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Process philosophy has drawn attention to the world as ambiguous and ever changing, however, also enactable. This makes entrepreneurship a processual phenomenon, rightly addressed as ‘entrepreneuring’. Recognizing not only their cognitive, yet also affective and conative capabilities, makes it possible for human actors to mobilize forces that bring the world to a standstill long enough to create a venture for value creation. This, however, calls for insight that is different to universal scientific knowledge – episteme and techne – namely situated insights addressed as m_tis and phronesis. M_tis then concerns alertness and shrewdness and phronesis is about prudence in the context of action. Academic education can only provide the latter competencies able to train for entrepreneuring by letting the students travel across the boundaries of the university. In addition, the dominance of management as an ideology must be pro-actively dealt with in order to create space for entrepreneurial practices. Three cases in academic training for entrepreneuring, all in the Swedish context, which show radically different ways of dealing with these challenges, are presented in a comparative analysis. The lessons are summarized as general conditions for providing training that advances entrepreneurship students’ situated and actionable insights.