“What we face may look insurmountable. But I learned something from all those years of training and competing. I learned something from all those sets and reps when I didn’t think I could lift another ounce of weight. What I learned is that we are always stronger than we know.” — Arnold Schwarzenegger

It recently occurred to me that there is one person I don’t feature in The Obstacle Is The Way but easily could have. Because like Rockefeller, Edison, Earhart, and especially Theodore Roosevelt, there is a man who proves and has lived the message pretty clearly: Arnold.

I mean, look at this. Or, if you don’t have time, just listen to his commencement address:

  • 1961: Arnold doesn’t like soccer, the sport most children played in his native Austria, so he tries weightlifting instead. He became so dedicated to bodybuilding he began breaking into his local gym on the weekends when it was closed so he could train: “It would make me sick to miss a workout… I knew I couldn’t look at myself in the mirror the next morning if I didn’t do it.”

  • 1965: Arnold served in the Austrian army to fulfill his one year service requirement. He ends up going AWOL during basic training so he can compete in the Junior Mr. Europe contest and ends up serving a week in military prison because of it. He won the contest.

  • 1968: Arnold arrives in America with little money and can barely speak English. Because bodybuilding doesn’t pay, he begins a bricklaying business with a fellow bodybuilder, mixing cement and knocking down walls with a sledgehammer.

  • 1970: Arnold won his first Mr. Olympia title at 23, making him the youngest Mr. Olympia ever, a record he still holds today. He would go on to win it six more times.

  • 1971: Arnold’s brother Meinhard died in a car accident in which he was killed instantly. Arnold would later pay for Meinhard’s son Patrick’s education and his emigration to the United States.

  • 1972: Arnold’s father, Gustav Schwarzenegger, dies from a stroke. Arnold was unable to attend his funeral because he training for  a bodybuilding content.

  • 1980: Arnold was a color commentator at the 1980 Mr. Olympia competition when he announced at the last minute he would compete in the contest. Schwarzenegger had been retired from competition but had been secretly training for the event. He won it with only seven weeks of preparation and after being declared Mr. Olympia for the seventh time he officially retired from competition.

  • 1984: Arnold appears in James Cameron’s The Terminator. Of his early acting career, Arnold said, “It was very difficult for me in the beginning – I was told by agents and casting people that my body was ‘too weird’, that I had a funny accent, and that my name was too long. You name it, and they told me I had to change it. Basically, everywhere I turned, I was told that I had no chance.” Basically, Arnold turned all those ‘negatives’ into a totally unique and iconic package.

  • 1991: Arnold reappeared as the title character in Terminator 2: Judgment Day, which was the highest-grossing film of 1991.

  • 1993: Arnold stars in Last Action Hero, which did poorly at the box office, opening opposite Jurassic Park. It is one of many failed movies in his career–as he admits.

  • 1994: Arnold’s movie career bounces back when he reunited with James Cameron for the popular sky film True Lies.

  • 2001: Arnold broke six ribs and was hospitalized for four days after a motorcycle crash in Los Angeles.

  • 2003: Without any previous political experience, Arnold wins the California recall election for governor by 1.3 million votes. (I actually attended his kick off rally in Sacramento. Twisted Sister performed)

  • 2006: Arnold wins re-election for Governor of California by well over one million votes.

  • 2009: He gives an epic and philosophic commencement address to USC students.
  • 2013: Arnold restarts his acting career with his first leading role in 10 years with The Last Stand, and his first co-starring role with Sylvester Stallone in Escape Plan. Also cooly embraces reddit and social media to great results.

“So let me tell you, as you prepare to go off into the world, remember six rules: Trust yourself, Break some rules, Don’t be afraid to fail, Ignore the naysayers, Work like hell, and Give something back.” – Arnold Schwarzenegger

What Arnold shares with all the figures in the The Obstacle Is The Way is that stoic idea of self-direction, self-discipline, self-mastery. He faced innumerable problems and obstacles in his life—some of which he created for himself, as we know—but what mattered more than that was how he responded.

He saw, as Marcus Aurelius wrote, that the impediment to action can advance action. He saw that the obstacle is the way.


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“Over the last 14 days, I have carried one book in my backpack to cope, all day and every day: The Obstacle Is The Way.” — Tim Ferriss

For the many of you who asked, I can now proudly announce that the audiobook edition of The Obstacle Is The Way is now available. And there’s an exciting piece of news about it that I’ve kept secret until now: Tim Ferriss is publishing it. 

Tim and I spent some time in Amsterdam in 2013 when I was finishing the book and I showed him a copy of the manuscript. He liked it so much that he went straight to my publisher, Portfolio/Penguin and bought the rights for the audio edition. This was an ideal collaboration because not only did Tim give excellent notes on the book that helped improve it, but his massive distribution network helps put the book in front of lots of new people. As his May selection for the Tim Ferriss Book Club, The Obstacle Is The Way will get all sorts of new readers I could have never expected otherwise.

