‘‘In the midst of order, there is chaos; but in the midst of chaos, there is order’’, John Gribbin wrote in his book Deep Simplicity (p. 76). In this dialectical spiri we discuss the generative tension between complexity and simplicity in the theory and practice of management and organization. Complexity theory suggests that the relationship between complex environments and complex organizations advanced by the wellknown Ashbys law, may be reconsidered: only simple organization provides enough space for individual agency to match environmental turbulence in the form of complex organizational responses. We suggest that complex organizing may be paradoxically facilitated by a simple infrastructure, and that the theory of organizations may be viewed as resulting from the dialectical interplay between simplicity and complexity.