TORAH → TRIPLESAY Issue 1092 · December 24, 2025

When Is Guilt Healthy?

“Guilt isn’t Jewish, because it keeps you stuck, stops you from growing. Regret is Jewish because it’s the catalyst for growth”

When Is Guilt Healthy?

Facilitated by Faigy Peritzman

Q:

Like any “good” Jewish woman, I find myself confronted by guilt on a regular basis. If I do chesed, I feel guilty that it came at the expense of my family or my self-time, etc. If I don’t do chesed, I feel guilty that I lost a chance to do a mitzvah. I find guilt follows me throughout the day, confusing me every time I have a decision to make. How do I know when guilt is a healthy wake-up call, and how do I know when it’s self-sabotaging?

Antithesis to Growth
Ruchi Koval

OY!Let me challenge your very first sentence. “Like any good Jewish woman….” Yeah, you put “good” in quotes, but we all know what you really meant. You meant good — unironically.

Sadly, the notion that guilt is good is way too prevalent in our culture. You know how I know guilt isn’t good? Because it usually keeps us stuck and sad. I vastly prefer its virtuous and lovely twin, regret.

“Regret” in Hebrew is “charatah,” and it’s one of the beautiful steps of teshuvah (that’s how we know it’s virtuous and lovely). The difference between guilt and regret is this: Guilt — I did bad (or someone thought I did bad) so I am bad and I don’t know what to do about it. Regret — I did bad, but I’m not bad, so let me distance myself from my mistake and improve so I become the kind of person who acts in alignment with my higher values.

See the difference? Guilt isn’t Jewish, because it keeps you stuck, stops you from growing. Regret is Jewish because it’s the catalyst for growth. One might even argue that if you never regret your previous behavior, you’re never growing. If you look back at your previous self from five or ten years ago, and you have all the same beliefs and habits and you regret nothing, you know what that means? It means you haven’t grown a whit. Growth, by definition, means we’ll notice that certain behaviors aren’t in alignment with our values. Then we calibrate and adjust and course correct.

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