The surprising truth about regrets
Stories of my mistakes, and retakes.
File this under “stumbled upon”: here’s the World Regret Survey which has collected more than 26,000 regrets from people in 134 countries.
Since resolving regrets is a major part of “coming of aging” - making peace with the past and opening to the rest of life - lead author Daniel Pink’s findings caught my attention.
Pink found that nearly all regrets, no matter country or gender, sort into 4 categories: foundation regrets, boldness regrets, moral regrets, and connection regrets, summarized in this article.
Foundation regrets. Many of our education, finance, and health regrets are expressions of the same core regret: our failure to be responsible, conscientious, or prudent. Our lives require some basic level of stability. Yet sometimes our individual choices undermine this long-term need. We overspend and undersave. We adopt unhealthy habits. When such decisions cause our futures not to live up to our hopes, regret follows.
Boldness regrets. One of the most robust findings in the academic research, and my own, is that over time, we are much more likely to regret the chances we didn’t take than the chances we did. What haunts us is the inaction itself.
Moral regrets. Most of us want to be good people. Yet we often face choices that tempt us to take the low road. When we behave poorly, or compromise our belief in our own goodness, regret can build and then persist.
Connection regrets. Our actions give our lives direction. But other people give those lives purpose. A massive number of human regrets stem from our failure to recognize and honor this principle.
The shoals of regret
Once watered by “coming of aging” attention, my own unconscious regrets, like dormant seeds in my soul, sprouted into a Scrooge-like reckoning with my past.
I clearly recognize my regrets in each of Pink’s categories:
Foundation Regrets:
After college, I took the road taken by the psychedelic revolutionaries of the late 1960s. At the time, I threw caution to the wind in favor of seeing through altered eyes the glories of love, truth and beauty. By convoluted chance, this path lead back, 20 years later, to the kinds of influence I was destined for - authoring Your Money or Your Life, thinking it could “change the world”. I had no intellectual foundation however. No grad school. No profession. No ladders climbed in any business. Intuitive and a quick study, I’ve joined many disciplines - personal finance, dialogue, food and farming, aging - as a raconteur and “possibilitarian”. I’ve been like Forest Gump, stumbling into group pictures with experts and leaders. I’d ended up there by dint of sheer luck and fierce will to understand and influence the disease of disconnection our capitalistic ways create.
To symbolize this, I used to point out that I was in the same graduating class from Brown as Janet Yellen. She continued on, year by year, opportunity by opportunity, to earn a seat on, and then the chairman of, the Fed. Yes, I eventually shepherded a 2 million copy best seller about money. You could say we each influenced how Americans earned, spent, saved and invested money - but my seat was the seat of my pants, and hers on the Federal Reserve. What might I have become had I, as advised by my mother, gone on to grad school, a PhD (probably in social psychology or journalism) and into leadership in institutions instead of this zig-zag, hodge-podge life of trying to make a my scratch on eternity.
One doesn’t correct such a foundational regret by getting a masters at 70, at least not this one. One forgives and gets over oneself.
Boldness Regrets:
In my twenties I stumbled into a toxic relationship. I froze rather than fought my way free. This cost me many years of potentially sane relationships. As with most regrets, I’ve learned to accept what I cannot change - that past - and change only my shame and judgement about it. Who says I would have gotten an A+ in loving relationships had a fled the one that hurt? The lessons learned needed to be learned one way or another. As with all regrets, acceptance of what is - and isn’t - is the key.
I do not have boldness regrets in my work though. I’ve been kick ass and shown up again and again, many books, projects, fields, countries, opportunities. One does not balance out the other, they are all part of one life, my life, my little minuscule role in the great dramas of history. I have a walk on part. We all do. Ultimately, we play our part in service to the magnificent show of the times we’re born into. In some plays, we are bit players. In some we get a speaking role. Ultimately it’s the larger story that matters, and the privilege of being part of it at all.
Moral Regrets:
These have been the hardest for me. In adapting either to outer expectations or inner fears, I have treated people badly according to my own moral compass. Every time I see another moral misstep with someone, I let the sorrow of that sink in, seek the person out, if possible, and apologize. Some have softened and accepted the apology. Others have not. From this I am becoming more Velveteen Rabbit-y - more humble, human and lovely to be around.
I have also learned how to heal regrets and more easily own and clean up my errors when I see them. Why not? By now in life, what is there to defend? And do I want to do this as my death approaches? Nah.
Connection Regrets:
My earlier life experiences left me with an unrequited longing to belong and a sense that, for some reason, people I count on will not be there for me if I fall. It’s a hidden distrust (a psychologist friend explained it through Attachment theory) masked by a sunny personality. It feels like trying to knit a fabric of belonging and, every time I turn my back, someone pulls a thread. It’s taken a long time to unearth this pattern and understand it as a pattern from childhood, not a reality of disloyal friends. In fact, I am blessed beyond measure with generous, connected relationships. My work is believing that. I am not alone in this, though. Most movies, novels, and plays are about the longing to belong (to a person, a family, a group) and a gazillion ways that can go wrong - and be righted.
Regrets, according to Pink, make us human and make us better.
Coming of Aging is healing regrets
In Coming of Aging, the process of going from older to elder, our regrets turn out to be the tools of transformation. We heal as we learn to go towards the center of sorrow, not stay on the periphery of shame.
Our regrets are the narrows we pilot through as we get out of the harbor of the middle of life with all its markers of responsibilities, duties, roles, recognition, success. They are dangerous - our fragile ego hulls can break on these hidden boulders.
With attention, we find the channel of deeper water that takes us beyond the breakers which once seemed the far horizon of our lives but become the past through such careful navigation of the shame and sorrow.
Beyond those breakers is a wide open sea. Life is vaster than we ever knew.
Owning and blessing our past, no matter what, restores the eyes of wonder. What an amazing world we live in. How much can we taste of every flavor, bitter to sweet to sour to tasty, of existence before our time is over.



Most people see regret as something to get rid of.
I don't.
I see regret as one of wisdom's teachers.
Regret occurs when we finally see something we could not—or would not—see before. We recognize a choice, an action, a failure to act, or a missed opportunity and realize its consequences.
Without that realization, there is no regret.
And without that realization, there is often no wisdom.
The question is not whether you have regrets. Any honest life will contain them.
The question is: What do you do with them?
Many people use regret to punish themselves.
They replay the past.
They relitigate old decisions.
They become prisoners of what cannot be changed.
That produces suffering, not wisdom.
Wisdom begins when regret becomes instruction rather than accusation.
Instead of asking:
"Why did I do that?"
the wiser question becomes:
"What did that experience teach me that I could not have learned any other way?"
Regret can teach humility.
It softens certainty.
It exposes self-deception.
It deepens compassion for others' mistakes.
An Elder doesn't ask:
"How do I get rid of my regrets?"
An Elder asks:
"What wisdom is this regret trying to teach me?"
This is wonderful, Vicki! I plan to write about my own inventory of regrets. I don't think there are many, but the ones I hold deeply remain vivid in my memories. I've been thinking about my mom, who died at the end of 2021, and how the last few years of her life were spent confronting her less-than-healthy decisions and deep regrets, much of it rooted in desperate attempts to be loved.
There's a new book called From Mistakes to Meaning: Owning your past so it doesn't own you, and the authors have given several interviews and discussions and are on YouTube.