I’ve always had trouble relating to kids in my generation.

Other than my wife and a few exceptions, most of my friends are much older and always seem to have been. As I’ve achieved some semblance of success, my peers have tended to be older too.

The result is that I feel old all the time. When I watch a show like Girls it’s usually with a mix of horror and confusion—probably like an ill-humored liberal watching the Colbert Report. What is going on here? Do monstrous people like this really exist? I honestly am not sure if the show is satire or criticism or portraiture.

The first time I met the writer Liana Maeby these feelings were very much in play. It was at a barbeque on the front yard of a house in Culver City. Drew Grant from the Observer was there. So was Daniel O’Brien, a senior editor at Cracked. I remember walking through the house—whoever’s it was—and thinking: I have nothing in common with most of these people.

As we all stood outside and talk, Liana told me she was a writer and working on a novel. I’m sure my reaction was feigned interest. I can’t imagine I ever expected to hear about it again. Because millennials are always talking about stuff they never actually end up doing, especially when it comes to art.

At first, I felt some relation to Liana’s character—someone I assume is at least partially autobiographical since she basically has the same name (Leila Massey) and from what I know of her, the same backstory. Leila is a young screenwriter who everyone sees as the next big thing. She has heat, she has momentum, big jobs come her way. I’ve been there. I’ve felt that.

This relation was short-lived. Because the writer throws it away. Drugs. Alcohol. Work aversion. Pointless travel. The momentum is frittered away. The career torpedoed.

Why? Angst. That perpetual ruiner of promising young talent.

Perhaps that’s what I have trouble relating to and what makes me feel apart. The only angst I’ve ever felt is over not working enough. I don’t fear missing out, I worry constantly that I’m being irresponsible. Like, am I investing enough for retirement? Am I turning things down out of youthful ego or entitlement? When I dropped out of college, it wasn’t because the traditional path scared me—it’s that I wasn’t moving along it as quickly as I desired. I wanted it all now: job, relationship, house. I wanted freedom, but only to skip the dicking around that seemed baked into the process.

At most parties, I’m the only one not drinking. I never really have and don’t quite see the point. Liana joined me in abstaining at that party, for reasons that were much clearer after reading the book. This desire to obliterate oneself—endemic to the binge culture of my young friends and peers—is another one I’ve always had trouble understanding. It’s part and parcel with the angst. It’s a cycle—unhappy and unfulfilled, we make poor choices, which lead us to the escapes that make reality more tolerable. God forbid you were born with the wrong biochemistry and the cycle can be nearly impossible to break.

It fascinates me to see others struggle and rebel against themselves, as the character in her book seems to. Why the self-destruction? Why the idleness? Where does the inability to make decisions come from? Why can’t they commit? What if early on they had lost themselves in something different—work, purpose, relationships?

It’s said that millennials—graduating into the Great Recession—are the Lost Generation. This has always felt like an excuse to me. The directions are the same as they’ve always been. Nobody wants to look them up and follow them. Because it’s somehow inauthentic.

There is a theme in Liana’s book that may hint at what lies at the root of it all. It’s a trait particularly potent to writers, but in a world where everyone publishes, everyone suffers from it. It’s as if the young writer sees her life as a work to be produced instead of to live. Leila, like Arturo Bandini in John Fante’s famous novels about LA, sees life happening “across a page in a typewriter.” Where Bandini saw every moment as a potential poem, a play, a story, a news article with him as its main character, Leila’s book actually lapses into script—literally, in a clever use of meta-fiction.

It turns out she was more than complicit in her own downfall. In fact, she was writing the film of her life. Justifying her addiction as part of a plan to hit “rock fucking bottom.” She brags to her agent that one day, they can “can make a movie about it” and the “town will lose its fucking mind.” The last words of the novel appear in script typeface: “WE FADE TO BLACK.”

It’s this obsession with performance—this performing for an imaginary audience—that makes the ordinary so difficult for most people. It’s something I’ve come to ascribe to a concept from Nassim Taleb—the narrative fallacy. This idea that your life is some unfolding story and it must be constantly exciting and compelling. It’s why young people have always been drawn to Los Angeles and New York, the places certified in the movies and television and books of their formative youth.

Work is hard to capture in an Instagram photo. A boring life centered around your craft doesn’t make for good blog posts. Living up to commitments and obligations and a sense of right and wrong—this violates the image we have of what a glamorous artist gets to do.

