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Over time, a black and white picture of optimism and pessimism has emerged. Early optimism research may have over-focused on advantages and understated potential costs of optimism, leading providers to overprescribe “positive thinking” hoping to improve well-being and enhance performance among pessimists. However, pessimism type is key in predicting performance, as findings reveal stark outcome differences for natural/hopeless versus strategic/defensive pessimists. Several studies suggest defensive pessimists perform at least comparably to optimists. Further, research indicates that attempts to encourage either defensive pessimists or strategic optimists to abandon preferred preparation methods in favor of opposing strategies often results in reduced performance.