After more than two decades of enduring global reforms, the current paper makes an attempt to investigate the fundamental prerequisites of a successful reform program. The study is particularly complicated by the ambiguity surrounding the very subject matter. While most scholars are united in the view that in order to facilitate a successful transitional process, transitional economies must execute fundamental grassroots reforms, there is no formally accepted universal blueprint of what is considered to be an acceptable transitional program. In an effort to broaden the scope of the investigation, the author probes into neoclassical economic thinking and examines ‘conventional reform indicators’ commonly associated with successful reforms. But the quest brings the author to the realization that mainstream neoclassical economic thinking by itself is not sufficient; it leaves behind unanswered fundamental questions which—for the sake of methodological and pragmatic necessity—demands resolution. Consequently, the author excavates beneath superficial philosophical thinking, and probes ‘mainstream theories’ for answers to valid problems confronting transitioning economies. The inquiry is not only beneficial for knowledge, but has implications for policy-making. The paper is sectioned into four parts: introduction is an appraisal of conventional thinking; section II examines reform pre-requisites and pragmatic questions; section III is an attempt to suggest answers to questions prompted in section II and rationalize unequal reform outcomes in reforming societies that execute identical reform program; the concluding section synchronously weaves together the different pieces and ideas by drawing attention on the uniqueness of contemporary reforms and lessons learned from past reforms.