marcus-quoteWhen I was nineteen years old I was told to read a book: Meditations, by the stoic philosopher emperor Marcus Aurelius.

Of course, I didn’t fully understand it at the time, again I was a teenager, but I immediately tore the book apart and made a million notes on it. It was for me, what the economist Tyler Cowen calls a “Quake Book.” It shook my entire (albeit limited) world view.

Though this book changed my life, it was really a single passage inside that book that made the difference. It’s a passage that has struck and changed the lives of many people in the two thousand years since it’s been written. One I’ve turned to again and again–when I dropped out of school, when I had problems at work, problems in my relationships, problem with employees, and just normal life.

The passage goes like this:

“Our actions may be impeded…but there can be no impeding our intentions or dispositions. Because we can accommodate and adapt. The mind adapts and converts to its own purposes the obstacle to our acting.

And then he concluded with powerful words destined for a maxim.

“The impediment to action advances action. What stands in the way becomes the way.”

These words were scrawled by Marcus Aurelius himself, to himself, likely on the battlefront as he lead the Roman Army against barbarian tribes or possibly at the palace amongst the intrigue and pressure. Not exactly a happy or encouraging place to be.

Yet in the years since I first read it, I’ve started to understand is that this little paragraph is the perspective for a special kind of optimism. Stoic optimism.

I’m sure that sounds like an oxymoron, but stoicism gets a bad–and unfair–rap.

What Marcus was writing—reminding himself—is one of the core tenets of Stoicism. What it is prescribing is essentially this: in any and every situation—no matter how bad or seemingly undesirable it is—we have the opportunity to practice a virtue.

An example: I’m writing this article and I hope that it is received well. But it could very easily bomb or get a terrible response. Now this would be a minor but rather undesirable impediment or an obstacle.

That’s probably what I would think at first too. But seen another way it’s…a chance for me to remind myself of humility, or learn from the feedback and improve my writing or even just accept that I can’t please everyone all the time.

A Timeless Idea

Over the years since I first read the book (and in the course of researching my own), I studied people in history who had made this each decision–willingly or by force of circumstance. People who’d faced an obstacle but saw it as the way. Which makes sense because stoicism is ultimately an art that is designed to be practiced, not spoken about.

Take John D. Rockefeller before he was…well John D. Rockefeller as we knew him. He was just a kid with a deadbeat dad. At 16 he took his first job as bookkeeper and aspiring investor.  He was making fifty cents a day. Less than two years later the Panic of 1857 struck. The result was a crippling national depression that lasted for several years.

Here was the greatest market depression in history and it hit Rockefeller just as he was finally getting the hang of things. It’s terrible right? Real investors who supposedly knew what they were doing lost everything.  What is he supposed to do? Rockefeller later said that he was inclined to see the opportunity in every disaster. That’s exactly what he did.

Instead of complaining about this economic upheaval or quitting like his peers, Rockefeller chose to eagerly observe the events that unfolded. He looked at the panic as an opportunity to learn, a baptism in the market.

It was this intense self-discipline and objectivity that allowed Rockefeller to seize advantage from obstacle after obstacle in his life, during the Civil War, and the panics of 1873, 1907, and 1929. Within twenty years of that first crisis, Rockefeller would alone control 90 percent of the oil market. His greedy competitors had perished and his doubters had missed out.

It’s a two part mental shift. First, to see disaster rationally. To not panic, to not make rash decisions. And second, like Rockefeller, we can see opportunity  in every disaster, and transform that negative situation into an education, a skill set, or a fortune.

Another example: General Dwight D. Eisenhower.

General Eisenhower—who men sniped behind his back was more of an organizer than a leader—had just pulled off the largest amphibious invasion in military history.

Slow going in the hedgerows of France had allowed the Germans to wage a series of counteroffensives—a final blitzkrieg of some 200,000 men. And now the Nazis threatened to throw them all back to the sea.

The Allies had a pretty understandable reaction: they just about freaked out.

But not Eisenhower. Striding into the conference room at headquarters in Malta, he made an announcement: He’d have no more of this quivering timidity from his deflated generals. “The present situation is to be regarded as opportunity for us and not disaster,” he commanded. “There will be only cheerful faces at this conference table.”

