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RyanHoliday.net - Meditations on strategy and life
Blog

Forget Armor

“The men in mail were somewhat of an obstacle, as the iron plates did not yield to javelins or swords; but our men, snatching up hatchets and pickaxes, hacked at their bodies and their armor as if they were as if they were battering a wall. Some beat down the unwieldy mass with pikes and forked poles, and they were left lying on the ground, without an effort to rise, like dead men.” Tacticus, The Annals

This is why efforts to be closed, protected, secure and insulated fail in a fluid marketplace. At Platea, a Persia general lay on his back weighed down by armor, impenetrable until a Spartan put a spear through the eye hole of his helmet.

You get the point. It doesn’t work.

There are too many people, they have too many resources and the speed of transactions, iterations and judgments are increasingly fast. So let go, be good and see what happens.

January 31, 2008by Ryan Holiday
Blog

On Positioning and a Life’s Pursuit

Every few weeks I wake up to something that makes me grin from ear to ear. Like ten thousand uniques overnight, a job offer, an email from an author I read, the front page of Digg, or a reminder of how good I have it. I get so excited that I don’t know what to do. That’s when I remember: “This is why I’m doing this. And I’m doing pretty well too.”

I’ve pointed myself towards a position that allows as many positive life-changing experiences to happen as possible. This is what Taleb talks about in The Black Swan. Is it more likely that an utterly unexpected event will wipe you out completely or put you on top of the world? If it all went to shit, at the absolute worst, I go back to school and start over. I did alright there. I’ll be fine. And no one can ever take away what happened, what I was able to do. The best case is almost too good to quantify.

I keep saying this but it is not easy. Most mornings you wake up and nothing happened. You get The Fear. You hold onto your principles, your faith in yourself contrary to all posted evidence. Sometimes you break down and have turn to some to someone and completely open up: “What the fuck am I supposed to do?” You see people and wonder what obliviousness feels like and maybe wish for it a little. The stress of knowing there is always something left undone, that you’re letting people down, that you got in over your head. The little twinge of accomplishment you feel at people’s jealousy–and the counterbalance of its loneliness. And of course, the Damoclean notion of knowing that others were here too and failed and got fucked. You worry about stuff that a 20 year old isn’t supposed to worry about. Like getting cornered, selling out, or being over exposed. Making sure you don’t spin off the planet.

We can sit here and talk about the strength it takes to push through. No question it is a requirement. Still, it is unrepresentatively glamorous. There is also the numbness. A internalized hardness that keeps the stresses from cracking the core. You need that. But it doesn’t translate well to the rest of your life. Nor is it a particularly pleasant state, to feel cold and apathetic.

Is it worth it? That’s not a question that I can really answer. See, I don’t have another choice. I can’t be anyone else. You’re only fucking fooling yourself if think you do either. Can you find yourself and be happy? Everyday, do you check a few things off that list? Homo faber. Have you positioned yourself for good gains and manageable losses? And then also understand that you still stand the risk of being totally fucked? If you still want to do it then you’re probably onto to something good. As Godin says, the Dip creates scarcity and scarcity creates value. There’s a reason this stuff is hard, it weeds out the weak. And unfortunately, sometimes the sane.

January 29, 2008by Ryan Holiday
Blog

Thinking Outside ‘Outside the Box’

-When a decentralized organization is attacked, it tends to become more decentralized

-When a centralized organization is attacked, it tends to become more centralized

The Starfish and the Spider by Ori Brafman and Rod Beckstrom

The logic of an entrenched player is to streamline the existing process. If you’re the US Military, you design a billion dollar top-down digital communication system that allows every soldier to carry a camera so that the Generals know exactly what is going on. You see yourself falling behind and finally start to address the problems you’ve been ignoring for a long time.

But in the end it is all strategically irrelevant. You’re never going to be able to add enough horses to the wagon to beat a car. The paradigm is shattered. Utterly shattered. The answer to massive efficiency disparities is not to think outside the box–Boyd told us that the notion of the box itself is constraining. The answer is to stop trying to win that way because winning is impossible. Centralized will never beat decentralized. And from that assumption you can find success again. Like the Stoics said, remember all the people that dug their heels in and fought, did they ever manage to defy nature or were they buried like all the rest?

What an innovative thinker would do is find a way to centralize your enemy (as you slowly decentralize). That probably means giving them power and letting it corrupt. Decentralized movements are able to survive off illegal enterprise, instead of attacking it and pushing them further into it, give them legal enterprise to centralize around. etc.

But look, chances are none of us are ever going to be in the position where we have to deal with a massively decentralized enemy. In real life, we have other concerns that make pure, logical business decisions difficult. That’s not why this important. It matters because it is strategic thinking at its very essence. Instead of looking at the situation from the framed lens you were given, what if you torn it all down? What if you took nothing for granted, got creative and came up with something inspired? I want to beat my fucking head against the wall when I talk to people about this stuff. They just.don’t.get.it.

You get all sorts of cognitive dissonance, rationalization, and this myopic focus on incrementally improving what we already have. That’s because they’ve tied who they are to that system–even if they were never a part of it, there is just too much uncertainty in chaos and speed and decentralization. These always have and always will be the fodder people. In business and especially in war, the last thing you want to be is fodder–a body that gets thrown at a problem. You want to be the person that transcends it. Ultimately, this all ties in to the stuff I have been trying to make sense of recently: vision, curiosity, contrarianism, relentlessness, and efficiency.

January 28, 2008by Ryan Holiday
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