Grief, Resentment and Compassion
By Rabbi Gabi Bookatz
Overview: A helpful guide to dealing with resentment in the context of bereavement.

Grief, like any other emotion, is fluid. It evolves, it rises, it recedes, it can explode, and it eventually settles. But it doesn’t follow any rules; there is no textbook for grief to follow.  

Even though Dr. Elizabeth Kubler-Ross famously describes the Five Stages of Grief (they are: denial, anger, bargaining, depression, and finally acceptance), they are not absolute, nor are they proscriptive. They are descriptions of a healthy process and the progress of grief.  

One of the challenges to attain the final stage of acceptance is anger. Some mourners are angry at themselves, others are angry at the deceased, while some are angry at other family members. This is all part of the healthy process of grief. But anger, if left unresolved, can lead to resentment, and resentment may be one of the most poisonous emotions – both morally and psychologically.  

In the world of addiction and recovery, resentment is known as ‘the number one offender’. It is one the biggest factors in the relapse to addiction. It’s an addictive emotion. It achieves the same goal as alcohol – it’s an anaesthetic. It is soothing to know that our suffering is somebody else’s fault. (This is why Step 4 of the 12 Step Programme is so critical in recovery. Step 4 is where “we make a searching and fearless moral inventory of ourselves”.) If we want to free ourselves from the clutches of resentment, find real serenity and achieve moral success, we need to take responsibility for own choices and behaviour. But it is also crucial that we change the way we see other people.  

Below is a correspondence that will help you change your view of other people’s behaviour. It is between me and a woman who lost her mother. 

Dear Rabbi Bookatz 

Thank you for your kindness and time to be there for our family at this difficult time.  

I guess it’s now just taking it a day at time. I was wondering if you had any advice or insightfulness into dealing with the disappointment and negative emotions.  

I found with my mom’s passing, it brought out the bad and good in people. I try focus on the angels – the people who went the extra mile. But then so many people I have interaction with daily who did less than nothing and weren’t even supportive and were not there for my parents.  

How does one forget what those people did and move on? My husband is telling me to be the bigger person and that I am the only one who can change the situation as all those people carry on with their lives and don’t give it a second thought.  

My mom’s passing is giving me time to reflect but I don’t have any new answers.  

Thank you.  


My reply: 

Dear XXXXX, 

I hope you’re well and finding comfort after the sad loss of your dear mother.   

I have thought deeply about your email and decided to give you a full answer which is meaningful rather than some short and superficial answer. 

To get straight to the main point of your email about disappointments, simply put, it’s not easy. But let me try and give you an approach that may help. 

There are a few things to contemplate when thinking about disappointments.  

One is simply that disappointments are the by-products of misplaced expectations. If we were less demanding or even pessimistic about our expectations of other people, we wouldn’t be so disappointed. If anything, we would be pleasantly surprised every time they did do something nice.   
Being pessimistic about people doesn’t mean that we view them as bad, cruel or uncaring, it merely means that we appreciate how hard it is to be human; how precarious living life is; it means that we relate to the fact that people put up a brave face but deep inside, like us, people are fragile, anxious, unsure of themselves and certainly not nearly as robust as they would like to be. It should be stated that obviously I’m only talking about moral/ spiritual achievements and nothing else. We can call this Compassionate Pessimism and it’s a very helpful tool in all our relationships. We should be hopeful and trusting of our own ability to achieve spiritual greatness and at the same time compassionately despondent of others. With this, we can and should only be disappointed with ourselves. This does not mean that there isn’t accountability in our relationships. But that’s another discussion… 

Another point to reflect on, which can help us deal with disappointments, (and related to the previous point) is charity. Let me explain. We all value charity as a universal symbol of humanity. All religions view charity as a fundamental pillar of their faith and their community. The reason we view charity as such a basic pillar of society is because we are aware that some people have been handed a bad lot in life and it’s often, to no fault of their own that they are in such a difficult predicament. We also appreciate that if we were in such a predicament, God forbid, we would like someone to give us a break and reach out to us with the compassionate hand of charity.  

We all know that charity is not limited to money; it can be the charity afforded by time, resources, or a shoulder to cry on. But there is another form of charity that few people practice; it is the Charity of Interpretation. The Charity of Interpretation is the kindness offered in the quiet space of the mind. We offer it by interpreting people’s behaviour in a kind, compassionate and forgiving way. All forms of charity require empathy to be genuine but none so much as the Charity of Interpretation. When we try and understand people’s behaviour that could be hurtful, offensive, or disappointing, we need to remind ourselves how hard it can be to be perfect, to never disappoint or to never fail. We would all like to be doing more, achieving more, loving more, contributing more and being more than we are currently, but we sometimes, to no fault of our own, find ourselves in a predicament that is a real obstacle. Most of us are haunted by some childhood experience, an over-controlling parent, an abusive sibling, an unforgiving teacher, or spouse etc. Maybe we suffered a physical or psychological trauma that we never properly recovered from. There are so many reasons that hinder us and prevent us from living up to our values and fulfilling our dreams. Empathy is required to have a charitable interpretation of people’s disappointing and offensive behaviour. This approach takes effort and may seem difficult but if we consciously engage in such an evaluation of people’s offensive and disappointing behaviour, we will be able to live a healthier life and build healthier relationships. 

Having said all the above, I believe that it is absolutely essential to create healthy boundaries in our relationships. Boundaries are about drawing clear lines about what behaviour is not okay. Healthy boundaries create respect and build trust in relationships. Just because we don’t expect perfection and can forgive, does not mean that everything is acceptable and people can behave in offensive and inconsiderate ways. I can engage empathically with almost any person, if I know that they are conducting themselves in sound boundaries. This is essential. 

In summary, we have two meditations and one practice. The first meditation we called Compassionate Pessimism and is about avoiding disappointments in the future. We must appreciate how anxious and confused most people are and that most people are not as robust as they pretend to be. This is helpful with regards to our expectations of people’s future behaviour and helps us avoid the disappointments and frustration in the first place. The second approach we called the Charity of Interpretation. It is thinking deeply about how so many people have had some painful and often terrifying experience in the past that, to no fault of their own, are now facing real obstacles in living up to their values. This meditation is relevant after the fact and helps us forgive and move on. The third point is about setting and articulating clear boundaries regarding which behaviours are not acceptable. Setting boundaries needs to be reinforced at both ends – for future and past behaviours.  

I hope this gives you some tools to work with and find some comfort in the turmoil of your grief. 

Best wishes,  

Rabbi Bookatz. 

Rabbi Gabi Bookatz
High School Teacher at Yeshiva College High School and Rabbi of Waverley Shul in Johannesburg, South Africa.