In a broad conceptual framing, cultural heritage is the result of humankind’s interactions with their environment and one another, both in its tangible and intangible expressions. Cultural heritage management is by nature a retrospective discipline, as the assessment and evaluation of cultural significance of heritage assets requires the passage of time. Practitioners often struggle with the evaluation and management of very modern and contemporary heritage items. There is a need to examine whether current approaches and practices are fit for purpose. Current cultural heritage theory abounds with the concept of heritage stewardship with the embedded futurist stance that we should hand on our heritage in good shape to the next generation, yet all approaches are retrospective and rooted in the values of the present. This paper examines to what extent stewardship, as well as two other futurist concepts, the precautionary principle and strategic foresight, are suitable tools for heritage management. Based on that review, this paper then conceptualizes and proposes an assessment model that positions the valuer into a strategic foresight-derived, modelled future ‘reality’ at a 15 to 30-year horizon, which then allows the valuer to apply standard heritage hindsight assessment methodology to contemporary heritage items.