This study addressed work and family enhancement and conflict among adults at midlife (N = 125). The study included personal well-being measured 25 years earlier. Participants were classified into groups on the basis of latent class analysis. Qualitative analyses of narratives within groups enhanced understanding of the experiences of those in the groups. The first of the three groups identified by latent class analysis consisted of a fairly large number of women who seemed to have achieved balance in roles and enjoyed marital and job satisfaction. The second group, almost exclusively male, was characterized by a low degree of work and family enhancement. In the small third group, a profound lack of marital satisfaction coupled with high work and family conflict and low enhancement identified men and women with seemingly enduring low levels of well-being. Narratives largely validated the quantitative analysis but also provided additional avenues for further research.