That Sin? Again?

Psychotherapist and renowned Buddhist teacher Mark Epstein writes that as a child, he suffered from a severe stammer. 

A compassionate speech therapist taught him that he was not alone in his difficulty, which brought him a measure of comfort. She also taught him techniques that he could use, including how to think ahead when he would soon need to pronounce a letter that he generally had difficulty with. He learned that he did not have to castigate himself for the difficulty and that he could use his mind to work with it productively. Epstein writes that the therapist’s essential teaching for him was that a trained mind can have power over everyday difficulties.  

This vignette has helpful implications for our collective practice of teshuvah (repentance) and self-examination during the upcoming High Holiday season. First, the confessional prayers are all framed in the first person plural and recited among large groups of community members.  Though our particular needs for atonement may be unique, it is obvious that everyone in the room has at some point failed themselves and others. Second, the problem with our everyday “sins” is not so much that we do things we regret, but how we respond to temptations when they arise and how we work with them afterward.

I often hear people talk about feeling frustrated that the same transgressions arise in our teshuvah work year after year. Maybe it’s being impatient with family members or co-workers or holding grudges we could let go of. Maybe it’s the irresistible temptation to speak ill of others or to speak disparagingly of them to get a laugh. Maybe, most often, it is ways we betray ourselves.

That sin? Again? I can hear the voice of a friend who often expresses this frustration with the teshuvah process and the discouragement about the possibility that this year will really be different.

I wonder if it would be useful to think about our own characteristic shortcomings as something like Epstein’s childhood stammer. Although he would have liked for his stammer to completely go away (as it mostly did, but only in adulthood), he did not have to beat himself up every time he experienced it. He had learned that he could anticipate the letters and words that might trip him up. He also realized he could use physical or mental techniques to help him produce that word effectively.

So too, we need not think of each failure to live up to our vows from last year as a source of shame. Maybe instead we can notice the unique patterns in our own mistakes. We can get curious about why a particular behavioral pattern is so compelling for us. Why can’t I prevent myself from engaging in gossip, even though I know I really want to stop? Why do I so regularly get reactive with a certain loved one or co-worker? What kinds of statements and facial expressions regularly trigger me to say hurtful things I immediately regret?

In Everyday Holiness: The Jewish Spiritual Path of Mussar, author Alan Morinis writes that everyone has their own “soul curriculum,” a particular set of traits and tendencies that make up their personality and moral self. Most of us middle-of-the-road people are neither entirely “sinful” nor unfailingly virtuous. We each have certain traits that come easily to us. 

For example, I don’t have to work hard to refrain from stealing. But there are other traits that I labor over all the time, regularly failing to meet my own standards for myself. We can’t completely change the contours of our soul. But with awareness and intention, we can grow wiser and more graceful in how we anticipate challenges that may arise and in how we respond when we fall short. 

I find this an important response to the frustration of encountering the same offenses each year.  Yes, it’s true that I have once again violated some of my own principles this year. Of course I have. That’s because I am still a human being, both glorious and imperfect. And I want to do better in the coming year. I am more likely to do so if I engage in less metaphoric breast-beating and instead bring more compassion and curiosity into exploring what circumstances make it more and less likely for me to make those mistakes. 

Have my patterns changed this year?  When have I been more reactive than usual? Have I grown more timely and more genuine in making amends for my failings, not just around Rosh Hashanah and Yom Kippur, but every day?  How have I grown in bringing to myself the love I offer to ourselves? What we learn in response to these questions may lead us to specific plans to be better in the coming year.

One of my favorite passages in the Torah appears in this week’s parashah. “This mitzvah [which some commentators take to mean teshuvah] that I command you this day is not unattainable to you, nor is it beyond reach. It is not in the heavens … neither is it beyond the sea…. Rather, the thing is very close to you, in your mouth and in your heart, to do it.” (Deuteronomy 30:11-14)

This process of teshuvah is hard work, but it is not beyond our reach. Our tradition and our community provide just the support we need. May it be a fruitful holiday season for you and for all of us.

(First posted at J Weekly 9/3/26 https://jweekly.com/2026/09/03/why-we-end-up-repenting-for-the-same-mistakes-and-flaws-year-after-year/ )