It’s all very fitting because Tim and I first connected over our love of Seneca back in 2007. Tim was the one who prompted me to write this post on stoicism for his blog in 2009, which resulted in my first inquiry from a book publisher. It was then that I realized I might be able to actually pursue this all as a career. And now here we are publishing a book together.

Anyway, enjoy. You can also listen to this podcast that Tim and I did about the book (which tied with James Altucher’s podcast was one of the most fun and thought provoking interviews I have ever done).

You can also purchase the The Obstacle Is The Way audiobook here:





Note: The events in this post occurred in February 2014. The original column ran in the New York Observer.

screen shot 2014 02 18 at 12 30 56 pm A Burglar Stole My Engagement Ring — And It Made My Proposal

About seven years ago I met a girl. It was at a college party–a “kickback” if I recall the distinction made by the host at the time. She was tall, she was blond, she had short hair. She was sitting in a cardboard box for some reason. Her name was Samantha.

We were essentially children, then, but over these intervening years became adults together. From 19 to 26 she walked me through dropping out of collegebeing embarrassed, moving across the country, writing books, having breakdowns. She was the long-suffering girlfriend, content with meager indulgences: a puppy and that pink bike I got her after my first five-figure check at 20 and later, a goat.

But eventually, I got it together. Or so I thought: I bought us a house. I bought her a ring. I even bought myself a safe to put the ring and all the other adult things in. I did everything I was supposed to.

Deciding to ask Sam to marry me was a process many years in the making, one that, honestly, I didn’t totally understand but knew was time for me to get on with. I found what I thought was the perfect ring while in New York on business: a 115-year-old Victorian piece that I put a better diamond in. I planned to propose during an upcoming vacation in Hawaii. I was pretty damn proud of myself.

I put that little ring in that little safe and forgot about it. In California for a few days, starting to recover from what was already shaping up to be terrible week, Samantha took a phone call: Your house has been broken into. Everything was stolen. Everything ransacked and destroyed. That safe? Yeah it was broken into as well–busted completely open and cleaned out.

The horribleness of it all came together for me as we huddled next to each other outside a restaurant, 2000 miles from home, her on the phone with the police relaying me questions. What did you have here? Who do you think could have done this? Where there any valuables in the safe we should know about?

She could see the answer in my eyes the second she passed along their question. She’d probably already had some idea and now the suspension of disbelief was no longer possible. But we kept up the external charade anyway–it was too much to talk about. She handed me the phone and I handled it with the cops. They’d left the box, but the ring was gone. Gone before I could give it to her.

So much for being an adult. So much for those best laid plans. For the illusion of having a handle on my life.

I’m sure a lot of guys have had to awkwardly return to the jewelry store where they bought their engagement rings. Some guys dejectedly inquiring about return policies. Others dragged in by the ear by a dissatisfied gold digger. Me? I had to walk in and say: “Umm…I’m going to need another one.”

Shopping for your first engagement ring is exciting, because you can do no wrong. That’s the beauty of an engagement ring. She’s going to like it. It’s part of the unwritten contract. Boy buys ring, girl melts when she see’s it–even if it’s hideous or way too small.

Round II is a little different. I may have been loaded with insurance money but the giddy confidence was gone. I may be able to gamble thousands of dollars on a surprise once, but in the cold light of morning, I couldn’t do it again.

It was one of the moments where you feel very much like a teenager in over his head, where you’d usually call someone else older and more responsible than you to help get you out of the mess you’d created. I’m sure this bled through in all my interactions with the police, with the insurance companies, with the jeweler: just tell me what to do here. This shouldn’t be my problem. What about my perfect plans? I can’t deal with this. But of course, none of that matters.

One of the ironies of being with someone you really love for a long time is becoming completely incapable of handling stressful or difficult things by yourself. Make a big decision and not tell them about it? That defeats the whole point of the relationship. It’s just not done.

I broke down and told her, though she’d clearly deduced it already. I showed her the ring I’d bought and she cried. It was exactly what she wanted, yet by definition irreplaceable. So we looked at rings together, over the phone. Thank God, because everything else I thought she’d like she didn’t. My first guess had been right–but now it was clear that it had been beginner’s luck.

Sam didn’t say it expressly but I knew how unfair this all was. The thieves had stolen something she could never get back. Something that after several years in a rather untraditional, basically common-law relationship endured with total patience and selflessness, to which she was more than entitled. Not the ring, the moment.

