In my thinking, if you give until it hurts, you gave too much. This isn’t meant to dispute the value or ideal of charity, but to some extent I do dispute the idea of extreme altruism. If we believe that we it is a good thing to make others happy and/or to alleviate their suffering, then we cannot rightfully cause our own suffering (other than in non-fundamental and temporary ways) for the sake of others. So if you give until it hurts you are giving out of ideology rather than from a healthy generosity of spirit.
There is no rational nor true spiritual basis for considering others to be of more importance than ourselves. Consider for a moment, if a man looked at two people and told you, “that person is entirely worthless, and that one is important.” It would seem presumptuous, certainly, but also unfair, unnecessary and unreasonable to be making such absolute moral judgments about the value of different individuals. One person might be more useful as an employee, another might be a better singer, but by what right or reason can we say who is better than another in an absolute sense (if there even is such a thing)? And what, then, makes it reasonable to say that anyone is better or more important than yourself?
What I see in this world and in my experience is that we do value other people, and we are generous when our needs have been met and our minds have matured. Therefore we want to help other people. But do we have an obligation to help others? Is there a moral imperative that says when and where and how much we should give of ourselves. I am skeptical. Even if I had such a belief I would be skeptical of anyone’s right or ability to say exactly how much I owe and who I owe it to.
I see generosity as enlightened selfishness more than altruism or self-abnegation. I think one’s concept of self expands with time and awareness (to the extent that we do mature), and so ones normal and healthy self-interest expands as well. We very naturally want to help our children or other loved ones because in a real sense they are a part of our lives. That feeling radiates outward–and more so when we have more to give. We also create the world we live in with our actions and the mindset they create in us. When we are generous we (at least psychologically) live in a world of generosity, just as when we are narrow-minded, self-cenetered and suspicious we live in that kind of world.
So when I say that giving to others can be good, I mean it not from a religious perspective or an ideological one which requires self sacrifice. I mean it can be good for the receiver and the giver. But it goes too far when the good is not acheived, meaning when it hurts the giver.
This issue is deeper than it might look at first glance. For example, when you give in order to fufill some religious or other ideology, you are not truly giving from your heart, but from what your mind tells you must be done. You are therefore trying to meet some moral dictate, to satisfy some rule. Wise giving is therefore less likely, since the focus is not a heartfelt understanding and response to the true needs of the recipient, but a way to (metaphorically at least) buy your way into heaven.
In addition to the lack of wisdom in the gift, there is also a tendency to stop your own growth when you act from ideology alone. Whereas you might have done the inner work necessary to see your commonality with others and in the process become more naturally generous, your “following the rules” excuses you from that effort. When we give ourselves a simple formula for redemption we close our hearts to the complexity and subtlety of love and life.
Give until it hurts? Never. If it hurts you are giving too much. If you grow as a person you might give much more someday, but without the pain. In the meantime give until it feels right and drop the ideology that says you must suffer so others may not. It makes no sense at all.



