If a person does something wrong then regrets it, accepting upon himself not to do it again, and then later does the same thing again, over and over, repenting then transgressing, does that help at all? Is there any purpose after a certain point of even repenting?
Our Sages taught (Mishna, Yoma 85b), “One who says to himself, ‘I’ll transgress then repent, transgress then repent’, from Heaven he will be prevented from repenting”. This is because he intends to abuse the special rectifying power of teshuva by using it in order to be able to commit more sin. Such an audacious approach undermines the purpose of teshuva and, therefore, the teshuva of such a person is undermined.
However, one who transgresses and truly regrets, accepting upon himself to refrain from this in the future, and then falls into sin again, is granted the ability to do teshuva. And even if this happens many times (as is usually the case), a person is still required to repent, and this repentance, if sincere, is accepted.
Lest one query, “How sincere must he have been if he turned around and sinned again?” The answer is that he was as sincere as he was. This may not have been enough to prevent him from transgressing again, but at least it was not his intention to repent in order to be able to sin. And the truth is, in reality, even very strong conviction often melts in the face of temptation. So the main thing is to be as sincere as possible and to regret and express one’s full-hearted intention not to sin again.
And even if this happens time and time again, one must not give up hope by saying, “What’s the point, I know I’ll do it again”. This is exactly what the evil inclination desires. It lures and prods one into sinning, and then dissuades one from repenting because of it. To this our Sages referred in the last blessing of the evening Shema, “remove Satan from before us and from behind us”. This is as if to say: G‑d, please remove Satan from before me luring me into sin. But even if I do sin, stop him from afterwards preventing me from doing teshuva.
That being said, despite our appreciation for the curative and correcting power of teshuva and our faith in G‑d’s helping hand, as taught by the Sages (Kiddushin 30b), “If not for G‑d’s help, one could not overcome it [the evil inclination]”, we are of course required to make practical, tangible steps to improving our situation. So, it’s not enough to genuinely repent and pray for future Divine intervention, but rather on the crest of the wave of teshuva, one must think of and execute strategies that will help prevent one from being challenged again.
This is perhaps the hardest part of teshuva, because it demands a change in inner orientation and commits us to change our ways of life. More often than not, one will initially view this as great sacrifice and extremely limiting. However, with conviction and fortitude, one will come to appreciate the liberation from the strangle-hold of the evil inclination.