Amid a long period of deskilling in art school curricula, craft has been denigrated as inferior to art and confining for artists, but can craft liberate imagination? The purpose of this study was to understand the relationship between an adult learner's self-perceived capacity for imaginative expression in representational drawing and the development of her artisanal judgment during a self-directed program of classical study, online and in-person, over a period of 22 months (mostly during the coronavirus pandemic). The researcher created, coded, and analyzed drawings, photographs, field notes, diaries, and video recordings to track cognitive events and situative factors encountered in the process of learning to draw. Rooted in Kantian philosophy and guided by Polanyi's theory of tacit knowing, an analytic interpretation of findings revealed the role of knowledge (empirical, axiomatic, tacit) and epistemically felicitous falsehoods in achieving constructive perception, a capability suited to imaginative expression in drawing and the predominant challenge of navigating complex attentional dynamics. Findings also described the role of embodied modalities, which constituted a somatic activity system, in grounding cognition and supporting learning transfer. Exploration of communities of practice served as a rite of passage, bringing to light artistic apparatus and valuable opportunities for peer learning. The inquiry exposed the author's unhelpful assumptions about imagination and identified methods for developing it that could be earned, not merely gifted: elaborative sketching, engaging with art, visual research, perceptual and recollective drawing, constructive drawing, and problem finding. This firsthand processual account of adult learning recommends a holistic approach to constructivist pedagogy over naive, or trivial conceptualizations of constructivism in drawing curricula. In addition to helping novice artists heal the breach between skill-building and imagination, the study contributes to literature, in educational psychology and social sciences generally, on adult learning and cognition in the arts. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]