Sometimes Low Self-Esteem Comes From Pride
I believe that one of the main reasons that I was always hurting so much inside and felt so down on myself, was that in the things that really mattered, I honestly and innocently expected unrealistic things for myself. It was torture. I felt it was a great injustice that I was not considered one of the best guys in the beis hamidrash - yet I am a mediocre lamdan. My guts felt that I was such a loser that I was not on as high a madreiga as some others I saw - yet I really am in need of much growing up and other work. It all put the spotlight on my weaknesses and I needed to shift the blame and find a nechoma. Everyone deserves a nechoma from pain. Even innocent fools.
But once I finally got comfortable with the facts about myself, I began to get comfortable with my life, with the people around me, and of course, with Hashem. See, I was helped to see that the thing that made me feel so sure that I was a pathetic excuse for a yid was: my Pride! I had an inflated self image that was killing me, not just a deflated one. I expected R' Akiva status - though I am just Dov, and need a lot of basic work.
This perspective has shocked the heck out of more people than I can count, for we were always led to believe that 'poor me' is a symptom of low self-esteem. That is often a lie. So pumping up the self-image is the exact wrong way to go, if I want to really stop needing artificial things to alleviate me of my great disappointment.
And I believe that the common taina that "once I am convinced that I have (oversensitivity, and inflated self-image and expectations, fear, and other) character defects, I will give up and just not try to grow at all in the beis midrash, learning, avodah, and lose ambition" - is not true, either. Quite the opposite happens to everyone I know who has ever done their 4th step. They feel that for the first time they now have the tools to be realistic and effective and to grow, unfettered by irrational and childish thinking. I started to slowly get happy after my 4th step, more than any other.