There is a lot of talk in education these days about allowing room for risk and for failure in the learning process. Trying to create a high school culture that allows such space is a challenge, particularly considering that the college process looms at the far end of the curriculum. At times it can seem as if colleges, particularly those considered to be “top tier,” want students who have failed and risked only if those failures and risks are packable in the confined space of an application essay and only if the failures do not leave a discernible mark on the transcript. While the relative truth of this perception is highly debatable, its cultural pervasiveness is not, and thus our students can feel hamstrung—we tell students to take risks in their learning, while we tell them the price of failure is exorbitantly high. The result can be a kind of paralyzing student cynicism at the very moment they should be most open to possibility, and they can end up feeling like passive bystanders at the very moment they should be emboldened by a burgeoning sense of autonomy as students, servants, and leaders.The difficulty may be summed up this way: risking failure in a demanding academic environment feels as if it may compromise a student’s ability to demonstrate the kind of achievement rewarded in the college process. Interestingly at odds with this paradigm, however, great achievement in the world beyond school is only available to those who are willing to risk forms of failure along the way. Therefor in schools we can fail to connect dots that are forever linked in the world beyond our campuses.While I can offer no complete answers regarding how a high achieving high school student population might fully overcome the obstacles that the awkward combination of risk, failure and achievement presents, I have been thinking recently about how the adults in their lives—parents, teachers, and community members—need to model risk-taking and manage failure with humor, resolve, honesty and grace. Such modeling is surely among the best teaching tools we have.