Let me start by talking about the term you used; “sin”. I believe this is a misnomer, which misleads people. Sin seems to be used more in a non-Jewish context.
I would suggest that from a Jewish perspective, or a Reform Jewish perspective at least, there are two kinds of behavior that are sometimes lumped in as ‘sin’.
(1) Errors in judgment or other lapses in our behavior that can negatively affect others and/or ourselves, and,
(2) Outright Moral failings that might properly be called Transgressions or Trespasses, each of which injure/affect three parties: ourselves, other people, and (it is thought) G-d.
I would say that most of the time, we are talking about the first kind. This is referenced in the Yom Kippur liturgy as ‘missing the mark.’ Reasons for this sort of failing might be when we don’t do our best, we simply don’t pay attention, we forget, or when we fall short of what we can/should do. This action (or inaction) may not affect anyone else, so we may be the only one injured; or it may be the case that this injures someone else as well. In either case, it is a disappointment and should serve as a spur to try harder.
When we talk about missing the mark, we are not usually describing a grievous criminal act or a major moral failing; overeating, forgetting someone’s birthday, misplacing trust in someone, being late again; these are all in this category. It is difficult for me to see any of them as an affront to G-d, so the use of the term ‘sin’ seems quite inappropriate. We should seek to rectify these failures, and to ameliorate whatever damage we may have done to others, but it does not strike me as what would be a ‘sin’.
The second kind of failing seems more serious. A transgression or trespass could be when we aren’t careful or don’t think about what we say, and we enjoy a bit of gossip about a friend that gets spread around, eventually gets back to them, and causes them injury or hurt. In this instance, we see three parties injured; the person who gossiped, the person who listened, and the person who was gossiped about. In this, we might also hold the view that G-d is affected and offended as well, because we have transgressed one of the guidelines for living a good, moral, and godly life by gossiping, and our action has upset the order of the world around us – injuring G-d’s creation. This is indeed a failing that requires we do all we can to rectify it; but even so, this does not seem to me to rise to the level of a ‘sin’ as it is commonly understood.
A sin, it would seem to me, would be a direct affront to G-d. Not too many things other than murder, worship of idols, or defaming G-d’s name seem to fall in this category, as I think about rabbinic writings. And for these, there is no practical forgiveness; the murdered person cannot forgive, and G-d is not obliged to offer forgiveness when one has rejected G-d by the very action that violates G-d’s guidelines/commandments and offends G-d. In my mind, then, a ‘sin’ is not forgivable – and we should be very cautious about using this term.
Back to your question. When we miss the mark or transgress, we must perform Teshuvah (Repentance), which includes recognizing our failure, asking forgiveness from those affected, making restitution where possible, avoiding the same action in future, and seeking forgiveness from G-d. This is the process we are encouraged to follow for Yom Kippur.
As you see, it doesn’t say seeking forgiveness from yourself, which is the heart of your question. I would suggest that this is implicit in the procedure set out. Before you can ask forgiveness (from others or from G-d), I would say that you must feel that you are ready for it, and deserving of it. To arrive at that point, you must find the means to forgive yourself before, or simultaneously when asking others.
I would also argue that after fulfilling the process outlined, if one finds that they feel guilty or undeserving of forgiveness, it is because they are re-visiting the transgression and re-imposing the guilt, instead of letting it go and being done with it. Another way to say this might be to say that they are second-guessing themselves and the process (effectively, discounting the other people and G-d) by which they were forgiven, perhaps feeling it was not harsh enough. In American jurisprudence, we would call this ‘double jeopardy’ – being prosecuted more than once for the same crime; and it is forbidden. So should it be in this arena as well.
Even worse, as you imply in your final question, some refuse to forgive themselves, and then feel guilty for not forgiving. This is a complete catch-22 position; it is insoluble. In no way can I imagine that this would be the desired outcome from the system outlined. Neither would I imagine G-d creating this as the way the world should work, even in the most capricious and arbitrary behaviors that are attributed to G-d in the Hebrew scriptures or stories, nor would I imagine that G-d would wish for such an unfair and disastrous outcome to a transgression.
I hope that this is helpful.
Rabbi Joe Blair
Answered by: Rabbi Joseph Blair