This essay will focus on three factors that may help to explain why it seems to be so difficult for many lawyers to escape the confines of a narrow, legalistic framing of issues-or more poetically, why they may be predisposed against looking down "the road less traveled by." These factors should be taken into account as challenges to the widespread adoption of innovative, more humanistic approaches to lawyering. First, the essay will turn to research regarding the psyches and psychological needs of the people who choose to attend law school and become lawyers. Second, the essay will consider what is required from lawyers to sustain the autonomy and privileges of their profession. Third, the essay will examine the demands of the business of law. Finally, the essay will consider the potential role of legal education in helping lawyers to develop an integration of thinking and feeling like a lawyer.