Inaccurate self-observation

I’ve been doing some thinking about inaccurate self-observation and the narratives that people build around it, and I’m curious to hear about other people’s experiences. I find that often when my boyfriend and I disagree about something, he thinks he holds the “truth” for the interpretation of events he is involved in. When it comes to feelings, he has invalidated mine because he thinks they are an inaccurate representation of both his intention and his actions. Ironically, while he thinks that my feelings misconstrue his actions, I think he often has an inaccurate notion of how his actions affect my feelings. We have finally made some progress with this lately and I think he is paying more attention to not only the way things affect me, but also my right to have my feelings. 

That being said, I am more hands-off (or at least trying to be :p) when it comes to issues that don’t directly involve me. He was recently fired from a job and is having a lot of trouble getting another one. It was his first job out of law school, and he didn’t hold it in high esteem because he claimed it was boring and easy. I suspect that issues with inattention to detail, forgetfulness, and lateness had something to do with his being let go, but I haven’t said that to him. (I should mention that he is not currently treating his ADD and hasn’t fully accepted that he has it. He knows what he struggles with, but doesn’t think of it under the ADD umbrella.) He seems to be full of excuses as to why he is better off without the job, how they messed up more than he did, etc. Apparently when he was hired, they told him he could work whenever he wanted because he was hourly. A few weeks later, they told him that he needed to pick a schedule and be consistent with it (something he has trouble doing). He thinks it is their fault that they weren’t clearer with their expectation; I think it is always assumed that an employer doesn’t want you rolling in at 9am one day and 11:30am the next, even if they offer flexibility.  He also seemed unable to put most of his focus into the work and was distracted by long drives to band practices and back to his parents’ house, when he had arranged to stay with relatives that lived closer to the job.

His dad defends my bf and his siblings from any outsider’s criticism through rationalization and joking threats. I have seen my bf do this in defense of his brothers too. His family is very insular and he still lives with them. Just when my bf stopped getting paychecks, his parents wrote him a big check for the money they were going to finish off paying for his college loans because they “wanted the responsibility off [their] chests.” I see this as coddling and enabling; he is unemployed and they just put thousands of dollars in his pocket. My bf is not going to pay off the loans yet because he wants to get a job with a loan forgiveness/repayment plan and pay it off at once with his law school loans, or have them be forgiven. That program takes 10 years to complete, and he has not been hired anywhere yet!

To make a long story short, I know my bf is talented, but I don’t understand the stubborn resistance to self-reflection. I know a fragile ego might be a factor. I am worried that if he carries on this way, I am looking at a future with a partner who might not be able to hold a job. I am financially independent and I feel like whatever is preventing him from growing is also preventing our relationship from growing. I’m wondering how you all have dealt with things like this and what I can do/should look out for.