I’d not push him either. I don’t think it’s a good idea to push people to change careers.

I agree it’s not your place BUT if he asks you for money and for you to buy stuff, then it kind of becomes your place. It’s like when kids turn 18 and argue they are adults and it’s not your business to tell them what they do. Sure. But next time they ask you for money, it becomes your business and your place. Within reason of course.

That’s how I look at it. No one can tell me what to do. But I also don’t ask anyone for anything. When I’ll start asking, they’ll have rights to tell me what to do (within reason).

Just my opinion of course