The purpose of this study was to examine how preservice music teachers navigate 21st-century skills in their lesson planning and field experiences. Among the various skills, we focused on the Partnership for 21st Century learning and innovation skills. Over 8 weeks, 10 preservice music teachers designed lesson plans focused on creativity, critical thinking, communication, and collaboration, and peer taught their lessons in an elementary music methods class as well as in their field placements. Our data sources included participants' post-field teaching self-evaluations and post-project reflective essays, as well as instructor and supervisor field notes and face-to-face participant interviews. Through the data analysis, we identified three central concepts: (1) Curriculum-as-lived: Teaching like improvising; (2) Balanced in-betweenness: Structure and freedom; and (c) Collective efforts: Stepping away from comfort zones.