The mature age learner’s re-engagement with a formal learning environment may be somewhat akin to the novice Paintball player, who unless well positioned and attuned to the rules of the combative game, is bombarded and worn down by constant ‘hits’. For the mature age learner, such ‘hits’ may come in the form of tensions surrounding institutional protocols, social interactions with other peers, and personal challenges related to other life role responsibilities. Transformative learning theory (Cranton, 2006; Mezirow, 2000) accounts for the often erratic and contradictory trajectories of personal change that some mature age learners make manifest. Findings in this article suggest that these trajectories need to be taken into consideration by educators through the assurance of appropriate, meaningful curricula, and the promotion of learning communities (Gabelnick, MacGregor, Matthews and Smith, 1990) that build resiliency (Knight, 2007; Goleman, 2002; Resiliency Initiatives, 2001) and empower mature age learners to cope with the challenges that will inevitably confront them.