I don't think therapy would help me to be honest. My problem is not psychological; it's that I need more money to buy my time and freedom. One time I was earning a modest passive income for about 3 years while working on open source projects; I was quite happy then and the fact that I didn't trust anyone was not a problem as I wasn't forced to interact with anyone.
I guess one positive aspect about this feeling of 'not caring' and putting on a mask is that it comes across as confidence and it gives me more control. I can say unexpected things and control other people's emotions to some extent.
When you're always willing to throw away the entire relationship in every interaction, people tend to respect you more for some reason. It's like; if you don't value the relationship, it signals high status or something. I suppose this is the trick that psychopaths use?