For most of us who are from the frum world, throughout our development, there was an implicit trust in the system we were raised in. We believed it to be true, to be good, to be the epitome of righteousness and the path to a truly happy life. But inevitably, at some point in our journey, something happened which altered our perception of our sheltered world, and triggered a reassessment of our society. It may not have been a catalyst for discarding all of our beliefs, but that first encounter had a lasting impression on our views about Yiddishkeit.
For me, it happened when I heard a mussar shmooze (lecture on character improvement). The Rosh Yeshiva had given a most inspiring shmooze on the power of tefila (prayer), how it can change our lives, how it can overturn the worst gezeira, how it can erase the worst aveiros, blah, blah. So moving. So uplifting. At shacharis the next day, I must have really shaken things up in heaven with my prayers. Some time after that, maybe a week or two later, he gave another shmooze, this time on the damaging effects we can have with the improper use of speech (lashon hara, bitul torah, nivul peh, blah, blah). In this shmooze he told us how even the most powerful tefila can be prevented from being answered if the person had corrupted their speech.
Like any typical yeshiva guy I wasn't much of a critical thinker, but for some inexplicable reason I realized that this idea totally contradicted what he said a week ago. Of course I knew that the whole point of these things is just to encourage us to better ourselves, and it doesn’t have to make total sense how he arrives at his conclusions (at least when the conclusion is as self-evident as these were), but I suddenly realized that I can’t really trust anything that a person tells me is from the torah. It suddenly became clear to me that any person who is knowledgeable enough, and has learned enough torah, can probably find a support for any position he wants to present. So if that’s the case, how can I trust anything that is "proven from the Torah"?
It didn’t make me totally stop trusting rabbis or the truth of torah (or even start to question all those things which are supposedly based in torah), and I don’t think any significant changes came as a direct result of this particular epiphany, but from that point on, whenever someone would try to convince me of a particular position by citing some source in a gemara or whatever, I would just tell them the two mussar shmoozes and they’d shut up with their proofs.
It would be a long time before I followed this idea to it's next logical step but it's clear to me that this experience further reinforced the inner distrust that would later reveal itself in my thought.
At what point did the crack in your wall of trust first appear?