A Dozen Ways to Avoid Regret (and a Warning about Endless Therapy)


When we suffer regret we are, by definition, occupied with the past. We lament things we did or didn’t do, time lost, vanished opportunities. Perhaps, however, it would be useful thinking about how to avoid regret going forward. Here are a few guidelines:

  • Recognize life’s limitations, learn from failure, and don’t stop trying. Anyone with imagination can think of several possible lives to lead, places to go, experiences to pursue. If  you are honest you can even envision a different spouse or children, no matter your great good fortune in those you have. Thus, the world is like a candy store in which only so much consumption of sweets is possible, to borrow a metaphor from Haruki Murakami and Forrest Gump. The earlier you recognize this the more you are forced to refine and narrow your choices. Moreover, you must reach for some of those candies without ever having tasted them and before obtaining experience in how to grasp each one artfully, a guarantee of mistakes.
  • We can only learn from disappointments and try again. Live your values as best you can: dive deep into those few candied heaps of life you deem worth the effort in the short time permitted. Don’t end your days saying, “I should have” or  “Why did I waste my time on … ” Or, worst of all, “Why didn’t I?” Michael Jordan, basketball hero, said:

I’ve missed over 9,000 shots in my career. I’ve lost almost 300 games.Twenty-six times I’ve been trusted to take the game-winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.

  • Improve your choices. Moving through life, take stock, reflect. Write down your analysis, perhaps every five or 10 years. Look where you’ve been, where you are, and where you would like to go. I’m talking about what career you might still pursue, what you’d like to learn about, how much of yourself you hope to devote to relationships, what personal characteristics you still wish to alter, where you’d like to live, what you’d like to see, and the legacy you might leave behind. No one can do everything, be everything. Too much candy, too little time, too much indigestion.
  • Since we can’t invent more hours, we are left to determine how best to spend our allotment. If you hope to become World Champion in the art of perusing and responding to tweets, stop reading this now. You are wasting minutes you could devote to your curious focus on 280 characters or less. For myself, I watch TV/video less than an hour a day on most days, except for those in the baseball season! Why? Because I value the time spent in the company of fine novelists, historians, and ancient philosophers more than what is on the tube. Some of this might strike you as elitist, but no.
  • Literature isn’t automatically “superior” to TV, film, or theater. I’ve simply made a choice: my personal preference. You can find superb TV shows if that is what you believe is a good use of your day. I’m suggesting you think through choices. Assuming you are mature, the most satisfying life possible for you will be a life designed by you — not a consequence of habit or the persuasion of advertising, the boss, or friends. Quiet consideration of how you spend your waking hours is essential to the success of your plan, especially if you are not happy.
  • Be active, take risks, always seek to grow. Some of these endeavors will assume the form of self-disclosure and vulnerability, some the shape of honest self-reflection, some the act of trying new things. The courage to know yourself and then be yourself is never easy. The ground is shifting under all of us. Move, don’t sit still. Reinvent yourself, at least a bit. Proceed, don’t rush, but live with intensity. Walter Pater wrote:

To burn always with this hard gem-like flame, to maintain this ecstasy, is success in life.


  • Be wary of bucket lists. I’m referring to the postponement of activities until late in life, the things you want to do before you begin residence below ground. Several problems come with delay: a) you might not live long enough. b) if you are forever looking forward you won’t live in the moment and experience joy in the now. c) bucket lists assume excellence at predicting what will bring fulfillment in 10, 20, or 40 years. We are poor at this. Research on “affective forecasting” (being able to predict how life events will influence our emotions) affirms the weakness. Richard Posner, in his book Aging and Old Age, puts the dilemma of anticipating our future self this way. Say we sentence a 20-year-old to life in prison. Are we punishing the same person when he is 65? That is, does a man change over time? Possibly deepen, mature, give up old hobbies and take on new ones, learn more; become enriched and transformed by love or literature or experience, turn grateful or embittered, for or against life?
  • Unless we can predict the manner in which events and people will work on us and how we will work on ourselves, we might realize a long postponed trip to Paris would have been better in life’s springtime; or, in my case, a Chicago Cubs World Series victory would have meant more to me at 20, when I lived and died by the team’s fortunes, than it did in 2016. By the way, I didn’t plan on morphing into a less avid fan. I simply changed.
  • Regret can be a result of idealization. As Janet Landman observes in her book, Regret: The Persistence of the Possible, this emotional state is akin to the aftermath of a decision made at a fork in the road. We reach the divide and must choose. Proceeding down the chosen path, past the time of easily retracing our steps, we think: “I was mistaken. The other way was better.” But really, do we know?  We only understand the lived experience of the choice we made. The other avenue is easy to idealize because it exists in imagination, because we didn’t encounter the imperfections one can only suffer by a different choosing. Do you wish to spend a lifetime lamenting a mirage?
  • Ask whether there is another side to losses, mistakes, and missed opportunities. I am not Pollyanna. Few who read my writing regularly would think so, I suspect. I will say, however, that I have learned far more from the “slings and arrows of outrageous fortune” than from any other source.
  • Not every mistake can be rationalized, not every loss offers even close to equal compensation in some other form. But before you devote the rest of your days to regret, take a few moments to seek what can be learned from life’s hard and unequal distribution of pain. Perhaps you can create some good out of your awareness of those things you did or didn’t do, the words you said or didn’t say, the chances missed and the poorly chosen roads endured — if not for yourself, then for someone else.
  • Remember that research says you will be happier if you take newfound money and buy a cup of coffee for a stranger than if you use the gift for yourself. King Midas wasn’t a happy guy, was he? Take a hard look at your desire to gain triumphant, towering status and wealth.


