9th grade came around, which was a whole new level. Yeshiva Ketana is 3 years of “Junior High school”, which meant a different part of the neighborhood, finishing at 9:30 every evening, and studying Gemarah for the first time.

If I thought Mishna was difficult, Gemarah was a whole new level of density, sentences and concepts that didn’t make sense and questions that had no answers. I would dread class every day, because it represented another page that I had to absolutely master, with blood tears and toil, day after day. Again, no one else seemed to struggle as much, mostly because they didn’t care as much.

And I was obsessed with remembering it all. Every day I’d get tested on that day’s material and knew it by heart, but I needed to remember everything I’d ever learned. There’s a phenomena, we were told, that if you didn’t review Torah you’d just forget it (unlike other subjects, which supposedly you studied once and remembered for ever. We knew no other subjects with which to compare it to). That way you’d always be busy and never get into trouble.

So I read most of tractate Shabbat over 24 times, which is the equivalent of reading all the Talmud once. But I could not find happiness, because for everything I remembered, there seemed more that I forgot.

In my second year, I was put in the more advanced class with Rabbi Boaz Kaplinsky. He was a short, potbellied man, who was tremendously entertained by his own intellect and sharpness of mind. He would utter nuggets of Talmudic wisdom and complex logic while smirking in the most self-satisfied way possible, and I did not understand a thing.

This was my first experience with someone who moved their lips and words came out, but for the life of me I couldn’t understand a fucking word he was saying. I became incredibly frustrated, and it was only after my parents threatened to switch me schools was a moved to the lower class, where I did much better. Rav Boaz later died in a car crash along with his wife.

We were all post bar mitzvah, and at my school they didn’t just wear Tefillin during morning prayers. They wore them all day. The kids would run around like animals during recess wearing little leather boxes that were supposed to remind them of God’s constant presence. I never felt worthy of wearing these throughout the day and I found mine, which were larger than average, to be physically uncomfortable. Some rabbis pressured me to do so anyway, but even when I did I would take them off during recess.

It was during this era that I also discovered pornography. I was always anxious, and escaping into porn was a logical turn of events for me. This was the age of dial up, and I’d sneak on to my father’s computer whenever I could get my hands on it. It started out with some innocent searches and spiraled rapidly, and every day saw me compulsively binging, then guiltily running back to school feeling like a terrible human and trying my hardest to outweigh my sins with the virtue of study.

At the time, I harbored a lot of resentment towards my parents for letting me access unfiltered internet. I wished they’d remove the temptation, but of course I could never overtly ask for that – half of me wanted to continue binging, plus it would be an admission of wrongdoing, a mortifying thought. To this day, I wish I’d been exposed to sex in a more healthy way – I learned how babies are made from an encyclopedia entry and cemented my understanding with some good old fashioned porn.

One Friday afternoon, after finishing school at 3:30, I spent my last hour before Shabbat expressing my creativity by creating a religious parody of The Matrix. I was charedi Neo, with a black hat. My sister Tema was Trinity. I cast my Hebrew-speaking neighbors in supporting roles, feeding them their English lines word by word. My father filmed. It was epic. The following week I was called to the principal, who always knew everything, and was told to never do that again. It was years until I did.

I used to miss an hour of school every week to take a guitar lesson. I considered this tremendously open minded on the part of the school, to let me “have an outlet”. I was the nerd who played classical guitar and listened to classic rock while everyone around me listened to the terrible excuse for disco and brass hits that is Charedi “music”.

Overall though, my years in yeshiva ketana were my best school years. There was the right mixture of structure and independence, and I was able to get into a flow. I would spend long hours in self-directed study under the watchful eye of the rosh yeshiva, Rav Yirmiyeh Zilberman.

He would sit at the back of the room, like the train robber with the shotgun, so you never knew if he was watching or even there at all, without turning around. But that was alright with me, because I knew what the right thing to do was, and to the best of my ability, I was doing it.

Full chapter list (Available in eBook Form)

1. Kindergarten
2. Cheder
3. Mishna
4. Good and Evil
5. Gemara
6. Yeshiva Gedola
7. Ramat Shlomo
8. Beitar
9. More of That
10. The IDF
11. Mitzpeh
12. Darkness
13. Independence
14. Shitting on the Parade
15. Light
16. Detox
17. Spreading Wings

12th grade is the first year of Yeshiva gedola. Literally the big leagues, this is the first year of the rest of your life. You enter a study hall that could literally be the place you sit for the next 50 years. My classmates are still there 12 years later.

Now your hours go until 11 oclock at night, so if you live outside the neighborhood, you definitely need to live in a dorm and come home to visit every couple of weeks.

In yeshiva gedola, all structure drops out from under your feet. No one gives a shit anymore if you are there or not. It’s at this age that wayward yeshiva bochurim start getting into epic trouble because no one is preventing them from doing anything, they just get caught and punished after the fact.

I was not prepared for this total lack of structure. I was not disciplined enough, nor did I enjoy studying enough, to just do it on my own. So I spent a lot of time in my bedroom playing guitar licks and avoiding my mother’s reproachful questions of “don’t I have school?”

Eventually, it became apparent that “it was time for change”. For years my parents had mentioned how one day I would move from my unusual information-focused school and into something more “conventional” where logic and conformity are key.

I’d held out at my school, despite some rocky patches, for 11 and a half years, but now it was time to transition to a “mainstream” school where I would certainly be happy because “I’d get my questions answered”.

Apparently, my entire dissatisfaction with school, according to my parents, was that I was not stimulated enough. If I would only go to a place that studied “B’iyun” surely there I would fly. A bunch of “experts” told them this, so there was no doubt this would be the case. I believed it as well.

In fact, remember Reb Avrohom Cohen from Chapter 2? He, and several other people over the years, was hired to study with me at nights, to prepare more for “mainstream” yeshivas. In those places, they spent years stretching their minds to the extremes of logical debate, and I needed to be up to par with all that practice.

I remember exhaustedly blinking at the page evening after evening as some rabbi tutor enthusiastically tried explaining to me the nuances of in-depth study. It’s only years later that I realize that the exhaustion had nothing to do with physical tiredness.

It was time to move schools, and once I started wandering, I never stopped.

Full chapter list (Available in eBook Form)

1. Kindergarten
2. Cheder
3. Mishna
4. Good and Evil
5. Gemara
6. Yeshiva Gedola
7. Ramat Shlomo
8. Beitar
9. More of That
10. The IDF
11. Mitzpeh
12. Darkness
13. Independence
14. Shitting on the Parade
15. Light
16. Detox
17. Spreading Wings