Tyler was on a quest of "minimizing his ego" most of his life. At some point it became a problem when he discovered his... personality. And that's where things went north.
You can't keep beating yourself up about stuff sometimes. Some things are parts of yourself which you can't and wouldn't want to change. They hurt no one. Except it's possible to hurt yourself over being some way that doesn't fit an idealized image. I know he struggled with that. He had to give up his ideal and struggled with that too.
Every time he tries to open up a little, the old chain yanks him back. The pull of it is too strong, so it's possible that he's still struggling with going between finding what he wants and cursing himself for wanting anything ever at all.