Wrestling with Regret



“Yom Kippur is about atoning for your sins to others, but what if you’ve screwed up your own life. How do you atone for that? “

I’m sitting on a tiny plastic folding chair that doesn’t support my entire rear end, shivering in the fall night air under a huge tent at the Woodstock Jewish Congregation’s High Holy Days Services. Everyone is wearing white, which is what you’re supposed to wear on Yom Kippur. I’m wearing a peasant dress with a loud pattern. Why the hell couldn’t I have worn something white, or at least beige? Mentally, I survey my closet and notice some white garments I overlooked. I’m upset about my sartorial faux pas. In fact, I’m so upset that instead of focusing on atoning for my sins to others, which is what the ten introspective days between Rosh Hashanah and Yom Kippur are supposed to be about, I am yet again indulging in a litany of regret—giving myself a hard time for what I’ve done to myself.

How unspiritual can you get?

I watch the crowd of more than a thousand people who are singing, swaying and praying in what resembles a Jewish tent revival. Rabbi Jonathan, a youthful, folk-singing cross between Pete Seeger and the Bal Shem Tov, leads us in singing rounds. I cry during Avinu Malkeynu, an ancient, haunting, melody.

When it’s over, I cross the aisle and greet my ex-husband and his new wife, the woman he left me for, who are sitting with my daughter and ex-mother-in-law. I wish them a Happy New Year, and they all look stunned, as if I’d caught them in an embarrassing indiscretion. His wife —homely and pudgy-faced, though much younger than me — turns reluctantly toward me, her mouth twisted in a smile facsimile; my ex-mother-in-law glares at me with blatant hostility; he is polite and returns my greeting. I actually feel good that I managed to be the one to put animosity aside for this one day. But I know that for the rest of the year, I’ll be wrestling with regrets about marrying him in the first place.

I used to think that surely by now I would be busy radiating spiritual beneficence, would have laid to rest all the ghosts of my past and be enjoying the wisdom I had attained in my life. It never occurred to me that at this late date I would be struggling with regrets like, Why did I marry Mr. Wrong? Why wasn’t I a better mother? And why haven’t I morphed into the wise, compassionate, spiritually evolved elder that I aspired to be by this age?


Yom Kippur is about atoning for your sins to others, but what if you’ve screwed up your own life. How do you atone for that?

Looking for answers, I go back to see Jim, the psychotherapist I was seeing when I married my husband. Jim is in his 80s now and his body is frail, but his mind is as sharp as ever.

“Why didn’t you warn me?” I ask as soon as I sit down. “Ira was such an angry guy. Why did you let me marry him?”

“I missed it, I just missed it,” Jim shakes his head ruefully, running his hand through his still-thick white hair. “So much of my work was based on wishful thinking for people.”

I feel bad for him. It must really suck to be a shrink and realize you made such a bad call that your patient is sitting in front of you 25 years later blaming you for it.

“Could I have done something else at the time? Was I totally trapped?” I ask.

“Yes, you were trapped,” he insists.

“How it went was how it had to go,” Jim insists.

“We learn things through taking beatings and through fumbling and failure,” he tells me, shaking his head regretfully. “Our successes don’t teach us much at all,”


We Americans believe you can always start over, no matter what you’ve been through. I can’t count the times I’ve heard, “It’s never too late” when I complain about being lonely. Everyone knows someone who found true love at 85.

Bullshit, I tell myself. Some losses are permanent, emotional damage runs deep, opportunity is finite and some people never bounce back. Doors keep slamming shut as we get closer to death. But in our relentlessly upbeat Facebook culture, we’re expected to have no regrets.

“Life is too short, time is too precious, and the stakes are too high to dwell on what might have been, ” Hillary Clinton advises. The traditional wisdom has worked admirably for her, but for me, not so much.

I’m a Jew. I dwell.


I do a little internet research and find that there are more nuanced takes on regret.

“There is no shame in wondering whether or not things could have been done better or differently,” Rabbi Wayne Allen advises. Healthy regret is not a fault but a manifestation of a thoughtful and self-evaluative soul.”

Henry David Thoreau agreed: “To regret deeply is to live afresh.”

As an introspective sort, I find these sentiments comforting.

So is meeting an ebullient 92-year-old woman a few days later over dinner. She mentions that her son died in his 60s because he didn’t take care of himself. I know I would have blamed myself if it were me. How did she manage to keep her spirits up after the loss of a child, I ask her, and what was the secret of her longevity. She tells me, “Never look back. Only forward.”

I find her matter-of-fact attitude remarkably refreshing. I’ve always felt that regret is somehow obligatory—that I’m condemned to obsess about the past. But if she can move on after the death of an adult child, maybe I can move on, too.

