Thank you to this week’s guest writer for their insights.

There are few things stronger to remind you about the approaching Yamim Noraim than walking through the front iron clad security gates at HM Prison Wandsworth. As I walked through the second-stage of security, it suddenly hit me that I would also be facing a trial, a judgement and a sentencing on Rosh Hashana. It also reminded me that I might also have to make an appeal in the Supreme Court of Courts on Yom Kippur, judging my behaviour and actions over the last year.

Six months ago, I joined an educational training provider and was tasked with project managing their new employment courses across several prisons across the UK. In short, I was to help prisoners coming to the end of their sentences to complete an intense five day course, where we help them build a digital CV, and prepare both a cover letter and the all important ‘disclosure letter’.

The CVs that are created are generally interesting: some of these criminals have had quite “illustrious” careers…However, the most thought-provoking and interesting document created through the programme is the disclosure letter. Editing these letters has provided me with a deeper insight into the process of rehabilitation as well as a new approach to the way I should conduct myself through the teshuva process.

Disclosure letters come in all forms and sizes and provide a window into the rehabilitation process of the prisoner. Some letters are a couple of lines with relatively little meaning, whereas others can be a few pages long. It should be noted that in general, those who take the disclosure letter seriously, who invest time and effort into it and who have demonstrated regret for their crimes they have committed are far more likely to find stable employment and be reintegrated into society. In direct contrast, those who only write a few lines are less likely to be employed, are at a higher rate of reoffending and might well end up back behind bars. The rehabilitation process is dependent on the effort of the individual – and our approach to teshuva is exactly the same.

It is not easy for a prisoner to write out and disclose their crimes. Many prisoners often refuse at first due to the fact that it can be an emotional process. We should realise this first hand, not because we have spent time in a jail (hopefully) but rather, because we experience a similar process through the entire month of Elul and during the Aseres Yamei Teshuva. Every year during the selichot process as well as on Yom Kippur itself, we openly admit our crimes:

“We have become desolate, we have betrayed, we have stolen.”

If taken seriously, this should be an emotional process, leaving people feeling ashamed and embarrassed about the way they have behaved, as well as creating a sense of yearning to improve in the future.

With this in mind, I decided for the first time that this year, in addition to verbally admitting my mistakes, I would write a disclosure letter of my crimes and sins against my friends, family and the Almighty. It should be noted that it would be impossible for me to disclose all of my sins: it would take longer than five days and Rymans would run out of paper. However, I wrote down the sins which I committed on a regular basis, the areas in avodas Hashem which needed improvement – and through this process of disclosing my weaknesses, I was able to gain a deeper insight into the flaws and traits of personality. I was able to establish which areas needed drastic improvement and was able to create a concrete plan on how I was going to accomplish this. It was a humbling and extremely healthy teshuva experience. It provided me with a stronger sense of clarity than I have had for years. It became the core part of my teshuva.

When it comes down to it, disclosing our crimes is not only a healthy process for one to acquire teshuva, but a necessity. It is the reason why the Rambam opened up his sefer on Teshuva with the requirement to orally disclose our crimes through the viduy process:

If a person transgresses any of the mitzvot… when he repents… he must confess before God… as it states: “If a man or a woman commit any of the sins of man… they must confess the sin that they committed.”

This year I decided to take an additional route in the process. I wrote out my faults in Elul as a constant reminder of where I needed to improve. We are in the final couple of days when we can admit our inadequacies. Time is running out! Let us not waste this opportunity. Let us admit our faults in a healthy and productive way, let us disclose our crimes and let us continue to work on bettering ourselves.

May you all have an easy fast and if you ever end up in the slammer, you know who to contact.

B’hatzlachah, and k’siva v’chasima tova!

The Working Jew.