In the surging counteroffensive, Eisenhower was able to see the tactical solution that had been in front of them the entire time: the Nazi strategy carried its own destruction within itself.

Only then were the Allies able to see the opportunity inside the obstacle rather than simply the obstacle that threatened them. Properly seen, as long as the Allies could bend and not break, this attack would send more than fifty thousand Germans rushing headfirst into a net—or a “meat grinder,” as Patton eloquently put it.

Eisenhower’s ability to not be overwhelmed or discouraged by the German Blitzkrieg allowed him to see the weaknesses within it. By defusing his fear of the German counteroffensive he uses his optimistic attitude to find its weakness.

And then there is Thomas Edison. I don’t think that inventing the lightbulb was the craziest thing the guy ever did.

At age sixty-seven, Thomas Edison returned home one evening from another day at the laboratory. After dinner, a man came rushing into his house with urgent news: A fire had broken out at Edison’s research and production campus a few miles away.

Edison calmly but quickly made his way to the fire looking for his son. “Go get your mother and all her friends,” he told his son with childlike excitement. “They’ll never see a fire like this again.” Don’t worry, Edison calmed him. “It’s all right. We’ve just got rid of a lot of rubbish.”

That’s a pretty amazing reaction. It’s what the stoics might refer to as amor fati–loving the things that happen to us. 

Edison wasn’t heartbroken, not as he could have and probably should have been.

Instead, the fire invigorated him. As he told a reporter the next day, he wasn’t too old to make a fresh start. “I’ve been through a lot of things like this. It prevents a man from being afflicted with ennui.”

Within about three weeks, the factory was partially back up and running. Within a month, its men were working two shifts a day churning out new products the world had never seen. Despite a loss of almost $1 million dollars (more than $23 million in today’s dollars), Edison would marshal enough energy to make nearly $10 million dollars in revenue that year ($200-plus million today).

So…how can we cultivate this fortitude and ingenuity?

The answer, I say, is with philosophy–practical philosophy. With Stoic optimism, we can be Edison, our factory on fire, not bemoaning our fate but enjoying the spectacular scene. And then starting the recovery effort the very next day—roaring back soon enough.

How about a business decision that turned out to be a mistake? It was a hypothesis that turned out to be wrong, like a scientist you can learn from it and use it for your next experiment. Or that computer glitch that erased all your work? You will now be twice as good at it since you will do it again, this time more prepared.

Perhaps you were injured recently and are stuck in bed recovering. Now you have the time to start your blog or the screenplay you’ve been meaning to write. Maybe you’ve recently lost your job. Now you can teach yourself the skills to get the job you’ve always wanted. You can take a careless employee’s mistake that cost you business and turn it into a chance to teach a lesson that can only be learned from experience. When people question our abilities that means we can exceed their lowered expectations of us that much quicker.

Easier said than done, of course.

In each of the three situations above, the individuals faced real and potentially life-threatening adversity. But instead of despairing at the horrific situation—economic panic, being overrun by the enemy, a catastrophic fire—these men were actually optimistic. You could almost say they were happy about it.

Why? Because it was an opportunity for a different kind of excellence. As Laura Ingalls Wilder put it: “There is good in everything, if only we look for it.”

I’m not Eisenhower. You’re not Rockefeller. Our factory has never burned down, so we don’t know how we would react.

But I don’t think it’s as super-human as it seems at first glance. Because there is a method and a framework for understanding, appreciating, and acting upon the obstacles life throws at us. Like Rockefeller too we can perceive events rationally and find the fortune in downturns. Like Eisenhower, we can disengage from our fears and see the opportunity inside our obstacles. Like Edison we can choose to be energized by the unexpected circumstances we find ourselves in. We know it won’t be easy but we are prepared to give it everything we have regardless.

In our daily lives we forget that the things that seem to be blocking us are small and that the obstacles blocking us are actually providing us answers for where to go next. It’s a timeless formula that can be revisited again and again.

All I can say is that this attitude is something I try to think of always. I try to envision these people facing much more significant problems than me, and seeing it not only as not bad but as an opportunity.

