Sunday, September 19, 2021

The Joyful Progression from Yom ha’Kippurim through Sukkos

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Artwork: Team Pennant, by Anna Fehr

The Joyful Progression from Yom ha'Kippurim Through Sukkos

According to the Abudirham, the sounding of the shofar after Ne’ilah is followed by the recitation of the pasuk: “Go and eat your bread with joy and drink your wine with gladness, for God has already approved of your deeds” (Koheles 9:7). He explains that the source of this minhag is a midrash (Koheles Rabbah 9:7) which says: “When the Jews leave shul at the conclusion of Yom ha’Kippurim, a heavenly voice goes forth and proclaims: ‘Go and eat your bread with joy, for your prayers have been accepted before Me as a pleasing aroma.’”

The Aruch ha’Shulchan (OC 624:7) states that all four days between Yom ha’Kippurim and Sukkos are characterized by the selfsame joy of Motzai Yom ha’Kippurim. They are considered “days of simchah,” which is why we don’t say tachanun or tzidkasecha tzedek. The midrash (Tanchuma 23:18) relates this joy to the Yom Tov of Sukkos itself:

To what may the matter be compared? To two people who entered into judgment before the king, and no one but the king knew what [transpired] between them. The king judged them, but the other people [outside] didn’t know who won. The king said, “Whoever emerges with a palm branch in his hand – it will be known that he won.” So too, Israel and the nations of the world enter into judgment on Yom ha’Kippurim, and nobody knows who won. Ha’Kadosh Baruch Hu said: “Take your lulavim in your hand, and they will know that you were meritorious in judgment.”

On the surface, these sources seem to be at odds with the atmosphere of dread and uncertainty on Yom ha’Kippurim itself. Throughout the Yom ha’Kippurim davening we repeatedly acknowledge that our lives hang in the balance. We continually remind ourselves that one more mitzvah or one more aveirah has the power to seal our judgment for life or for death. We continually underscore the notion that our salvation is not guaranteed, and that teshuvah, tefilah, and tzedakah are our only means of removing the evil of the decree. How can we reconcile the mood of apprehensive contingency on the Yom ha’Din with the assurances of our success at its conclusion?

I believe that an answer can be found in the Rambam’s explanation (Moreh ha’Nevuchim 3:36) of the reason for viduyim, korbanos for sins, and taaniyos. After classifying teshuvah as one of the “doctrines which are indispensable for the well-ordered society of Torah adherents,” the Rambam writes:

If man were convinced that he could never straighten his crooked ways, he would forever continue in his errors, and maybe even increase his disobedience if he believed there was no alternative. But with the belief in teshuvah, he will come back to the good and will return to an even more perfected state – even more perfected than he was before he sinned. For this reason, [we are commanded] in many actions which strengthen our belief in this very beneficial principle [of teshuvah]: for example, the viduyim, and the korbanos for sins … and the taaniyos.

The chief purpose of Yom ha’Kippurim is to reinforce our belief in the efficacy of teshuvah. If we didn’t believe in the power of teshuvah to change ourselves and our fate, we would persist in our harmful ways. But in order for the institution of Yom ha’Kippurim to function in this manner, we must allow ourselves to feel that our teshuvah was accepted. If Yom ha’Kippurim ended and we still felt totally in the dark as to whether our teshuvah, tefilah, and tzedakah paid off, we simply wouldn’t put in the effort in the first place. Imagine a struggling student who is encouraged to improve her grades so that she can graduate from college, but is never informed whether she actually graduated, and is never allowed to celebrate success. How could we expect her to put in the hard work without any hopeful promise of joyfully crossing the finish line?

Thus, the urgency and uncertainty we feel on Yom ha’Kippurim and the relief and joy we feel at its conclusion serve a common goal: to strengthen our belief in the efficacy of teshuvah. With this in mind, "go and eat your bread with joy" this Chag ha'Sukkos, knowing that you are priming yourself for greater teshuvah in the future.
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Monday, September 6, 2021

2020-2021 Torah Content Retrospective (and Personal Favorites Award Show)

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2020-2021 Torah Content Retrospective (and Personal Favorites Award Show)

Introduction

Today is Erev Rosh ha'Shanah - the eve of the new year. I was reflecting back on the teaching I've done during the 2020-2021 academic year, thinking about which of my own shiurim, podcast episodes, and articles stood out the most in my mind as having the greatest personal impact or significance in my life. I figured that this would be a good way to reflect on the year as a whole, since my life has been interwoven with my teaching and learning. 

