The Limits of Strategy

Inner Peace Wins

The relationship between philosophy, strategy, and self-help is something I think a lot about, and this is just a sketch of what requires a longer treatise:

Strategy is the art of getting what you want, typically by overcoming some obstacle. To be a good strategist you need to know where you want to go and what stands in the way. But strategy, even grand-strategy is also short-sighted because getting what you want proves less dazzling once you get it. You soon realize that B is just a means to C and C a means to D and all of a sudden the pursuit of a goal leads to an infinite regress and you end up philosophizing, “Why is this my goal?”

The ancients understood the limits of strategy and thus it was said that you couldn’t judge a life successful except in the moment that a person died: did the person look back on their life and think it was a good one? But even this metric seems limited. Why should we trust the judgment of a single moment in time? Maybe the dying person overestimates or underestimates her life? If we are opaque to ourselves, how can we judge the worth and success of our own lives?

Another reason to resist the lure of strategy is that you end up focusing on what can be won instead of something more long-term and ambitious whose problem-set is less defined and more directional. What do you want to be true in 1,000 years that you can help with now? The ruthless strategist may balk at this question since there is no way to control the outcome or be judged for it in 1,000 years (we think, anyways).

The strategic reason to be a reluctant strategist is that when you are less expectant and more open, good outcomes seem to happen, whereas when you are desperate and anxious for them to happen, they don’t. I don’t think this is just a bias of perception. Confidant people, optimistic people attract better outcomes than those with low-self esteem and limited beliefs in part because their energy is a kind of magnet for the same kinds of people. Doing nothing is a bad strategy, but acting simply to act is also not a great life strategy. To check yourself, you need to ensure your motives are non-reactive. Otherwise, you win the battle but lose the war. Self-knowledge is one way to inner peace and inner peace is the one way to protect against a life in which the goal posts always move away. If you know that you are going in the right direction and will get there, you’ll be less anxious about the specific path you take (your sense of success won’t be path dependent) and this will in turn make for both a better experience and a better outcome. So, to achieve the good outcome, kill the idolatrous urge to conflate a specific, momentary triumph (or failure) with a life strategy, which must remain open.

Being too proud and being too despondent are two sides of the same coin: disbelief in oneself. To cure disbelief, don’t focus on outcomes. That makes your worth dependent and contingent. Focus on the nobility of the effort, the nobility of the aim, the nobility of the search. If you do that, you’ll get to where you need to go, and the world 1,000 years from now will also be better for it.

In short, strategy is limited by the goal, and a life strategy is limited by the fact that the goal of a successful life is incoherent. Embrace this truth and you will paradoxically have a successful life filled with many normal victories that even an amateur strategist would want.