LT
It's nice he replied. Most T's and decent humans would be supportive of someone doing something good for themselves. You are right though, you need to do it for you. It's ok to have support along the way, cheerleaders and such but it has to be for you. I hope you are able to do that
I feel like, and maybe I'm off, but you seem to constantly seek approval from him. I'm unsure why? Part of a T's job is to be supportive and non judging, he has proved time and time again, that he is ok with you. I wouldn't expect much different from a T. I think, and I lack this too so it's not judgmental, you need to find some true and real self love. You need to approve yourself. I struggle with it too but I'm trying, making a list of things that scare me that I want to do and things that can build my confidence. I don't hate myself but I sure don't love myself.
Hopefully in time, we can both get to that place where we can love ourselves and approve of ourselves and achieve the goals we want for ourselves. Good luck to you with it all