“Unetaneh Tokef,” or “Let Us Cede Power,” a stark and powerful Yom Kippur prayer about fate gives me some guidance. Essentially, it says there is no escape from fate. We all suffer and die, and God decrees what’s going to befall you in the year ahead. But that’s not the whole story. We can mitigate God’s decree by performing Teshuvah, tefillah and tzedakah (repentance, prayer and charity). According to Rabbi Helen Plotkin, “It is not what will happen to you that makes your life meaningful. That power is in your hands, as you cultivate the self to whom it will happen. Teshuvah, tefillah, and tzedakah are there to help you write yourself into a role worth reading.”

I’m not much for repentance and prayer, but this year I resolve that I will finally cultivate the self by doing something to help others. I will find some way of participating in social action — in tikkun olam or repairing the world.  It’s clear that I’ve been focusing too much on my own misery and not enough on Tzedakah, an obligation for a Jew. Helping those who are in need, no matter in what capacity, is crucial and “holy” work, and it will undoubtedly help me to “never look back. Only forward.”


Erica Manfred is a journalist, essayist and humorist who writes about everything from dentistry to divorce to fantasy fiction. Friend her on Facebook.


Featured image: Maurycy Gottlieb, Jews Praying in the Synagogue on Yom Kippur,” 1878



9 responses to “Wrestling with Regret

  1. Thank you, Erica.

    This was beautiful and I’m sure will speak to many readers, and I’m just as sure that whatever you do to give to the world will speak to you..

    Meanwhile, I get by with a little bit of wisdom from a friend when I look back on a decision I now think I should not have made: “It seemed like a good idea at the time.” Which is, I’m sure, what Hillary Clinton must be thinking these days about her private email account. And you’re berating yourself???

    And you should commend yourself for going over to give your former husband and his (and your) family members good wishes. This was a gesture I venture to say you’ll never regret.

  2. I’ve invented an acronym (which is already ridiculous – any bunch of letters isn’t an invention) but here it is: SLAGIATT meaning “seemed like a good idea at the time”. That’s why we marry the wrong guys, take the wrong jobs, have the wrong babies… uh, no wait… I’m just saying most of the time we do our best. Then we beat ourselves up. STOP IT! Most of the time we can make some mistakes and live through it. No body’s keeping score but you.

    So, let’s all give ourselves a break. Somebody out there is a way bigger fuckup than you could ever be!

  3. Thank you for sharing the feelings so many of us have – regardless of what event brings about our discomfort. I was reared and remain Methodist where it is decreed that my future is not based on my good works but on God’s will – which would seem to let us off the hook except that it leaves us solely responsible for our choices, our works, and how we feel about the results. Since my husband died 12 years ago, I have almost constantly sought to replace the sense of well-being and belonging that he took with him. And I have been diligent, perhaps excessively according to my friends, yet I have failed. The thing is, I have caring family and friends, but it is not enough. I’m not sure whether anything is expected of me by God or my fellowman, but I am positive there is something I’m supposed to learn or do that will restore contentment. I am not hunting for the meaning of life, just to live daily in a meaningful way amongst a group – small or large – that shares my quest. So, I’m hunting my tribe…and if I don’t find them soon, I might just start my own.

  4. I have always tried to live in the present, knowing that I made the decisions in my life based on what I knew at the time, not on what I have since learned. That philosophy is harder and harder to maintain as I get older, and now, on the verge of retirement at age 66, I do look back and wonder what if way too often. I try to remember what I learned from taking one road and not another, and using all I can to give others the gift of my time and knowledge. It’s funny how it comes back to the wisdom of elders, the wisdom we refuse to acknowledge when we are young. So mch of life is hugely the same through the years. We don’t think our elders can possibly understand what we are going through, but their experences are pertinent, and by listening, by empathy, we can better navigate our lives no matter what our age.

    1. I find that people under 40 have no interest or wisdom. They want to avoid or destroy history. My knowledge is useless to them and I could give countless examples in our society. They want us out of the way at least or preferably dead.

  5. I find the idea that we learn through failure and heartache a load of nonsense but it seems to be a common theme. Like everyone I have had very good times and some very bad times and quite frankly I could have lived quite happily without the bad times. Did I learn anything from the bad times – only to try and make sure it never happens again.

    I have seen people destroyed by heartache and failure and the idea that they learned from these experiences is completely false.

    Failure is not a teacher and the 92 year old is absolutely correct – always look forward. You cannot change the past and if you could it might have been worse.

  6. Thank you for this! Some 20 years ago I sat with a friend in that very same tent, shivering with cold and regret. Since then, I’ve lost a job, gained and lost and gained apartments, lost my parents, gained and lost a boyfriend, gained two cats, gained friends, and gained the courage to get onstage for the first time since high school. Back in my forties, I expected to have more by 60-something than I do now — but then I remember that, in my 20s, I couldn’t imagine making it past 40. I find tremendous inspiration in women like your 92-year-old friend, and I focus on cultivating “the self to whom it will happen” and on writing myself “into a role worth reading.”

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