This chapter acknowledges that as parents the people are far from perfect, and therein lies opportunity. It is all about the love of risk-taking. The payoff from being an open-to-learning parent comes in times of conflict, whenever there are differences in views or performance is unsatisfactory. There is a dignity of risk that parents need to teach their children. In some societies (e.g., Eastern Confucian-based countries) saying ‘no’ is to be avoided, and often it is better to avoid answering or deviate the conversation so a no or refusal is not provided. Perfection is not the goal. The parent’s role is to be open to learning opportunities, create high levels of trust and safety to make and learn from mistakes, and teach a child what reasonable means in risk-taking and how to say and react to ‘no’. The boundaries between risk and safety and between yes and no are too often fuzzy and not strong demarcations.