Most Orthodox Jews were born into this way of life. Converts and pentitents (baalei teshuva) get media attention but are not terribly significant in Orthodox Jewish numbers.
As a convert to Orthodox Judaism, I have no problem understanding the main reason why people leave — it is a very difficult way of life. I suspect that religiosity and the ability to conform to a stifling community are in part genetic and some Orthodox Jews are not going to have that genetic ability and so they leave.
I don’t know if there’s much to be learned by dialoguing with those who’ve left the path, but others disagree.
Much of life can be understood by simply asking — what’s easiest? Most people most of the time will do what is easiest for them. The reasons people give for their behavior usually have nothing to do with their real reasons, which they may not even be conscious of.
