The purpose of this article is to share wisdom collected from the field and offer a view of meaningful learning, explore the tensions that exist in educators’ work, and invite conversation about the future of educational practice. The anecdotes and data come from a series of research studies conducted from 2001 to 2011 by a cadre of middle grades researchers— university faculty from public and private universities across Oregon. Over the past decade, we studied the perspectives of middle grades principals, middle grades teachers, university faculty, and district personnel directors representing distinct communities (urban, suburban, rural), disparate demographics (e.g., low SES to high SES), and varying school size (i.e., small to large middle schools). We guided each study with research questions such as: How are national policies affecting how teachers view the nature of their work? How does national policy affect the way middle school teachers balance the academic-cognitive needs of young adolescents with their social-emotional needs (Dalton et al., 2004)? How have high-stakes accountability measures based on yearly academic testing influenced teachers’ curriculum, instruction, and assessment practices (Greene et al., 2008)? What are the perceptions of middle grades university faculty, classroom teachers, and principals regarding well-prepared middle grades teachers (Samek et al., 2010)? We used a variety of data collection methods including surveys, interviews, and focus groups to build an understanding of school and university perspectives.