Feelings of anticipation and hope can underpin the decision of the mature age learner who returns to the formal learning context. However, once part of the new context, exposure to worldviews, social practices and perspectives incongruent or different from their own can trigger feelings of self-doubt and uncertainty, as long held self-perceptions and views of reality are unsettled and challenged. Compounding the challenges associated with the new identity of ‘student’ are other identities attached to the various life roles the mature age learner fulfils. As each identity jostles for attention, the mature age learner’s trajectory of personal change can be erratic and emotion laden. For some, it may feel akin to the novice paintball player, where unless well positioned and attuned to the rules of the combative game, small and large ‘hits’ can constantly bombard and wear down the defences. In the formal learning context, such ‘hits’ may be representative of institutional practices and protocols or social interactions with others from different backgrounds and beliefs; they can also be ‘hits’ in the form of personal challenges that arise from other life role responsibilities. Drawing from the findings of a qualitative study for a doctoral thesis, this paper builds on transformative learning theory as a way to explain the often erratic and contradictory trajectories of personal change made manifest by a small group of mature age learners who engaged in the full-time, thirteen week, face-to-face Enabling program known as STEPS. Findings that point to the emotional toll these trajectories can elicit have serious implications for educators of mature age learners in terms of appropriate curriculum design and the establishment of learning communities that build resiliency, empowering the learner to cope with whatever challenges may confront them.