In Sierra Leone, transactional relationships - so-called agreement relationships - have a life-course dimension. Not only are they employed by young people but they are equally important among elders, and they serve different purposes as people age. Long-term ethnographic research with the elderly uncovers that they remember the past and engage with the present through agreement relationships. The elders' love and life histories from the 1930s to today form 'accumulated history'. They reveal a shift from kin-based rural hierarchies, where agreement relationships were carefully concealed, to larger, more dynamic urban networks that are openly held together through such relations. Leaving the former and finding one's feet in the latter become possible through transactional relationships that provide alternatives to fosterage and strategies of fictive or aspirational kin. The case of Sierra Leone invites us to rethink the focus on transactional relationships at a specific point in time for a life-course perspective that reveals the enduring nature of the phenomenon and sheds light on its changing texture in individual biographies, with the potential for capturing large-scale social trajectories within and across countries.