In this study, we share our collective experience of designing a course to provide a space for individual and collective ontological inquiry as a part of a freshman seminar program operated by a university in the United States. Building upon the inquiry-based learning approach that has been implemented in higher education settings, this study forges opportunities of creating a holding environment for the transformation of those who are experiencing learning through a developmental truce (Kegan, 1982). The central design principle of the course was generative pedagogy (Nicolaides, 2015), which treats learning as ways of being and becoming scaffolding affirmative ethics (Braidotti, 2019) in response to ambiguity and complexity. (i.e., Nicolaides, 2013; Nicolaides & Lim, 2020; Nicolaides & Yorks, 2013). By exploring opportunities and challenges of designing an inquiry-based course that amplifies ontological inquiry onto ways of being and becoming, our aim is to start a conversation on how to engage philosophy in the practice of learning effectively. By doing so, this study will address some ethical challenges that the practitioners and scholars may face in implementing adult learning pedagogy that taps into deeper levels of self and identity.