When my dad pushed me to do or decide things I usually didn't do them, or did them with much anger and frustration, even if it was my original plan and decision. So, I think you pinpointed (at least part of) the reason there. People like to feel free in their actions and decisions. I think it's better to let your son decide by himself with support and gentle guidance from you and his father if he is willing to listen. Feeling free is as important as feeling secure if not more important, at least for me. Good luck to your son