Leaders often try to manage risks of all sorts by developing scenarios that are highly probable. Using probability thinking, they make decisions. They might also create contingency plans for very unlikely events if they would be devastating. Most leaders don’t bet the farm on highly improbable events. Small bets with guard rails, sure.
Sometimes leaders, even those who quite naturally use probability to manage all types of risk, go off the rails when it comes to organizational or people decisions. This is even more obvious when justifying their own behavior. If they can call upon an exemplar whose behavior gives further credence to their actions, so much the better.
Steve Jobs was a remarkable leader. He was also tyrannical. Using his example as a reason to behave in ways that are destructive is foolish. Steve Jobs succeeded because of and despite his eccentricities. He had few peers.
Mimicking either generic leadership advice or a single exemplar should not take the place of thoughtful, mature judgment.