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