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Years ago, as a counselor at a Jewish summer camp, I watched a teenage camper leave a shiur in tears after hearing a well-meaning speaker describe the need to do teshuvah for mitzvot. The speaker challenged the campers, “Were your mitzvot performed with all their details correctly? Did you have the correct intentions in mind?” That we all have sins is a given, but did you realize your “good” deeds were not even good enough? Overwhelmed by the vision of a heavenly scale weighed down by both aveirot and sub-par mitzvot towards a guilty verdict, the camper picked herself up mid-shiur and left in despair. (From a 2019 article by Dr. Chaya Sima Koenigsberg on OU’s website.)

This story illustrates a fundamental problem that I wonder about every Elul, and I suspect I am not alone. It’s the problem of teshuvah anxiety. Think of it as the autumnal analogue to Spring’s chametz anxiety:

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In springtime, we start to see crumbs everywhere, and sometimes to imagine them – in the pages of books; between floorboards; in corners of drawers that never, ever saw a piece of bread.

And after Tishah b’Av, we start to see aveirot everywhere – in our speech, in our thoughts, and apparently, according to the above story, even in our mitzvot.

In truth, I think teshuvah anxiety isn’t a major obstacle for most people. When I was learning in yeshiva we had teshuvah anxiety. We emphasized intense mussar in Elul; my friends would take on taaniyot dibbur, refraining from speaking for days; we increased our learning; no one went out for shwarma, and so on.

It was a fearful and tense month, but we made it.

In fact, that kind of teshuvah anxiety was probably good for us; it spurred us to true cheshbon hanefesh, examining our behavior in meaningful ways, repairing our wrongs and insufficiencies, and developing plans for growth. Shlomo HaMelech advised, “Fortunate is the man who lives in perpetual fear; one who hardens his heart will fall into evil” (Mishlei 28:14). Sefarim like Sha’arei Teshuvah and Mesilat Yesharim don’t seem too concerned about the possibility that teshuvah anxiety might be a problem.

But I think there is a danger for some people, perhaps best illustrated in a century-old poem.

A little over 100 years ago, the poet T. S. Eliot published The Love Song of J. Alfred Prufrock. The poem is delivered in the voice of a middle-aged man who wishes to ask for a woman’s hand in marriage, but fears what people might say and think of him. He tries to bolster himself with sweets, thoughts of religion, and even his own death, but he can’t move forward. He muses,

And indeed there will be time
To wonder, “Do I dare?” and, “Do I dare?”
Time to turn back and descend the stair,
With a bald spot in the middle of my hair –
(They will say: “How his hair is growing thin!”) …
Do I dare
Disturb the universe?…
Should I, after tea and cakes and ices,
Have the strength to force the moment to its crisis?
But though I have wept and fasted, wept and prayed,
Though I have seen my head (grown slightly bald) brought in upon a platter,
I am no prophet – and here’s no great matter;
I have seen the moment of my greatness flicker,
And I have seen the eternal Footman hold my coat, and snicker,
And in short, I was afraid….

* * *

Everyone deals with uncertainty; to live is to be uncertain. The Talmud depicts the demonic Ashmedai laughing at people who claim great knowledge; a Yiddish adage says Der mensch tracht, und Gott lacht (Man plans and G-d laughs). And normally, we accept that lack of clarity. But sometimes that uncertainty overtakes us, as it does Prufrock. His uncertainty drives him to despair.

I’m not speaking about pathological anxiety; I am not a psychologist, and I would never oversimplify a complex medical condition. The advice I’m going to offer is not addressed to that situation.

As far as I can tell, Prufrock is not ill, but he’s also not among those who handle uncertainty easily. He’s in the middle, and the reader laughs as Prufrock dithers – but Prufrock’s is a serious inability to live with uncertainty.

Which brings me back to the girl in the summer camp story, and teshuvah anxiety. That counselor may be right, mitzvot may need improvement too, but not everyone can deal with that intense message. Some people – those in the middle, like Prufrock, and certainly those whose condition is more extreme – will despair. Then what happens when we despair of changing, of growing, of earning Divine forgiveness? And even for those who don’t give up, what if the search for improvement becomes less about drawing close to Hashem, and more about silencing that internal voice that says we are inadequate, trying to satisfy ourselves?

How can we balance the need to build intensity, to challenge ourselves and examine ourselves, with our need to avoid the trap of turning Elul, for some people, into a month of stifling uncertainty and anxiety?

