Students increasingly appear anxious, risk-averse, and worried about getting things "wrong." They may appear to lack intellectual curiosity, and be unwilling to engage in independent study. This essay explores how teaching and assessment in theology and religious studies might help students learn to take intellectual risks, and increase their resilience. One approach is to encourage students to experiment and "fail safely," to increase their confidence that they understand what is expected of them, and to help them begin to understand learning as more broadly formational, not always directed toward a grade. I suggest three strategies: more formative assessment; a stronger narrative about the purpose of formative assessment; and an appeal to values, virtue, and the cultivation of character. Via these approaches, students might be encouraged to understand assessment in less utilitarian terms and increase their resilience for a world characterized by volatility, uncertainty, complexity, and ambiguity, prepared both critically and dispositionally to thrive and contribute positively to society.