The Five Biggest Regrets and Why They Might Not Apply to You


My mother used to say, “Regret is a painkiller for fools.” Her early life was tragic and her words were — I think — a way to justify her decision never to look back. But mom’s aphorism does raise a question: how much attention must one pay to those who tell us about their poor life choices as they reflect on their past? Are we smart to use their experience — what they wish they did or didn’t do — to change our plans?

Not necessarily.

Here is an example of the kind of “wisdom” I’m talking about. A palliative care nurse, Bronnie Ware, wrote, The Top Five Regrets of the Dying.* Her list comes from her work with those near death:

  1. I wish I’d had the courage to live a life true to myself, not the life others expected of me.
  2. I wish I hadn’t worked so hard.
  3. I wish I’d had the courage to express my feelings.
  4. I wish I had stayed in touch with my friends.
  5. I wish that I had let myself be happier.

Let’s look at these and see if we agree.

I’ll combine regrets 1, 3, and 5. The courage to take risks is the link among them. Indeed, the word courage appears in two of the three regrets I’m talking about.

Ware heard patients lament giving-in to others, doing what was expected, and failing to push back when pushed around. In order to be true to yourself you must take charge of your life and disappoint or anger some others. True, “the courage to express (our) feelings” is dangerous, since most of us find disapproval unpleasant, and vulnerability an invitation to attack. The reward, however, can be great. As to letting yourself “be happier,” Ware observed that many of her patients — only too late — recognized the need to break out of safe routines and travel outside of their zone of comfort. This, they believed, was the road not taken: the path to happiness.

Oscar Wilde’s witticism encapsulates much of the last paragraph: “Be yourself; everyone else is already taken.”

I applaud Ware’s odd-numbered reminders to lead a courageous, assertive life. I’m less sure, however, about regret #2: “I wish I hadn’t worked so hard.

Here is what she wrote:

This (regret) came from every male patient that I nursed. They missed their children’s youth and their partner’s companionship. Women also spoke of this regret, but as most were from an older generation, many of the female patients had not been breadwinners. All of the men I nursed deeply regretted spending so much of their lives on the treadmill of a work existence.”

One important consideration eludes nurse Ware: regrets can also pertain to a less work-driven life: “Gee, I should have accomplished more. I ought to have been a better provider for my family. I might have made a name for myself.”

Marlon Brando said something similar in the 1954 movie On the Waterfront, playing a washed-up boxer:

I could’a had class. I could have been a contender. I could have been somebody — instead of a bum — which is what I am.

Rational or not, men, in particular, live with the genetic drive to make their way in the world. Many do regret having worked too much, too hard, too long — regret the loss of time with spouse and children. A different life, however, might have caused them not only end-of-life regrets, but disappointment in themselves for most of the preceding years.

Ware’s last item describes the elderly who told her, “I wish I had stayed in touch with my friends.

Philosophers as far back as Aristotle would say Ware hit the target here, and are supported by psychological research on what brings life satisfaction. Nonetheless, maintaining friends is a time-consuming task: making phone calls, writing email, traveling to those chums who don’t live nearby, remembering work buddies when you leave the job, and sending birthday cards. Your vocation, as well as the spouse, children, and laundry contend for the hours available on the clock. We are never permitted more than the usual 24.

A couple of additional considerations: Bronnie Ware’s dying patients were living in a different body with a different agenda than their younger selves. The seniors looked back and judged from a once-in-a-lifetime perspective — literally. When they weighed their life experience on the equivalent of a bathroom scale, did they get an accurate result?

Here is what Nobel Prize winning psychologist Daniel Kahneman wrote on how we think about past experiences when we reflect on our memories of those experiences: “Confusing experience with the memory of it is a compelling cognitive illusion … The remembering self is sometimes wrong, but it is the one that keeps score and governs what we learn from living … ”

Kahneman gives an illustration of this phenomenon:

(A man) told (me) of listening raptly to a long symphony on a disc that was (damaged) near the end, producing a shocking sound, and he reported that the bad ending ‘ruined the whole experience.’ But the experience was not actually ruined, only the memory of it. The experiencing self had had an experience that was almost entirely good, and the bad end could not undo it, because it had already happened. My questioner had assigned the entire episode a failing grade because it had ended badly, but that grade effectively ignored 40 minutes of musical bliss. Does the actual experience count for nothing?

Which self should count? The self who lived the experience or the one who recalls the events through the imperfect, sometimes warped lens of time?

