“The test of a first-class mind is the ability to hold two opposing views...at the same time and still retain the ability to function.” (F. Scott Fitzgerald) In distributed, complex socio-technical systems, risks increasingly originate from multiple sources, affect multiple agents in diverse ways, and thus become systemic. The traditional linear causal model of risk control and an individual decision-maker orientation is no longer adequate to contain such risks. This paper reports a detailed case study of a highly complex architectural project by the architect Frank Gehry and his firm Gehry Partners, L.L.C. Gehry and his partners successfully used the 3D representation software Catia to construct radical architectures with dauntingly complex geometric surfaces in spite of increasing systemic risks. Our findings suggest that, in order to successfully combat such risks, organizations rely upon organizing mechanisms characteristic of high reliability organizations (HROs). Our analysis also indicates that creating and maintaining a collective mindfulness is critical for risk control and mitigation in complex socio-technical systems. IT artifacts such as Catia, in combination with other social/technical elements such as skilled workers, contracts, and communication protocols, can enable the five cognitive processes underlying collective mindfulness: preoccupation with failure, reluctance to simplify interpretations, sensitivity to operations, commitment to resilience, and under-specification of structures.