What is it that makes you feel generous? Do you give a dollar to a panhandler and assume it will go for drink or drugs? Do you put a dollar in the collection plate because it’s expected? Those may look like generous actions, but the motivation that would make the act genuine is lacking. Generosity is one of the 6 “perfections” that Buddhists aspire to practice, and the following is the most beautiful instruction I have ever found on what makes an act one of generosity. It was written by Geshe Tashe Tsering and is quoted from his book, The Awakening Mind.
To friends, give with nonattachment. To enemies, give with love. To strangers, give with closeness. To those with good qualities, give with aspiration. To those with faults, give with compassion. To those who are inferior, give without arrogance. To those who are equal, give without competition. To those who are superior, give without jealousy. To those who are rich and happy, give without resentment. And to those who are miserable and destitute, give with deep compassion.
The point is to give what is needed in a genuine gift. If there are any strings attached, or any aversion or negative emotions to the recipient of the act, we aren’t really being generous, we’re just pretending. That doesn’t mean we have to hug the homeless person on the corner or to be indiscriminate in what we give: It means we need to remember that the individual is alive and has needs, just as we do. We have to care about helping in some small way and not regret giving or puff ourselves up at a demonstration of our self-worth. We have to let go of the gift with grace and stop investing ourselves in what the recipient does with it. That makes it truly generous.