There are lots of ways to answer that so let me take a few stabs at that question:
- I think it's often helpful to define terms and so I would ask, "What does it mean to help someone?" Is helping them doing what they ask of you or is it doing what will lead to true freedom? If the victim in Jesus' parable was able to talk and they asked you to carry them rather than put them on the donkey, would that truly help them? Probably not because it would overwhelm you so much that you too might be lying beside the road near death.
- Because this question is so tricky it requires significant input from both God and wise counselors. So it's not a time to isolate and try to solve things on your own. People who like to be enabled are great at manipulating you through guilt so it's important to have clear voices speaking truth into your situation and not letting someone pull your strings. The more wisdom we receive the less conflicted we feel.
- Shame based people are easily manipulated because they feel like they aren't good enough and maybe if they try to help lots of people with their problems they'll prove that they really are good enough and get the approval that they've always wanted. That's a black hole. Don't go there! If you recognize that shame is an issue in your life I'd get counseling for that before I tried to solve the world's problems.
- Finally, I think you have to assess the fruit of your "help". If the person you are "helping" isn't getting any better, then maybe you aren't helping them after all, only enabling their bad behavior. Some times we help by doing nothing or doing the opposite of what seems like help (calling the police, exposing a problem, etc.)
There are no easy answers to the conflict that often comes with trying to help someone. Jesus taught us that it's always the right thing to do to help others in need, just make sure that you are truly helping them and not making matters worse.