I like what Feldman says about letting go not being a matter of deprivation at all but rather a way toward happiness.
We believe that it is difficult to let go, but in truth, it is much more difficult and painful to hold and protect. Reflect upon anything in your life that you grasp hold of--an opinion, a historical resentment, an ambition, or an unfulfilled fantasy. Sense the tightness, fear, and defensiveness that surrounds the grasping. It is a painful, anxious experience of unhappiness. We do not let go in order to make ourselves impoverished or bereft. We let go in order to discover happiness and peace.
The only things we can keep are the things we freely give to God. What we try to keep for ourselves is just what we are sure to lose.
-- C.S. Lewis