This was no easy task. By my count, I gave somewhere in the neighborhood of 760 recorded shiurim, along with 50-100 unrecorded shiurim. It was difficult to remember what each shiur was like, especially back in the haze of the lockdown months (September 2020 - January 2021).

Soon after beginning this project, I thought to myself, "Hey! Why don't I make an 'awards show' style list of my personal favorites?" I figured this would be a nice way to preserve my impressions of this year so that I could look back on it in the future (God willing) and recollect what I thought and felt at the time. Plus, this will be the closest thing I have to a list of recommendations - although, as you'll see, my personal favorites don't necessarily line up with the shiurim I would recommend for others. Most of my selections were chosen based on personal associations.

I'm going to structure this like the Academy Awards. There will be different categories, each of which will have one winner and four runners-up. Each entry will be accompanied by a short summary of what the shiur was about and why it was chosen. Each entry will be hyperlinked to its corresponding YouTube video, podcast episode, and/or article. 

It goes without saying that these "awards" are entirely subjective. Hence, my use of the word "favorite" instead of "best." It also goes without saying that this is a very self-indulgent exercise - and yet, so is my entire teaching career. 😅 

Favorite Shiur of the Year: 
Date: 2/19/21     Audio
Comments: This was, hands down, the most important shiur I gave this year. As the subtitle suggests, the ideas in this shiur reflect an epistemological upheaval in my own learning and the way I relate to knowledge. The impact of this shiur can be measured by the number of times I have referenced it in my other shiurim and conversations, most often by exclaiming the word, "WOLVES!" - without any prior context. It is somewhat ironic that my favorite shiur of the year is relatively sparse in its Torah-content. Someone even criticized me for spending too much time on wolves and not enough time applying it to Torah. I didn't have the heart to tell him that this was by design. I wanted to fully explicate what I learned about wolves, and then open the doors to the implications for our Torah methodology without spelling them out in too explicit of a fashion. I plan to eventually write this up as an article, and maybe even give a Sunday shiur on it. If I do, there's a good chance I'll make the Torah implications more explicit, now that the upheaval has had time to settle. We'll see.
Runners-up

Favorite Sunday Shiur of the Year: 
Date: 4/18/21     Audio     Article (note: this is NOT a written version of the shiur, but the article the shiur was based on)
Comments: It was hard to pick a winner in this category. I chose this one because I think it captured many of the hallmarks of my teaching and learning style. It focused on methodology and educational philosophy, it highlighted the importance of pshat, it exhibited organization and presentation of the material, it drew upon my experience as a teacher, it incorporated real-world examples, it sparked questions and discussions, etc. In other words, this felt like my Torah. I enjoyed giving the shiur and was happy to be able to making a small contribution of my Torah to a community in which there are chachamim who make me feel like a grasshopper in comparison.
Runners-up
  • Kiddush: The Universe of Torah in a Glass of Wine (audio): This is a good example of taking a familiar maaseh ha'mitzvah and bringing out the ideas of chochmah and perfection within in a manner which is actionable and causes the mitzvah to "light up" when you perform it. 
  • Elohai Neshamah Upon Waking (audio): This shiur exemplifies my approach to tefilah as applied to a berachah - perhaps the most impactful berachah I say each day.
  • Yom ha'Kippurim 5781: Ralbag on the [13] Middos [ha'Rachamim] (audio): Before I gave the Wolves Shiur, this was my favorite shiur of the year. I had wanted to write an article on this topic for many years, but felt it was too daunting. Strangely enough, it ended up being easier to give a shiur on it than to set it down in writing. Unfortunately, the video of the shiur wasn't recorded. Even though it was the afternoon of Erev Yom ha'Kippurim, I decided to give over the entire 90 minute shiur again to record on video, since I felt that the PowerPoint presentation added so much. I'm glad I did.
  • Tishah b'Av 5780: Methodology of Kinnos as Applied to Kinah #31 (Eish Tukad b'Kirbi) (audio): This shiur was initially intended to only be for the members of my shul in Mercer Island who were interested. At the very last minute - maybe 30 minutes before? - I found out that nobody in yeshiva was giving shiur at the time, so I opened it up to anyone who was interested. Attendees included members of the community, former talmidot from Shalhevet, and a shul in Virginia. There ended up being a very diverse group of over 100 participants, which made for a great learning experience. The majority of them stayed to the end, even though it ended up being 2.5 hours long! 