We all face tough situations on a regular basis. But behind the circumstances and events that provoke an immediate negative reaction is something good—some exposed benefit that we can seize mentally and then act upon.We blame outside forces or other people and we write ourselves off as failures or our goals as impossible. But there is only one thing we really control: our attitude and approach

Which is why the stoics say that what blocks the path is the path. That what seems to impede action can actually advance it. And that everything is a chance to practice some virtue or something different than originally intended. And you never know what good will come of that.

The obstacle is the way.


When we shopped for our first house, I told my girlfriend (now wife) that most of the decision was up to her. I had worked out what we could afford, but in terms of what house, where and what style, I wanted whatever she wanted.

We were coming from New York and so everything seemed bigger in Texas. A real estate agent showed us a “small” place that was “only” 1,500 square feet. We didn’t have enough stuff to fill half of that. We ended up with a two story, two bedroom with a small fenced in yard, at just under 900 square feet. It was perfect.

Except the day we moved in, she said to me, “You know, I’ve always wanted to live on a farm.”

When I moved to the South for the first time in 2011 I thought it would be a good place to write. What I could not have anticipated is how good a place it was for just about everything. I certainly could not have anticipated that just a few years later I would live on a twenty acre ranch with more animals I can confidently account for (it’s somewhere around 20 but if you include the cattle that live on the land, closer to 50).

Our house. (Photo: Ryan Holiday)

A few years ago, Tyler Cowen wrote a Time Magazine cover story about why everyone was moving to Texas. There is a bunch of data behind it, but I can lay it out pretty simply:

-It’s cheap.

-It’s beautiful.

-It’s awesome.

It’s a chance at the life.

It’s easy to say about a lot of places, I suppose. But let me tell you what they actually mean in Texas.

First, there is no state income tax in Texas. Some people know this and some don’t—few really grasp what it means practically. It means that if you make decent money and decide to move here and rent something affordable, it’s essentially free to live in Texas. If you make $150,000 a year, your state income taxes in California are roughly $12,000 per year (in NYC it’s closer to $15,000). Or, you can put a thousand bucks a month toward your rent here. If you decide to buy, property taxes are high—but what you get for the money more than makes up for it. My editor at the Observer recently tried to cajole me into coming back to New York. Our house now—which has its own lake and is 29 minutes from the airport which never has lines—costs less than the rent we were paying for our lofted studio apartment in Midtown. Are you kidding?

New sign for the front gate. Truer words never spoken. (Photo: Ryan Holiday)

Second, I’ve driven across the United States many times. I am continually shocked at how beautiful Texas is. The vastness of Texas means it has essentially every kind of climate you can think of from plains to swampland to pine forests to the coast to deserts and even some mountains (topping out at 8,750’). I could go on about the many beautiful features of Texas but I thought I would just pick one thing and it’s so unexpected: water. Barton Springs in Austin is probably one of the most amazing natural swimming pools in the world (rivaling Australia’s rock pools). There is a college campus near San Antonio that has a swimmable river in the middle of it(with its own rare species of grass at the bottom). In a place called Wimberley, there is a 120 foot deep blue hole that you can rock dive into. There’s another stream nearby called Wimberley Blue Hole and a thing called Hamilton Pools, which is one of the largest natural rock grottos on the planet. Out in the middle of nowhere, there is a park in Toyahvale that happens to have the largest spring fed pool in the world. In some random town called Luling, there’s an Old Mill turned into a swimming hole that looks like something out of Mayberry. Honestly, the only water that isn’t nice in Texas seems to be the ocean.

Third, it’s awesome. Like really awesome. In East Austin, where we used to live, we had two small pet goats. We were not the only ones. Another neighbor had them too. Oh, and apparently other people did too because one day someone found one wandering the streets—wandering the streets of the fastest growing city in the US—and gave it to us. His name is Watermelon.


In Dallas, a guy named Jason Roberts created a program called Better Block Projectthat has become the model for urban revitalization. A friend of mine started the best hostel in Austin out of an old Victorian mansion and a month after opening, it’s fully booked almost every night. They’re building the first Wavegarden surf park in Texas and a brand new F1 racetrack sits right outside Austin. They say the state bird of Texas should be the construction crane—that’s how much it’s being built out.

