The practice of generosity takes us out of the acquisitional paradigm of happiness that most of us get — particularly if you grew up in a Western culture — that your happiness and well-being will ripen when you get that degree, that job, that house, that relationship, or whatever it is. We’re taught to condition our happiness on these things, and we yet don’t always get what we want. Even when we do get what we want, it’s very challenging, if not impossible to maintain a perfect set of conditions.
Ultimately and perhaps more importantly, real generosity is mostly about letting go. Gil Fronsdale said it’s an antidote to our stinginess and feelings of scarcity. This is intimately connected to Buddhist practice, particularly The Second Noble Truth, which is that all of our mental anguish comes from clinging and aversion. So anytime we’re practicing strengthening this muscle of letting go, it’s right in the heart of the path of practice. Ajahn Cha said, “If you let go a little, you have a little peace, if you let go a lot, you have a lot of peace, if you let go completely, you’ll have complete peace.”
As a child in India, I experienced that there’s a level of generosity that is often- inversely proportional to people’s resources. The people who have the least seemed to have the most generosity. It reminds me of a story about this anthropologist who went to a remote part of Appalachia, and he was interviewing this woman living in a dirt floor shack with no plumbing and no electricity. He asked the woman “What would you do if you came into a large sum of money?” She thought about it for a minute and she said “I guess I’d give it to the poor.”
What this story demonstrates is that sometimes the spirit of generosity comes with a with a feeling of abundance, or at least sufficiency. This woman, who by our standards has almost nothing, doesn’t see herself as poor. This points to the saying from the Buddha, that “if people knew the results of giving in the way I know them, even if it were their last morsel of food, they would not eat without having shared it if there were someone to share it with.”
– excerpt from Gullu Singh’s talk True Generosity: The Gift of Letting Go