Tip: Practice Saying “I Don’t Know” + “I Don’t Care”

As we’ve discussed, Ryan Holiday is a modern Stoic. I think of him several times a day when I take his “Memento Mori” coin out of my pocket and flip it as I do my warm-up hike on...

+1 inspired by Note: The Daily Stoic

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Conquering Digital Addiction & Stoicism

conquering-digital-addiction memento-mori Mind Philosophy stoicism technology Wisdom

Pankration = "All Strength"
#571

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Q: What Kind of Boxer Are You?

In our last +1, we talked about being an Optimus-Champion in our Big 3. We had fun with one of my new mantras: Champ Champ Champ. (Laughing.) (You come up with a mantra that makes your soul smile?) Today I want to talk a little m...

+1 inspired by Note: The Daily Stoic

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Antifragility & Confidence

antifragility confidence courage Grit Mental Toughness Mind persistence

The Optimizer in the Arena
#572

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Daring Greatly Daily

In our last +1, we talked about daring greatly, being willing to enter the arena of life and getting up every time we get knocked down. If that isn’t the perfect segue into Theodore Roosevelt’s wisdom from what is now known as his “Man in the Arena” speech, I don’t know what is.

+1 inspired by Note: The Daily Stoic

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Masterpiece Days & Modern Hērō

Actualization big-picture commitment courage masterpiece-days modern-hero soul Spirit

The Optimus Medallion
#708

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Coming Soon to a Pocket Near You!

As we prepared for our inaugural Optimize Coach program, we were thinking about some cool stuff we could send our Coaches that would symbolize our commitment. Of course, everyone will be getting an Optimize-blue t-shirt but we were trying to come up ...

+1 inspired by Note: The Daily Stoic

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Greatest Year Ever & Modern Hērō

Areté big-picture Coach Eudaimonia greatest-year-ever modern-hero soul Spirit Virtue

Use It or Lose It, a Case Study
#729

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Aka: Where’d My Left Forearm Go?

In our last +1, we had fun hanging out with my new bionic arm as we stepped into the stimulus-response gap to choose our optimal response to life’s inevitable challenges. I briefly mentioned the fact that, the...

+1 inspired by Note: The Obstacle Is the Way

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Antifragility & Learning

antifragility Body Gratitude Grit Learning memento-mori Mental Toughness

At Least THAT Didn't Happen
#849

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Something to Consider

The other day I was out on the Trail enjoying a run. Then I kinda tripped and then slipped and then caught myself before falling. Oops. 😲 Good news: I didn’t fall hard on the pretty-much-healed but still-not-quite-100%-healed arm. Not so good news: The way I kinda caught myse...

+1 inspired by Note: The Daily Stoic

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Conquering Perfectionism & Modern Hērō

conquering-perfectionism equanimity Gratitude Happiness Mind modern-hero tool

You and Your Gordion Knots
#860

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Conquering Our Super-Tricky Challenges

Skipping the longer philosophical chat about the ethics of being a conqueror, Today we’re going to chat about Alexander the Great. More specifically, we’re going to talk about him and a knot. The Gordion Knot. You know the story? Wikipedia tells us that legend has it th...

+1 inspired by Note: The Obstacle Is the Way

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Antifragility & Stoicism

antifragility equanimity Mental Toughness Mind Philosophy stoicism

Got Firm Determination?
#861

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Resolving to Untie the Knots in Our Lives

In our last +1, we hung out with Alexander the Great and watched him cut the legendary Gordion Knot. We ended that discussion with a couple questions: Got any seemingly impossible knots in your life? And… Is there a more direct and/or forceful approach to resolving the is...

+1 inspired by Note: The Obstacle Is the Way

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Antifragility & Confidence

antifragility commitment confidence courage Grit Mental Toughness Mind

The Daily Stoic Kid
#891

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What Coin Will YOU Pick Today?

