• Shterna Ginsberg


Updated: Sep 13, 2021

Nobody enjoys feeling regretful. But feeling regretful means you’re able to enjoy life.

R’ Yisroel Neveler ע”ה told this story:

A group of the Baal HaTanya’s chassidim sat around the table, taking time to absorb the Torah and chassidus that they’d been learning. One of the chassidim was asked: “Where have you been all these years? What brought you to this table?” The chassid shared his story:

As a young yeshiva student, I was a serious masmid (intense learner) and my life was satisfying. Only one thing bothered me. When I davened and said the word “חטאתי – I have sinned,” I felt like a liar. I was perfectly strict in my observance of halacha; I never did anything wrong, so how could I say that I have sinned? I felt guilty of dishonesty. This bothered me for a long time until it occurred to me that since I’m part of K’lalYisroel, I can say “I have sinned” and it won’t be a lie – because other people, like Zanvil, sin all the time. I was relieved.

One day I learned about the importance of looking favorably at every Yid. The words resonated with me and I realized that when I say “I have sinned,” it’s not proper to think of other Yidden as sinners. I started searching for new meaning.

I learned about the value of developing good character traits and the quality of overcoming misery, jealousy, resentment, worry and anger. This gave me plenty of things to think about as I said the words “I have sinned” because I often felt jealous, resentful or angry. But I still felt like a liar, because even as I said “I have sinned,” my heart felt no regret. After all, these feelings are not sins; they are a natural part of the human experience. I couldn’t feel genuine regret for behaviors and attitudes that were impossible to change.

Then I came to the Baal HaTanya. I learned Who Hashem is, I learned who I am and I learned what my life is about. I learned that I can choose what I think, say and do – and I learned that my every choice matters. Suddenly, I started believing what I was saying; I cried out from the depths of my soul: “I have sinned! Oy, gevald! I have sinned and I never want to do that again!”

What happened to this chossid? How did he come to feeling a sense of regret? And what’s valuable about his experience?

Nobody enjoys feeling genuine regret. But the qualities that can give birth to sincere regret are also the very same ones that propel us towards infinite, joyous possibilities.

Let’s take a look at these qualities:

  • Choices & responsibility: We can only feel regret for our behavior when we realize that we can choose what we think, say and do. If we don’t recognize our ability to make choices, we can’t feel responsible – and sometimes regretful – for our choices.

  • Self-respect: We can only feel true regret for our choices when we value who we are. The more we respect ourselves, the more we realize that our behavior has an impact on other people.

  • Awareness of life’s purpose: Knowing the purpose of our life makes us feel regretful when we get distracted from our purpose. Without knowing our purpose, we can’t feel regretful for veering away from it.

When we taste something delicious, we want more of it. When we taste what it’s like to live with these qualities, we never want to live any other way! We want these qualities. They give us a way to navigate life’s twists and turns with dignity and with peace of mind and heart.

Before I learned how to feel regretful, I thought that a good day is something I get to have when good things happen to me, or when the people around me are pleasant to be around. When I didn’t have a good day, it was (I thought!) mainly because of people’s faults and because of circumstances that were beyond my influence of change. My choices? I was too focused on others to fully see my own self.

If there was tension in my marriage, if my baby was cranky, if the doorbell was ringing, the toilet overflowing, the kids arguing and the soup burning all at the same time and I snapped at someone who did something that I experienced as annoying, I wouldn’t feel deep and true regret.

Of course, I’d apologize. Here’s what that sounded like: “I’m sorry, but there was so much going on and you knew how much it means to me that you ___________________! I told you a million times!”

Writing about it now, I am laughing. The thought of blaming circumstances or another person for my behavior (as a way of apology, no less!) is ludicrous. Back then, it wasn’t funny. I found myself sitting with Misery and Resentment – and there was nothing I could do to change it.

A page in my G-d-centered reality is completely different, even when all the same bells are ringing. Here, a good day is something I can do, by putting my G-dly Self in my driver’s seat. By choosing how I want to show up; making choices, one moment at a time. Standing in my G-dliness, I respect myself and I own my ability to make my life the beautiful one that I want to live.

And sometimes I slip back into my old way. My Animal Self way. In the Animal Self way, the people and situations that surround me become Powers that drive my behavior. In that space, I am diminished by my mistakes and failures; I could shrink when I compare my scruffy shoes to someone else’s elegant heels. I am pushed and pulled by circumstances and conditions. I find my spirit rising and falling with the moods of people around me.

In that mindset, I can speak unkindly to someone who triggers my discomfort. But then, as soon as I realize that I’ve slipped, I truly feel regretful. With my whole heart, I say, “I am sorry.” No buts. No limits. No fine print and no exclusions. I am simply sorry because I caused hurt to a person; I don’t want them to be hurt. And no matter what happened before those words popped out of my mouth, no matter how worthy my agenda was or how perfectly right any observer might think I am, my G-dly self doesn’t say hurtful words. My G-dly self is a shining light that warms and nourishes; it never criticizes or notes the weakness of other people. My G-dly self does what’s right regardless of others’ wrongs. My G-dly Self is strong and rich enough to share smiles even (or especially) with someone who gives me nothing in return.

When we get into an argument with someone, do we walk away feeling right? When we let off steam in her face, did she deserve it? Did his stubborn, obnoxious behavior leave you with no choice but to withhold your love?

When our Animal Self is in our driver’s seat, these questions seem like no-brainers. Of course we’re right! We may apologize, but (in the context of the full story) we were never really wrong. It’s the other person who was wrong. Even when we can admit that we did something wrong, we’re still right compared to the other person. Or we’re right considering the circumstances.

When our G-dliness is driving us, we think on an entirely different wavelength. Our behavior, our choices, are between us and Hashem. If it’s good by Him, it’s good. If He doesn’t like it, it’s not ok for me. Nobody else is responsible for my choices. Even when my circumstances or situations are limited, nothing can take away my dignity or my power of choice.

It’s so liberating to live this way! And yet living this way also comes with feeling regretful at times.

These days, when I let my Animal Self drive me, I know that I have betrayed myself. My life depends on Hashem. I never want to be disconnected from Hashem; never want to be disconnected from my inner G-dliness: Oy, gevald! I have sinned and I never want to do it again.

In the last month, have you felt sincere regret in any of your relationships?

What strengths did your regret come with? Where did it lead you to?

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