The fact that everyone says, “Oh, but this will make for such a great story” wasn’t any comfort. I owed it to her to make it better. I needed her help to get through it myself, but I couldn’t let that deprive her of something she deserved. I didn’t understand that before, I didn’t get what this whole thing was about. I’ll be honest: it was a box I was checking, an item on a to do list.

The impediment to action advances action, Marcus Aurelius once wrote. This was not how I had originally intended it to be. That original plan was interrupted. But as it is often is, what came of it was so much better.screen shot 2014 02 18 at 12 30 44 pm A Burglar Stole My Engagement Ring — And It Made My ProposalI bought the ring I knew she liked but was too shy to demand, but I said nothing, I said we’d find something later. They’d had it at the place the first time, but I’d ignored it because it wasn’t my taste. White gold, 1920’s vintage Art Deco, with blue sapphires around the diamond. I had to dodge questions for the next month or so. I had to politely discourage her “research”–just in case she found something else.

Would you believe I refused to put it in the new safe? I hid it instead, in a hollowed out book. I waited, again, but this time for the moment, not some arbitrary plan. Last week, we went to the Hamilton Pools in Texas, undoubtedly one of the wonders of the world. It’s an enormous natural stone grotto–seen in countless Pinterest slideshows but assumed to be some exotic locale.

For a twenty minute window there wasn’t a soul in the place and I asked. Total surprise. And she said yes for real and that was that. Even better than whatever half-thought gesture I would have tried to pull off had everything gone as planned.

Yes, it will make for a great story. But not because of what happened, but because of what happened because of what happened. It was what I needed. Which is a lot like life.

You do certain things and check certain boxes and think you’ve got it. But of course you don’t–you don’t have a clue. You never do, not until after. Not until the shit that happens in life teaches you.

This column originally ran in the New York Observer. Comments can be see there.

The day has come. The Obstacle Is The Way: The Timeless Art of Turning Trials into Triumph is now out. I’ve written a ton of pieces about the book, I produced content and images to support the book and of course, there is already all sorts of press about the book out. I want to use this post (which will be updated for the next couple weeks) as an archive of all of that—or as a place to get started if you’re new to me and my work.

Upcoming Events/Appearances:

5/5: Book signing @ Garden District books in New Orleans

5/7: Book signing @ Book People in Austin

5/14: Marking Rockstars Austria

5/18-20: Google Create UK

5/21: The School of Life Workshop London

5/28: Book signing @ Book Soup in West Hollywood

6/6: Vivid Sydney

Articles I’ve Written For TOITW:

Huffington Post: How Dr. Drew Pinsky Changed My Life

Cracked: 7 People Who Overcame Huge Obstacles To Become Famous

Copyblogger: How I Wrote Three Books In Three Years

FastCompany: 7 Ways To Turn Your Opponents Into Opportunities

Art of Manliness: Finding the Opportunity Inside the Obstacle Turning Crisis Into Opportunity: 5 Ways To Deal With Hardship

800-CEO-READ: The 3 Stoic Disciplines: How to Turn Your Obstacles Into Triumphs

Upstart Business Journal: Why Amelia Earhart’s 1925 Gamble Should Inspire Entrepreneurs

Thought Catalog: How You Do Anything Is How You Do Everything

Thought Catalog: Should I Drop Out of College?

Medium: Hey Millennials, It’s A Good Thing Things Are Bad

Psychology Today: The Importance of Negative Thinking A Lesson From The World’s Worst Week A Practical Philosophy Reading List Nine Ways To Turn Your Obstacles Into An Advantage


Forbes: Ryan Holiday: How Challenges Become Opportunities For Entrepreneurs

800-CEO-READ: Think In Residence: A Q & A with Ryan Holiday

Art of Manliness: The Obstacle Is The Way with Ryan Holiday American Apparel marketing director Ryan Holiday on Stoicism

Lewis Howes School of Greatness: The Philosophical Guide to Turning Trials Into Triumphs with Ryan Holiday

Big Think: Read Stoicism

Art of Charm: The Obstacle Is The Way A conversation about obstacles and old books with Ryan Holiday

Intrepid Radio: The Obstacle Is The Way

The New Man: Ryan Holiday – The Obstacle Is The Way

Evidence Magazine: The Obstacle is the Way: A Timeless System for Transforming Challenges into Opportunities

The Phat Startup: How To Destroy Any Obstacle – Ryan Holiday Interview

A Closer Look Radio: Turning Trials Into Triumph with Ryan Holiday

Yo Pro Wealth: Create Your Future, Do What You Love – Ryan Holiday

Press About The Book:

Bittorrent: Every Obstacle Is Also An Opportunity

London Evening Standard: How to avoid a work crisis with a ‘pre-mortem’

Huffington Post: 9 Essential Habits Of Mentally Strong People

Huffington Post: 10 Reasons to Love the Obstacles in Your Life

Linked In: Do Bad Odds Help Us Perform Better?

