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A reason why industry incumbents seldom survive technology transitions is their strong reliance on an efficient, but inflexible organizational system. We studied three digital transformation initiatives that created fast progress in a struggling newspaper group by working against the industry logic and established thinking in the area. This chapter argues that management succeeded in introducing a new strategic practice through these transformation initiatives. We focus on three factors contributing to the success: complexity management, short time development of a long-term vision, and the introduction of impossible goals.