Starting with my acquaintance with W. Ross Ashby, this paper offers an account of one aspect of his work, information theory. It shows his motivation to embrace information theory, how he extended it, where it failed while fertilizing reconstructability analysis, and what it took for a solution to emerge. Based on Ashby‘s recognition of the material limits of computation, the paper continues his concern for transcomputational phenomena and proposes a paradigm shift to cope with what probably is one of the most complex system we face today, cyberspace. Replacing the epistemological stance of discovery with that of design, the paper discusses how the enormous information quantities of cyberspace implicate human agency, a concept necessary to explain the ecology of electronic artifacts that populate cyberspace. It suggests a new direction for constructing theories of complex systems involving their human constituents not recognized by Ashby but derivable from his ideas.