Favorite Methodology Shiur
Date: 5/5/21     Audio
Comments: I didn't plan on giving this as a shiur in yeshiva, but that day I had "teacher's block" and felt like I needed to go back to my roots. My roots as a teacher are Bruce Lee. I decided to give my talmidim a taste of how integral Bruce Lee's teachings were in my own development, and how relevant his principles can be in helping them to become better thinkers, and to gain the most methodology from their learning in yeshiva.
Runners-up
  • The Curious Tale of Sasson and Simchah (audio): This shiur was the fruit of the learning I did over my lonely COVID Sukkos spent in NY - the only time I haven't gone back home to spend Sukkos with my family. Thankfully, a good friend and chavrusa came over to learn, and we took up this midrash in the Gemara which brought up some important methodology points.
  • Koheles Part 05: Scrapping the New Approach and Returning to My Old Approach (audio): When I began my twice-a-week Koheles shiur this year, I intended to try to come up with a new approach based on Metzudas David. After four sessions, I realized that "this too, was futile." This was the shiur in which I scrapped the attempt to come up with a new approach, and instead, went back to teaching Koheles the way I had successfully taught it in high school for years. The shiur began with a very Kohelessy way of arriving at that decision. 
  • Introduction to Sefer Mishlei (The Book of Proverbs) (audio) (article): I've taught many students in high school how to learn Mishlei, but this was the first time I recorded an Intro to Mishlei shiur. It was also the kick-off of my beloved Monday Night Mishlei shiur. 
  • How to Become Wise (Part 1 Part 2) (audio part 1 and audio part 2): This one made the list not because the content was my favorite, but because of the decision I made in giving this shiur. I had been slated to give two methodology shiurim. I chose the first siman of Darchei ha'Gemara by R' Yitzchak Kanpanton, in which he focuses on the importance of learning through the same text multiple times, and not letting yourself think you've mastered it even after 100 times. I wasn't sure what to do for my second shiur, and then it hit me: I'll follow R' Kanpanton's advice and give the same shiur on the same text a second time! Of course, it didn't end up being the same shiur, which validated the point he was making! 

Favorite Mishlei Shiur: I CAN'T CHOOSE! 😬😵😶
Date: 5/5/21     Audio Version
Comments: I gave 165 Mishlei shiurim this past year: a morning Mishlei shiur Monday-Thursday for the yeshiva guys, and a Monday Night Mishlei shiur for the community. As far as I'm concerned, ALL of them were a wonderful blur of Shlomo's chochmah and joyous analysis and discussion. I loved each of the two Mishlei shiurim for its unique group of participants. So instead of choosing one winner and four runners-up, I've selected five shiurim which represent various things I loved about all the shiurim.
Representative Favorites
  • Mishlei 10:15 - The Self-Perpetuating Psychological Impact of Wealth and Poverty (audio): To be honest, I don't remember exactly what this shiur was about, but judging by the description I gave it, it was a typical "jam-packed with methodology" shiur, so I feel confident in choosing it as a representative of our Monday-night Mishlei shiur, which was typically more methodology-heavy than my morning shiur in yeshiva. I've chosen this both as representative of the methodology aspect of my Mishlei shiurim, and because I love learning with our Monday night Mishlei Crew (and the "Mishlei Afterparty" which typically follows).
  • Mishlei 18:8 - Mishlei on Complaining (Part 1 Part 2(audio part 1 part 2): I chose this because it is emblematic of what Mishlei is all about: practicality. This pasuk still stands out in my mind as one of the most practical. Based on feedback I've received, many students feel the same way, which is why I chose it as the representative of Mishleic practicality. (This also happens to dovetail quite well with Stoicism.)
  • Mishlei 18:22 - Finding a[n Intelligent] Wife = Good + Favor (audio): I chose this because it's the ONLY shiur of mine - on Mishlei, or on anything! - that I've actually gone back and listened to in its entirety. I initially started listening to it in order to find a specific reference, but ended up listening to the whole thing. As I listened, I thought to myself, "I LOVE learning and teaching Mishlei with these talmidim!" I'm choosing it as representative of my morning Mishlei shiur with my talmidim in yeshiva.
  • Mishlei 10:21 - The Foundational Egotism of the Eveel (Pleasure-Seeking Fool) (audio): If there's one thing Rabbi Moskowitz taught me, it's that if you approach everything you learn with a fresh mind, then you're bound to see chidushim and experience constant "level-ups" (my term) and revolutions in your understanding. In this shiur I presented my new understanding of the eveel. I chose this shiur as a representative of Mishleic chidushim.
  • Rabbeinu Yonah on the Naar, the Pesi, and the Ksil (audio): As a matter of fact, I gave shiur on this same Rabbeinu Yonah much earlier in the year, on 10/2/20, after Trump was diagnosed with COVID-19. I'm sure there's some overlap in the two shiurim, but it might be worth watching/listening to both, since the earlier shiur deals with a real-world example. Here's the link to the video and audio for the Trump version.

