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Most educators today are likely to proclaim a commitment to teaching critical thinking. Willingness to take intellectual risks such as questioning orthodox teachings or proposing unconventional solutions is an important component of critical thinking and the larger project of liberal education, yet the reward structures of educational institutions may actually function to discourage such risk-taking. In light of the extra importance placed on grades and high-stakes entrance exams in an increasingly competitive educational marketplace, this problem might presumably be magnified among honors students. This essay concludes by calling on honors educators and other interested parties to contribute their voices, their questions, and their proposed solutions to a new JNCHC Forum focusing on the tension among talented students between taking intellectual risks and a desire to avoid the personal struggle and possible failure that sometimes come from taking such risks.