18 yr old kicked out

My son dropped out of school when he was 16 became addicted to weed, started drinking.
I'm a firm believer in tough love, but my mom has always enabled him by sending him money and at times I Felt guilty for staying with a man I didn't love etc and would give in to my son to keep him from telling my parents about him.

I did give my son a firm warning that if he did not wish to obey the rules when he turned 18 I would kick him out. Shortly after his 18th bday, I did it. There was police involvement, a retraining order with a move out order, but I did it. And despite how horrible I felt, and how many hateful texts I received, I did not maintain a relationship with him for at least 9 months.

My mom is back at it though, giving him money and whatever he wants and it frustrates me because in the end, he has learned nothing. He makes us all feel guilty about tough love and it is hard not to help him out, but for every step forward, he takes two steps back and I don't know how to tell everyone to stop enabling him as he needs to learn to do things for himself.

I'm guilty of it too, but not to the extent of what my mom does... How does one deal with this though and not help out your own child when you know they need you? Of course, what they need in reality is to rely in themselves! So frustrating. When and how do we stop when they just can't go forward ... Eventually they will have to right?

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