Favorite Rambam Shiur: 
Date: 8/4/21     Audio
Comments: I actually didn't choose this particular shiur because of the content, but for what it represents. This took place during our yeshiva's summer program, and was the last Rambam Bekius shiur of the year. In the 130 Rambam shiurim, we covered all of his introductory material - and I mean all of it - Hilchos Yesodei ha'Torah, Hilchos Deios, many other sections focusing on inyanei d'yoma, related material in his other works, and other areas of interest. This final shiur was especially meaningful to me because ALL of the "Rambam Bekius regulars" were able to attend, even though this was during the summer. In the last 10 minutes of the shiur, we all spoke about what we gained from Rambam Bekius. It was a really special session.
Runners-up
  • The Mitzvah of Anochi (Part 1) Hilchos Yesodei ha'Torah 1:1-6 (audio): I'm not gonna lie: this choice was somewhat arbitrary. Why? Because even though I thoroughly enjoyed giving Rambam Bekius shiur four times a week all year, I have virtually no recollection of the shiurim I gave during the Fall Semester, during the months of COVID lockdown. The memories of the shiurim from the Spring Semester feel fresh in my mind, and I found myself impelled towards those as my four runners-up. I'm choosing this single shiur from the Fall Semester because it was the beginning of Hilchos Yesodei ha'Torah, after we spent three months going through the introductory material and had established our groove. This is also where we outlined our plan for doing this as "bekius." Lastly, how could I not choose the beginning of Hilchos Yesodei ha'Torah?
  • Understanding Exceptions to the Rule of the Middle Path (Hilchos Deios 2:3) (audio): This runner-up and the next one are part of our multi-shiur endeavor to understand what the Rambam means by the term "deios" and what, exactly, his approach to the middle path is. If I remember correctly, this was a particularly productive session where a lot of our prior analysis came together. I chose this because it's a good example of our "bek'iyun" approach.
  • Refining Our Understanding of Silence and ALL of Hilchos Deios (2:4) (audio): This shiur began with an attempt to refine our understanding of the Rambam's position on the deiah of silence, but led to an overhaul of our whole understanding of Hilchos Deios. I chose this because it's a good example of how our persistence in our "bek'iyun" approach continually yields new insight.
  • How Can the Rambam Permit ANY Lying? (Hilchos Gezeilah v'Aveidah 14:12-13) (audio) So much of our learning of the Rambam's Mishneh Torah this year was "intertextual." By that, I mean we used the Rambam as a commentary on himself. I could have picked a number of examples, but this one was relatively fresh in my memory, which is why I chose it as representative of the overall feature.

Favorite Chumash Shiur: 
Date: 9/16/20, 9/23/20, 10/1/20     Audio Part 1, Part 2, Part 3
Comments: No introduction to Chumash as had a greater impact on my learning than that of the Ralbag. I have wanted to give shiur on this for a long time, and once I knew I was giving a Chumash methodology shiur, this was at the top of my list. This year I plan to give an updated version of this as my first Sunday Shiur of this coming year. 
Runners-up

Date: 5/24/20    Audio
Comments: I chose this for two reasons. The first is that it's the only shiur I've given in which I (a) summarize my entire understanding of tefilah, (b) summarize my methodology of tefilah, and (c) engage in a full analysis of a berachah using that methodology. The second reason is that this was the first Sunday Shiur I ever gave in yeshiva, and has sentimental value for me for that reason. (Note that at this point in 2020, I didn't even know I'd be teaching at yeshiva full-time for the following academic year.) The third reason is that I gave a smaller version of this shiur at the beginning of the pandemic in Shalhevet, which has a different kind of sentimental value for me. 
Runners-up
  • 3rd Berachah of the Amidah: Kedushas ha'Shem (Sanctity of the Name) Exploration Part 1 Part 3 (audio Part 1 Part 3): Towards the beginning of the year I focused more on tefilah than Tehilim. I chose this shiur as a good example of how the proper analysis of a familiar berachah can lead to a completely new understanding which can affect how we live. 
  • Chanukah 5780: Asking for Miracles on Chanukah (audio): This was a Lomdeha Seminar shiur, but since it was about tefilah (the al ha'nissim insertion for Chanukah and Purim) and dealt with how we request things in tefilah, I chose it as one of the runners-up.
  • Insights into Tefilah from a Nun (audio) There were a number of tefilah-related discussions I had with my talmidim and talmidot which were not recorded. The catalyst for this shiur was the death of my great-aunt ("Sister Susan") from COVID. She was a Catholic nun, and I found a written piece in which she expressed part of her view of prayer. We started by comparing and contrasting her approach with that of Judaism, and this led to a general discussion about tefilah.
  • Some Applications of "Radical Acceptance" to Tefilah (audio) I chose this as a representative of another "genre" of my tefilah shiurim, namely, the results of my relatively new immersion in the world of mindfulness and meditation. I gave this shiur while reading Radical Acceptance, by Tara Brach, which led to the insights I shared. 