Business Insider: The Simple Strategy Alabama Coach Nick Saban Used To Create A College Football Dynasty

Farnum Street: The Obstacle Is The Way — Turning Adversity Into Advantage

Small Business Trends: “The Obstacle Is The Way” Gives Unusual Advice for Success

Stoicism Today: “The Obstacle Is The Way” by Ryan Holiday

Medium: Resilience — The Obstacle is the Way

Uncollege: Review: “The Obstacle is the Way,” By Ryan Holiday



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“Rehearse them in your mind: exile, torture, war, shipwreck. All the terms of our human lot should be before our eyes.” – Seneca

A lot of bad stuff happened to me last week.

I know the philosophers say there is no such thing as good or bad events–that there are only our perceptions which make things one or the other.

But my week began with a near fatal car accident on a dark highway and ended with someone breaking into my new home, ransacking it and stealing most of what I own–and destroying what they left behind. For good measure, my pet chickens were later decapitated and disemboweled by an unknown animal.

Why this happened and who or what is to blame, I’m not sure. But I can tell you for sure where the biggest problem lay: I was not at all expecting it. Not at all. And so it felt terrible.

We can easily accept in the abstract that there is no good or bad, that we create definitions and categories for objective events outside of our control. Yet, when it happens to us in reality, particularly as a surprise, our very human side kicks in.

It’s bad. We feel bad. Real bad.

Over the last few years, I have noticed something strange. The more in my head my career has taken me, the more vulnerable I have become. In some ways this is good. Writing forces you to become more in touch with your emotions; writing is often inherently an empathic act, so practicing it makes you more empathetic. So does reading. In my relationships, this has all made for positive change.

But there is another part of this vulnerability. Sensitivity to loud noises, to temptations, to moods–these are increased the more in your head you get. For instance, it makes many of us addicted to our routines and leaves us exposed when that routine is interrupted.

I think when you manipulate your own mind and your work all day, it feels natural to assume the rest of the world is like this too. You need things your way, and need them to happen on your terms. This is most definitely a weakness. Vulnerability is a good thing, up until it becomes an entitlement.

Not all of us are artists, I understand, but the point stands for everyone else too. Inured from harsh realities humans once accepted as commonplace–from sudden and unpredictable weather to sudden and unpredictable death–we can forget how capricious events can be. We deliberately do not think of these possibilities because we don’t want to ruin our (delicate) moods or disrupt our routine.

Life does not tolerate this for very long.

Fate often lulls us into complacency before reminding us that life is wicked and unpredictable.

As Euripides put it: “Foolish is the man who delights in his good fortune, supposing it will never leave him.”

The mathematical law of the universe says it more clearly: Everything regresses towards the mean.

The mean in life, we must never forget, is punctuated bursts of violence and destruction and someone else’s whim.

In a second, it can all change.

An accident. A diagnosis. A news alert.

Tomorrow, someone could blow up our economy and you could lose everything you have. A dictator could move the world towards war. Or, someone could slam into you in an intersection. Or they could come through an upstairs window and make off with your most valuable possessions.

This is life. These things will happen. Or maybe they won’t. No, they definitely will–the variability lies only in the degree and the ETA.

In your reaction to such inevitable events, you will undoubtedly ask yourself a million questions. Most of them will be pointless. One of them truly matters. Ask yourself: If it happens again, are you better prepared?

I don’t mean what you think I mean. Not: did you buy a bigger safe? Or did you set up security cameras or run a practice drill for some calamity? (Though all those things are important and helpful). Because by “again” I don’t mean the exact same event. I mean fate, misfortune, unpredictable and unpleasant circumstances.

So: Are you now mentally prepared for a world you cannot control? Now do you finally understand how random and vicious the world can be? Did you learn from your last reminder?

Because, to come back to those philosophers from earlier (whose advice about responses is a little more practical), we have only one choice. That choice is acceptance. See, we don’t control what happens to us. No amount of technology or civilization will ever make a difference in that regard, except at the margins.

What is in our control? Well, after our biology and psychology run their course–like shock for instance–all that’s left is our response. We control how we act, we control the stories we tell ourselves afterwards.

We choose whether we will make ourselves vulnerable. We choose whether we will get soft. We decide if we’ll be delusional.

We can also choose to prepare ourselves for a savage world. To use philosophy as a weapon in our defense. Bad things will happen. They will knock us on our ass. But we have the choice now to dull the surprise in advance and quicken our recovery time.

It’s up to you whether you’ll take it.

This post originally ran on Comments can be seen there.