Paideia, a Classical ancient Greek notion of education, encompassed both holistic formal instruction and art (particularly poetry) as means to develop cultural values and understanding. This dissertation examines how the new media arts—as a transdisciplinary and computational field—can be leveraged to fulfill a contemporary notion of paideia in both its practice and instruction, demonstrated through respective artistic and pedagogical proofs-of-concept. Specifically, we analyze the ways in which the computational platform can facilitate the creation and readability of causal relationships across information to embody value, meaning, and holistic thought. We examine how we design affordances—formal qualities that constrain an object’s possible uses by an agent—for guiding participant behavior (observed or enacted) and interpreting meaning as part of experiential learning. We will achieve this through artistic installations and objects. We discuss pedagogical strategies with a cross-disciplinary conceptual framework to support holistic thinking through digital design-based learning. We compare these new efforts toward paideia with ancient Greek media and approaches. Toward imparting values, the cybernetic nature of physical computing and other interactive systems offer a means to model or to incentivize (and thus train for) certain kinds of participant actions and behaviors. We present an original body of performance and installation work designed to cultivate the values of social cooperation and attention to nuance. Toward shaping meaning, we propose that complex non-verbal ideas may be communicated by strategic formal design that 1) follows “natural [somatic] mappings” or culturally established associations and/or 2) explicitly defies them, directing attention through “strangeness.” To this end, through a theoretical framework and artistic proofs-of-concept, we explore how computation facilitates abstraction and metaphor via operations of mapping, analysis, and execution. Lastly, to promote trans-paradigmatic thinking, media arts education and practice through fictional worldmaking can provide a means for organizing complex knowledge and systems. We discuss conceptual framework contributions within the THEMAS (STEAM + creative Humanities) pedagogical model (as originally conceptualized by Marcos Novak). In these ways, building upon ancient roots, this research both informs the field of media arts and technology and informs education through design strategies for (artistic) experiential and making-based learning.