Favorite Tehilim Shiur: How to Learn Tehilim: A Crash Course 
Date: 11/17/20    Audio     Article
Comments: This is my favorite Tehilim shiur because it's the most important one. This is where I spell out my whole methodology and approach to the sefer. It's the foundation of all the other Tehilim shiurim I give. 
Runners-up
  • Tehilim 92 (Mizmor Shir l'Yom ha'Shabbos) (audio): I chose this because it's the first actual Tehilim shiur I gave this year, in which I applied my methodology. I happen to think that this perek is the best perek to start with because it's relatively accessible and exemplifies my methodology, and that of Dovid ha'Melech.
  • Tehilim 118 (Hodu la'Shem Ki Tov) Part 5 (audio): I chose Part 5 of this five-part shiur because of the discussion which took place. After beginning with our perek, we quickly ended up having a discussion about what "The Good" is, according to Judaism and Stoicism. It was a great discussion, and I definitely experienced a major level-up from it. 
  • Tehilim 1 (Ashrei ha'Ish): Parts 1, 2, 3, 4, 5 (audio parts 1, 2, 3, 4, 5): I chose this because it was my favorite perek of Tehilim that I learned this year. The particular ideas, as explained by the Meiri, were really beautiful, and - unlike many of the ideas in Tehilim - I felt like it is relatively within my grasp to live according to them. 
  • Lessons in Bitachon from 2020 + Tehilim 114: b'Tzeis Yisrael mi'Mitzrayim Part 2 (audio): I chose Part 2 of this two-part shiur because of the discussion that occupied almost all of the time. Since this shiur was given on December 31, 2020, I decided to reflect back on the lessons I learned about bitachon during that tumultuous year. It was a good reflection which was in line with the objectives of Tehilim.

Favorite Hashkafah / Lomdeha Friday Seminar Shiur
Date: 10/23/20    Audio
Comments: I don't know whether this is actually my favorite, but this was one of the first shiurim I gave in the year which I'm the most proud of. I think I did a clear job of presenting the questions and problems, regardless of what one thinks about the answers. It's a topic I had been asked about a lot as a high school teacher, and I think I did it as much justice as I am currently capable of.
Runners-up
  • How the (Seemingly) Outdated Elements of Torah Are Evidence of Its Perfection (Part 1 Part 2): (audio part 1 part 2) This was the other contender for being the winner. I think this is probably one of the more important Friday Seminar shiurim I gave, since it addresses a whole host of questions that are raised in this modern age. I do think that there's room for improvement (which is true of all my shiurim), I'm really happy about this first iteration. 
  • Some Guidelines for Thinking About Biblical Historicity vs. Archaeology (Part 1 Part 2): (audio part 1 part 2): This is a great example of a shiur in which the majority of the material is not mine, but which I feel I contributed through my organization and presentation. like the last three shiurim, this is especially important for the present generation of Modern Orthodox Jews, who will inevitably be challenged by arguments against Biblical historicity. I hope that I did a good job in providing ways of thinking that can bolster their conviction in Torah and give them some tools to navigate these treacherous waters.
  • Is Judaism FOR or AGAINST Free Thinking? (audio) I've noticed that so many of these choices have to do with the threat of ever-present threat of heresy. Well, this shiur addresses that topic square-on, asking the question: Are we allowed to think about these dangerous things? I hope this answer I gave is adequate!
  • Three Schools of Jewish Thought (audio): The inspiration for and structure of this shiur came from a shiur Rabbi Fox gave at NYHS. I took the basic elements from him and developed my own approach. Like many shiurim on the list, this is a work in progress. Giving this shiur over in yeshiva and at Lomdeha led to new questions and avenues of thought, not only in my stuents, but also in myself, which is why I chose it. 

