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

Stillness Is the Key

by Ryan Holiday

This is our fourth Note on one of Ryan Holiday’s books. Ryan is one of my absolute favorite writers. One of the testimonials in the front of the book perfectly captures my sentiment. Screenwriter and director Brian Koppelman (Rounders, Ocean’s Thirteen and Billions) puts it this way: “I don’t have many rules in life, but one I never break is: If Ryan Holiday writes a book, I read it as soon as I can get my hands on it.” (btw: Cal Newport’s the first testimonial. He says: “Some authors give advice. Ryan Holiday distills wisdom. This book is a must read.”) Penguin Random House sent me an advance copy of this book. As I knew it would be: It’s fantastic. Of course, the book’s packed with Big Ideas and I’m excited to share some of my favorites so let’s jump straight in!

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Confidence & Stoicism

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

Ancient Wisdom Best of Optimize Modern Classic Top 101 Work

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

Best of Optimize 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

Best of Optimize mental training Modern Classic Philosophy Top 101 Work

+1s Inspired by Ryan Holiday All +1s

How to High Five Your Inner Daimon
#3

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: Unhappiness. The trick to closing the gap between who you...

+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

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.” Ryan Holiday wrote a book inspired by that wisdom called The Obstacle Is the Way. It’s brill...

+1 inspired by Note: The Obstacle Is the Way

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Antifragility & Stoicism

Acceptance Best of Optimize challenges courage Growth mental training omms Philosophy success Work

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 knowing yourself and having the courage to wal...

+1 inspired by Note: Ego Is the Enemy

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Purpose & Stoicism

Actualization Authenticity Best of Optimize 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 we remain exclusively (!) in our busin...

+1 inspired by Note: The Daily Stoic

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Conquering Anxiety & Stoicism

Power self-awareness success Work

Infinite Optionality
#191

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The Ticket to Antifragility

Let’s talk some more about how to become Antifragile. We’ve already talked about it on a high level. Super quick recap: If you’re fragile you break easily. If you’re robust you withstand more pressure until you break. If you’re ANTIfragile, you actually get stronger the more you’re knocked ar...

+1 inspired by Note: The Obstacle Is the Way

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Antifragility & Confidence

antifragility confidence Hope journal-exercise Mental Toughness persistence Strategy Work

The Big Picture
#194

Zoom In + Zoom Out

Let’s do one more to round out our little series of +1s on how to become more Antifragile. It’s easy to fall into the trap of thinking that whatever challenge is capturing our attention for the moment is EVERYTHING!! If we aren’t mindful, we can feel so attached to the outcome of that challenge tha...

+1 inspired by Note: The Obstacle Is the Way

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Antifragility & Purpose

antifragility Mental Toughness Philosophy self-awareness tool Vision Work

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 Seneca used to describe that feeling of calm confidence we have when we’re living an authentic, s...

+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 returned!! And, lo and behold, the horse bro...

+1 inspired by Note: The Daily Stoic

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Antifragility & Stoicism

Growth self-awareness Wisdom Work

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 my Trail every morning and when I’m out walking during the day—by myself or with the kids. In fact, ask Emerson what...

+1 inspired by Note: The Daily Stoic

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Conquering Digital Addiction & Stoicism

Best of Optimize conquering-digital-addiction memento-mori Philosophy stoicism technology Wisdom Work

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 more about the sport of mixed martial arts. We may think it’s a new thing a...

+1 inspired by Note: The Daily Stoic

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Antifragility & Confidence

antifragility confidence courage Grit Mental Toughness persistence Work

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 with something cool and then it hit us. Here’s the qu...

+1 inspired by Note: The Daily Stoic

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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 day after the surgery I was told they put 18 screws into my arm to connect the two titanium p...

+1 inspired by Note: The Obstacle Is the Way

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Antifragility & Learning

antifragility Energy 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 myself and kept myself from ...

+1 inspired by Note: The Daily Stoic

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Conquering Perfectionism & Modern Hērō

conquering-perfectionism equanimity Gratitude Happiness modern-hero tool Work

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 that, once upon a time, the ancie...

+1 inspired by Note: The Obstacle Is the Way

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Antifragility & Stoicism

antifragility equanimity Mental Toughness Philosophy stoicism Work

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 issue than you may have tried so ...

