Chapter 14 addresses the meanings and value of observation in drawing more explicitly, by reflecting on the idea of practice. I begin by contrasting drawing to practice skills or to make preparatory studies for other works with the more comprehensive idea of drawing in the sense of a practice. I introduce conceptions of “marginal practice” and “focal practice” originated by the philosophers, Herbert Dreyfus, Stuart Dreyfus, and Albert Borgmann, whose thinking about the impact of technology has been influenced by the work of Heidegger. I examine the strength of drawing as a “marginal practice,” and as a “focal practice” suggesting that the enduring significance of observation drawing is to be found in the ways in which it differs from dominant practices in contemporary culture. These ways of thinking about practice illuminate questions of skill, work, and pleasure, and provide a means of reconsidering the meanings of observation drawing.