I can't help but feel like Phil has some sort of disability that makes him incapable of imagining himself as someone else.
You know how there are conditions like aphantasia, where a person who has it can't visualize anything? It's just impossible to them, they can't think of a banana and "see" it inside their mind.
It's like Phil has some condition that makes him incapable of role playing. Every fucking game he has to say "uhh, this is stupid, I can't make a choice here". It's not you, dumbass, it's the character. Stop self-inserting and play as the character.
Jesus, imagine Phil playing a tabletop RPG. He'd have to play as a Human Beggar otherwise any other character would have him saying "uhhhh, no, I can't use magic in real life, why would I use it here??? Nuhuh".