Dear Rabbi,
I recently became observant and have done Teshuva for a certain sin. Sadly, I fell into this sin again and I again did Teshuva. However, when I initially sinned it was out of fear and now it is out of love.
My question however is: How do I know if my repentance is enough. I feel constantly saddened that I was able to go against G-d and I feel I let G-d down. How do I overcome this?
Best,
Baruch
Dear Baruch,
Great to hear about your journey in coming close to G-d! May you only have continued success and grow and enhance that connection every day!
The concept of proper teshuvah and what constitutes it, is a long and nuanced subject – beyond the scope of this letter. I will though attempt to address some aspects as it relates to the issue at hand.
Concerning Teshuvah, there are various aspects, there is the “commandment of Teshuva,” the reconciliation of teshuva, and the spirit of Teshuva. Each of these aspects is somewhat unique and entails different acts.
The basic commandment of Teshuva is to “leave sin.” It is the firm resolution that the person will never sin again. While this is the bare minimum of command there are other aspects as well in the repentance, they are regret and admitting the sin. While somewhat beyond the purview of this letter, the reason that a person need regret one’s actions is that every matter in this world is comprised of body and soul. The soul of a mitzva is the intent and enjoyment that one receives in fulfilling it, the body is the actual commandment.
The same is with sin: The body of the sin is the actual sin itself, its soul is the enjoyment and lust that a person has in sinning. When a person recites the vidui – an action – they slay the action part of the sin, but to slay the soul one must regret their action. As long as a person does not regret their action, they are emotionally and psychologically connected to the act even if they resolve never to act on it again. It is self-understood that this regret is more difficult and there are layers upon layers of the degree of regret that a person can have. It’s explained in chassidut that this is a level of repentance that is constant, as the verse states (Tehillim 51:1) “My sin is constantly before me.” A person must always at some level be aware that they sinned, and constantly strive to reach higher and higher levels of repentance.
This is all the “command of repentance” there is however the reconciliation of Teshuva: There is an aspect of repentance that is similar to something that one does to their fellow. True the person is forgiven, but to bring the relationship back to the level before the sin, more is needed. This is accomplished in various manners. The simplest manner is through charity and through using the negativity as an impetus towards good. Just as a rubber band must be pulled back to leap forwards, one should use the negativity as the springboard for goodness. Doing so transforms the sin into positive – as it is the sin that propelled the person to a deeper connection with G-d.
The spirit of Teshuva though is something that transcends sin. At the heart of the matter, teshuva means to return. It means coming close to G-d. Now, no matter how close we are there is always infinite levels to return to an infinite G-d. This is the main aspect of Teshuva that we must do with love. Teshuva means to be obsessed with G-d and reach higher and deeper levels of intimacy with Him every moment of the day. It is this aspect that we should be primarily be focused on. For when we reach a level that we are one with G-d there is no sin.
Concerning your question about being sad etc. On the contrary Teshuva is the greatest connection that a Jew has with G-d. It is a level where G-d says no matter what you may have done, I still love you as you are my child. One should do all mitzvot with joy especially the Mitzvah of Teshuva, which as Nachmanides and others explains is indicative of the deep connection that one has with G-d. While sadness indeed has a place in Teshuva, one should be very weary of it. It is often a tool of the Evil Inclination to make a person depressed about themselves and their sin.
When the person focuses on their negativity it creates a cycle where the negativity causes the person to be stuck in a rut and to sin more. So while surely a person should be sad that they sinned they should be exhilarated that G-d gave them the chance to reconnect. In truth sadness and happiness are the same. One is sad for what they became far from G-d, but happy that they can reconnect to G-d and come close to Him. That being the case, why focus on how far you were, when you can focus on the joy of coming close again.
I hope this clarifies some of your questions and I wish you luck in the eternal mission of coming close to G-d once again!
