Living through radical historical and social changes can be challenging for people as they go through personal transitions and developmental stages across the life course. Research has shown that living through disruptive social changes influences one generation’s health and wellbeing and those of generations to follow. The research shows how the need to navigate social transitions shapes people’s mental health and wellbeing. Using cultural phenomenology as a theoretical foundation, I focus on lived experience to integrate psychological and physiological processes. I embed life story narrations and daily activity observations in a larger socio-historical context to discuss how people from various age cohorts who grew up in vastly different historical periods orient towards a future of uncertainty. In this context, I define embodiment as a way people use their bodies to interact with the world and base their sense of self on the processing and expression of bodily sensations, social relations, and existential concerns. I identify and illustrate three major themes that are both culturally specific values and under a global scope: 1. People could no longer resolve their existential crisis by merely relying on the traditional kinship system and moral obligations, which results in their exploring and establishing new ways of communication and interactions. 2. Surviving through radical social structural changes, the ideological conflicts across generational groups became challenging for people to live through uncertainty at the current life stage and towards the future. Descendants from families who experience historical trauma are more likely to experience mental health issues, especially across personal or social transitions. 3. There are gaps between the mainstream cultural norms and how people are encouraged to fulfill their aspirations and ideals. The existing patriarchal system and neoliberal cultural trends cannot satisfy people’s growing needs for wellbeing or resolving existential tensions. Vulnerable social groups, especially women, suffer more from the neo-Confucian cultural systems. This dissertation is written at the cross-section of phenomenological anthropology, Chinese studies with broad East Asian cultural impact, and global mental health. The analysis and findings will help understand mental health and psychological wellbeing across the life course, focusing on cross-generational impact and socio-historical transitions.