Kobayashi Maru the unwindable situation.
The Kobayashi Maru scenario was an infamous unwinndable situation part of the training for command-track cadets at Starfleet in year the 2285. It was basically used to test a cadet's ethical decision-making and leadership.
The dilemma becomes complex on the situation of having to protect and save civilians while entering to a neutral zone, that become a violation of a treaty that is considered a declaration of war, or letting the civilian ship at the mercy on the Klingons. Your task is to choose the least bad of two bad options.
James T. Kirk decided not to believe that such a no-win scenarios were possible, his impulse was to look for possibilities to save the Civilian ship and save her own ship from being attacked. So he reprogrammed the simulation. That remain to be controversy were some Trekkies consider that he cheated. It's good to question if a situation that we take for granted is really fixed or changeable, We have two bad choices, why not to try a third, fourth or fifth possibility that is less obvious. That optimism showed by Kirk that proven to motivate creativity and thinking outside the box.
The most important thing to take from the test from that episode is understanding the limits of your power. Hardly anyone likes to lose, but sometimes we have to exercise original thinking to figure out which of the two bad options at sight is the most like winning. 
If we are calculating wins or losing on the basis of the outcome that we produce, the impact against hypothetical better outcomes that we have not knowledge or power to make it happened, then we are bounded to lose at least once. But we have to figure out a way to go ahead and do it.
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