How do organizations survive in the face of change? This is a key question for Western military organizations after the Iraq War and its consequences. All human crises are manmade because of we are human beings. The spreading of individual risk also increases systemic risk. The root cause of the problem is what has been termed “rational irrationality” – behavior that, on the individual level, is perfectly reasonable but that, when aggregated in a complex system, produces calamity (Alpaslan & Mitroff, 2010, xvii). From the perspective of organizational adaptation and learning, March (1991) argues that a significant number of competencies needs to be learnt and unlearnt during each and every process of change. According to Birkinshaw and Gibson (2011, 2004), in many sports, ambidexterity is a competitive advantage. Footballers are encouraged to use both left and right foot; left-handed batsmen have a slight advantage against right handed bowlers; the southpaw boxer presents a rarely encountered challenge to a boxer with an orthodox stance; some ambidextrous tennis players even use both hands, separately, to play strokes during a rally. And while some individuals are naturally two-handed or two-footed, many work hard to gain an advantage by practising until they master ambidexterity. The challenge for public security and safety organizations is that with terrorism and changes brought on by cyber-security they are faced with their greatest challenge since the end of World War Two. Not only are the structures and operating procedures undergoing change but also attitudes and values are pressed on by a changing society. Rational black and white thinking no longer functions when immigrants, various ethnic backgrounds, social media and the operating mechanisms and values of market economy force their way into the training grounds of military bases and battlefields. This article examines the usefulness of the concept of ambidexterity as part of the Comprehensive Approach planning and decision-making process adopted by Western military organizations.