Favorite Lomdeha Weekday Shiur: 
Date: 9/10/20
Comments: Surprise surprise! My favorite Lomdeha weekday shiur was not a limudei kodesh shiur, but an English class! I designed this as the first class of my AP English Language and Composition curriculum. I've shared this lesson with thousands of AP Comp teachers around the country, many of whom have given it in their schools and shared the feedback with me. I'm quite proud of this lesson plan. And lest you think this has nothing to do with Torah, you would be wrong! Teaching AP English Language was worthwhile to me for many reasons, but the sharpening of my own rhetorical analysis skills was definitely a major takeaway, and my "rhetorical analysis toolbox" has contributed to my Torah development in a number of ways.
Runners-up: Note that there were many Lomdeha shiurim I didn't record or didn't upload. As a result, I didn't have a ton to choose from. The most enjoyable and memorable Lomdeha shiurim to me were the ones that weren't recorded. Especially the Q&As, the explorations, and the candid "life discussions."
  • Avos 2:4 (Don't Believe in Yourself) (article): I chose this one as representative of my entire Lomdeha experience. It was the first day of class, and the first day teaching my Shalhevet Class of 2021 in person, since the day before Purim. It felt great to be teaching these specific talmidot, and it felt great to be teaching in person again. I also happen to like this idea. 
  • Iyov #01: Introduction to Sefer Iyov: I chose this as representative of my entire Iyov course at Lomdeha. Fortunately, my Iyov classes led to lots of interesting discussions. Unfortunately, they don't always lend themselves to good recordings, which is why I only posted them on YouTube but not as podcasts. 
  • Hilchos Teshuvah 2:9-10 (Interpersonal Teshuvah): I chose this one not for the Rambam content, but for the Atomic Habits intro. In August of 2020 my friend, Abby B., introduced me to Atomic Habits, by James Clear. I was so enthralled by it that I incorporated it into the first part of my Jewish Ethics class during the days surrounding the Yomim Noraim. I chose this particular day because it features "temptation bundling" and "habit stacking" - two of the more useful techniques I gained from the book. In other shiurim I linked Clear's techniques with explicit examples in Hilchos Teshuvah. 
  • Riaz vs. Rambam (and Thomas Jefferson vs. Pirkei Avos) (audio): This was a wacky one! I found a letter from Thomas Jefferson in which he criticized Judaism's approach to ethics, based on a methodological mistake - the same mistake made by a certain rav in his analysis of the Rambam's view of the ikkarim. In this shiur I addressed both of those mistakes with an emphasis on methodology.

Favorite Episode of The Stoic Jew Podcast: 
The One Most Relevant To My Current State of Mind
Comments: Okay, I cheated again. So sue me. I can't choose a favorite out of the 192 episodes, and any time I think I've found my favorite, I realize that it's because the ideas in that episode have been on my mind or particularly relevant lately. I do think I've narrowed it down to at least five episodes that I think about more often than all the others. Again, this shouldn't be taken as an indication that these are the best, or even the ones I'd most recommend (since there are more fundamental ones which just aren't chidushim to me anymore). Instead, here are some representatives of the subcategories of favorites.
Representative Favorites

Date: 8/30/21     Audio
Comments: As I explain in the audio version (which is definitely superior to the written version!), I didn't even plan on writing this until I watched the video by Rhystic Studies and got this name stuck in my head during a bout of insomnia that night. As I tossed and turned, I associated to this Rambam, and when I gave up on sleep and got out of bed, I knew I had to write and record this! 
Runners-up

Favorite Article: 
Date: 9/18/20     Audio
Comments: This isn't my best article, but of everything I wrote in 2020-2021, this most captures my state of mind. I had just lived through the first part of the pandemic and the overturning of my own life and was about to head into the new year with my new jobs. This article, which originally was just write-up of some thoughts I jotted down on Erev Rosh ha'Shanah, really sums up the essence of what 5780 was and what 5781 would be.
Runners-up

Favorite Unscripted Moments: 
Date: 7/27/21     Time-stamp: 6:15 - 6:45
Comments: Isaac, my talmid-chaver, has been a valuable presence in my shiurim for many reasons. One of these reasons is his memory. He attended nearly all of my morning Mishlei shiurimi and all of my Rambam Bekius shiurim in 2020-2021, and I could always rely on him to recall what we said in a past shiur, or at least remember it better than I did. This unscripted moment took place during our summer program the day after Isaac got married. I did NOT expect him to attend Rambam Bekius that entire week. In shiur we had just arrived at a question on something we said earlier in the year, which none of us could remember. I shook my head and said aloud, "If only Isaac were here" - and that VERY second, he appeared! I was SO happy, and I'm glad I caught the moment on video.

