How are employment and family experiences simultaneously linked to the timing of retirement? Based on a life course perspective, this article aims to understand the way in which different work and family statuses accumulated throughout adult life, lead to early, on-time, or late withdrawals from the labor market. We focused on Switzerland, a country characterized by a liberal and flexible pension structure that provides widespread institutional mechanisms for both early and late retirement. Using longitudinal methods such as multichannel sequence analysis and event history analysis, we have created types of interlocked employment and family trajectories from age 20 to 57, and estimated their effects on the risk of retirement after age 58. The data come from the retrospective survey SHARELIFE, focused on ageing topics. The results show particularly that whereas early and “on-time” retirement is not likely for individuals—mostly women—with trajectories characterized by housework responsibilities, part-time jobs, and investments only in the public pension fund, late retirement is associated with the absence of a partner’s financial support. In the conclusion, we argue that the Swiss retirement institution should consider alternative mechanisms to offer more balanced retirement opportunities to its citizens, especially to those following less advantaged employment–family trajectories.