Hope automatically implies the possibility of hopelessness. To think you're happy instantly taints, however subtly, the purity of that happiness with the worry of its opposite. Yet the problem is not being happy but our need to label "happiness."
If we make the label for happiness, we simultaneously create labels for sorrow and thus simultaneously create experiences we hope to avoid, even though we know they'll inevitably come anyway. And until they do, we avoid and resist.
As they come even closer, we try to coerce or change the future in order to fend off hopelessness. Therefore hopelessness and other fears chase us constantly, and as we run we never get the chance to stop and take a look at the illusions they are.
We even come up with brilliant devices in order to help us keep up the avoidance, such as sayings we brand as wise like, "When you have nothing to lose you have everything to gain." That's relieving for a while, but it doesn't leave the realm of illusion. For once you start to believe in gain you'll also begin to remember everything you have to lose again.
If in contemplative meditation we begin to dialogue with whatever it is we feel we need, we usually find that something within us tries to coerce or change our problems so that they can reinforce and adapt to our hopes. In other words, we work on gratifying our hopes rather than working on the illusions of hope itself. In the first case you can have endless scenarios to gratify your self, and in the second all you can do is come to a state of acceptance or "witnessing."
So do you really want to engage and perpetuate this any further? Perhaps you will until you're old and wise or completely tired of it.
Though not easy, you only need to see beyond the illusions of duality and into the peace and power of One Absolute, where life becomes not an everlasting contest against opposites but an Absolute Marvel in which experiences can expand beyond the limits of names and labels. It's where winning and losing, first and last, pleasure and pain are realized as illusions, evaporating within deeper and deeper experiences of Absolute Unity.
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