Runners-up
  • Real-world Rhetorical Transaction: During one of our first English Composition classes, shortly after I had introduced students to the rhetorical triangle and the rhetorical appeals (ethos, pathos, and logos), we were interrupted by the past-president of the shul whose space we had rented. He popped his head in and wanted to introduce himself. We had a brief conversation, and immediately afterwards I took what we were learning and applied it to the conversation we just had. It was a great "real-world rhetorical analysis" moment which had an impact on my students.
  • Miniseries Outtake: During one Shabbos meal a long time ago, Avi Markowitz pretended to not know how to say the word "miniseries." He kept on pronouncing it as "mih-NIZ-er-eez" and for some reason, it tickled my funny bone to no end. I had so many failed attempts to make this video because I kept on cracking up at the very beginning whenever I thought of him saying "miniseries."
  • Mishlei 18:14 - Mishlei on Mental Health (In Memory of Yocheved Gourarie): It feels wrong to call this a "favorite" unscripted moment, since it was one of the least favorite moments in the year. But since it was so impactful, on myself and (I hope) on others, and it was unscripted, then I want to include it here. The night before this shiur I had learned that one of my first students in Shalhevet, who I taught from 2010-2012, had died. I hadn't spoken about it or dwelled on it, but I wanted to address it at the beginning of my Mishlei shiur. As soon as I started, I broke down crying. I managed to get out the idea, which had to do with mental health, and I think it was sufficiently clear. I didn't mention her name because I suspected it was a suicide (which it was) and I didn't know whether the family wanted it publicized. This led to a period of personal grief, mourning, and depression - which I'm sure had been exacerbated by all of the difficult months of COVID leading up to it. I gave a shiur in memory of Yocheved on Asarah b'Teves and raised close to $9000 for Amudim, a Jewish organization which offers services for mental health. I chose this shiur because it reminds me of all that. 
  • Whoops!: There was a moment in one shiur in which a student forgot that we were recording said something negative about another institution. I intended to edit the recording immediately afterwards, but forgot, and by the time we remembered, we forgot which shiur it was in and where in the shiur the statement was made. We tried tracking it down, but to no avail. We don't even know if it's audible in the recording, since he was sitting far away and said it under his breath, but we want to eliminate it if at all possible. It has become our "white whale." If you ever hear it, please let me know ASAP! 

Favorite "Successful" Teaching Experiment: 
Comments: I didn't have to record my shiurim, and even if I did, I didn't have to upload them publicly. I chose to do so for several reasons: (a) I knew it would make me a better teacher, since everything I taught could be scrutinized by any and all listeners; (b) I knew that making my Torah content available and accessible to everyone would be a beneficial thing to do; (c) since I knew I would have to supplement my income with tutoring, I wanted to "get my Torah out there" so people could see for themselves whether it was something they liked. It's hard to believe that the only thing I did at the beginning of the year was to launch my YouTube channel. I launched my Mishlei and The Stoic Jew podcasts on December 10th, 2020, I launched the Rambam Bekius and Machshavah Lab podcasts on December 29th, 2020, and the Tefilah podcast on January 10th, 2021. What a different year this would have been without this decision!
Runners-up
  • The Stoic Jew Podcast: Not many people know how this experiment began. It began with me wanting to break the habit of being on my phone while in the bathroom. I decided to replace it with substantive reading. Since I had wanted to get back into reading the Stoics, I decided to leave my copy of Marcus Aurelius's Meditations in the bathroom to read whenever I went there instead of using my phone. I soon discovered that I needed to find a way to think into everything I read with more deliberation. I decided to record my own meditations on his meditations in the form of short WhatsApp voice messages, which I sent to anyone who was interested. That population grew, and so did my meditations. In December I decided to start a podcast. The podcast grew and evolved into what it is today.
  • Patreon: Were it not for my Patreon supporters, I would not be able to produce the Torah content that I am currently producing. Those hours would instead be spent tutoring. I think we can all agree this this is a better use of my time, insofar as the net Torah-goodness is concerned.
  • The One-Page Article Experiment: This was BIG! Without going into details, I wanted to devote this summer to self-care and working on my mental-health game, so as not to burn out in 2021-2022 like I did in 2020-2021. I drastically reduced the number of chavrusas and activities I had during the summer. The question was: Would I write daily articles, like I had for nearly all past summers? Part of me wanted to say "no," because that would create too much pressure. The other part of me knew how much I thrived during "writing season." The One-Page Article Experiment was my compromise - and it was fantastic! It allowed me to write productively every day but without going overboard. It opened my mind to new ideas, as I wrote about in Hunting for Treasure vs. Panning for Gold on the Beaches of Nome. It led to far more readers than I would have gotten if I wrote my typical 3-10 page articles. It made me a more concise writer (not obvious from this post, lolz!). And I'm fairly certain that this format will allow me to write throughout the year in a sustainable manner.
  • Audio Versions of Articles: I was worried that making audio versions of all my summer writing would be a waste of time. Turns out that this not only helped me to put the finishing touches on my editing process, but it also got my Torah out to way more people than it otherwise would have. Plus, it didn't even end up being so time-consuming! One small regret: I started to make audio versions of old articles, but didn't end up doing that many. That would have been time consuming, because I would have been tempted to edit as I went, and I don't need that kind of black hole right now.

