Life as a Grand Strategy

I used to carry a lot of fear. What if I lose this? Or, ‘I have to monitor that in case something bad happens.’ Worse, I would be unsure of how to act in certain situations, whether to advance or maintain or do whatever else somebody asked me to do right away. I was petrified of anything that could be considered a step backwards. I think I once wrote that I promised myself I’d never work on a wage-basis ever again.

Now I’m starting to understand that this was foolish. It’s an attitude prevalent in what Robert calls “tactical hell.” After I formulated, at least ephemerally, what I was after, the feelings melted away. In fact, in laying out and looking at the chessboard I saw instances where there was not only nothing shameful in taking a job like that but doing so would be the best possible move.

This is what is known as Grand Strategy. It means knowing in a very deep way what it is you’re trying to accomplish. It’s important because once you understand where you intend to finish in that distant, far off sense, you can take in, in perspective, how insignificant many individual decisions are. Left or right, what does it matter? Take this, leave that – knowing how you can turn either to a productive, contributive step means you’re less dependent on circumstance and less anxiety for you to carry.

Let’s say you wanted to become something like Tyler Cowen. Tactical hell would be thinking of ways to acquire what he possesses – getting a huge audience, bothering an editor at the New York Times Book Review, setting up a blog and trying to get linked by other important writers. It would be hell because you’d probably fail at each of these things. Grand strategy would be to think of what and why you want to be like Tyler. Perhaps, it’s that he’s paid to be curious or that you think you’d find fulfillment in the intellectually productive life he appears to lead. The separation of the person and the position leads to an understanding that latter flows from the former. The grand strategy is clear.

Whether you choose this class or that one, work or travel, books or people, these are small, tactical decisions. You know that the standing order is to turn each into an interesting, engaging process; everything is a challenge to examine and a chance for insight.

Think about Fight Club. The whole, it’s only after you’ve lost everything that you’re free to do anything. Well what does he really mean? I think what he’s saying has little to do with possessions. He means that after you’ve cleared out dependency and distractions, you acquire, in a way, a kind of grand strategy: a sense of self. When that becomes your only guiding principle, what is happening on the outside is irrelevant. You’re free because grand strategy gives way to formlessness. And formlessness to peace and calm and self-assurance.

Written by Ryan Holiday
Ryan Holiday is the bestselling author of Trust Me, I’m Lying, The Obstacle Is The Way, Ego Is The Enemy, and other books about marketing, culture, and the human condition. His work has been translated into thirty languages and has appeared everywhere from the Columbia Journalism Review to Fast Company. His company, Brass Check, has advised companies such as Google, TASER, and Complex, as well as Grammy Award winning musicians and some of the biggest authors in the world. He lives in Austin, Texas.