It is a common misconception, perhaps derived from the wider Christian culture, that Yom Kippur - the Jewish "Day of Atonement" - is predicated on guilt. Teshuvah, the act of penitence for transgression, which is the foundation for atonement received on Yom Kippur, is not about guilt. In Rambam’s Hilchos Teshuvah (the laws of Teshuvah, one among the many volumes of his Mishneh Torah) he writes the text of the essential confessional prayer: I implore You, G-d, I sinned, I transgressed, I committed iniquity before You by doing the following. [List sins] Behold, I regret and am embarrassed for my deeds. I promise never to repeat this act again.
This is the gold standard of verbal confession and articulation of sins before G-d, which is a positive command.
Guilt and remorse are very different concepts. Guilt is selfish, “I feel bad because X”. The focus is within, on “I”, on me. If “I” didn’t feel bad, there would be no problem, nothing to fix or apologize for. In contrast, remorse looks externally, at the consequences our actions have - it’s not about “me”, about how "I" feel about my actions at any given point, but understanding the negative impact my actions created. Even if “I” don’t feel particularly bad about something, I can become more sensitive to the damage my actions caused and seek a way of rectifying that damage, and preventing myself from repeating that mistake in the future.
Teshuvah is not about imposing something alien on ourselves, beating ourselves up for the theater of satisfying some vain emotional need for a positive self-image. It is a substantive return to our essence, to our spiritual core and mission, which persist, independent of and untainted by our actions. Teshuvah is not about guilt, it is about repair, a release of the burden holding our future hostage to our past, a coming home to our true self. In so doing, teshuvah offers a path of transforming past transgressions into future merits.