Finances with my 16yo son have been an issue. I take care of his essentials. He's responsible for anything extra. My desire is to teach him to be more independent. "Figure it out," is my mantra.

I have a concern this may have been counter-productive. He has pursued two avenues.

1) Doing house work for his girlfriend's dad. The amount varies but yesterday he landed $60. This I don't have an issue with. He figured it out.

2) He asked his mother for $200. I believe this is in addition to the $20 he already received from her to resolve his negative bank balance.

He does not have a job though his grades are good and he participates in after-school activities. He can get a job, but would be limited to around 5-10 hours a week.

I have an issue with #2 and I'm trying to work it out in my head. Reasons to not care:

1) It doesn't concern me. I told him to figure it out. He's doing just that. It is only my responsibility to hold my line and hope he'll someday come around.

Reasons to care:

1) His mother is teaching him exactly what I am trying not to; to be dependent on others.

2) His mother lives in squalor. He knows. Yet, this doesn't seem to bother him. IMO, this touches on something deeper but I acknowledge this is me getting inside of his head when I shouldn't.

3) His basic ignoring of core responsibilities.

My deep instinct is to confront him and say, "relying on friends and family to support you financially will only get you so far. You're 16. No driver's license (though he's coming around on this). It's time to start stepping up and being more responsible." I think at a minimum this is the wise choice. However, I also want to take it further, contact his mother, and ask her to stop (I know she won't). If I did take that route, I know I'd have to leave it at that; mention it once and let it be.

What is the advice of the RP Dad's out there?