Epistemic Status: Simple point, supported by anecdotes and a straightforward model, not yet validated in any rigorous sense I know of, but IMO worth a quick reflection to see if it might be helpful to you.

A curious thing I've noticed: among the friends whose inner monologues I get to hear, the most self-sacrificing ones are frequently worried they are being too selfish, the loudest ones are constantly afraid they are not being heard, the most introverted ones are regularly terrified that they're claiming more than their share of the conversation, the most assertive ones are always suspicious they are being taken advantage of, and so on. It's not just that people are sometimes miscalibrated about themselves- it's as if the loudest alarm in their heads, the one which is apt to go off at any time, is pushing them in the exactly wrong direction from where they would flourish.

Why should this be? (I mean, presuming that this pattern is more than just noise and availability heuristic, which it could be, but let's follow it for a moment.)

It's exactly what we should expect to happen if (1) the human psyche has different "alarms" for different social fears, (2) these alarms are supposed to calibrate themselves to actual social observations but occasionally don't do so correctly, and (3) it's much easier to change one's habits than to change an alarm.

In this model, while growing up one's inner life has a lot of alarms going off at various intensities, and one scrambles to find actions that will calm the loudest ones. For many alarms, one learns habits that basically work, and it's only in exceptional situations that they will go off loudly in adulthood.

But if any of these alarms don't calibrate itself correctly to the signal, then they eventually become by far the loudest remaining ones, going off all the time, and one adjusts one's behavior as far as possible in the other direction in order to get some respite.

And so we get the paradox, of people who seem to be incredibly diligently following the exact wrong advice for themselves, analogous to this delightful quote (hat tip Siderea) about system dynamics in consulting:

People know intuitively where leverage points are. Time after time I’ve done an analysis of a company, and I’ve figured out a leverage point — in inventory policy, maybe, or in the relationship between sales force and productive force, or in personnel policy. Then I’ve gone to the company and discovered that there’s already a lot of attention to that point. Everyone is trying very hard to push it IN THE WRONG DIRECTION!

The funny thing about cognitive blind spots (and that's what we're looking at here) is that you can get pretty far into reading an article like this, hopefully enjoying it along the way, and forget to ask yourself if the obvious application to your own case might be valid.

If so, no worries! I developed this idea an embarrassingly long time before I thought to ask myself what would be the constant alarm going off in my own head. (It was the alarm, "people aren't understanding you, you need to keep explaining", which was a huge epiphany to me but blindingly clear to anyone who knew me.)

And the framing that helped me instantly find that alarm was as follows:

What do I frequently fear is going wrong in social situations, despite my friends' reliable reassurance that it's not?

That fear is worth investigating as a possibly broken alarm.