Ben Chorin has a great piece explaining his fondness for people (and blogs) that challenge the status quo in the frum world. He writes:
"The yiddishkeit taught in cheder, or the more modern equivalent, is filled with simple-minded myths designed to give meaning to our traditions."
If I could expand on that idea a bit, I’d say that the problem isn’t just that people retain these juvenile perspectives. It’s that we’re expected to! True, no one frowns upon a person that studies more and develops a "greater appreciation" of these narratives and teachings, but that’s only if the person is still spouting the original idea as truth and only using his newfound appreciation as a way of expanding on the original concept. However, if a person were to study anything which could (chas v’shalom!) cause him or her to reject any of those original ideas... well, that’s already stepping over the line.
Basically, in the frum world, when you reach adulthood you’re expected to have essentially the same views on Yiddishkeit that you had when you were in 3rd grade. And probably nothing would make our rabbeim prouder if when we died at a ripe old age we still thought everything we read in The Midrash Says really happened.
This idea of being frozen in one’s intellectual development (or better said, it being a one-way street) can also be seen in the more general idea of overall religious development: No one has a problem with a person that adopts a new chumra. No one sees that as illegitimate. (Although some might rightfully have a problem with chumras because they are often just superficialities, most often, a sincerely and properly done chumra isn’t considered inappropriate.) But if a person takes a good look at themselves and decides that something they’ve been doing for the past ten years is just not right for them, that they’d be much better served using their time or energies in a manner that’s not stipulated by the mishna berura, then it’s something that’s got to be opposed.
It seems to me that there is no real concept of growth in the frum world. Yes, there is some sort of notion that is often spoken about called “growth in frumkeit”. And of course, “growth in learning”. When people talk about “growth in frumkeit” what they really are saying is that the person has developed an increased tolerance for the annoyances of halacha. Either he has adopted some practice that’s even more restrictive and frustrating than previously or he has just learned to accept the aggravation quietly.
Sorry, but that's not real growth. As Ben Chorin says: “This process of rebellion and return can repeat itself many times in a person's lifetime.” True growth can be in any direction. That terrible moment of confusion when you sadly realize that you don’t have a clue as to how things are, when moments earlier you thought you had it all figured out – that’s real growth. Gaining a better sense of self-awareness - that's real growth. Even if that awareness is something which frightens you. (Oh my gosh! Does this mean I don't want to stay in kollel the rest of my life? Nooooooooo!!!)