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Taking Shame out of Teshuvah  

How regret can open the door to real growth

What if we went through the Aseres Yemei Teshuvah and took full responsibility for our mistakes without shame distorting the process? An eye-opening approach

I

once had a client — let’s call her Rikki — who had an almost physical aversion to teshuvah. Owning up to her mistakes felt so painful that she spent each day trying to act perfectly, hoping to avoid anything she’d later have to apologize for.

The feeling of being in the wrong was so excruciating for her that when she did mess up, she’d apologize in a way that made things far worse. Like the time she skipped a scheduled date with her husband. A bit of context: Rikki is highly involved in community matters so her phone rings — a lot. The constant stream of calls in the evening caused tension in her marriage, so she and her husband made a joint decision to end every night with a walk and conversation. Quiet, sacred time to reconnect.

One evening, Rikki took a phone call that ran long. Her husband waited — tired but hopeful — for 45 minutes before eventually falling asleep alone. When he expressed his disappointment the next morning, Rikki sputtered out a quick apology, followed immediately by a string of explanations: “I’m sorry, but it was really important. I’m helping so many people. I tried to get off, but the woman wouldn’t respect my boundaries….”

If you’ve ever received a half-apology like that, you know how it feels — infuriating. There’s no true accountability, no pause to ask: How did my behavior impact you? What followed was predictable: silence, tension, and distance between them for days.

Still, Rikki preferred this painful cycle over the discomfort of full accountability — the very thing that could have brought real repair and closeness.

Why is doing teshuvah so hard? Why is admitting that we’ve made mistakes — and then actually apologizing — so difficult? I wonder if it’s because somewhere along the way, many of us absorbed the belief that to repair our relationship with Hashem, others, and ourselves, we need to shame ourselves first.

But here’s the thing: Shame is something our system simply can’t tolerate. We’d rather do almost anything than feel that sting of humiliation. In fact, Chazal teach us that feeling ashamed is like a form of death. So many addictions are just desperate attempts to drown out that unbearable shame.

Because we instinctively flee from shame, many of us have short-circuited the teshuvah process. We’ve given up on full teshuvah… which means we’re also missing out on the full healing and reconnection it creates.

Shame on You!

We humans have this fascinating tendency: We hold fast to an extreme, convinced it’s the answer — and then, when we see its damage, we swing all the way to the opposite side.

For decades, shaming people was the tool to get them to change — or at least to scare them into it. I still remember standing outside one afternoon when I overheard an elderly woman shouting at her grandchildren: “Shame on you!” I remember feeling this jolt in my chest — not just from her words, but from how instantly they landed. The kids shrank back, shoulders slumped, heads down. They swallowed the shame without even questioning whether they deserved it.

We now know that “shame on you” rarely leads to better behavior — it just breeds more shame and more hiding. But maybe, in our instinctive urge to protect ourselves from the pain of shame, we’ve swung too far the other way. Now we’re so afraid of shaming anyone — including ourselves — that we avoid accountability altogether.

Have you ever heard someone say, “I did the best I could” or “I’m only human”? These words often come from a genuine place. They’re meant to express vulnerability, to acknowledge our limits — and sometimes, that’s exactly what they do. But other times, without us even realizing it, they can become a quiet way of stepping back from responsibility. It’s hard to sit with the sting of regret or shame, so we cushion the fall. We mean well, but in trying to protect ourselves, we might miss the deeper invitation to grow.

As a general rule, our relationship with others is a reflection of our relationship with ourselves. So if I’m harsh with myself, I’ll be harsh with others. Even if I manage to control my words, inside I’ll still hold impossibly high expectations of the people around me. Since the way we treat others is like a mirror, when we start avoiding real accountability, we stop holding others accountable, too… even if we’re really hurting from something they did.

I see this all the time in my practice: a deep lack of internal accountability, which spills over into our relationships. When I ask a client what she’s afraid might happen if she told someone how deeply their broken promise, avoidance, or sharp words hurt her, the answer is often, “I just feel like that’s so mean.”

Calmly admitting that someone’s actions hurt you can be very difficult. Not just because it’s vulnerable, but because if the person doesn’t know how to handle the “pinch,” they might react in a way that creates more distance. That’s what happened to my client Abby. She spent weeks mustering up the courage to tell her sister how her critical comments — which were said out of habit, almost unconsciously — were affecting her. But instead of really hearing her, her sister sunk into shame.

