My first Rosh Hashanah sermon was a disaster. In my effort to explain repentance, I asked members of the community to recall the worst sin that they had ever committed. I watched as they revisited their sins, expecting to see signs of remorse, but instead, smiles spread across their faces, their eyes glazed over and they started to drool.

“Guilty pleasure” exists, but guilt can also be debilitating. And on Rosh Hashanah when God examines and judges every single one of our actions, that can feel overwhelming (Mishna Rosh Hashanah 1:2).

In her autobiography “The Choice”, Edith Eger offers a masterclass in guilt management. Edith grew up in Hungary where she was a member of her country’s Olympic team. But in 1944, together with her family, she was forced out of her home into a ghetto and from there to Auschwitz.

Eger survived the camp and a death march, but by the time the liberators arrived, she was so sick that she was taken for dead. Her body was tossed onto a mound of corpses, she was only saved because an American soldier spotted a slight movement of her hand.

Following her recovery, Edith married, had children and built a successful practice as a psychologist. Yet, she remained deeply traumatised. Her suffering affected every area of her life, until she decided that she had to return to Auschwitz to exorcise one particularly painful memory.

At Auschwitz, Edith relives every moment of her arrival there decades earlier. We accompany her as her mother coaxes 16-year-old old Edith to fasten her coat and stand up straight so that she will survive the selection.

But Dr Joseph Mengele has a different concern. He turns to Edith and pointing at her mother asks, “Is this your mother or your sister?” At this moment, Edith is so overwhelmed by the desperate need for maternal love that without thinking, she blurts out, “mother”. Mengele responds by directing her mother to the line for the gas chambers.

Edith was haunted by that memory. She spent years trying to banish it from her mind. Her return to Auschwitz enabled her to reopen it, to apologise at her mother’s final resting place and to choose to focus on building a better future for herself, rather than living a life consumed by guilt. This experience forms the basis of the psychological support she gives to her patients who wrestle with guilt.

Rabbis also deal with guilt, particularly in their responses to questions posted on religious internet sites. One questioner heard a psychologist state that guilty feelings are unhealthy. He wanted to know if Judaism concurred.

The rabbi answered that Judaism doesn’t want us to ignore, deny or shake off our guilt. Rather, it wants us to process it, purging it through repentance. By confessing our sins, making amends, and committing not to repeat our errors, we achieve atonement – at oneness with God; leaving us guilt-free.

This is why in response to an enquiry from a thief, the rabbi concurs that, his guilty conscience is a good thing. It should spur him to repentance.

Many enquiries come from young people from religious homes who are struggling with shame and guilt over sexual misdemeanours which may sound minor to a secular audience. One woman is concerned because she had a physical relationship with a previous boyfriend. She now fears that this was a betrayal of the man she is currently dating and whom hopes to marry.

Another woman is haunted by the fact that her wedding dress was immodest. She cannot bear to look at her wedding photos and she feels trapped in a secular lifestyle she regrets adopting.

Such questions are answered by Shai Piron, a distinguished rabbi and former Israeli Minister of Education. Recognising that those questioners have undergone significant pain and penitence, he tells them that too much guilt is destructive. They should not focus on the past, but on the future.

“Guilty feelings”, he says “are not an engine for growth, but frequently, they guarantee decline”.

If too much guilt is destructive, a little may propel us to put matters right, especially where the wrongdoing is not just against God, but against another person.

One questioner accidentally bashed another car and then drove off without leaving her details. She wants to let go of the guilt which is consuming her. The rabbi reassures her that she is not destined for hell, but he also reminds her that Jewish law requires her to do everything in her power to trace the victim. She must apologise and recompense him, even if this requires her to take out a loan and pay it back over time.

If she can’t find the owner of the damaged car, she should donate the money to charity. Only then, will she legitimately be relieved of her guilt.

Guilt can move us to do the right thing, but it can also be inflated. Ba’alei Teshuvah – the newly religious- are particularly susceptible to the stress of exaggerated religious guilt.

One man from a secular home has become observant, but he still enjoys playing football and going out with his friends. He feels guilty about this and regrets that instead of bringing him joy, his religious path is causing him anxiety.

The rabbi responds by reminding him that everyone needs relaxation. The rabbi advises the young man to take a more holistic approach to Judaism by recognising that his legitimate leisure activities need not be a distraction from his relationship with God, they can be part of it.

Sometimes our guilt is not just inflated, it is misplaced. One questioner suffers from intense anxiety over the minutest details of his religious observance. He agonises over the possibility that he mispronounces words during the evening prayers. The rabbi reassures him that his prayers are perfectly acceptable.

This man does not require religious guidance, he is suffering from Obsessive Compulsive Disorder and he needs therapy.

Our rabbis recognise that sometimes people feel so paralysed by guilt that they cannot bring themselves to engage with God. When repentance is impossible, they recommend putting the past to one side and focusing on the positive by doing as many good deeds as possible to get ourselves back on track (Yalkut Shimoni, Hosea 13: 12).

But in the main, Judaism’s approach to guilt is positive. Guilt may be troubling, but it is also a powerful engine for change. Someone who feels guilty will be forgiven not just for one misstep, but for all their sins. (Berachot 12b).

Rabbi Kook, who was Chief Rabbi of the land of Israel during the period of the British mandate suggests that this is because our consciences mirror the state of our souls. Shame and embarrassment are spiritual symptoms of sin.

They draw us closer to God, automatically triggering repentance and divine forgiveness. Such feelings are not so compartmentalised that they apply only to a specific sin. Our relationship with God is holistic, so repentance for one sin leads to repentance for them all (Orot Hateshuvah 14: 24).

Once we have fully repented for our failures and reconciled with God, then our sins are erased and my slate is wiped clean. Our relationship with God is not only restored, but better than before. Like two quarrelling lovers, when we make up, we become closer than ever.

Yet, for all his positivity about guilt and repentance in the lead up to Yom Kippur, even Rabbi Kook recognised that the intense soul- searching we do during this penitential period can be soul-destroying.

Rooting out our wrongdoings can crush our joie de vivre. For this reason, Yom Kippur is followed by Succot – the festival of joy to reignite our energy for a pristine and positive start to the new year (Orot Hateshuvah 9: 10).

Gideon Sylvester is the United Synagogue’s Israel rabbi