Proposing a major (though envisaged synergetic) shift in the knowledge management (KM) paradigm needs to convince a skeptical audience. This article attempts such a feat and motivates its conceptual considerations by fusing a wide scope of theoretical KM-related foundations in response to current KM unsustainabilities and emerging enabling technologies. The envisioned workflows, infrastructure, affordances, and impact resulting from the progressing design science research and prototyping efforts are consolidated and reframed, guided by a five-step visioneering process and twelve triple-criteria-clusters combining innovative, technological, and vision-related qualities. Inspired by Bush’s “Memex”, a desirable vision never realized since its suggestion three quarters of a century ago, the novel KM system (KMS) pursues the scenario of a mutually beneficial co-evolution between individual and institutional KM activities. This article follows up on the unsatisfactory and unsustainable state of current KM affairs suffering from accelerating information abundance, invisible work, structural interdisciplinary holes, lacking personal tools, and widening opportunity divides. By portraying a potentially transformative and game-changing technology, the crafting and drafting of a desirable, sustainable, and viable KMS vision assures transparency and can be more easily shared with a critical mass of stakeholders as a prerequisite for creating the respective future KM reality. The drafting of the “Desirable Sustainability Vision” is envisaged to assist a currently accepted KMS start-up project and investment.