The construction of future technological systems in work domains that do not yet exist, known as the envisioned world problem, is an increasingly important topic for designers, particularly given the rapid rate of technological advancement in the modern era. This paper first discusses the theoretical underpinnings of using cognitive work analysis (CWA) for developing a decision support system (DSS) situated within the envisioned world problem and recasts the problem as pathway-dependent processes. Using this pathway-dependent framework, each stage of the envisioning process is described to reveal how human factors experts can link existing work domains to envisioned instances. Finally, a case study example of the envisioning process that incorporates CWA modelling is demonstrated as it pertains to the advancement of the human spaceflight domain. As a result, this paper provides a unified treatment of the envisioned world problem with an end-to-end example of one approach to designing future technologies for future work domains.