JPG, this is exactly what so many of us are going through. The FOG (fear, obligation, guilt) that keeps us doing things for our kids, even when we know we are enabling rather than helping.
I’m glad to hear you’re in therapy. It is very helpful to develop boundaries with your adult children. I know it’s hard to cut off support when you’ve been providing it for a long time, but you will probably find that your son will not make progress towards taking care of himself as long as you are providing money. I have a policy I try to keep that I only provide help when it goes towards a one-time expense that looks like it will provide a step forward towards more independence. (Though as you can see from my recent threads, that doesn’t always pan out.) in general, I do not provide money towards daily upkeep. I’ve broken that occasionally when something seems especially dire, but my kids know by now the answer will usually be no. They also know I don’t do bail, legal fees, court costs, tickets, or other bailouts from self-inflicted problems. That one I’m firm on. So, need help getting set up in sober living or need books for trade school? Sure, that’s what moms are for. Perpetually need gas money or come up $150 short on the rent every month? Sorry, that’s on you to manage your life better. Does that make sense? Like I said, I’m not perfect at this - but this is the balance I’ve been striving for personally.
Your son is going to have to arrange for his own support. No job is beneath someone living in his car. He’s going to have to lose the attitude, the pride, or the chip on his shoulder that’s keeping him from waking into the local subway or similar and talk to the manager or turn in an application. Getting a little hungry or running out of gas may be just the incentive he needs. Prepare for him to be mad. Don’t let a tantrum destroy your resolve. For many of our kids, this is the only way they will learn. If he gets mad or abusive hang up the phone, ignore the texts and wait for him to calm down.
I understand all to well the guilt that comes from raising kids in an abusive and chaotic environment. We did the best we could do. We can’t change the past. All we can do is move forward.
I also understand the worry. It’s so hard having a son that is homeless. A car would be a step up for mine. We have to remember that their lives are the result of their own choices, though, and the power to change their circumstances lies with them, not with us.
Did you read the article on detachment? I have found it really helpful. I have to go back to it often.