What it takes to be generous is to challenge the inner "should", like "this should be this way", or "I should not feel this way". I think it requires sacrifice: not the grudging sacrifice of resentment, but more like a genuine sacrifice that comes from "nothing to lose". Sounds a bit contradictory, I admit, because quite often the connotation around sacrifice is that it is a real giving of something that we feel loathe to part with. But I don't think this is the true meaning of sacrifice. More to the point, sacrifice has to come from a truly free offering that, again, comes from a genuine sense of "nothing to lose". The real heart of sacrifice is this nothing to lose part, because without it, sacrifice becomes little more than a token gesture.
Another way I am thinking about it is to see generosity as a venturing or perhaps "an adventure" in letting go---trying to see what it would be like to give time and resources to others that I would otherwise wish to have for myself. This is the heart of serving and a real contemplative practice that doesn't take place on the cushion.
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