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Chapter 1 approaches managerial theory as an entry point for examining the relationship between jazz and risk. If management theorists have looked to jazz practice as an analogy for risk-taking, jazz affords us with a powerful window onto a more complex narrative of risk in American life. This chapter develops a distinction between risk and uncertainty crafted by economic theorist Frank Knight, where uncertainty implies a conception of risk in which the parameters of risk are impossible to quantify. Chapter 1 culminates with an examination of postbop, as it was realized by the 1960s Miles Davis Quintet and subsequent artists: the embrace of “controlled freedom” by the Davis Quintet brought an unprecedented level of virtuosity to bear upon improvisatory risk-taking.

This chapter outlines the history of the Miles Davis Quintet, one of the most important and influential performers of jazz music. It examines their compositions, recordings, and their working methods inside the studio. It describes how their conventional practices of extended improvisation and heightened group interaction were groundbreaking, contributing significantly to the jazz repertory. Their innovations also serve as a cornerstone of contemporary jazz composition. Great importance is put on the quintet's departure from chorus structure, and their experiment of “controlled freedom”, where they maximized their creativity, spontaneity, and interaction. The chapter also discusses the background careers of each of the members, highlighting in particular what they brought into the quintet.

This chapter provides some general analytical frameworks relevant to the Davis quintet studio recordings. It defines terms such as “modal jazz”, and provides overviews of strategies used by the group in refining their improvisational techniques. On the topic of pitch, it considers the motivic cells, motivic improvisation, and phrase overlap. In the area of meter, it covers accentual shift, metrical conflict, and metric modulation. It examines the interaction of larger metrical groupings or hypermeter and form, and suggests how the quintet enhanced formal ambiguity in improvisation by masking sectional and formal divisions. It also delves further into the idea of “controlled freedom”, describing the group's interest in uniting traditional jazz approaches with avant-garde ones, and how this affected their approaches to improvisation by indicating a series of intermediate levels between strict adherence to chorus structure on the one hand, and its complete abandonment on the other.

This chapter looks at another of Narayan’s novels, The Bachelor of Arts. The training of the mind of a Narayan hero is properly launched by Chandran in this novel. By the end the struggle yields results; Chandran has gone through a self-devised schedule, of self-education. This young man could be a novitiate in a monastery cutting himself off with a will from the world. His self-training is self-launched. He has come a long way, from an assertion of ‘freedom’ to a voluntary control of freedom, even to a determined self-regulation of it. The moral dividend is a spiritual poise, though a balance achieved by youth.