Favorite "Failed" Teaching Experiment: 
Clarification of Category: The word "failed" is in quotation marks because none of these were actual failures. They produced a significant amount of good, and they yielded a lot of data. They only "failed" in the sense that the projects didn't continue. 
Comments: At the very beginning of the year, when I first launched my YouTube channel, I started a series called 5-minute Kavanah (named after the 5-minute Energy drink). The idea was to have high-density mini-shiurim on the tefilah based on the teachings of the Rishonim and to post one shiur each day. Don't get me wrong - this was a fantastic idea! It just wasn't sustainable, given my intense teaching schedule. Taking deep and complex ideas and reducing them to a five-minute video, complete with a PowerPoint presentation, is VERY time-consuming. I would totally take up this project again if I had the time. I just don't think I will in the near future.
Runners-up
  • "The Onkelos Initiative": I've done Shnayim Mikra with Onkelos for 20 years. I'm always saddened when I hear about people who do Shnayim Mikra with Onkelos but don't gain anything from it. I'm even sadder when I hear that people don't do it because they don't gain anything from it. To help remedy this, I started a WhatsApp group devoted to Onkelos. The idea was for all of us to share insights, observations, and questions with each other, and have an ongoing Onkelos discussion throughout the week. I was going to say that the group only lasted for a month or two, but I just checked, and it looks like it was going strong through January 2021. Then, for unknown reasons, it petered out. Maybe we should start it up again? I certainly gained from it. 
  • Koheles Shiur: I've taught Koheles for many years in high school. I foolishly thought that I could give a Koheles shiur twice a week in yeshiva, on Tuesdays and Thursdays. I did for a while, but then I hit the part of Koheles that I hadn't taught in high school before (due to time constraints). At that point I quickly realized that it takes WAY too much preparation to be able to sustain a twice-weekly Koheles shiur of a yeshiva-level caliber. I don't even think I could do a weekly shiur. Suffice it to say, my fluency in Koheles is not nearly at the point of my fluency in Mishlei, or even Tehilim.
  • (Regular) Tefilah Shiur: At the beginning of the year my morning Mishlei shiur was only twice a week, and the other two days were devoted to a tefilah shiur. Shortly after the year started, I nixed the tefilah shiur and made all four days into Mishlei. I did this for two reasons: (a) it was too hard to generate material for a twice-weekly tefilah shiur, and (b) I just wanted to learn more Mishlei! That turned out to be one of the best decisions I made all year.
  • WhatsApp Ideas: Very early on it was suggested that I use WhatsApp to record little ideas, questions, and insights that I'd share with those who follow me on WhatsApp. In theory, that sounded nice, but it didn't last. Instead, I folded those types of ideas into The Stoic Jew podcast, which was a far more natural home for them.

Concluding Thoughts

Well, that's it for my self-indulgent year in review! I hope this ends up being beneficial for others besides me, but even if it doesn't, I certainly gained from these lists. I'm sure there are other candidates for these shiurim which I've forgotten about. Feel free to remind me. This is yet another benefit of the decision to record and upload the vast majority of my shiurim: without that decision, a retrospective like this would have been impossible. 

I hope and pray that Hashem grants me another year of learning, teaching, and development, and I hope that you can join me for the ride! 
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