Despite the acclaimed potential of industry 4.0 for efficiency and growth, statistics show that the majority of firms’ digital transformation programs fail to meet their objectives. We provide a plausible explanation of this understudied phenomenon through theoretical discussions on the four overlooked paradoxical characteristics found between digitalization activities. Further, using the lens of lean and dynamic capabilities theory, we propose strategies for firms to transcend the paradoxes and in turn, realize their expectations of the transformation initiatives.