The Transforming Learning for the Third Century (TLTC) initiative funds projects that seek to promote students' self-agency and their ability to innovate and take risks. The Provost Task Teams on Engaged Learning and Digital Instruction define this learning goal as follows: "Students must know how to observe the opportunities and capacities of human communities, understand where new or existing ideas or systems could bring value within those communities, and be able to act effectively in order to drive sustained and positive change to provide that value" (Third Century Initiative Student Learning, http://thirdcentury.umich.edu/ student-learning/). This paper begins by defining the interrelated concepts of self-agency, innovation, and risk-taking. After discussing the relevance of these capacities for student development, effective approaches to fostering them will be offered. The paper concludes with a selection of appropriate measures for assessing these outcomes.