How Do We Deal With Sin: An Analysis of A Strange Aggadeta

דתניא, רבי אילעאי אומר: אם רואה אדם שיצרו מתגבר עליו – ילך למקום שאין מכירין אותו, וילבש שחורים ויתעטף שחורים, ויעשה מה שלבו חפץ, ואל יחלל שם שמים בפרהסיא.

For R. Il’ai says, If one sees that his inclination is gaining sway over him, let him go away where he is not known; let him put on black clothes, don a black wrap and do what his heart desires rather than profane the name of Heaven openly.

-Moed Katan, 17a

It’s Elul, so a lot of people are talking about repentance; what is repentance, how to repent, what repentance means, etc etc. Which is all well and good, as repentance is probably one of the more important concepts in Judaism to be aware of and to practice in one’s own life. But let’s go a little bit deeper than that. For repentance can only be possible when there is sin. So let’s talk about sinning. We don’t often talk about sin. We talk about avoiding sin. We talk about why people sin. We talk about feeling sorry for sin. We don’t often talk about sinning itself, even though everyone sins, and sins more or less constantly. Some people do big sins, most people do small sins, but we all sin. That’s pretty much undeniable. 

So first of all, what is sin? My personal favorite article on the subject is by Francis Spufford, who happens to be my favorite religious thinker from outside the Jewish tradition, for his passionate, thoughtful, and occasionally profanity-laced version of religious existentialism. I highly recommend the first half of his book, “Unapologetic“, and its worth buying just for that, even if the second half he turns towards talking about Jesus which is of little utility for an Orthodox Jew (though maybe some Hasidim.) But anyway, in his book, in an excerpt that can be found here, he attempts to come up with an understanding of the concept of sin that actually resonates with people instead of the titillating connotation it has acquired in our society. What he hits upon is what he calls HPtTFU, an abbreviation for “The Human Propensity to (word that starts with F) Things Up”. In his words,

“It’s our active inclination to break stuff — “stuff” here including moods, promises, relationships we care about and our own wellbeing and other people’s, as well as material objects whose high gloss positively seems to invite a big fat scratch.”


Sin, thus defined, is our propensity to do things that are destructive, whether to ourselves or to others we care about, a group which would include families, friends, even deities. We do these things for a variety of reasons, expedience, greed, anger, lust, but the common denominator is that we don’t really want to do them. We want to be good friends, good family members, good Jews, and we identify ourselves accordingly. But we, to paraphrase Spufford’s phrasing,  eff things up for ourselves. We crack under pressure and do things that are wildly out of sync with the people we wish to be. 

Now, how do we deal with that? Much ink has been spilled on how to avoid sin. Much ink has been spilled about how to feel sorry about having sinned. But how does one sin? This is a question which is obviously difficult to address, as it may seem as a tacit excuse, even approval, for sin. But people sin, and they do so constantly. So what does one do if they have already lost the battle that raged in their soul against the parts of themselves that are incommensurate with the person they wish they were? What is there to do at that point? Repentance is not an option yet, for repentance cannot be possible while one is yet involved in the sin! How should one, in the moment in which they have yielded to temptation, understand what is happening to them? 

I believe that the strange aggadeta cited at the top of the page points the way towards an answer. R. Il’ai states that if someone knows that he is going to sin, he should wear black, go to a place where no one knows him, do what he needs to do, and not desecrate God’s name in public. Now, a surface, perhaps cynical reading of this aggadeta would be that R. Ilai is saying “If you’re gonna do something stupid, at the very least try not to do it in public”. But were that the case, why the dressing in black? Why the going to a different town? Just say, “do it in private not in public?” What’s the point of the extra stuff? 

It thus seems to me that there is a deep psychological insight into the human condition and the nature of sin being made by R. Il’ai here. Let us put ourselves in the minds of the sinner spoken of here. He has tried to resist temptation. He has tried to be the person he wants to be. He has sent the forces of his will out to battle against the forces of his inclination. And they have been roundly defeated, and they have beat a hasty retreat. The battle is over, and he has lost. 

But there is still a war, the war for his soul, and for his identity. He may justly conclude from the fact that he has sinned that he is a sinner, that there is no hope for him to become the person he wishes to become, that he is doomed to not just sin, but be a sinner. The battle outside the walls of the city has been lost, and the enemy now knocks at the gates, waiting to storm in and conquer. The end of the war is in sight. 

To have any hope in the long run, our sinner must use any means at his disposal to defend his sense of self, and not become a sinner, though he has sinned. He must defend the city wall with everything he’s got, with the last of his ammunition and anything that can be loaded into a cannon. He must fight tenaciously for every possible inch, because giving any more inches is a death sentence. 

How does he do this? R’ Il’ai gives us two ways that seem at odds but are accomplished with the same prescription. The first is to disassociate one’s identity from the act he is committing. R. Il’ai’s directions are not just for the purpose of hiding from the judgement of one’s peers, they are to strip the sinner of any identification with the self that is committing the sin. He is to dress head to toe in black. He is to go to another town where he is unknown, without an identity. He is to do his sin in private, so that he not become publicly identified with the sin he commits. He is to do all that he can to ensure that, though he may sin, he does not become a sinner, that the sin not become part of his identity. 

The second is to conserve one’s desired self by any means available. One could have said to the sinner in question that if you don’t care about whatever sin you’re committing, why should you care so much about Chillul Hashem, such that you dress up in black and go to a different town? What kind of hypocrisy is this, that he should care more about possibly causing a chillul hashem than the act he is committing? But R. Il’ai takes a different route. Not only should you not despair of keeping the rest of the mitzvot, but you should be just as concerned, perhaps even more concerned and extra punctilious in your observance of them. Even when you fall victim to temptation, you should be asking yourself “Ok, but how do I do this without causing a chillul hashem”, as jarring and hypocritical as that sounds. You need to grab every opportunity you can to reassert the fact that you are in fact a person who wants to be a good person and a good Jew. And you should remain a good Jew even as you  sin, even when you lose the battle against yourself, because that is the war you are fighting. 

R. Il’ai’s advice, essentially, is if you sin, (and you will, because you’re a human being), you need to do everything you can to avoid becoming a sinner. This is a problem that I feel a lot of Orthodox Jews have. As R. Yitzchak Hutner once wrote in a letter, we tend to see our great people as men without fault, sin, or struggle, and when we sin, struggle and have faults, as we’re bound to do in a religion with 613 different ways to do so, we view ourselves as incapable of greatness, as sinners, not people who sin. And that’s unhealthy. We need to be able to not just do good things, but know how to properly process and bounce back from the bad things we do. And I think this is an important thing to keep in mind for Elul and the Aseret Yemei Teshuva. The goal of our endeavors over this time period should not just be to klap al chet and feel bad for the bad stuff we did, but actively try to reaffirm ourselves as good Jews and good people.