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A Burglar Stole My Engagement Ring—And It Made My Proposal

May 5, 2014 — 9 Comments

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.

Welcome To The Obstacle Is The Way: The Timeless Art of Turning Trials into Triumph

May 1, 2014 — 20 Comments

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

Entrepreneur.com: 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

RyanHoliday.net: A Lesson From The World’s Worst Week

RyanHoliday.net: A Practical Philosophy Reading List

Beliefnet.com: Nine Ways To Turn Your Obstacles Into An Advantage

Interviews:

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

BoingBoing.net: 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

Bitehype.com: 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

Slideshares:

Trailers:

A Lesson From The World’s Worst Week

April 28, 2014 — 20 Comments

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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 ThoughtCatalog.com. Comments can be seen there.

The Obstacle Is The Way Book Trailer & Book Signings

April 22, 2014 — 3 Comments

Here is the first of two trailers for The Obstacle Is The Way (done by Simplifilm). The second one, which is coming soon, is about the story of Ulysses S. Grant and the siege of Vicksburg.

Also there are three signings set for the book so far. All are welcome. I hope to see you there:

May 5th
Garden District Books
New Orleans, LA
7pm
Click here to RSVP

May 7th
Book People
Austin, TX
7pm
Click here to RSVP

May 28th
Book Soup
West Hollywood, CA
7pm
Click here to RSVP

I am also speaking at Marketing Rockstars Festival Austria, Google Create UK, and The School of Life Workshop – London in May and VIVID Sydney in Australia in June. Though these events may require tickets or conference entry.

Many, many articles on and from the book to come. I will post them here for your enjoyment. Thanks to everyone for their support and don’t forget to take advantage of the pre-order bonuses while you still can.

Also here’s a Slideshare preview from the book

A Practical Philosophy Reading List

April 21, 2014 — 23 Comments

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Very few people wake up and think “I need philosophy.” This is perfectly understandable. But of course, everyone has their own problems and are dealing with the difficulties of life in some way or another.

The irony is this is actually what ancient philosophy was intended to ameliorate. “Vain is the word of a philosopher,” Epicurus once said, “which does not heal the suffering of man.” Centuries later, Thoreau expressed this same thought: “To be a philosopher is not merely to have subtle thoughts, nor even to found a school . . . it is to solve some of the problems of life, not only theoretically, but practically.”

Suffering might be a strong word to describe most our travails in love, in business, with our egos, with our urges, with our jerk of a neighbor who keeps stealing our parking space. But it turns out that this was exactly what philosophy can help with.

Whatever problem you’re facing right now, someone else probably already went through it. And their advice and wisdom comes down to us through philosophy. It was jotted down by slaves and poets and emperors and politicians and soldiers and ordinary men and women to help with their own problems and with the problems of their friends, family and followers. This wisdom is there, available to us.

Some of the best philosophers never wrote anything down–they just lived exemplary lives and provided an example which we can now learn from. That too, was philosophy. It was practical and it was applicable and it made life better.

In a humble continuation of that tradition, I’d like this post to serve as a quick introduction to the world of practical philosophy–philosophy you can actually read and use in your own life. I won’t pass along any of that academic stuff that Schopenhauer once dismissed as “fencing in the mirror.” I want to give you the opposite of what you probably experienced in college, which despite the good intentions of your professor, you understandably resented and immediately forgot. I’m also giving you only the original texts, all of which I promise are totally readable and will change your life.

Meditations by Marcus Aurelius

Meditations by Marcus Aurelius

Meditation is perhaps the only document of its kind ever made. It is the private thoughts of the world’s most powerful man giving advice to himself on how to make good on the responsibilities and obligations of his positions. Trained in stoic philosophy, Marcus stopped almost every night to practice a series of spiritual exercises–reminders designed to make him humble, patient, empathetic, generous, and strong in the face of whatever he was dealing with.

Well, now we have this book. It is imminently readable and perfectly accessible. You cannot read this book and not come away with a phrase or a line that will helpful to you next time you are in trouble. Read it, it is practical philosophy embodied. Letters from a Stoic

Letters from a Stoic by Seneca

Seneca, like Marcus, was also a powerful man in Rome. He was also a great writer and from the looks of it, a trusted friend who gave great advice to his friends. Much of that advice survives in the form of letters. Now we can read those letters and they can guide us through problems with grief, wealth, poverty, success, failure, education and so many other things. Seneca was a stoic as well, but like Marcus, he was practical and borrowed liberally from other schools. As he quipped to a friends, “I don’t care about the author if the line is good.” That is the ethos of practical philosophy–it doesn’t matter from whom or when it came from, what matters if it is helps you in your life, if only for a second. Reading Seneca will do that. (Other collections of his thoughts are great too: Penguin’s On the Shortness of Life is excellent.) The Moral Sayings of Publius Syrus

The Moral Sayings of Publius Syrus

A Syrian slave in the first century BC, Publius Syrus is a fountain of quick, helpful wisdom that you cannot help but recall and apply to your life.

“Rivers are easiest to cross at their source.”

“Want a great empire? Rule over yourself.”

“Divide the fire and you will sooner put it out.”

“Always shun that which makes you angry.”

Those are a few I remember off the top of my head. But all of them are good and worthy of re-reading in times of difficulty (or boredom or in preparation of a big event). Fragments by Heraclitus

Fragments by Heraclitus

This is as ephemeral as I am going to get. While most of the other practical philosophy recommendations I’m making are bent towards hard, practical advice, Heraclitus might seem a bit poetic. But those beautiful lines are really the same direct advice and timeless, perspective-changing observations as the others.

