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[A]ny system which leaves the individual upon one horn of the dualistic dilemma is at best the achievement of courageous despair.

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Despair is the result of each earnest attempt to go through life with virtue, justice and understanding, and to fulfill their requirements. Children live on one side of despair, the awakened on the other side.

When a man is in despair, it means that he still believes in something.

An individual in despair despairs over something. So it seems for a moment, but only for a moment; in the same moment the true despair or despair in its true form shows itself. In despairing over something, he really despaired over himself, and now he wants to get rid of himself. For example, when the ambitious man whose slogan is “Either Caesar or nothing” does not get to be Caesar, he despairs over it. But this also means something else: precisely because he did not get to be Caesar, he now cannot bear to be himself. Consequently he does not despair because he did not get to be Caesar but despairs over himself because he did not get to be Caesar.

The individual is in a dilemma: either he decides to safeguard his freedom of choice, chooses to use traditional , personal, moral, or empirical means, thereby entering into competition with a power against which there is no efficacious defense and before which he must suffer defeat; or he decides to accept technical necessity, in which case he will himself by the victor, but only by submitting irreparably to technical slavery. In effect he has no freedom of choice.

"Thus when the ambitious man, whose slogan was "Either Caesar or nothing", does not become Caesar, he is in despair over it. But this signifies something else, namely, that precisely because he did not become Caesar he now cannot bear to be himself. Consequently he is not in despair over the fact that he did not become Caesar, but he is in despair over himself for the fact that he did not become Caesar."

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With despair, true optimism begins: the optimism of the man who expects nothing, who knows he has no rights and nothing coming to him, who rejoices in counting on himself alone and in acting alone for the good of all.

I once heard theologian Rob Bell define despair as “the belief that tomorrow will be just like today.” When we are in struggle and/or experiencing pain, despair — that belief that there is no end to what we’re experiencing — is a desperate and claustrophobic feeling. We can’t figure a way out of or through the struggle and the suffering.

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Despair in our culture tends to produce wild activity: change the job, change the partner, replace the faltering ambition instantly. We fear passivity and prize action, meaning the action we initiate. But the self cannot be willed back. And flight from despair forfeits whatever benefit may arise in the encounter with despair.

There’s a really interesting thing about despair, I think. It has a spark in it of deep motivation. I think despair can be described as looking at every possible scenario and seeing no hopeful one. But what that means is, if you can present someone in despair with one scenario that looks hopeful – that looks like a real possibility – then there’s this immense wealth of motivation to drive toward it, because despair is not a nice place to be.

Someone in despair despairs over something. So, for a moment, it seems, but only for a moment. That same instant the true despair shows itself, or despair in its true guise. In despairing over something he was really despairing over himself, and he wants now to be rid of himself.

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