“I’m so sorry,” she said. “I know, I’m the worst. I never get anything right.” She went on and on, lamenting about how she’s always making mistakes. Abby felt awful, like she’d wounded an already-wounded person. She didn’t share to shame her sister — she shared because she wanted to feel closer. But when someone is drowning in shame, there’s no one left to connect to.

What if there were another way? A way to hold ourselves (and each other) accountable — without shame distorting the process?

There is. And it’s life-changing.

Ayekah: Where Are You?

This year, during Aseres Yemei Teshuvah, what if you tried something new? Instead of beating yourself up for all your mistakes, what if you got curious about the longing underneath your miss?

The Hebrew word for cheit, often translated as “sin,” actually means “to miss the mark.” We usually fixate on our failed attempt to hit the target instead of exploring the loss of it — the loss of what could have been. If your grown child tells you, “That really hurt me,” it stings because they’re only telling you this because they trust you had the potential to show up differently. That’s a loss — a missed moment — and it feels uncomfortable.

That discomfort is sacred, though, because it’s where our true strength lies. When we’re willing to feel that pinch, and let others feel it, too, we can repair our relationships.

When I share my own missed opportunities, I want to share them with people who can sit with me in that place of loss — not rush to reassure me, or tell me that I shouldn’t feel bad. Just like we sit with someone during a shivah, we can sit with ourselves — or each other — in the ache of what could have been.

That ache, that feeling of loss, carries within it the seed of something new. Because beneath every regret is a deep, holy longing for who you could be. Who you want to be. Who you know you truly are.

When I let myself feel that honest pinch of regret, I find that longing. I reach for it by saying to myself, “Instead of doing this, I wish I would have….” That simple shift connects me to the part of me that knows I can do more. That longing becomes an invitation — and even an excitement — for next time. I see what I wish I could do differently, and suddenly it feels so much more possible to show up that way when I get another chance.

As we approach the Yamim Noraim, it’s easy to feel dread because we’ve learned to see accountability as shame. But Hashem’s accountability isn’t about shame — it’s about love. Shame says, “You’re bad.” Hashem says, “Where are you?” — just like He asked Adam: Ayekah?

When you have a “miss,” Hashem notices because you’re needed, you’re invaluable. What you do matters because you matter.

A woman once shared how hard it is for her to believe she’s capable of accomplishing much. She said she grew up with “laid-back” parents — but as an adult she realized they simply weren’t emotionally available enough to truly parent her. She remembers one day in high school when report cards came out. Her best friend locked herself in a bathroom stall, hysterically crying, saying she couldn’t go home because her father would kill her for getting a bad grade. This woman felt so envious. She knew that no one at home would even look at her report card. That longing — to matter enough for someone to expect more of us — lives deep in every soul.

I’d like to emphasize that busha is different from shame. The Gemara in Nedarim (20a) teaches: “Whoever possesses busha will not easily sin, and whoever has no busha… his ancestors did not stand at Mount Sinai.” Busha s a beautiful middah, one of the core characteristics of a Yid. It is the inner reflection that arises when a person recognizes the gap between who he could have been — his ideal self, his tzelem Elokim — and how he acted.

Rather than being destructive, that gap humbles us and points us back toward our true potential. This is in contrast to kalon — a degrading shame that strips a person of dignity, making him feel low and empty (Malbim, Mishlei 3:35). Unlike busha, which stirs a return to one’s greatness, kalon (“shame”) demeans, shuts a person down, and says: “I’m bad — so why bother?”

Blame and Shame

When people ask me to summarize my work with couples, I often say: Couples usually fight about one thing — “Who’s bad?” We’re so conditioned to see the world and our relationships through the lens of “Who’s right and who’s wrong?” The shame and rejection of being “wrong” is so intolerable that we end up spending enormous energy proving it can’t be us — it’s the other person.

One fear many couples carry is, “Who will be blamed (read: shamed) when our kids struggle?” That’s when the blame game starts — the subtle (or not so subtle) story that it’s our spouse’s fault more than ours.

I had a client who, for years, would look at me and plead, “Just tell me — who’s right, me or him?” It’s so beautiful now that she can look back at all those sessions and laugh. She feels deep gratitude that she no longer sees the world — or her relationship — that way.

When we’re in pain, instead of asking, “Who’s right? Who’s to blame? Who’s worse?” a much wiser question is: “What’s my contribution here?”

This question is a true sign of maturity. And when you take an honest look at yourself with compassion and love — not shame — reflection feels far less scary. Then you can say, “I see how I contributed by… not being honest, complaining instead of expressing, giving unsolicited mussar, holding resentment….”

