This chapter explores the factors that contribute to free and happy families using research done by my colleagues and me with individuals from multiple generations. We examined how creative individuals who reported that they came from happy families conceptualized that happiness. While there were some slight differences, particularly across generations, the factors that contributed to this happiness were found to be factors that contributed to the individual’s sense of freedom and ability to be creative. Their families spent large amounts of time doing fun activities that bolstered closeness, feelings of mutual appreciation, and strong support systems for everyone in the family. Freedom to explore and exist without the need to conform to stringent rules along with the instillation of values rooted in love and respect for others appeared to be strong factors for individuals experiencing a sense of freedom and creativity. The availability of stimulating activities that could be shared in with other members of the family was found to not only boost the individual’s sense of autonomy but also allow the opportunity to explore who they were and what they wanted out of life.