Against the backdrop of escalating contradictions and critiques of the digital economy's trajectory, this study analyzes how the emerging digitalization issues might be philosophically understood from a systems viewpoint. Five systemic digitalization challenges including the circular economy (CE), cyberphysical systems (CPS), sharing economy (SE), digital transformation (DT), and smart systems were identified (SS). To investigate digitalization challenges, the machine, organism, cultural/political, societal/environmental, and interrelationship systems metaphors were used. The machine viewpoint demonstrates that the circular economy challenge may be examined utilizing Hard Systems Thinking (HST) methodologies, with a focus on sufficiency via product design and business model innovation. The organism approach demonstrated how the digital twin notion may be investigated using Socio-Technical Systems (STS) and the Viable System Model (VSM) to diagnose and forecast CPS viability in an increasingly linked Industry 4.5/5.0 environment. In analyzing SE's rentier capitalism, the cultural/political viewpoint demonstrated the applicability of purposeful systems techniques for "people complexity." The societal/environmental viewpoint stressed emancipatory systems approaches to "coercive complexity" as crucial to evaluating the perpetuation of digital exclusion by DT from an emancipatory systems perspective. The interrelationship viewpoint emphasized the significance of systems approaches for researching "structural complexity" in intelligent systems. These viewpoints aid decision- makers in identifying problem-solving strategies based on systems thinking.