Digitalization primarily takes place in and through organizations. Despite this prominent role, however, the importance of organizational structure-building processes in the digital transformation is still underexposed in discourse. The fact that ongoing digitalization is linked to an established phenomenon and its own logic, is regularly not addressed due to the attraction potential of the semantics of the digital revolution. Digital revolution and the reordering of societal relationships, though, manifest themselves primarily in processes of reorganization. Structural automation processes in the ongoing digital transformation are limiting the scope for action, necessitating forms of structural structurelessness in organizations that cultivate opportunities for chance. Since organizations realize their operations as a dual of structure and individual, and the principle of organization is therefore based on the complementarity of structural formality and unpredictable informality. The paper discusses the topicality of the classical form of modern organization in the digital age and reflects on approaches to a contemporary design of spaces of opportunity. The reflexive handling of future openness is the central task of management and leadership in order to enable variation and innovation in organizations.