LB –
“Background: Recently I talked to my Rebbetzin about how sometimes when I listen to shiurim, I feel terribly guilty afterward. Even if I do more mitzvot after, I still feel horrible and like I don’t do enough or learn enough and am not enough.”
Now here is the key question – why and in what way do you feel “guilty”? Is it something that YOU are at fault and is brought out through (I assume) Mussar kind of shiur? Or, is it something in the sense of a shiur reflecting the negative part of the human.
Better know in the terms of Hashkfah “Shiflos haAdom” vs Gadlut HaBorah” which has been an ongoing debate.
In any case, there were Mussar Movements like Novardak that reflected the above i.e. of “perfecting” the faulty human nature to its best possible, via working on eliminating all faulty human acts “shiflos haAdom”, and is a whole topic on its own. But as far as I am aware, that method is no longer followed even by the most extreme Yeshivish mussarniks and, was never used for women.
Furthermore, I don’t think anyone will disagree that being ‘depressed’ about Mitzvos etc is NOT the way.