Here’s a recent account from a member online, of his experience becoming skeptical about his beliefs.
[For those who are unfamiliar with the term “OTD,” it refers to the phrase Off The Derech, which means someone who has left the fold of orthodox belief and/or observance]

Why I went OTD

by Hillel Ari Ess

I used to love Yiddishkiet (this was one of the most difficult things preventing me from going OTD later in in life). I was a masmid who learned most of the day and late into the nights. You could say I was a normal ben Torah; but with a knack for intellectual honesty. I always craved the truth. I assumed the Torah as true because that’s how I was raised, so my pursuit for truth always revolved around the Torah.

When challenges arose either from Tanach, chazal or hashkofa I would look earnestly for ways to reconcile them. When I found answers that suited me, I would eagerly share them with others. This pursuit for truth in light of the many questions that arose drove me close to many big rabonim and kiruv professionals. In time I myself became a resource for hashkofic-related questions on Yiddishkeit, besides being very learned by that point. I loved this. The pursuit for teaching others the Torah’s truth was in my bones.

As I became older, though, I started seeing through many of the answers I had so desperately clung to in my youth, and I started discovering there were many, many more questions for which there were absolutely no adequate answers. Many of the oft-given and accepted “answers” were simply clever deflections or – I began to discover, when I was old enough to thoroughly investigate – either partially or fully distorting the source literature, imbuing upon it meaning, in the interests of reconciling the challenge on the Torah.

Upon pressing big rabbis with many of these questions, and realizing they had  no answers, they would dissuade my from my pursuit. “Just work on your faith,” they’d tell me. By this point I was well immune to the kiruv techniques of wowing and distracting the listeners from their real questions with some interesting correlations (the Purim code for example). The reality dawned hard on me after extensive pursuit of rebbeim and bakiim on these issues, that there really was no reconciliation for these questions. This jarred me deeply. I started looking at everything anew. And suddenly I saw that chazal, in perceiving how difficult Tanach was, protected it by throwing on layers and layers of interpolated meaning to avoid these issues. Yet even those commentaries themselves were riddled with endless faults. The midrashim only made it worse trying to embed fantastical narratives into the text.

This is the backdrop of my story. I still live in the religious world and have a religious family, but I no longer observe or believe inside.

-Hillel