You can answer Kahneman’s question for yourself. To me, the notion of 25-year-olds being subjected to the “wisdom” of 75-year-olds cannot always result in proper guidance for the young. The same caution applies if the 25-year-old and the 75-year-old are different versions of one person. Your 75-year-old judgment cannot do justice to your 25-year-old’s life choices any more than your 25-year-old self can anticipate the manner in which he will judge his life at 75. If you are in life’s first half, then you must live by what counts as wisdom for the body you inhabit, the instincts you have, the great ideas you’ve read about, and the thoughtfulness only someone in your life-situation can possess.

Among the most perceptive observations about the human experience comes from the Stoic philosopher Seneca in his treatise, On the Shortness of Life:

Small is the part of life that we really live. All that remains of our existence is not actually life but merely time.

If Seneca is right then the best advice is easy: live.

*Thanks to my wise buddy John Kain for calling Bronnie Ware’s work to my attention. The top photo is called Mood Disorder, by Specialtoyoutoyou. It is sourced from Wikimedia Commons.

12 thoughts on “The Five Biggest Regrets and Why They Might Not Apply to You

  1. This is really interesting and challenging, thank you 🙂 I particularly liked:
    “Which self should count? The self who lived the experience or the one who recalls the events through the imperfect, sometimes warped lens of time?” I spend a lot of time trying to ‘recall’ in therapy – and much of the time I can’t recall specific actions or feelings, just a ‘sense’ of how it felt or of what was going on, and a fuzzy sense at that. A lot of weight seemingly gets given to those recollections and how they might be interpreted, however fuzzy they are – which is not necessarily to say that they _count_ more, but they _do_ have an important impact on how I view where I have got to, and how I make sense of things now……


    • Thank you. Not to confuse things, but we all think of certain memories as akin to photographs in their accuracy. The research says otherwise. Given the lack of certainty about our memories, one might ask how much weight we should put on them. Eye witnesses to events often give conflicting accounts. Sometimes, too, our therapeutic dilemma is how much time we wish to devote to a backward look. I certainly encouraged my patients to look back when there appeared to be unresolved issues. The issue of experience and memory — the experiencing self and the remembering self — are fascinating. The Kahneman passages I quoted come from his book, “Thinking Fast and Slow.”

      Liked by 1 person

  2. Thanks for another interesting article, Dr. Stein. I would like to comment on No. 4: “I wish I had stayed in touch with my friends.”

    I agree with you that “maintaining friends is a time-consuming task…” Just keeping up with those friends currently in our lives can consume the available time that we have. I do believe that those friendships that are meant to last a lifetime usually do so. Most of the friends along the course of our lifetime only enter our lives for a short time.

    What I strive to do is to be fully present when I’m with the people in my life at any given moment. When with friends, I try to be true to myself; express their importance in my life; and enjoy their company. When the time comes for us to part, as has happened recently, I have no regrets, only a sense of loss.

    Liked by 1 person

  3. Thank you, Rosaliene. Your comments often suggest to me a life well-lived, although (of course) we don’t know each other directly. Not a perfect life, but the life of an intelligent woman who shows courage, lives in the moment, and learns from experience. That is the best any of us can do.

    Liked by 2 people

  4. A very interesting subject Gerald. I’ve tried not to get to caught up in dwelling for long periods of time in reflecting on regrets or wishing things were different than what they are. I know to that my mum has suffered a lot because of regretting some of the decisions she made or didn’t make that affected her children for the worse, because she didn’t understand at the time. On the whole not much is accomplished other than putting yourself through a lot of guilt about things that you can’t change. If you can learn the lessons from regrets to do things a different way or repair relationships, that’s useful, but other than that I find for me it uses up a lot of mental energy and emotion that I need to spend on dealing with the reality of how my life is at the moment. Wishing it to be something else is pointless. I am who I am now because of all my life’s experiences. Anyway I think on the whole most people do the best they can at the time with what they have, sometimes that not much and you only learn that in the future when the consequences hit.


  5. Well said, Claire. Regret certainly can be a time waster. The past is over and can’t be changed, the future is yet to be and may not happen at all or unfold in the way we expect. The present is the only thing we really “live.”


  6. I’ve read this list in a few different “inspirational” articles. I really like your perspective on it though. Very interesting indeed.

    I’m currently going through your archives, so you’ll probably still have me “pop up” quite often. 😛


  7. One of the pieces of poetry I wrote is similar to Seneca:

    I live and make do with what I have, now. Personally, I find it useful to think of my ‘task’ in life to negotiate between the past and present to bring forth future.


  8. …oh, what I mean is this:
    “To Live, and to Live!
    that is All.”


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