Children are, rightly, viewed as vulnerable and in need of safeguarding. However, protecting children from harm should not eclipse their need to learn about managing risky situations and those in which they are vulnerable. How adults view risk and vulnerability will affect the way in which they enable children to learn through activities which carry a degree of risk. Community practitioners may be well placed to discuss with parents how the risk and benefit of various activities can be considered, and children enabled to learn and develop resilience through acceptable risk taking activities. This paper discusses the challenges which community practitioners may encounter when working with parents on enabling them to achieve a balance between risk and safety for their children. It presents some key concepts and perspectives which may assist them to facilitate discussions with children and families.