I’ve written about this before. I’ll try to be more clear about it in this post.
You cannot enable homelessness. You can, though, enable the conditions that lead to homelessness.
Homelessness happens as a result of a person’s inability to engage society in a successful manner. It is a relationship issue between the individual person and his or her world, alone.
What you can enable are the conditions that, in turn, have an effect on a person’s ability to engage society. If a person is an alcoholic, you can do things that will enable their alcoholism, like giving money to a panhandler. If a person has mental health issues, you can treat them in such a way that their mental health becomes worse instead of better, such as by denying them the respect every person deserves.
Many people will say that by giving compassion to homeless people, you are enabling their homelessness. Nothing could be further from the truth. Compassion is a restorative action that has the ability to heal people of their assorted problems. And it’s that healing that helps improve a person’s ability to successfully engage the world, and thus leave homelessness.
Be compassionate, be supportive, don’t abandon homeless people.