Leading with care and compassion, critically reflecting on our teaching practices, and collaboration has always been central to our pedagogical practices. Participating in the #ONHumanLearn project, an initiative designed to humanize learning in higher education, we began to notice a growing divide between our engaged and disengaged students. As we learned/unlearned/relearned to take our professional practice one step further, we started to notice our own sense of powerlessness intensify alongside feelings of fatigue and frustration for our inability to reach the disengaged. We wondered what we could be doing differently to reach them. As we reflect on the process, we humbly accept that leading with care also means caring for ourselves, and that any initiative working to humanize higher learning ought to firmly embed and embody co-learning as a relational and reciprocal approach. In this paper we pay attention to inequities that became more apparent or were created as we sought to humanize education, the opportunities we have found, and our developing awareness of what is needed to sustain change.