This paper reports the results of a qualitative study of parents’ perceptions of risk and the influence these perceptions had on children’s access to age-appropriate risk taking activities. Thirty-seven parents, aged 28–55 years, participated in semi-structured, in-depth interviews after completing a card sort of the attributes they most desired for their children. Parents formed two groups; one (n = 18) comprised parents who had encountered significant risk in their lives; the second (n = 19) had lived relatively risk-free lives. All parents focused on one of their children, aged 5–17 years, as they engaged in the interviews. We based our analysis of participants’ narratives on an adaptation of Charmaz’s approach to social analysis and Packer’s perspective of hermeneutic interpretation. While all parents provided their children with autonomy support (i.e., structure, guidance and connectedness), parents who had experienced significant risks themselves were better able to balance safety and adventure and offer their children opportunities to manage everyday risk and uncertainty. These parents focused on the benefits of participating in age-appropriate risk taking activities to develop life skills. Parents who had relatively risk-free lives focused more on protecting children from harm and preventing them from making mistakes. These parents’ narratives reflected their concerns about whether they were doing the right things for their children and whether others viewed them as good parents. Results suggested that when parents balanced telic (i.e., serious, cautious, goal-oriented, arousal-reducing) and paratelic (i.e., playful, adventurous, activity-oriented, arousal-seeking) motivations and offered children opportunities to engage in age-appropriate risk taking, their children also learned to move between telic and paratelic motivations flexibly. We conclude that risk and uncertainty are not only valuable, but necessary, contributors to children’s healthy development of happiness, well-being and resilience.