Grand strategy is hailed by some as a silver bullet for resolving policy drift, while others reject it as a hubristic term. William James argues that expectations of this concept need to be revised. The first half of this article addresses the study of grand strategy. James identifies and critiques the prominent conceptual frameworks for evaluating grand strategy. He offers an alternative approach for measuring the quality of a state’s grand strategy, based on the notion of proportionality. The second half is tailored towards policymakers, as the article assesses the ways in which grand-strategic thinking can be improved in government.