+1 inspired by Note: The Obstacle Is the Way

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Antifragility & Confidence

antifragility commitment confidence courage Grit Mental Toughness Work

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 coins so Emerson and I cou...

+1 inspired by Note: The Daily Stoic

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Fatherhood & Stoicism

Emerson equanimity Fatherhood memento-mori Philosophy stoicism Wisdom Work

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 Premeditatio Malorum coin. You know, the one featuring a ship in stormy...

+1 inspired by Note: The Daily Stoic

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Fatherhood & Stoicism

Emerson equanimity Fatherhood Grit Philosophy stoicism Wisdom Work

Antifragile Fuel
#898

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Aurelius on How to Make Flame and Brightness

Have you ever had an experience that annoyed you? (Hah.) Or, perhaps, a particular person who seems particularly skilled at annoying you? (Hah x2.) Me, too. (Hah x3!) So… I’m currently experiencing one of those moments with a particular individual who shall remain anonymous. 😘 We’ll skip the det...

+1 inspired by Note: The Daily Stoic

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Antifragility

antifragility confidence Grit Growth Mental Toughness Work

How Is This Making Me Stronger?
#899

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Well, How Is It? Add Fuel to the Fire!

In our last +1, we talked about making flame and brightness out of everything thrown into our blazing fire. (Thank you Ryan Holiday for the connection to Marcus Aurelius’s wisdom.) How’d that go for you? Shall we practice again? (Remember: The only way to get good at A N Y T H I N G is to practice it...

+1 inspired by Note: The Obstacle Is the Way

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Antifragility & Conquering Anxiety

antifragility conquering-anxiety Grit Growth Mental Toughness Practice Work

Problems vs. Conblems
#966

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Throw Challenges FORWARD Not Backward (or Under the Rug!)

Before we took a (longish) tangent into the power of words, we were talking about our session on the sixth Optimizing fundamental: Prosper. I briefly mentioned the fact that I shared 11 “Pro” words to move forward with hope. One of my absolute favorites? Problem. Of course, simply thinking about “p...

+1 inspired by Note: The Obstacle Is the Way

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Antifragility

antifragility emotional-stamina Growth Mental Toughness prosper Work

Antifragile Propellant
#968

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Flip the Switch for Fast and Furious Goodness

Today I’d like to revisit our “How to Prosper” theme for a moment (or two) longer. In almost all of the Mastery-Coach sessions, I emphasize the importance of being Antifragile—using life’s (inevitable!) challenges as a source of fuel. So… As I was preparing for the lecture, I planned to talk ...

+1 inspired by Note: The Obstacle Is the Way

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Antifragility & Confidence

antifragile-confidence antifragility confidence Growth prosper Work

How to Avoid Being Miserable
#992

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William James on Habits

Ryan Holiday has written a bunch of great books. The Obstacle Is the Way. Ego Is the Enemy. The Daily Stoic. His latest? Stillness Is the Key. It’s fantastic. The book is all about how pretty much all wise teachers across pretty much all cultures have used “stillness” as a cornerstone to peak perfo...

+1 inspired by Note: Stillness Is the Key

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Algorithms & Habits

algorithms Best of Optimize carpediem Coach Habits Mastery productivity Systems Work

Spiritual Windshield Wipers
#993

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Eudaimonia, Journaling, and the Science of Writing Down Our Goals

In our last +1, we talked about some William James wisdom from Ryan Holiday’s new book Stillness Is the Key. Recall: According to Professor James: “There is no more miserable human being than one in whom nothing is habitual but indecision, and for whom the lighting of every cigar, the drinking of eve...

+1 inspired by Note: Stillness Is the Key

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Habits & Productivity

big-three carpediem Coach Eudaimonia Habits productivity Work

Death's Interest Rate
#1031

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Schopenhauer Says: It’s Paid by Sleep

Not too long ago, we chatted about Ryan Holiday’s latest book Stillness Is the Key. (Since then, he and I connected for an interview you might enjoy.) Today I want to chat about another brilliant passage from that book. This one’s on sleep. Here it is. Ryan says: “The philosopher and writer Arthur ...