* * *

I think one answer lies in recognizing that Judaism is an optimistic religion, and so we don’t need to despair. It is axiomatic that Judaism is sanguine in its view of human nature and the possibility of meaningful growth.

  • Moshe optimistically promised us that national teshuvah will happen: “The day will come when you will return to Hashem your G-d and you will listen to His voice, and on that day Hashem will have mercy upon you.” (Devarim 30:2-3)
  • Rabban Gamliel lived at a time when we were crushed by the Romans, and still he envisioned a Messianic day when, miraculously, childbirth would occur without gestation and trees would bear fruit without a growing season. (Shabbat 30b)
  • The Torah has an optimistic view of our personal future, too. Witness the classic Gemara in Kiddushin: If a man says to a woman, “Marry me on condition that I am a tzaddik,” then even if he has been fully wicked in the past, if she accepts his offer then she is married. Why? Perhaps he contemplated repentance at that moment, and that is sufficient to label him a tzaddik.
  • And most directly the words of Rav Avraham Yitzchak HaKohen Kook, “The world is guaranteed to come to complete repentance. The world does not remain in one place; it perpetually evolves.”

Because of this optimism, a Jew should not yield to despair.

* * *

Even as I claim that Judaism is optimistic, I must acknowledge that this is a partial picture; there is plenty in the Torah to argue that human beings are doomed to fail. But nonetheless, we should act as though Judaism is 100 percent optimistic, and push ahead with our teshuvah.

The navi Chaggai presents a perfect example of this attitude. Chaggai says to the Jews in Eretz Yisrael who have stopped building the second Beit HaMikdash, “This nation says the time has not yet come, the time for the house of Hashem to be built” (Chaggai 1:1-10). As Rashi explains: You think you’ve made your calculations and there has been no geulah, and so you despair because you believe that you are beyond geulah.

And Chaggai replies, “Is it time for you to sit in your homes? No! So says Hashem…, Pay attention to your ways! Ascend the mountain, bring wood, and build the Beit HaMikdash! I will desire it, My honor will be in it!” Optimism!

And then Chaggai inserts his own pessimism! He omits the letter hei in the word v’ekavdah (“My honor will be in it”), and Chazal explain that Chaggai hinted that the second Beit HaMikdash would truly be inadequate, lacking an aron, keruvim, fire from Heaven, the Shechinah, Divine inspiration, and the Urim v’Tummim worn by the kohen gadol. But he told them to go ahead anyway, because a Jew should never despair, even when we know our dreams are unrealistic.

We may not be 100 percent optimistic, but we should act as though we are.

Rambam conveyed this message, too. In his Laws of Repentance, after talking about the wonders of teshuvah, Rambam published a list of behaviors and traits which defy teshuvah, like the person who sins with a plan of repenting, and the one who causes the public to sin. Now, that’s an instant recipe for teshuvah anxiety – how can I take an optimistic approach to teshuvah when you’re telling me that some aveirot are irreparable?

But the Rambam, like Chaggai, said not to despair. At the end of that long chapter detailing all of the ways a human being could go wrong and teshuvah could become impossible, he said, “All of these [aveirot] and similar activities, even though they obstruct teshuvah, they don’t prevent it. If someone repents of them, he is a baal teshuvah, with full entry into Olam Haba.”

Rambam, hard-headed rationalist with the highest halachic standards, is not willing to give up entirely. Yes, it’s hard. Recognize the fear, recognize the cause for despair – and then proceed anyway, because we are optimists.

* * *

To me, this is the answer to Prufrock in Elul. True, the daunting task of identifying our wrongs, defining paths of repair and embarking upon those paths is intimidating. Anyone who takes Elul seriously is apt to spend some time asking, Do I dare? Do I dare? But to them, Elul responds: Dare!

The Torah is optimistic – so tackle your thoughts during Shemoneh Esrei, apologize and rebuild a relationship; work on a midah that has been hard to repair before, such as anger or laziness. And see what happens.

May we, this Elul, defeat our inner Prufrock and our doubts about whether our mitzvot are mitzvot, recognizing the optimistic message of Chaggai and the Rambam, and so merit to truly feel the words of Kohelet (9:4): “For all who are connected to life, there is faith.”

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Rabbi Mordechai Torczyner served as Rosh Beit Midrash of Toronto's Beit Midrash Zichron Dov from 2009 until 2023. He is the incoming Rabbi of Eitz Chayim of Dogwood Park in West Hempstead, NY.