The first thought I had: why do you keep pushing therapy given that it always makes you feel badly, and in more than one way?

I relate to what stopdog said and am in a similar position. I personally don't give a damn to many of the so-called socially respected values such as property, getting married, having kids etc. I value education so I have chosen to put a great deal of energy into that in many ways but am not moved by credentials per se. Perhaps more than anything, I value personal freedom and have set my life to have quite a lot of it, which meant choosing not to get into certain kinds of positions and status as it would limit the level of freedom and autonomy that I like. For me, a therapist is definitely not someone I would ever want to trade lives with. I definitely have regrets and would change some decisions and strategies if I could go back, but oh well.

It sounds to me, Sarah, that you have some ideals that are just not compatible with your reality but you keep chasing them. I would ask myself the question why? And, even more, can there be a different way, something that fits with who you? It sounds like you want to live someone else's live and kinda ignore and devalue your own. Of course depression can do that... but therapists get depressed and chronically dissatisfied as well. I personally know quite a few that are some of the most effed up, insecure, lonely, disrespectful people I have met. There is often a lot of talk about such therapists here on PC. I don't think there is anything magical about status, wealth, property.... many people who have them complain about all the maintenance and stress those things can come with and wish they had chosen differently.