Despite the common misconception that people who are born into wealth don’t (or shouldn’t) have problems, there are many challenges that rising generation family members face. Interviews with inheritors often reveal with themes of flagging self-identities, fear of failure, isolation, and lack of motivation. The roadblocks on the path towards thriving experienced by the next generation of affluent families are often unseen and generally not acknowledged. What can look like poor behavior – entitlement, disengagement, apathy, and lack of motivation – is often camouflaging deeply-felt confusion, self-doubt, fear, shame, and anxiety. Those next generation family members who adopt a mindset of hope, growth, and a willingness to persevere and find their own voice and path are referred to as the “rising” generation. This paper explores what traits and skills support inheritors to become members of the rising generation. Based on semi-structured interviews with rising generation exemplars, this research identifies four positive psychological skills or traits – growth mindset, grit, mastery experiences, and positive relationships – that are commonly present within the rising generation family members who have overcome the pitfalls of inherited wealth in which many of their peers become entrapped. Additionally, this paper outlines how both parents and their children can begin to cultivate these skills and traits.