Sometimes, when I sin, I know its because I have not fully explored the deepest meaning possible of what lies at the heart of the transgression, yet at the same time, it also draws me closer to HaShem, because I realise how weak I am before HaShem; my pride is taken from me in that lowly state. Rabbi Nachman said something about one having to begin again and again. I find that by having to return to the beginning, I gain a deeper insight into the nature of the matter yet feel this is paradoxical, for I also need to not return to that sin. Any advice please?
It is wonderful to see someone so deeply thoughtful about Teshuvah (repentance) and how to most effectively change oneself and be closer to Hashem. If I understand your question correctly, the tension that you describe is one that lies between actions and character traits (middot). The action in which you are engaging is wrong and thus takes you further from Hashem, but in your sense of distance you feel small and that it therefore lessens the character trait of pride that you feel is a block between you and Hashem. Could it possibly then be that doing something against Hashem’s directions to us could bring a person closer to Hashem?
As a general rule, a study of Talmud and the works of classical Jewish thinkers indicates that the answer is “no”. While there is indeed a concept of errors and sins being transformed into merits (Talmud Yoma 86B), that is something that happens after a person has done teshuvah and ceases to engage in those activities anymore. The person changes himself or herself and no longer does these things, and thus what was once a problem in their relationship with Hashem has now been transformed into something that prompted teshuvah and growth and thus became a good thing in retrospect. But as long as one is still repeating the error, it lacks redeeming value. Thus, the same page in the Talmud also brings a debate as to whether people are even permitted to confess sins that they have already confessed in the past but to which they have returned, comparing it to “a fool repeating his folly” (Mishlei/Proverbs 26:11).
In a similar vein, the Rambam (Maimonides) critiques the notion of choosing to sin even with a plan to repent. In his Laws of Repentance (4:1), he notes that one who makes a plan to sin and figures that he will rely on repenting afterwards will have a very difficult time accomplishing that teshuvah. While it is understood that human beings make mistakes and will at times fall prey to temptations, we are not permitted to choose to go down that path light-heartedly with rationalizations of future spiritual growth.
The issue that you raise of pride getting in the way of your relationship with Hashem is indeed quite an interesting and complex topic. Arrogance is treated as a deeply negative character trait. The Rambam lists it (Laws of Deot 2:3) as something that has no constructive use and that a person should avoid at all times. However, arrogance is not the quite the same thing as pride. Arrogance is dismissive and generally directed outwards towards others, whereas pride can in many cases be an appropriate sense of the value of oneself and one’s accomplishments. Indeed, there was an entire school of Mussar self-development called Slobodka, whose focus was on helping people recognize their own greatness. In seeing and feeling deeply how truly valuable they were, people would naturally rise to the high standard of behavior that fit a person of their level of greatness and character.
It is often assumed, and likely incorrectly, that feeling low and small is an inherently good thing in one’s spiritual development and relationship with Hashem. However, the definition of true humility may be quite different. The Torah (Bamidbar 12:3) describes Moshe as being the most humble of men, but clearly Moshe did not assume himself to be lowly or a “nothing”. Far from it, he took on the role of being the greatest of all prophets and the leader of the Jewish people! A man who thought he was nothing would not have been able to assert himself in the ways that Moshe did.
So it seems that a different definition of humility may be in order here. The Talmud at the very end of Tractate Sotah (49B) quotes Rav Yoseph as correcting those who claimed that there were no longer any truly humble people around, “because I am here.” While it seems like the punch line of a joke to point out to others that “I am humble,” there are those who explain that humility doesn’t mean thinking that you are small and incapable but rather “thinking about others.” That could mean thinking about other people, as well as thinking about Hashem, but thinking as little as possible about oneself. The arrogant person thinks primarily about himself, and the humble man thinks about others (while maintain the awareness that he is a worthwhile human being.)
We do indeed begin again and again, and part of Rebbe Nachman’s teachings is that one should never give up. Even at the lowest moment, we are capable of change and can start moving in a better direction right now. Hashem did not create human beings to be perfect, and expects us to make mistakes. Rather, our job is to aspire to spiritual greatness and to try our best to get there.
Sin can indeed make you more aware of Hashem, for it shows you how far you are from what Hashem stands for and demands of us. Still, even though we all sin, the Jewish tradition, unlike Calvinism, does not want us to dwell on that or to see ourselves without worth. On the contrary, we are, as God's creatures created in the Divine image, both able and required to try to imitate God as much as we can.
So the direct answer to your question is this: It depends on the nature of the sin. If you are hurting others -- physically, financially, psychologically, socially, or otherwise -- then you indeed need to stop the behavior immediately, for someone else's welfare is at stake. Furthermore, you must, as according to the steps of teshuvah, recognize that what you did constitutes a sin, have remorse, apologize, compensate the victim to the extent that you can, and take steps to make sure that you do not do what you did again. Again, depending on the nature of the sin and the harm it caused, these steps might include getting therapy to learn how to avoid this harmful behavior in the future. Therapy may give you insight not only in how far you are from what Hashem wants of you, but also how to diminish that gap. If the sin is between you and God, then, again, the steps of teshuvah are what is required, but here talking with a rabbi is probably advisable about how to avoid the temptation that is prompting you to sin in this way. You might also look at Rambam's Hilkhot Teshuvah (Laws of Return) and Rav Soloveitchik's book on Teshuvah or my own treatment of this subject in Elliot N. Dorff, Love Your Neighbor and Yourself: A Jewish Approach to Modern Personal Ethics, Chapter Six, to understand the process of teshuvah better and to get the strength to do it effectively so that you do not sin in this way again.
This is a most interesting question on a variety of levels.
As I understand you, you say that you don't want to sin but that, when you sin and then repent, you feel closer to God. So the question becomes, how is it that sinning has been the only way to connect to God? I don't think Rab Nachman had it in mind to sin and again and again so that we can experience God. This is a very unhealthy way to live as it is akin to diving into cold water again and again so that you can feel how good it is sit by the fireplace to get warm. Surely there are other ways to connect with God without having to go through the sinning first to get there.
I would suggest that repentance is a first step to becoming aware of our vulnerability and weakness before God. But it ought not to be the goal of who we are as Jews. Repentance turns us into the direction we ought to go. It is not the direction itself.
Once a commitment is made to God, that is repentance. The next question is, what now? Over the millenia, the answer has always been acts of gemilut hasidim and study. What was true those many years ago is equally as true now. Repentance focusses the mind and heart - study and tzedakah bridge the gap that we promised God we would bridge.
There are dozens and dozens of readable and understandable books on bridging these gaps. Birkat Avraham, Noam Elimelech, Likutei Moharan, etc. Aseh lecah rav - find yourself a teacher and explore the bridge between you and God. You can walk it and you don't have to revert to sinning again and again to feel God's presence.
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