The chapter examines how evolving cultural discourses and social circumstances influence strategies for cultivating a sense of hope, while integrating insights from psychology and social sciences on life’s meaningfulness and resulting life strategies. The findings highlight variations arising from changing cultural contexts (social relationships, attitudes, and values). The chapter introduces a theoretical model for fostering hope, categorising strategies into four groups: securing one’s life (hope for recovery from illness, overcoming poverty, managing old age), reproduction (continuity through children), preservation of memory and reputation, and transcendental hope. This dynamic is illustrated through case studies drawn from Roman history writing, funerary inscriptions of children, and late antique Christian discourse.