I have only glanced at the Off the Derech: Why Observant Jews Leave Judaism and my reaction to most of what I saw was pshita, mai kah mashma lan. I was far more captivated and entertained by Shalom Auslander's Foreskin's Lament, which I just finished reading. Auslander was raised in Monsey, attended Yeshiva of Spring Valley and then MTA, went to Neve in Israel, and from adolescence onward has drifted further away from Judaism and grown angrier with G-d. The book (note: I give it an R rating, just to forewarn you in care you want to read it) describes his personal experiences and reads like a late night comedy skit.
So what drove Shalom away? Was it the fact that his father was a drunk, his mother was a typical guilt-inflicting jewish mother, and his home life was filled with conflict? Was it incidents in his yeshiva eduction, such as when a Rebbe told the class, after announcing that a student's father has passed away, that Hashem punishes parents for the sins of children (how's that for motivating kids to learn?) Was is the hypocrisy he witnessed? Or was it the pull of drugs, pornography, and hedonism in secular society that drew him in? Perhaps it was all of the above.
I found it interesting that Auslander and I are about the same age (based on the years he said he was in MTA), yet we are so radically different. That difference has little (I think) to do with religion and more to do with personality -- I have as little desire to smoke pot or hang out in Times Square as Auslander probably does to observe Shabbos. I honestly cannot think of an "answer" or approach that would inspire the likes of Auslander because I simply cannot empathize with his needs and lifestyle. That says as much about me as it does him (and is why kiruv is not what I do for a living).
On that note, I got a definite sense that his teachers had no idea of the world Auslander lived in -- what meaning could a gemara or Nach shiur have to a boy living interested in drugs, girls, and shoplifting. In that regard the system did fail Auslander and it continues to fail many like him. What parent wants to hear from a Rebbe, "No we have not learned a single word of gemara this year because there are bigger issues we need to work on." Yet, if our schools are honest, that's exactly what needs to happen in many, many cases. Don't get me wrong -- I am not advocating the coddling, no rules approach. Auslander had that too and it did not make any difference. A teenager who is smart enough to read Beckett on his own and skips school to hang out at the Met and Moma because he senses there is something real and deep there is being done a disservice by a hands-off approach. What he needs is a hands-on approach that would show that there is something real and deep to what religion offers beyond technical legalism and threats of next and this-worldly punishment.
Auslander comes across as angry -- angry at G-d, angry at his parents who do not accept him for what he is, angry at the community in which he cannot find a place or earn acceptance because he just won't play by the rules. On the one hand, does Auslander not realize that his choice to define himself as an outside carries the consequences of being treated as such? On the other hand, in some sense I commiserated with Auslander -- a third grade Rebbe telling children that G-d kills parents because of their sins is stupid. How do we respond? Some would defend the authority of the rebbe at all costs. Some, like Auslander, drop out. Both of these approaches fail because they do not separate the values of religion from its mere supposed representatives on earth, who unfortunately are often fallible and even stupid.
As far as his skills as a writer, Auslander is funny and cute, but at the same time I felt he was superficial. The book makes for a nice comedy skit and a quick read, but I would have appreciated more intropection on his part. By comparison, l'fi aniyus da'ati the best young American writer who happens to be Jewish is Michael Chabon, whose Kavalier and Clay places him in a different league entirely than Auslander.
My wife half-humorously warns me that admitting to reading Auslander and such kefirah is a black mark in the shidduch world. Since I'm married I don't care : ) -- let my kids fend for themselves when the time comes in a few years. But I will say that closing our minds to the Auslanders of the world will not make them go away. Perhaps every Rebbe in MTA and the likes should read this book. These are the kids in our system as they really are, without sugarcoating, at there very worst. What are we going to do about it?