
Even when I would not be caught dead in other Jewish spaces, I always went to services on Yom Kippur and Rosh Hashanah. In part, this was because my father stressed how important it was not to work on the High Holidays. “Don’t give the anti-semites an excuse to put down the Jews who do care by going to work yourself,” he would say to me. And he was and is right.
But that did not mean that I had to go to services. There was something else, a renewal that came from the exercise of looking within and trying to improve myself. I loved the long lists of sins. I read them carefully. But there was one problem:
I felt shame every time I found a sin that applied to me, which was frequently.
Rabbi Brene Brown defines shame as “the intensely painful feeling or experience of believing that we are flawed and therefore unworthy of love and belonging – something we’ve experienced, done, or failed to do makes us unworthy of connection.” She further teaches that while guilt is a healthy, adaptive trait to help us feel bad when we fail to live up to our values, whereas
“Shame corrodes the very part of us that believes we are capable of change.”
Shame is not the point of Yom Kippur. Indeed, if shame was making it harder for me to change, it was undermining the opportunity for personal transformation that Yom Kippur brings.
Turning Shame To Sadness
When we do our spiritual accounting on Yom Kippur, we will find places where we missed the mark. How are we to react? If we don’t feel any emotion, we are unlikely to change. Yet if we feel too badly, spiraling into shame, we can paralyze ourselves into inaction. So lets try to find a different emotion.
Fear? I don’t like Fear as a motivator – indeed research shows it is effective for short term but not long term change.
So what about sadness?

Sadness, like guilt, is uncomfortable. It looks you in the eye, and leaves the door open to compassion. Compassion and self-compassion are exactly what we need in order to change.
If you start to feel that crushing shame, ask yourself the following 10 questions:
- Have I felt this feeling before?
- Did I actually damage the relationship?
- What can I do to repair?
- What happened?
- What is my reaction?
- What am I sad about in this situation?
- What will the impact be on me?
- What is God’s truth about the situation? (If you are unsure of the Divinity, think of it as looking at the Truth from the perspective of the Universe, that sees all sides and perspectives.)
- Who will I NOT talk to about this? (Here you are exercising the soul trait of Silence, to prevent you from amplifying and more energy to this negative situation that is required.)
- What other explanation is there for this?
By fully inhabiting the situation, you’ll open the door to transform those shame feelings into sadness. Rabbi Alan Lew of blessed memory called the High Holidays a journey from “hard-heartedness to broken-heartedness…the journey the soul takes to transform itself.” (This Is Real p.8)
Given the choice between shame, which undermines the ability to change, and sadness, a gateway to personal transformation, I’ll take sadness every time.
Which will you choose?
Want to know which soul traits might be making it hard to turn shame into sadness? Take the Soul Trait Quiz
Images by Kevin Jesus Horacio and Irena Carpaccio on Unsplash
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