Individual difference and diversity among older people alludes to the importance of creating flexible programmes facilitated in welcoming, person-centred, learning environments. In response, I present my ideas for developing a future online local history project involving older adults’ memories of childhood. Through my qualitative fieldwork interviews, I consult practitioners and learners who have experience using Information and Communication Technologies with, and as, older adults in education and training contexts. I invite these participants to describe the possibilities for, and challenges to, realising my ideas for the future project. Through documentary analyses, and my use of a recurring circle metaphor, I compare and contrast the participants’ expressed ideas with those I garner from among the literature. My intentions are to direct my project designs in response to the educational needs of older adults. I note EU and national policy responses to demographical trends as seeking to provide educational opportunities for older people based on their needs, motivations and interests. Despite tendencies to view these needs and motivations as homogenous, purported benefits to engaging older adults in education emphasise improvements to their personal and social well-being. I see policy regarding the provision of ICT skills training for older adults as suggesting two broad agendas: (a) social inclusion, and (b) economic need. Acknowledging further heterogeneity among older adults in respect of their varying degrees of interest in, and familiarity with, ICT, I argue that the acquisition and development of ICT skills may be incidental to their participation in the future project. I contend that more meaningful participation in the future project may be fostered through the adoption of an oral history dimension that recognises the value of contributors’ lived-experiences. Capturing the stories may present health benefits to these contributors, and offer a way of connecting to marginalised voices.