This chapter construes the digression, an act of stepping aside or aslant, as the basic building block in a more capaciously imagined digressiveness, enacted as style, praxis, and ethos. Distinguished from distraction—an ostensibly pervasive state in and of contemporaneity over which far too much hand-wringing distracts thinkers (ironically) from more interesting questions about attention, concentration, and perception—digressiveness has value when explored and expressed as a cultivated art of strolling. More specifically, this form of digressiveness can stroll to, with, and through an encyclopedic impulse without succumbing to the totalizing aggrandizements or pretensions to mastery that corrupt more rigid brands of encyclopedism. As Denis Diderot provides one sanguine exemplar of the dialectical interplay of digressiveness and encyclopedism, he also anticipates a closely allied version of that interplay, nonetheless specific to work in contemporary digital media. Journalist Rich Juzwiak uses the platform of his blog fourfour to enact just such an interplay, modeling likewise for the scholar paradoxical ways to stay a course by wandering and to collect (ideas, objects, and their collision) through dispersal.