Background This paper is part of the special issue “Reimagining Research and Practice at the Crossroads of Philosophy, Teaching, and Teacher Education.” Early childhood initiatives have joined a nexus of educational reforms characterized by increased accountability and a focus on measurement as a marker of student and teacher learning, with early education being framed as an economic good necessary for competing in the global marketplace. Underlying the recent push for early childhood education is what we see as a “discourse of improvement”—depictions of school change that prioritize achievement as reflected in assessment scores, data collection on teacher effectiveness, and high-stakes evaluation. These characteristics, we argue, foster increasingly inequitable educational contexts and obscure the particularities of what it means to be a child in the world. Purpose We use the practice of philosophical meditation, as articulated in Pierre Hadot's examination of philosophy as a way of life, to inquire into the logics of educational improvement as instantiated in particular contexts, and for cultivating cross-disciplinary partnerships committed to fostering children's flourishing. We link this meditational focus with feminist and de-colonial theoretical perspectives to make visible the role of power in the characterization of children's learning as related to norms of development, minoritized identities, and hierarchies of knowledge. Research Design: In this collaborative inquiry, we compose a series of meditations on our experiences with the logics of improvement inspired by 12 months of systematic conversation. Our data sources include correspondence between the two authors, written reflections on specific practices in teacher education each author engages with, and a set of literary, philosophical, and teacher education texts. Conclusions/Recommendations Our meditations illuminate the value of collective inquiry about what constitutes improvement in schools. We raise questions about how the measurement of learning is entwined in historical and present-day relations of power and idealized formulations of the universal “child” or “teacher” and argue that we must work together to reimagine the framings that inform our work. Ultimately and most directly, these meditations can support dynamic attempts to cultivate meaningful and more equitable educational experiences for teachers and students. Philosophical meditations at the crossroads of philosophy, teaching, and teacher education thus extend beyond critique toward imagining and enacting a better world in our classrooms, even though (and especially when) this path is not clear.