+1 inspired by Note: Stillness Is the Key

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Energy & Sleep

Energy Health memento-mori Recovery sleep

The Big 2 Virtues
#1032

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Can You Guess What They Are?

Not too long ago, we talked about the four cardinal virtues of ancient Stoicism then connected those virtues to the six core virtues of the modern positive psychology movement THEN distilled all those virtues into the four cardinal virtues of Optimize. Super-quick recap: Stoics said: Wisdom + Temperance ...

+1 inspired by Note: Stillness Is the Key

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Energy & Positive Psychology

Energy Fundamentals Hope positive-psychology Virtue

The 1, 2, 3 of Antifragility
#1108

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How to Operationalize OMMS

This morning I was out on the Trail enjoying (yet!) another stunningly beautiful Ojai morning. I was thinking about our Mastery Series Module on How to Create Antifragile Confidence, Heroic Courage, and Response-ability. The Theory side of that session will be stacked and we’ll have a range of Tool...

+1 inspired by Note: The Obstacle Is the Way

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Antifragility & Confidence

antifragility confidence Gratitude Hope Mental Toughness Work zest

How to Make an OMMS Sandwich
#1116

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Start with the Meaty-Obstacle + Add Goodness

Not too long ago we talked about how to operationalize Antifragile OMMS via a 1-2 then 1-2-3 process. Start with Wisdom + Self-Mastery then throw in some Gratitude, Hope and Zest and voila! Well… As I was falling asleep last night I was thinking about this whole process (“That’s like me...

+1 inspired by Note: The Obstacle Is the Way

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Antifragility

antifragility Growth Mental Toughness omms Virtue Work

“The Purgatory of the Idiot”
#1286

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vs. The School of Genius

As you probably noticed if you’ve been following along, I recently rebooted the PhilosophersNotes TV series. (Check it out on the App, on the site, on YouTube, on Instagram TV, on Facebook, on the podcast, and wherever else you mindfully consume your media!) As part of that relaunch after the two-year ...

+1 inspired by Note: Stillness Is the Key

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Conquering Digital Addiction

Areté conquering-digital-addiction focus iconoclast Mind mindfulness productivity

Numbing Our Souls
#1287

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Let’s WAKE UP and Stop Doing That (Today!)

In our last +1, we took a quick trip through the purgatory of the idiot (lol) that is the crowded and busy world of incessant inputs straight to the school of genius which is found at 101 Solitude Lane. Today we’re going to revisit Ryan Holiday’s great book Stillness Is the Key for another gem. Altho...

+1 inspired by Note: Stillness Is the Key

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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

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The Obstacle Is the Way #61

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Euthymia #100 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 Serenity Prayer #133 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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Infinite Optionality #191 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 Big Picture #194

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The 5 (Greek) Keys to Optimizing #200 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 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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Antifragile Fuel #898 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 Is This Making Me Stronger? #899 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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Problems vs. Conblems #966 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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Antifragile Propellant #968 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 Avoid Being Miserable #992 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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Spiritual Windshield Wipers #993 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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Death's Interest Rate #1031 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 Big 2 Virtues #1032 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 1, 2, 3 of Antifragility #1108 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 Make an OMMS Sandwich #1116 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 Purgatory of the Idiot” #1286 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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Numbing Our Souls #1287 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

Interviews with Ryan Holiday All Interviews

How to High Five Your Inner Daimon
#3

The Obstacle Is the Way
#61

Euthymia
#100

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The Serenity Prayer
#133

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Infinite Optionality
#191

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The Big Picture
#194

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 Optimus Medallion
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Use It or Lose It, a Case Study
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At Least THAT Didn't Happen
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You and Your Gordion Knots
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Got Firm Determination?
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The Daily Stoic Kid
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Stoic Shipwrecks
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Antifragile Fuel
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How Is This Making Me Stronger?
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Problems vs. Conblems
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Antifragile Propellant
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How to Avoid Being Miserable
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Spiritual Windshield Wipers
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Death's Interest Rate
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The Big 2 Virtues
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The 1, 2, 3 of Antifragility
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How to Make an OMMS Sandwich
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“The Purgatory of the Idiot”
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Numbing Our Souls
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