The age-normative framework has gained widespread acceptance among students of the life course since the pioneering work of Bernice Neugarten had her colleagues in the 1960s. Investigators have begun to call for new research in this area to determine how these schedules operate in contemporary American society, how they might vary by life sphere, and how they might operate differently for men and women or along other important social divisions. Building on interviews with a random sample of 319 adults in the Chicago metropolitan area, we turn our attention to cultural age "deadlines" for a series of general transitions related to education and work. While a rough, "normal biography" of educational and work life existed in the minds of our respondents, the deadlines attached to that biography were flexible guidelines for how those trajectories might unfold, not rigid, normative principles. We relate these findings to complementary evidence on family transitions, and we consider our findings in light of two lively scholarly debates. One debate concerns the degree to which various life spheres (e.g., family, education, and work) are more or less structured by age, and the other debate concerns the degree to which men's lives are more or less structured by age compared to women's lives.