I am not making any claims to stream entry, but I have had a lot of social anxiety in my life, and found some ways to deal with it. Feel free to ignore this reply if it is too unrelated to meditation...these are just some thoughts on what I have found personally useful.
The anxiety exists for a reason (your history). When you go searching for perspective, that history is going to come at you full-force. Your rational mind might tell you a story about how it's not really a big deal, and you should just get over it, but we both know you don't really believe that story. It has not been conditioned in you like the other one has.
These approaches don't work (at least not at a deep level):
- trying to lessen the anxiety or protect yourself from it
- trying to rationalize the anxiety away
- trying to be happy with the anxiety
- developing better social skills
Most therapists will encourage you to do these. It all sounds good in theory, because this is how we are socialized, but if you really examine it, they just can't work. As you have pointed out, the concept of the self is at the root of all of this, and if you are going to insist on taking the self so seriously, there's no way out.
The only thing that seems to work is to take the time and energy you are spending on those projects, and instead redirect it to something that is *actually* important to you. This is a radical perspective shift, and your mind might convince you that this is completely impossible. If you try it, you will see why and how that happens.
Your mind doesn't like contradictions and cognitive dissonance, but *you* can learn to embrace those, and you might find a great deal of freedom from the mind if you do. Have you heard of "shame attacking" exercises? This is a psychotherapeutic technique where you basically go out into public and do something extremely stupid (but harmless), for the sole purpose of learning to feel shame without identifying with it. I tried this, and I will say that it is very powerful.
I have had a few events in my life that have exposed a real "glitch in the matrix". I don't know how to force those to happen, but if you can increase the chances, it's probably helpful. Can meditation do this? I'm not really sure. I've seen it while meditating, but I have not had any apparently life-altering events while meditating. But, I have high hopes for meditation, because it seems like a fairly consistent and gentle way to practice these skills.
One type of therapy that I have found personally helpful is Acceptance and Commitment Therapy (ACT). I found that this book is well-written and has some great exercises in it, even if you don't suffer from depression:
https://www.amazon.com/Mindfulness-Acceptance-Workbook-Depression-Commitment/dp/1626258457 You can also look up the "ACT Matrix", which is very direct tool for practicing this perspective.
I hope some of that is helpful. I would be curious to hear the perspective of those who are further along than I am, too.