Maybe it’s not about the self and one’s “philosophy”. When I see a person begging (or otherwise doing something needy or disruptive), I ask the most practical question possible:

Has this person had a harder day/week/month than I have? In another phrasing, am I more privileged than this person, as a matter of luck?

The truth is, I know very little about the person except that they are (ostensibly) suffering. The idea that my “encouragement” is going to affect their behavior is terribly ignorant and self-centered.

They might be a wife-beater, or someone who’s simply been dealt a terrible hand and can’t take care of themselves. Or both.

The idea that my giving money will have a substantial negative impact on this person is small and unknowable. It’s outweighed by the likelihood of a positive impact.

This doesn’t mean I give a lot, or often. But I consider that a shortcoming, not a philosophy.