Maybe that’s Liana’s point. Maybe that’s the truth she’s trying to get at, having been to the other side and back.

Or maybe I’m just wired like a premature old man and I don’t get it at all.

But I’m glad she wrote it. I’m glad she shipped the book.

This post appeared originally on the New York Observer. 

A CEO calls her staff into the conference room on the eve of the launch of a major new initiative. They file in and take their seats around the table. She calls the meeting to attention and begins, “I have bad news. The project has failed spectacularly. What went wrong?”

The team is perplexed: What?! But we haven’t even launched yet…!

I know it seems strange and maybe even counterproductive to demand that employees think negatively instead of optimistically, but in business circles today, everyone from startups to Fortune 500 companies and the Harvard Business Review are doing this exact exercise. In a direct response to optimistic, feel-good thinking, these leaders are encouraging their employees to think negatively.

The technique that the CEO above was using was designed by psychologist Gary Klein. It’s called a premortem. In a premortem, a project manager must envision what could go wrong—what will go wrong—in advance, before starting. Why? Far too many ambitious undertakings fail for preventable reasons. Far too many people don’t have a backup plan because they refuse to consider that something might not go exactly as they wish.

In fact, I think more companies need a Chief Dissent Officer, someone to shoot down the bad ideas that our blind spots and naive optimism too often obscure. They can catch us when we are puffed up with visions of our own greatness and preordained success. Remember Netflix’s aborted attempt to split into two separate companies? Or when Google Wave was marketed as “the next Gmail,” only to be shut down in a little over a year? If only these great companies had stopped to envision the possible travails that awaited them, they might have been able to prevent them.

No one has ever understood this better than former heavyweight champion Mike Tyson, who, reflecting on the collapse of his fortune and fame, told a reporter, “If you’re not humble, life will visit humbleness upon you.”

The practice goes back much further than just psychology though. It dates back many thousands of years, in fact—to the great Stoic philosophers like Marcus Aurelius, Epictetus and Seneca. And they had an even better name for it: premeditatio malorum (premeditation of evils).

A writer like Seneca would begin by reviewing or rehearsing his plans, say, to take a trip. And then, in his head (or in writing), he would go over the things that could go wrong or prevent it from happening—a storm could arise, the captain could fall ill, the ship could be attacked by pirates.

“Nothing happens to the wise man against his expectation,” he wrote to a friend. “. . . nor do all things turn out for him as he wished but as he reckoned—and above all he reckoned that something could block his plans.”

By doing this exercise, Seneca was always prepared for disruption and always working that disruption into his plans. He was fitted for defeat or victory. And let’s be honest, a pleasant surprise is a lot better than an unpleasant one.

In a case where nothing could be done, the Stoics would use it as an important practice to do something the rest of us too often fail to do—manage expectations. Because sometimes the only answer to “What if?” is, “It will suck but we’ll be okay.”

We often learn the hard way that our world is ruled by external factors. We don’t always get what is rightfully ours, even if we’ve earned it. Not everything is as clean and straightforward as the games they play in business school. Psychologically, we must prepare ourselves for this to happen.

If it comes as a constant surprise each and every time something unexpected occurs, you’re not only going to be miserable whenever you attempt something big, you’re going to have a much harder time accepting it and moving on to attempts two, three, and four. The only guarantee, ever, is that things could go wrong. The only thing we can use to mitigate this is anticipation, because the only variable we control completely is ourselves.

The world might call you a pessimist. Who cares? It’s far better to seem like a downer than to be blindsided or caught off guard.

If we have prepared ourselves for the obstacles that are inevitably on their way, we can rest assured that it’s other people who have not. In other words, this bad luck is actually a chance for us to make up some time. We become like runners who train on hills or at altitude so they can beat racers who expected the course would be flat.

Anticipation doesn’t magically make things easier, of course. But we are more prepared for them to be as hard as they need to be, as hard as they actually are.

You know what’s better than building things up in your imagination? Building things up in real life. Of course, it’s a lot more fun to build things up in your imagination than it is to tear them down. But what purpose does that serve? It only sets you up for disappointment. Chimeras are like bandages—they hurt when torn away.

With anticipation, we have time to raise defenses, or even avoid them entirely. We’re ready to be driven off course because we’ve plotted a way back. We can resist going to pieces if things didn’t go as planned. With anticipation, we can endure.

We are prepared for failure and ready for success.

#stoicweek

When 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.

#stoicweek