A few reasons strategy is hard

  • Strategy is dynamic. The best strategies emerge as complex decision environments evolve.
  • Strategy is rarely predictable. Because predictions are rooted in history, they work best in environments that aren’t changing, that aren’t going through a regime shift. 
  • Strategy is hard to practice. That is, it’s hard to backtest, especially if facing an important decision in a rapidly-changing decision space. 
  • The most interesting strategies are created, and aren’t known in advance. They aren’t announced. 
  • The most impactful strategies have long tails. And impacts that are felt far beyond their domains. 
  • Strategy is human. If people are purposive (they don’t have to be fully rational, even boundedly rational will do), then strategy is one of the most human activities. Even an AI will struggle because of the benefits of seeing “beyond the board”. 
  • In strategy, the most important ones emerge when the decision space is infinitely-dimensioned. People may struggle with that complexity, but the remarkable ones will find ways around it – not just to simplify it, but to transcend it. 
  • Strategy is granular.