The contexts of design are constantly changing, sometimes to the extent that once a ‘good’ designerly response to an issue, over time becomes increasingly problematic. Therefore, there is often a need to rethink design and its concepts. Programmatic design research may provide an exploratory space for inquiry through specific examples in relation to certain theoretical and conceptual framings. In this paper, we explore [dis/re]orientations towards design histories for creating alternative programmatic research spaces. We work through an everyday challenge, ‘Terms of Service’ (ToS), a regulatory mechanism amplifying power asymmetries in relating to data-intensive things. Disorienting design by making an odd association between today’s ToS and the ‘ornament’ in early industrial design, we explore resulting reorientations to rethink designing in this domain. Finally, we outline how [dis/re]orientations could be considered a speculative method for making a kind of ‘Programmatic Time Travel’, using reflections of pasts to reimagine designing for just futures.