In this paper we discuss work in progress where we are studying the current issues, controversies, and trends associated with the pursuit of postgraduate credentials (e.g., advanced degrees, certificates) to enable career transitions. Given the proliferation of credentialing opportunities facilitated by the Internet, degree inflation, labor market trends toward global outsourcing of some forms of skilled labor (e.g., software development), and a variety of other factors, today's working technical professional contemplating career change is faced with much more complicated decisions than in past decades. We provide a framework for understanding these factors and guidance for those facing such decisions.