Followed by: “I wish I had done/said… instead.” Those words help you create a vision for the future. Notice how different they feel from the more typical, shame-inducing “I should have.” One draws you closer to the person you long to be; the other echoes like that elderly lady’s voice, scolding, “Shame on you. You should have acted differently.”

There are four steps in the teshuvah process (according to the Rambam). The first step is azivas hacheit — letting go of the mistake. When can we truly leave something behind? Only when we have something healthier to take its place. That’s where “I wish I would have…” comes in. As in, “I’m sorry I spoke passive-aggressively before. I wish I had just shared what I was really feeling — I think it would have helped us connect instead of creating distance.”

Next is Vidui — admitting. This is only possible when you refuse to shame or attack yourself. True admission comes from longing: I want to be closer to Hashem and others. I want more. I am more.

Then comes charatah — regret. This is so different from shaming yourself. Regret means, “I see I took a shortcut because it felt easier in the moment. But I know I’m capable of more — and I wish I hadn’t.” It’s remorse for the disconnection it caused.

And finally — kabbalah l’asid, the commitment for the future. When you reach step four, you’re not making a brittle, fear-based vow like, “I better never do this again or I’m a failure.”

It’s a more honest, heart-driven commitment: “This is who I want to be, and I want to align my actions with that.” That shift — from self-condemnation to self-alignment — is what makes the commitment sustainable and real, instead of reactive and guilt-based.

Asking for mechilah from others can be so empowering. It reminds you that you can do hard things. Hearing how your actions impacted someone else — and feeling that pinch of pain — helps you return to your truest self. Don’t run from it. Let it remind you that you want connection — with Hashem, with others, and with your highest self.

When we move from blame to responsibility (read: response ability), we free ourselves to grow. We free ourselves to choose, again and again, who we truly want to be.

Rikki’s story is one of my favorite examples of what real teshuvah can look like. Because after a lot of inner work, she was able to overcome the shame-teshuvah association that was so wired into her subconscious.

Last year, her father’s yahrtzeit fell out on Shabbos, so she and her siblings decided to spend Shabbos together at their mother’s house. Rikki was looking forward to bonding with everyone during such a sensitive time, but instead of it being an uplifting experience, she came home emotionally drained. The whole Shabbos, everyone had been on edge — so easily triggered and so quick to react, including her.

As she was describing the Shabbos to me, she slipped into a cycle: blaming others, victimizing herself, shutting down, shaming herself, and finally shaming others… round and round it went. And the more she did this, the more disconnected she felt — not only from her family, but from herself.

A week later, during our next session, I gently said, “It looks like you might be holding some grief.” She immediately started tearing up. Beneath all her anger and sadness was a deep sense of loss for the family bonding she had hoped for. It was from that place of disappointment that she had reacted to her siblings.

When I asked her how she wished she had shown up that Shabbos — to look at her actions alone — she felt that uncomfortable pinch. But she pushed through the pain and took an honest look at her behavior. She decided to write each of her siblings an email, owning the moments where she didn’t show up as her highest self. Each apology was followed by a sincere statement of how she wished she’d reacted instead.

“I’m sorry about that sarcastic comment I made,” she wrote to one brother. “It was out of line and disrespectful. I wish I would’ve just stepped away instead of reacting like that.”

After she sent the emails, she felt unbelievably empowered. “I have a new understanding of teshuvah now,” she told me. “I never knew I could feel so cleansed and light. I feel like I got a piece of myself back.”

Flawless Isn’t the Goal

When I first created my coach training program, I had certain requirements for certification. One of them was submitting a full 50-minute recorded coaching session that would then be graded.

But at some point, I had a realization: Wait a minute — I still have sessions where I’m off my game, blended, or completely miss something important. And that’s me, after years of experience.

It hit me that delivering a flawless session isn’t the most important thing in a coach. What matters more is: Can they reflect?

Can they catch themselves when they’ve missed something? Can they sit with the moment honestly — not to shame themselves or be harsh, but to get curious about what happened? Can they feel the loss of what they could have offered in that moment — and grow from it?

That’s the kind of coach I want to certify. So I changed my requirements. Now, they’re graded not just on the session itself, but on their ability to reflect on it. That’s the skill I’m watching for.

And lately, I’ve been wondering — maybe that’s how Hashem judges us, too. Not for missing the mark — but for what we do once we realize we’ve missed it.

 

Julie Lurie runs a private coaching practice in Chicago and is the cofounder of Connections — The Jewish Marriage Institute. She trains kallah teachers and coaches, leads supervision groups, and offers relationship and parenting classes to women around the world.

 

(Originally featured in Family First, Issue 960)

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