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Regret Letters

I was heartbroken to hear the deep-felt regret of a friend who believed she had not done enough to cheer her elderly father who had just died suddenly. “Not doing enough” is such a common lament and yet, so often, it is an unrealistic self-judgement.

The first thoughts I shared with her were that much of our regret springs from a scarcity of resources and our conflict about reconciling the distribution of our scarce resources. We each only have so much time and energy to allocate in a day. Many of us could fill several days with what we would like to accomplish in a given day. And we each have several ‘stakeholders’ in how we decide to share ourselves. We have the complex jobs of taking care of ourselves, being present with our spouses, and ‘negotiating’ with family and friends for how much they get of us each day. And for those not yet retired, there is that contract with your employer to give them first dibs at the biggest chunk of you from your prime time.

I reasoned that there cannot not be regret from the choices we make when allocating our scarce resources—there isn’t enough of us to go around. The best way I could see out of this bind was to routinely set priorities, adjust expectations, and to confront the frustrations and sadness of our shortages straight-on.

While further pondering her situation in hopes of finding the right words to sooth her, it dawned on me that what she needed was a letter from heaven so she could hear the other side of the story. Instead of me countering her laments, it would be so much more compelling for her to hear her father’s perspective, to make it a dialogue, not the monologue that it necessarily was.

Below are 2 sample ‘letters from heaven’ I wrote for her, one focusing on doing for another in general, the other more specifically on financial tensions. I hoped that with these examples, she would be able to write the letter she needed to receive from her dad. It’s a variation on “rewriting the ending,” a technic that some use to dislodge emotional pain, or writing a letter you don’t intend to send. Of course, the strategy might also help diminish regret in a relationship with a living person.

Dearest Sally-

I am horrified that you feel like you let me down, that you feel like you didn’t do enough for me in my final years and days. That is so wrong. You and George were wonderful, you were both so kind and generous and I could never repay you for all that you did.

I felt like I failed you and your mother as a provider. I didn’t make and save enough money to see us through to the end of our years on our own. That is so upsetting to me. But the 2 of you stepped up and filled my shortfall, for which we were so grateful. You bought us 3 cars over the years and furniture without flinching, and so many other things to keep us happy and comfortable.

You two were always there to take us to the hospital, to doctor’s appointments, and to make sure I got a coronavirus vaccine. You were on top of our needs to the end. George was so tender and caring in changing my bandages, something I couldn’t do for myself. There is no way that I could make it up to you. You both gave of your time, of your money, and of your love to make our later years the best they could be.

We both lived in fear of being forgotten in an old folks home but you took me in after mom died. I spent most of my time in my room at your place because I didn’t want to intrude any more than I already was doing. I wanted to be sure that you and George had as much private time as possible.

It was wonderful to be a part of your family life for years and to enjoy being around dogs again. I couldn’t help much towards the end, but I delighted in watching George do his projects around the house and wished that I’d been able to do the same when I was younger. I’m so relieved and happy that you have each other and I didn’t want to do anything that might spoil your wonderful relationship.

We never thanked you enough for all that you did for me and us. Thank you from the bottom of my heart. My golden years were indeed golden because of all of your love and support.




I am mortified that you are carrying regret about how you participated in my final years after all of this time. I am the one who wishes she could apologize, to have made things different. I was so humiliated and shamed by the way my life ended and am horrified that you have burdened yourself with regret for your efforts to improve my plight.

I just plain lived too long. I did my best to live a long, healthy life, but it went on too long. I knew what “too long” looked like from my elders and I desperately didn’t want to be like them, but there I was. The financial crisis was the final blow that shattered my vision of a different, more gracious end of life scenario.

My parents died poor and my life was focused on not dying poor, but I did. Your father didn’t like my parents and having to contribute to their support put a strain on our relationship. His parents died at younger ages, so he didn’t understand. I so very much wanted to be financially secure in my old age, to not be a problem for you two, but I failed. Everything was going according to my plans and then the financial crisis hit and wiped me out.

Like I had planned, I’d lived for decades on the interest from my assets, rarely dipping into the principle, until the crash. Suddenly, I needed to draw on the principle and it had simultaneously shrunk unimaginably. Like so many others, I was rapidly in financial ruin. I know you were impacted too. You asked if I would be OK if you cut back on the supplement you were so generously giving me for the extras and I wasn’t able to tell you the truth. It would have been so much better if we could have had an honest conservation about my financial situation, but I just couldn’t do it. It was a mistake, but it was the best I could do. Disclosing my health and financial information to you felt like a loss of independence for me and a burden for you. It would have been kinder to us all to be direct, to be forthcoming, but that wasn’t the way we did things.

I too am suspicious that all the stress and anxiety that I had about my financial ruin contributed to my stroke. Suddenly, there was yet another devastating loss of control over my life and more burdens for you.

I’m so sorry for the mess I created for you in so many ways. I know that you had to negotiate with yourself, your husband, and your sister on how best to manage my financial and health affairs. There were no winners in that process and I know that it still troubles you.

I also know that you felt that you weren’t doing enough to support me emotionally. That was another losing situation. I always valued my independence and wanted you to live your own life. I wanted to be a part of your life, but not the central focus. As I aged and became more debilitated, I unfairly looked to you to provide what I’d permanently lost and, of course you couldn’t do that, no one could. The person that I had been was gone and I was dissatisfied with what was left of me. You supported me in the many ways that you could but no one could provide what I yearned for, which was to be whole again.

I always wanted to die peacefully in my sleep, which I did, but not with the dignity I had dreamed. I wanted our relationship in the end to be joyful, not a tug-of-war over scarce resources of your time and money. I’m sorry that it degraded to that. I wanted you to remember me as a happy, independent, resourceful woman that loved you very much. I’m pleased that you keep several photos of me on your dresser to displace the sad images of my last years.

Let’s vow together to lay down our mutual regrets. We both did the best we could for each other under extraordinary circumstances. That does not diminish our lifetime of love and respect for each other. Let us focus on the bright side of our lives as individuals and as mother and daughter.