There is a certain freedom and ridiculousness to Texas that I love. Sure, let’s have a 20 oz. chicken fried steak for breakfast. Sure, let’s put queso on everything and have tacos for every meal. I remember shortly after moving there, asking an employee at Cabella’s if he had any recommendations for a gun safe. “Well, son,” he said to me in complete seriousness, “m’boy moved away to college a few years ago so I reinforced the door frame and just turned the whole guest room into a gun vault. Have ya thought ‘bout doing sumthin like that?” Good God, I thought. And then, when we moved into a new house this year, it had a walk in closet turned into gun vault.Welcome to Texas.

Some other awesome things: It’s a state with two football teams, three NBA teams, and two professional baseball teams (oh and pretty decent college and high school—including a 100,000 seat college stadium). It’s the setting for one of the greatest television shows and books of all time, Friday Night Lights. It’s one of only three states to ever be independent countries. There’s a fort in southeast Texas called La Bahia (arguably more important than the Alamo) that flew the flags of six different nations in its 294 year history. In East Austin, there is a French embassy. (Did you know the two countries almost came to blows over a pig that broke into the ambassador’s home?) Oh and my favorite, Texas is so big that the distance between its two furthermost cities Beaumont and El Paso is 26 miles more than the distance from Los Angeles to El Paso. Texas is roughly the size of France and Switzerland combined

And yet…it’s a four-hour flight to basically anywhere worth going in the United States. You can leave Texas on a 7am flight and still have a full day of work or meetings on either coast.

To me, the American Dream has always been relatively simple: The ability to live one’s life on one’s terms. That is: financially, recreationally, personally, and creatively. Texas offers that. Increasingly, America’s great cities and states make having all of that essentially impossible for the vast majority of people. They are culturally, financially or physically oppressive.

Of course, Texas is not without its flaws. Two cultural flaws are particularly odious and bear pointing out. One, the radical, delusional politics. Not because it’s a Red State—every state has the right to lean the way the population cares to (for the most part, as a liberal person I’ve never found conservatism in the South to be a bother). Instead, I’m speaking of the Jade Helm 15 variety of nutbags and the Overton Window that these views set. I’m talking about anyone who can’t see that Americans in Texas complaining about Mexican immigrants clearly doesn’t understand enough history to deserve the right to an opinion. The second cultural problem is a certain breed of NIMBY-esque hipsters—particularly in Austin—who constantly complain about the other Americans who dare to like their city enough to move here. In fact, I can already hear them complaining that I wrote this piece. Last week I shot a jack rabbit off my front porch, skinned and ate it. I’ve earned my stripes. I’m not the enemy.

But these are minority viewpoints and they’ll work themselves out. I’ve always found the South to be almost disconcertingly welcoming. It’s that they people seem to generally want you to live there, they’d like you to be a part of their community. Diversity—an essential ingredient to a happy life—has always been more tangible to me here than East or West, and not only by race but by occupation, lifestyle and beliefs. 2015-08-31 11-23-00

This too is part of the dream. This too is part of the rich life. Along with millions of other people, I found it and fallen in love with it here.

So I’m not saying everyone should move to Texas, but you should move to Texas.

This post appeared originally on the New York Observer

(from my poster with Joey Roth)

The story of Ulysses S. Grant at Vicksburg is the story of a central truth of history: that strength often becomes a weakness and weakness can be transformed into strength. The great strategist Saul Alinsky believed that if you “push a negative hard enough and deep enough it will break through into its counterside.” Every negative has its positive. And conversely, every positive–every advantage you think you have–has its negative.

Grant spent months trying to take Vicksburg, which looked down from its protected perch high on the cliffs of the Mississippi, strangling the most important river in the country. He tried attacking head-on and was repeatedly repulsed. He spent months digging a new canal that would change the course of the river. He blew the levees upstream and literally tried to float boats down into the city over flooded land.

None of it worked. But Grant refused to be rattled, refused to rush or cease. His next move ran contrary to nearly all conventional military theory. He decided to run his boats and men past the gun batteries guarding the river—a considerable risk, because once down, they couldn’t come back up. Despite an unprecedented nighttime firefight, nearly all the boats made the run unharmed. A few days later, Grant crossed the river about thirty miles downstream.

