Am an old man and a long time Trekkie and absolutely loved your post. You are so far ahead of the game, pondering such thoughtful things when the grand majority of the world is looking at how to accumulate more for themselves. If more people had your compassion and desire to reach out, think of what a beautiful place this world could be. I don't think you need to burden yourself with some measurement of what is "enough." I think you follow your heart in individual cases, building on successes and learning from failed gifts. It is hard to go wrong giving to others. It is a pay it forward thing. Even if the person you are generous with does not continue the chain and grow in giving to others themselves, this is on them. They will have to live with their lack of compassion, and you are still free to pass along in a new direction, with the new knowledge of that failed investment. If you chose to gift to your friend, enjoy this exchange and then watch how it blossoms. You will know that your heart is good, and you will be receptive to who should receive your blessing in the future. You have inspired me to look at my own finances and giving and to reevaluate if I'm truly doing my best or am I just "generous" when it doesn't really affect me. Thanks.