Let’s Be Honest: Regret, Guilt, and Shame

Let’s be honest, regret is the Jewish national pastime. Some nations play sports. We? We regret. We regret not calling our mothers enough, not saying the right thing at shul, not investing in real-estate or our children’s future.  

But here’s the thing: regret isn’t just emotional spam, it’s actually useful. Psychologists will tell you regret is one of the most human emotions. It sharpens our values, pushes us to grow, and reminds us that we do care. Without regret, we’d all just be running around making terrible choices with zero reflection. (Basically toddlers, but with mortgages.)

3 Things Science Knows About Regret

1. Regret makes us human. If you feel regret, congrats, you’re alive and your conscience works.

2. Regret makes us better. It tells us, “Hey, next time, don’t do that.”

   
   

3. Regret clarifies what we value. If you regret missing minyan, it’s because you actually care about davening. If you regret something you said, well, that’s because you care about how your communication is perceived.

Our tradition is way ahead of the curve here. Teshuva isn’t about wallowing in shame. The Rambam would actually agree with this modern psychology. He writes that teshuva is not about endless self-flagellation, but about taking regret and turning it into different action. Regret is meant to be a launchpad, not a permanent campsite.

The Four Core Regrets

Daniel Pink, a researcher on regret (yes, that’s a real job), found that regrets fall into four categories:

1. Foundation regrets: “If only I’d done the work.” Didn’t study, didn’t save, didn’t build healthy habits. Foundation regrets reveal we crave stability. Lesson: lay the groundwork now.

   
   

2. Boldness regrets: “If only I’d taken the chance.” Didn’t take the new job, didn’t apply, didn’t say what needed to be said. Boldness regrets reveal we crave growth. Lesson: take the shot.

   
   

3. Moral regrets: “If only I’d done the right thing.” You knew the halacha, you knew the right choice, but convenience won. This is the person who cut corners in business, or the teen who joined the lashon hara conversation instead of walking away. Moral regrets reveal we crave goodness. Lesson: do the right thing, even when it’s inconvenient.

   
   

4. Connection regrets: “If only I’d reached out.” Didn’t call, didn’t visit, didn’t apologize. The cousin you lost touch with, the friend you stopped calling after a dumb fight, the parent you meant to honor more while you could. Connection regrets reveal we crave love. Lesson: when in doubt, reach out.

   
   

It’s like Pirkei Avot says, “Who is wise? One who sees what is born.” Regret is our reminder to look ahead and not wait until the damage is done.

Guilt vs. Shame

Now, here’s where things get interesting. Not all regret is created equal. Some of it becomes guilt, which is good. Some of it turns into shame, which is deadly.

• Guilt says: “I did something wrong.”

• Shame says: “I am something wrong.”

  
  

Rabbi Abraham Twerski distinguishes the two, “Guilt is about what a person did … it can be a constructive feeling … Shame … is what one feels he is. With guilt, there is hope of improvement; shame leaves one unredeemable.”

Let’s be honest, guilt is Jewish. Shame is not. Think about Yom Kippur: we confess specific actions. “We have spoken gossip, we have stolen, we have acted disrespectfully.” The tefilah doesn’t say: “We are worthless failures who should give up.” No, guilt is about behavior and things we can fix.

Example: A parent snaps at their kid before Shabbat, regrets it, and thinks, “That was unfair. I’ll apologize, and next week I’ll plan better so I’m not rushing.” That’s guilt, and it leads to repair.

But if the same parent thinks, “I’m a terrible parent. My kids deserve someone else. I always ruin everything.” That’s shame. And shame doesn’t motivate teshuva; it motivates despair.

This is why we as Jews are obsessed with teshuva: it’s about transformation, not self-destruction. Rambam says the highest teshuva is when you’re in the same situation again and choose differently. That’s guilt harnessed into growth.

5 Jewish Ways to Turn Regret Into Action

1. Write a “cheshbon hanefesh resume.” List your biggest five spiritual screw-ups, what you learned, and how you’ll act differently. (Think failure resume meets mussar sefer.)

   
   

2. Talk about one regret at the Shabbat table. Not in a heavy way, more like, “Here’s what I messed up, and here’s how I’m growing.” Normalize mistakes as growth fuel.

   
   

3. Do a regret “pre-mortem” before an action. Imagine the project will fail. Why? Fix those reasons now.

   
   

4. Channel your inner Rambam. Ask: “If my better self took over today, what would he or she do differently?” Then… just do that.

   
   

5. Call your future self. What would the 2035 version of you say? Probably, “Don’t waste time. Learn more. Hug your kids.”

   
   

Let’s be honest, we spend too much time running from regret, when it might actually be one of Hashem’s greatest gifts.  Regret is the nudge that says, “You care. You can change.” Guilt is the engine that pushes us to teshuva. Rabbi Lord Jonathan Sacks writes “Guilt is the voice of conscience, and it is inescapable…Guilt is self-knowledge.” Shame?  Shame is the enemy of Teshuvah because it tells you redemption is impossible. That one we can leave outside with the recycling.

Because at the end of the day, regret isn’t about what you lost. It’s about what you value. And the Jewish response isn’t to wallow, it’s to act.

So let’s be honest, if you regret not calling someone, call them. If you regret not learning more, pick up a sefer. If you regret yelling, apologize. It’s that simple.

Regret doesn’t have to haunt us. It can refine us. Which is, after all, the entire point of being a Jew. Taking the raw material of our mistakes, and turning them into growth, connection, and holiness.