The Air Force Future Operating Concept identifies the goal to achieve Operational Agility, which is necessary for success in future combat against near-peer adversaries. In order for the U.S. Air Force to reach the goal of Operational Agility, as stated in the Air Force Future Operating Concept, the Joint Doctrine definition of risk must change, and the Air Force must adopt a bolder approach to risk, because current definitions conflate risk with hazards, and Air Force Risk Management measures, at best, hedge risk while ignoring the necessity to exploit risk. The International Standards Organization has adopted a generalized definition of risk that incorporates both up-side and down-side aspects of risk. Aswath Damodaran and Michael Mauboussin provide insights for understanding risk and its relationship with uncertainty and luck, and for approaching risk from a positive, risk-exploitation orientation. A new definition and positive, disciplined approach to risk will empower Airmen leaders at all levels to effectively articulate and, in turn, comprehended Commanders Intent, and thereby to distribute control, decentralize execution, and seize the initiative at the lowest possible levels. Moreover, without a bolder approach to risk, Airmen will miss opportunities for initiative and innovation critical in future multi-domain, anti-access and area denial operations. To succeed in those future battlespaces, the Air Force must develop and entrust Airmen leaders to exploit risk instead of fearing or completely avoiding risk, because the ability to discover and capitalize on unplanned but advantageous opportunities will be the decisive factor in future near-peer military conflict.