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.