The wish to have done things differently is painful. It is also, if you look at it carefully, evidence of something. The person who can see what they would do differently has grown beyond the person who did the original thing.
My grandfather, in the last years of his life, had a list.
Not a written one. A mental one — a set of specific moments he returned to, regularly, in the particular quality of silence that came over him in the evenings. The argument with his brother that was never resolved before his brother died. The year he stayed in a job that made him miserable because leaving felt too uncertain. The way he had been, for some years, too impatient with his children when they were young.
He never described the list as such. He described it in fragments, over years, in the way that people share the things they carry when they have finally stopped trying to carry them alone. Each fragment came with the same sentence at the end: “I should have known better.”
He was right that he should have. He was wrong about what that meant.
The wish to have done things differently is one of the most universal features of the life review that arrives in later years. It is painful in the specific way that retrospective clarity is painful: you can see, now, what you could not see then — and the seeing produces the wish to go back and apply the current understanding to the past circumstances. The wish is impossible to fulfil. It is also, if attended to carefully, something other than it appears.
My grandfather’s phrase — “I should have known better” — contained an error that I have heard repeated, in various forms, by almost everyone who has sat with their own version of the list. The error is in the tense. He did not know better, at the time. He knows better now. The “should” imports the current knowledge into the past circumstance, where it did not exist, and uses the gap between the two as evidence of a failure that was, in the terms available then, not a failure at all.
The Accounting That Uses the Wrong Ledger
The specific pain of retrospective regret is different from the pain of prospective regret — the regret of imagining what will be lost if you make the wrong choice now. Prospective regret is oriented toward action: it motivates the avoidance of the thing that will be regretted. Retrospective regret has no such orientation. The action has already been taken. The only thing available is the accounting of it.
The accounting tends to use the wrong ledger. It measures the past action against the current understanding — against the values, the knowledge, the emotional resources, the relational capacity that decades of living have produced. And it finds, unsurprisingly, that the past action falls short. Of course it does. The person who took the action had less — less experience, less self-knowledge, less capacity for the kind of perspective that the life review is now applying retroactively.
“I should have known better” is almost always true. It is also almost always unfair — because you didn’t know better then. Knowing better now is the proof that you have grown, not the proof that you failed.
The argument with the brother, unresolved until the brother died. My grandfather could see, by the time he was telling me about it, exactly what had been at stake — the pride, the fear of vulnerability, the habit of conflict that both of them had learned in the same family and never unlearned. He could see it because decades of living and loss had given him the understanding that the argument itself had not. The clarity is real. It is also a product of the journey that the argument was part of.
What Regret Reveals About Development
Erikson’s account of the final stage of psychosocial development describes the central tension as one between ego integrity and despair — between the acceptance of the life as it was actually lived, with its particular choices and foreclosures, and the despair of a self that cannot make peace with what was done and undone (Erikson, 1968).
What Erikson’s account illuminates is that the capacity to look back with clear eyes — to see what was done, what it cost, what could have been different — is itself a developmental achievement. It requires the kind of perspective that is only available after the fact, after enough distance has accumulated for the patterns to become visible. The person who, at forty or sixty or eighty, can see clearly what they could not see at twenty or thirty is not the same person who made the original choices. They are the person those choices helped to produce.
The regret, understood this way, is not primarily information about the past. It is information about the present. It is the indication that the self has developed beyond the point at which those choices were made — that the understanding now available was not available then, and that its current availability is a product of the very life, including its mistakes, that is now being reviewed.
My grandfather should have known better. He does know better — now, at the end of a life that included the argument and everything that came after it. The knowing better is not in spite of the life. It is a consequence of it.