“Try in vain with empty talk / to separate the essences of things / and say how each thing truly is.”

“Applicants for wisdom / do what I have done: / inquire within.”

“Character is fate.”

“What eyes witness / ears believe on hearsay.”

“The crops are sold / for money spent on food.” Man’s Search for Meaning by Viktor Frankl

Man’s Search for Meaning by Viktor Frankl

Man is sent to a concentration camp and finds some way for good to come of it. Finds some way to turn it into the ultimate metaphor for life: that we have little control over our circumstances, complete control over our attitude, and our ability to make meaning out of the things which happen to us.

In Frankl’s case, we are lucky that he was a brilliant psychologist and writer and managed to turn all this into one of the most important books of the 20th century. I think constantly of his line about the man who asks, “What is the meaning of life?” The answer is that you don’t get to ask the question. Life is the one who asks and we must reply with our actions. Essays by Montaigne

Essays by Montaigne

Montaigne was deeply influenced by some of the books I mentioned above. He was the epitome of Heraclitus’s line about “inquiring within.” So much so that he spent basically the entire second part of his life asking himself (and other people) all sorts of interesting questions and then exploring the answers in the form of short, provocative essays. (A favorite: Whether he was playing with his cat, or whether he was the toy to his cat). These essays are always good for a helpful thought or two–be it about death, about “other” people, about animals, about sex, or anything. Nature and Selected Essays by Ralph Waldo Emerson

Nature and Selected Essays by Ralph Waldo Emerson

While Montaigne’s essays are good for making us think, Emerson’s essays make us act. They remind us that we are ultimately responsible for our own life, for making ethical choices and for fulfilling our potential. I prefer Emerson to the more indolent Thoreau and because unlike most classic writers, he embodies that uniquely American drive and ambition (but in a healthy way). If you have not read Emerson, you should. If you have–and you remember fondly his reminders about recognizing our own genius in the work of others, or his reminders to experience the beauty of nature–that counts as philosophy. See how easy it is? Essays and Aphorisms by Arthur Schopenhauer

Essays and Aphorisms by Arthur Schopenhauer

Schopenhauer is another brilliant composer of quick thoughts that will help us with our problems. His work was often concerned with the “will”–our inner drives and power. “For that which is otherwise quite indigestible, all affliction, vexation, loss, grief, time alone digests.” But he also talks about surprisingly current issues: “Newspapers are the second hand of history”–and that the hand is often broken or malfunctioning. And of course, the timeless as well: “Hope is the confusion of the desire for a thing for its probability.” The Essential Epicurus

The Essential Epicurus by Epicurus

First off, Epicurus’ philosophy has almost nothing to do with our definition of the word “Epicurean.” I mean look: “Live your life without attracting attention.” He who has the least need of tomorrow will most gladly greet tomorrow.” “It is better for you to be free of fear and lying on a bed of straw than to own a couch of gold and a lavish table and yet have no peace of mind.” Epicurus was a teacher and a philosopher, and very little of his work survives. But the fragments which do are humble, noble and mostly about avoiding needless fear and anxiety in life. Those are all good things are they not? Ironically, Epicurus also has another more “scientific” side to him and there are few essays which go into great depth about “atoms.” I mostly skip those and stick to the lessons on imperturbability and self-reliance. This classic essay on the life of Epicurus is also great.

Misc Biographies

This last thought will probably get me into a little trouble because I am veering off what is more directly considered “practical philosophy.” But I think I am on good ground here. For starters, Cato the Younger–considered one of the most influential stoics–never wrote anything down. He was a philosopher by action and so many people studied his “work” through biography and anecdote. This was a Roman tradition. For instance, Plutarch wrote many biographies of famous historical figures–from Demosthenes to Mark Antony–which function as philosophy and moral example. A few biographies worth picking up for their practical philosophic value: Where Men Win Glory by Jon Krakauer (Pat Tillman embodies the tragic hero). Titan: The Life of John D Rockefeller (unflappable, disciplined, ultimately generous and humble–there are a lot of good stories here). I mentioned Cato earlier–the most recent biography by Jimmy Soni and Rob Goodman is quite good. I like Frederick Douglass’ autobiography, My Bondage and My Freedom as well as Xenophon’s Cyrus the Great (the modern business translation is most readable). I try to read at least one such biography a month, to get recommendations start here.


This list is by no means conclusive. Absent are many other great works of practical philosophy, and of course, other great works of theoretical and systemic philosophy. I’m not saying those are without value. I’m just saying that when most people wake up and try to make the most of their lives–or often, just struggle to get by–that’s not what they’re looking for.

They’re looking for help. Well, philosophy can be that help. Most of us are just suspicious because we wrongly associate it with long lectures or confusing translations. That’s a shame.

Because the works above have long been resources for people with all sorts of problems, from fighter pilots to kings to accountants to convicts to parents to athletes. In other words, unlike most of the big intimidating (usually German) philosophers whose names you cannot pronounce, this is philosophy for outside the classroom. Take it with you, use it, depend on it.

I’m sure some philosophy purists are going to object to my use of the books above and my characterization of some of their favorite thinkers. But I hope they understand that we have the same goal in mind: more people using philosophy as it was intended (improving lives).

I hope the rest of you find some solace, aid or inspiration in these recommendations. Those books changed my life and I hope they’ll change yours.

The post originally ran on ThoughtCatalog.com. Comments can be seen there.