The authors of this article write that, as college teachers, they continue to confront their own timidity, and fear of risk. They have had to ask themselves when, in lip service to academic rigor, they are just taking the safe way out. They say that they worry at times while admonishing students to think for themselves, come up with new ideas, and take intellectual risks if they have failed both in the design of their assignments, and in their assignment methods. Over the past few years, the two of them have experimented, played, and tried to push themselves away from their comfort zones to challenge themselves and their students in new ways. In the two sections presented here, these two authors discuss their attempts to encourage honors college students to take risks and to engage with course material in creative ways that develop their critical thinking skills. Kate Wintrol discusses her struggles in an introductory survey course to design creative assignments, that encourage critical thinking while Maria Jerinic analyzes her efforts in an upper-level seminar to encourage students to produce creative products that deviate from standard academic research assignments. They offer experiences in response to the public conversation surrounding the nature of U.S. education at all levels.