What the Research Finds About Regret and Growth
The psychological literature on post-traumatic growth — the positive psychological changes that can emerge from the struggle with highly challenging circumstances — has consistently found that the capacity to integrate difficult experiences, including choices that caused harm or pain, is associated with increased psychological complexity and what researchers describe as wisdom (Tedeschi & Calhoun, 2004). Wisdom, in this research framework, is not the absence of regret. It is the capacity to hold regret alongside a coherent narrative of the life — to see what was done, understand why it was done, acknowledge the cost, and integrate the whole into a self that is larger and more complex than the self that made the original choices.
Research on self-compassion and regret has found that the ability to extend compassion to oneself for past choices — to treat the past self with the same generosity one would extend to another person in equivalent circumstances — is associated with lower levels of chronic regret and higher levels of psychological wellbeing in older adults (Neff, 2011). The compassion does not require the minimisation of what was done. It requires only the accurate assessment of what the past self had available — the knowledge, the resources, the developmental capacity — at the time the choice was made.
The fair accounting measures the past action against what was available then, not against what is available now. This is not a lowering of standards. It is the application of standards that are proportionate to the actual conditions — which is, in fact, a higher standard than the retrospective application of current understanding to past circumstances.
The Wish as Testimony
The wish to have done things differently is not evidence of failure. It is testimony — to the growth that has occurred between the original action and the current moment of review. The person who wishes they had been more patient with their children when they were young is not the same person who was impatient. They have developed, through the accumulation of experience and loss and reflection, a capacity for patience that was not available at the time.
This reframe does not erase the harm that the original action caused. The brother who died with the argument unresolved is still dead. The children who experienced the impatience still carry it in some form. The harm is real. What the reframe changes is the meaning of the regret — from evidence of a fundamental character flaw to evidence of a development that, however painful its route, has produced something genuinely valuable.
The wish, held this way, becomes something other than self-punishment. It becomes a measurement of the distance traveled — from the self that made the choice to the self that can now see what the choice cost and what it would have required to make a different one. That distance is the life. The life is what the regret is proof of.
He Knew Better. That Was the Point.
My grandfather’s list was real. The argument was real. The year in the wrong job was real. The impatience was real, and so were its effects on the children who experienced it and who, in their own ways, still do.
What was wrong was the verdict. “I should have known better” treated the knowing-better as a prior condition that had been ignored — as if the understanding that came in the eighties had been available in the fifties and he had simply failed to apply it. It wasn’t available. It was produced, over decades of living, by the very experiences he was now reviewing.
He knew better by the end. That is the point. Not the consolation prize — the actual point. The life he lived, including its mistakes, produced the self that could see them clearly. The seeing is not separate from the living. It is what the living, done honestly and long enough, eventually makes possible.
The wish to have done things differently is valid. It is also, if you look at it from the right angle, a kind of gratitude — for the growth that made the wish possible at all.
REFERENCES
Erikson, E. H. (1968). Identity: Youth and crisis. W. W. Norton.
Neff, K. D. (2011). Self-compassion: The proven power of being kind to yourself. William Morrow.
Tedeschi, R. G., & Calhoun, L. G. (2004). Posttraumatic growth: Conceptual foundations and empirical evidence. Psychological Inquiry, 15(1), 1–18. https://doi.org/10.1207/s15327965pli1501_01
ON THE CHANNEL · PUBLISHED 30 MAY 2026
This article reframes the wish to have done things differently — from evidence of failure to testimony of growth. The video goes deeper into the specific emotional texture of this stage of life review: what it feels like to carry the list, what “I should have known better” is actually saying, and what changes when the regret is held as measurement of distance rather than verdict on character. I wish I had done things differently — Hidden Patterns
📖 IF YOU WANT TO GO FURTHER
The book that most directly addresses the relationship between regret, self-compassion, and growth in later life is Kristin Neff’s Self-Compassion. Neff’s research on the difference between self-criticism and self-compassion — and on what it actually means to extend genuine compassion to the past self without minimizing what was done — is the empirical foundation for the reframe this article offers. The chapter on self-compassion and personal accountability is the most useful thing I know for anyone working with a mental list.
