Good guilt is actually the remorse we feel for having sinned and distanced ourselves from G-d. This kind of guilt is completely contained, and serves as a motivating factor for us to resolve not to repeat sins and draw even closer to G-d than we were before. When we come close to G-d again and are positive that He has forgiven us, we feel very happy. Not only that, we will feel motivated to further improve our relationship with G-d by increasing in our Jewish observance. So this guilt leads to the ultimate goal – true happiness. (Imagine that you insulted your best friend. When you sincerely apologize and work to show that you do care, you will be overjoyed to find your friendship renewed and even stronger than before. And believe me, G-d is faster to forgive us than even the best of friends.)

The fact that you are CONSTANTLY guilt ridden means that you have spiritually unhealthy guilt. Unhealthy guilt causes the polar opposite effect of good guilt by making a person depressed, unenthusiastic, and spiritually lethargic. Eventually, a person wallowing in guilt will further decrease his Jewish observance and will indulge in further wrongdoing.

How does this happen to a person? We all have an evil inclination within us whose whole job is to tempt us to sin. Knowing how effective the guilt tactic is, he uses it as one of his favorite ploys. The guilt starts and we think that it must be a holy feeling trying to make us repent for our wrong doings. But gradually the guilt becomes overwhelming and constant, eventually bringing us to where the evil inclination hoped to lead us all along—the slippery slope of sadness and sin.

How do you escape the quagmire of bad guilt? First of all, identify that the guilt you have is the antithesis of good and be determined to overcome it. The evil inclination is so successful because he fools us into thinking that guilt is holy and admirable. Step number one is realizing that these feelings are actually unholy, unhealthy, and extremely harmful.

Secondly, good guilt MUST be relegated to specific times. Like when we pray for forgiveness in the Amidah prayer, before going to sleep at night, and on days like Yom Kippur. Focus these times on sincere remorse and future resolve, and find yourself happily connected to G-d. At all other times, guilt thoughts must not be entertained on the mind.