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Explore how mathematicians and people in general decide which problems are worth solving in this conference talk that examines the cognitive processes behind problem selection. Learn about recent research characterizing and computationally modeling people's judgments about unfamiliar games, including comparisons with large language models and alternative computational approaches. Discover how this framework extends to mathematics, with early findings on modeling evaluations of mathematical problems in both everyday and expert contexts. Understand the translational applications for benchmarking AI systems and designing more human-compatible artificial intelligence partners for mathematical research, addressing the fundamental question of how limited time and energy should be allocated to maximize meaningful problem-solving impact.