This article argues, from a critical realist perspective, that it would be beneficial to extend thinking on how personal and social education could become more central to students' learning. We explore how constructive-informed arrangements which emphasize cognitive skills and affective qualities could be realized through experiential approaches to learning. Our theorizing is informed by neo-Aristotelian thinking on the importance of identifying mutually acceptable value commitments which can cultivate practical wisdom as well as generally benefit society. Thereafter, we outline how the recent writings of Tiberius could inform thinking on how, epistemologically and ethically, a first person perspective on learning and personal growth could connect with normative decision making on how to make good life choices. We conclude by briefly highlighting the methodological potential of using outdoor learning environments to help students make informed and wise judgements which show evidence of discernment, deliberation and effective decision making.