While both society and astronomy have evolved greatly over the past fifty years, the academic institutions and incentives that shape our field have remained largely stagnant. As a result, the astronomical community is faced with several major challenges, including: (1) the training that we provide does not align with the skills that future astronomers will need, (2) the postdoctoral phase is becoming increasingly demanding and demoralizing, and (3) our jobs are increasingly unfriendly to families with children. Solving these problems will require conscious engineering of our profession. Fortunately, this Decadal Review offers the opportunity to revise outmoded practices to be more effective and equitable. The highest priority of the Subcommittee on the State of the Profession should be to recommend specific, funded activities that will ensure the field meets the challenges we describe.