The stubborn dominance of objectivity in child observation in pre-service early childhood education warrants letting go of as we confront its limitations as outdated, problematic, Eurocentric, neo-liberal and even racist. In the context of recent aims to establish 'critically reflective' practices, such as 'pedagogical documentation' and 'collaborative inquiry' as the 'new way' to 'do' early childhood curriculum planning in Ontario, Canada, the authors are concerned that the hard work of naming and creating conditions to 'think together' with concepts of subjectivity has been missed and misunderstood. The risk of missing this shared thinking and not persevering in the struggles of subjectivities, especially in curriculum courses and placement, underestimates and 'under-minds' the intellectual capacity of students and positions theory as neutral in its relation to practice. How, then, does one take up subjectivity and recognize its affordance in building the intellectual and relational capacity of pre-service students? What conditions need to be created to lead with critical thinking and engage in subjectivities in the context of early childhood education pre-service programs? Drawing on critical educational perspectives, the authors work to define subjectivity in the context of early childhood education; identify the conceptual barriers that they have encountered in their work as a professor and a field liaison; and propose potentially generative conditions for pre-service programs.