In his novel, "Zen and the Art of Motorcycle Maintenance", Robert Pirsig considers philosophical questions associated with Quality and Value from the perspective of maintaining the proper tuning and performance of a motorcycle for not only proper function of the cycle itself, but also from that of the cyclist being fully in tune with understanding the underlying forms of the mechanical systems and processes working together to propel the union of cycle and cyclist forward. Not only through time and space but toward enlightened understanding and quality of being. The purpose of this presentation is to highlight Robert Pirsig's discussions on quality and value, including the ideas of "value rigidity" and "stuckness", relating them to technological advancements and anxieties. Bringing the discussion to close with a brief reflection about today's smart-everything-technologies and how to apply "Zen" ideas toward maintaining them forward.