The enemy thought he’d given up. You have to ‘catch the rabbit’ before you eat it, Vicksburg’s newspaper taunted him. Lincoln had a replacement ready and primed to take over.

In fact, Grant had a bold plan: Leaving most of their supplies behind, his troops would live off the land and make their way up the river, heading east to take the state’s capitol in Jackson (which had been supplying the city), and only then circle back west towards Vicksburg, hitting it from the other side.

Finally, he laid in for a siege. On July 4th, 1863, Grant ate his dinner inside the city. He had caught the rabbit.

It seems obvious and clear in retrospect. By looping around the fortress and attacking from the rear, he pinned them inside their own walls. With a simple change–and an enormous gamble–he turned their impenetrable advantage into a prison of their own making.

That’s how it works–in war and in life.

It’s something I’ve talked a lot about with my friend, the designer Joey Roth. Why is it that entrenched players, with all their resources, can’t seem to innovate? Why do outsiders seem to respond better to disruption and changes? How does one learn to spot transformative opportunities?

At its core, Stoicism discerns from the things we can control from the things we cannot. Ego on the other hand, is incapable of making this distinction. It deludes us, it lies, it makes us soft and vulnerable. It takes for granted the protections of a fortress and refuses to see how the tables might be turned. On the other hand, the strategist–the stoic–allows us to see obstacles not as impediments, but as opportunities that guide our efforts.

As Joey put it when we were collaborating on a poster about this very idea:

When the competition is established, dug in and secure, it looks like an insurmountable obstacle, but in fact gives you freedom maneuver. This mirrors the agility of a startup vs. an entrenched player, or the beginner’s unencumbered approach beating the expert’s finely tuned but rigid technique. It’s also a reminder to stay flexible as you advance in your work and develop processes and expectations.

Being outnumbered, coming from behind, being low on funds, these don’t have to be disadvantages. They can be gifts. Assets that make us less likely to waste our time, our energy, or potentially even our lives in a failed frontal assault on whatever it is that we happen to face. “Obstacles” force us to be creative, to find workarounds, to sublimate the ego and do anything to win besides challenging our enemy where they are strongest.

In fact, having the advantage of size or strength or power is often the birthing ground for true and fatal weakness. The inertia of success makes it much harder to truly develop good technique. People or companies who have that size advantage never really have to learn the process when they’ve been able to coast on brute force. And that works for them . . . until it doesn’t.

At Vicksburg, Grant learned two things. First, persistence and pertinacity were incredible assets and probably his main assets as a leader. Second, as often is the result from such dedication, in exhausting all the other traditional options, he’d been forced to try something new. That option—cutting loose from his supply trains and living off the spoils of hostile territory—was a previously untested strategy that the North could now use to slowly deplete the South of its resources and will to fight.

In persistence, he’d not only broken through. In trying it all the wrong ways, Grant discovered a totally new way—the way that would eventually win the war.

In our lives, we can apply the same lesson–and ideally, not at such a high and violent cost. We can learn from our obstacles, and they can show us the way. We can remind ourselves to see the counterside to every negative (as well as every positive.). And understand that it’s our obligation to push through.

All it takes is mobility, creativity and a little bit of risk.

This post originally appeared on Thought Catalog

It’s been a busy first half 2015. In case you don’t follow me everywhere (twitter is best for articles), I wanted to put together a quick roundup of all the writing I’ve done so far.