In our last +1, we talked about going deep to serve profoundly. Immediately after finishing that +1, I went downstairs to hang out with the family. But… Before I stepped out of the office to check in for some Deep Love time, I actually grabbed my new collection of Daily Stoic co...

+1 inspired by Note: The Daily Stoic

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Fatherhood & Stoicism

equanimity Fatherhood memento-mori Mind Philosophy stoicism Wisdom

Stoic Shipwrecks
#892

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And Kids at the Park Biting You

In our last +1, we had fun reflecting on a new ritual Emerson and I are having fun with. It’s been super fun to reflect on ancient Stoic wisdom via Ryan Holiday’s modern medallions. (Thanks, Ryan!) Today I want to chat about that P...

+1 inspired by Note: The Daily Stoic

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Fatherhood & Stoicism

equanimity Fatherhood Grit Mind Philosophy stoicism Wisdom

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Ryan Holiday

Prominent writer on strategy and business.

PhilosophersNotes on Ryan Holiday's Books All PhilosophersNotes

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+1s Inspired by Ryan Holiday All +1s

How to High Five Your Inner Daimon #3 Get instant access to all +1's! Join nearly 10,000 members in the 1,000-Day Epic Optimizing Challenge and start optimizing your life today. Join Now

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You, a Farmer and His Horse #375 Get instant access to all +1's! Join nearly 10,000 members in the 1,000-Day Epic Optimizing Challenge and start optimizing your life today. Join Now

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How to Reclaim Lost Time, Energy + Brainpower #557 Get instant access to all +1's! Join nearly 10,000 members in the 1,000-Day Epic Optimizing Challenge and start optimizing your life today. Join Now

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Pankration = "All Strength" #571 Get instant access to all +1's! Join nearly 10,000 members in the 1,000-Day Epic Optimizing Challenge and start optimizing your life today. Join Now

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The Optimizer in the Arena #572 Get instant access to all +1's! Join nearly 10,000 members in the 1,000-Day Epic Optimizing Challenge and start optimizing your life today. Join Now

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The Optimus Medallion #708 Get instant access to all +1's! Join nearly 10,000 members in the 1,000-Day Epic Optimizing Challenge and start optimizing your life today. Join Now

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Use It or Lose It, a Case Study #729 Get instant access to all +1's! Join nearly 10,000 members in the 1,000-Day Epic Optimizing Challenge and start optimizing your life today. Join Now

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At Least THAT Didn't Happen #849 Get instant access to all +1's! Join nearly 10,000 members in the 1,000-Day Epic Optimizing Challenge and start optimizing your life today. Join Now

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You and Your Gordion Knots #860 Get instant access to all +1's! Join nearly 10,000 members in the 1,000-Day Epic Optimizing Challenge and start optimizing your life today. Join Now

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Got Firm Determination? #861 Get instant access to all +1's! Join nearly 10,000 members in the 1,000-Day Epic Optimizing Challenge and start optimizing your life today. Join Now

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The Daily Stoic Kid #891 Get instant access to all +1's! Join nearly 10,000 members in the 1,000-Day Epic Optimizing Challenge and start optimizing your life today. Join Now

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Stoic Shipwrecks #892 Get instant access to all +1's! Join nearly 10,000 members in the 1,000-Day Epic Optimizing Challenge and start optimizing your life today. Join Now

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Interviews with Ryan Holiday All Interviews

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How to High Five Your Inner Daimon
#3

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The Obstacle Is the Way
#61

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Euthymia
#100

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The Serenity Prayer
#133

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The 5 (Greek) Keys to Optimizing
#200

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You, a Farmer and His Horse
#375

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How to Reclaim Lost Time, Energy + Brainpower
#557

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Pankration = "All Strength"
#571

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The Optimizer in the Arena
#572

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The Optimus Medallion
#708

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Use It or Lose It, a Case Study
#729

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At Least THAT Didn't Happen
#849

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You and Your Gordion Knots
#860

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Got Firm Determination?
#861

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The Daily Stoic Kid
#891

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Stoic Shipwrecks
#892

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