Does Judaism endorse guilt trips? It sounds so self-righteous to feel really bad about committing a sin, thinking about it all day to the exclusion of all else.

In fact, it’s downright dysfunctional. Even worse, it’s counterproductive.

It becomes a vicious cycle. If at work or throughout the day you are focused on your mistakes and defects, then you are bound to feel down about them. Which makes you susceptible to tripping and indulging even more in the very things you are trying to avoid.

So how should you deal with depression over spiritual downfalls? By exposing the guilt for what it is—a clever ploy of the evil inclination to make you battle-weary, and more likely to give in to lust and temptation.

There is a healthy alternative to dealing with your mistakes: setting aside intentional time in the evening, not while at work or play, to review your behavior. With a clear mind, you can make an honest reckoning of where you need to make improvements. You can then rest assured that G‑d forgives you completely . . . and move on.

Tanya Bit: Strategize for the future rather than obsess over the past, ensuring that it is productive and not destructive.

(Inspired from Chapter 26 of Tanya)