Amor Fati: Learning To Love And Accept Everything That Happens

If You Do This, You’re A Monster

Here’s Your Productivity Hack: Go The F*ck To Sleep

Shut Up When They’re Talking To You: Always Say Less Than Necessary

I Just Turned 28: Here’s What I’ve Learned In Another Year

Tell Me Who You Spend Time With, And I Will Tell You Who You Are

Anything Can Have Meaning If It Changes You For The Better

Things This Dropout Actually Learned In College

How To Learn The Art Of Speed Reading

Why I Run

24 Fiction Books That Can Change Your Life

9 Short Quotes That Changed My Life And Why

30 Things People (You) Need To Stop Doing Right Now

3 Questions You Need To Answer Before You’ll Have The Life You Want

This Is What Email Overload Looks Like

Man Drowning In Email Before Honeymoon Pens Epic Autoresponse

Three Positive Habits To Practice Every Single Day

24 Things That Only Writers Know (From Writers)

5 Documentaries You HAVE To Watch

33 Ways To Be An Insanely Productive, Happy Balanced Person

5 Life Lessons I’ve Learned From My Pet Goats

6 Reasons Your Book Will Fail

A Writer’s Routine

How To Be A Public Speaker — Or, The Art Of The Keynote Address



Is Gawker Destroying Itself From The Inside? Let’s Hope So.

I’m a Millennial and I Don’t Understand My Peers—Not Even a Little Bit

Why Ta-Nehisi Coates’s ‘Between The World and Me’ Is Not the Masterpiece We Hoped For

I’ll Miss Working With reddit’s Victoria Taylor

An Interview With the 16-Year-Old Media Manipulator Who Deceived The New York Times

Exclusive Interview: Meet Maddox, Owner of the Internet’s ‘Best Page in the Universe’

How Much Do I Love T-Mobile? You Don’t Want to Know

Here’s the Real Solution to Millennial Angst

Meet the Journalist Who Fooled Millions About Chocolate and Weight Loss

EXCLUSIVE: Behind the Facebook Prank That Gamed Reddit And Reached 1M Pageviews

EXCLUSIVE: ‘Digital Darth Vader’ Charles C. Johnson On Manipulating Politics and Media

5 Subreddits That Will Make Your Life Better

7 People Who Overcame Huge Obstacles to Become Famous

The Surprising Value of Negative Thinking

Journalism’s Biggest Problem Is Not What You’d Expect—And It’s Entirely Fixable

Things Heavy Metal Taught Me About Life

The 7 Strategies That Helped Me Write 3 Books in 3 Years

The Shame of Our Public Shamings

An Annotated Interview: The Superficiality Behind Viral Nova

A Guide to Stoicism, From One of NYC’s Greatest Stoics

The Perfect Spouse Is the Best Life Hack No One Told You About

The Hypocritical Degradation of Brian Williams

EXCLUSIVE: How This Left-Wing Activist Manipulates the Media to Spread His Message

I Discovered a Billion-Dollar Business, and All I Got Was This Free Self-Help Book

EXCLUSIVE: How This Man Got the Media to Fall for ShipYourEnemiesGlitter Stunt

Intentional Insanity: The Occupational Hazard of Writing Online for a Living



36 Books Every Young and Wildly Ambitious Man Should Read



How to Get More People to Actually See Your Work

Marginalia, the Anti-Library, and Other Ways to Master the Lost Art of Reading


‘The Canvas Strategy’ is the fastest way to become indispensable at work




The single worst marketing decision you can make



Everyday Philosophy: How to Turn Trials Into Triumphs

If you’re wondering where the May issue of my Reading List Email is…it sounds like we have a problem. It appears that Gmail’s tabbed inbox layout is finally starting to catch up with my newsletter because the email definitely went out. In the last few days, a bunch of readers on Twitter informed me that Inbox Tabs have been shuffling my Reading Recommendation newsletter into their Promotions tab–or worse, to Spam. For whatever reason, this month’s email had to lowest delivery rate I’ve ever had.

If you’re one of the 40,000 people who enjoys getting the recommendations each month, there are two ways to ensure that it always ends up in your Primary inbox where you can see it.

Drag and Drop

The easiest way is to drag and drop.

Locate the Reading Recommendation Email in your Promotions tab. Left-click and drag the email from Promotions over to Primary.


Once dropped, Gmail displays a yellow box that asks if you want to make this change permanent. Click Yes to ensure that all messages from appear in the Primary tab going forward.

Create a Filter

Locate one of my Reading Recommendation Emails in your inbox by searching for “Ryan Holiday” or “”

Create a filter for “” and check the box next to “Never send it to SPAM” on the second screen.


That should do it.

Thank you to all the readers who brought this issue to my attention. If you’re not already getting my monthly reading recommendations, you can sign up right here.