This document discusses barriers to transforming legacy organizations into those of the future. It summarizes 6 key barriers: 1) Management frames of reference that are rooted in the past and resist change, 2) Traditional management learning programs that do not adequately prepare leaders for transformation, 3) Narrowly defined management power that prioritizes short-term goals, 4) Regulatory capture that allows regulated industries to influence policy in their favor, 5) Media control through ownership and advertising that distorts reporting away from challenging the status quo, and 6) Powerful elites who have a lot to lose from transformation. Case studies are provided to illustrate how these barriers impede leaders seeking to reinvent organizations.