  • Be careful how much time you spend looking back. I am on thin ice in saying so. A good therapist begins with history. The untying of binding emotional knots is essential, often requiring discovery of how they came to be, where they remain, and more. Danger exists, however, in believing every knot requires attention, every cognitive or behavioral change demands agonizing soul-searching. Some will loosen with the passage of time, others aren’t too important. CBT (Cognitive Behavior Therapy) is able to master many without endless and wrenching historical probing. Meanwhile, weigh the time spent on a backward focus versus possible gains from attention to the now via action. Curtail whatever retrospective view isn’t essential to making a satisfying life.
  • Is this avoidance, cowardice? Only sometimes. Psychotherapy in-depth encourages a seemingly perpetual return to the bottomless gorge of your memory-distressed soul until you dredge up every dark thing at its floor. Sometimes we must put an end to reruns and begin a new season in the installment series of our lives. Your therapist might urge digging deeper. He may be correct. I’m here to say — on reflection — my patients sometimes knew when to stop when I didn’t.
  • Is there room for gratitude? Such a sentiment is hard to summon in the midst of despair, maybe impossible. The practice of routinely reminding yourself what is good can, nonetheless, diminish sadness much of the time.
  • Time is always moving forward and doesn’t permit time-travel for do-overs. Those facts set the stage for regret. Not because you made horrible mistakes, but because you are human and were thrown into a set of unalterable physical laws (as are all of us). The best way we can deal with what nature offers is to make good use of the present and plan for the future, even though the person for whom we are planning (our future self) may not be as thrilled as we hope with the baton we pass him.
  • Regret is inevitable because our genetic inheritance keeps us unsatisfied, always seeking more and better. Those early humans without such ambitions — those who were easily satisfied — didn’t survive, nor did their offspring become our ancestors. Evolution enabled the perpetuation of our forefathers’ genes in the form of their progeny, but offered no guarantee of joy in our status, our mate, or our job. Regret, therefore, is built into who we are: restless creatures still driven by the biological imperative to behave in a way that increases the chances of our genes surviving, even past our reproductive years.
  • Learn to forgive yourself. You cannot do everything, you will never be perfect, you will disappoint and injure others, your imprint on the planet will (unless your last name is Will Shakespeare or Hawking or Beethoven) be small. We are always learning and forever changing course. Do your best, try to do better, and leave it at that. Life is punishing enough for most of us without volunteering for the cross and offering to hammer in the nails, to boot. As a Christian colleague occasionally told her patients, “Get off the cross, we need the wood.”

You need the wood, too. Take the timber and carve a sculpture or draw a lovely image or build a house; or burn it to keep yourself and another good human warm. Leave the job of summing up your life to history, assuming history cares.

In my book that is enough.

The top painting is Impression, Sunrise by Claude Monet. The second photo is Sunset Over the Vercors Mountains, Seen From Grenoble by Guillaume Piolle. Finally, Sunrise with Reeds in Winter is the work of Benjamin Gimmel. All are sourced from Wikimedia Commons.

20 thoughts on “A Dozen Ways to Avoid Regret (and a Warning about Endless Therapy)

  1. Wow – too tired to comment more coherently than that , but wow 🙂 so much incredibly valuable stuff to think about; I’m not sure I know when to stop though I don’t have the luxury of being able to make that decision as I already know my therapy will end when my therapist retires over the next few years….thank you so much for writing this. The fear of regret is still one if my biggest fears….

    Liked by 1 person

    • I’m not suggesting anyone should stop therapy, but rather for us to break-through life’s sometimes deadening routine and consider our choices. Nor to stop with consideration of all the doors open before us (or how we can find some if they seem closed), which can be its own form of navel-gazing and take action. I pretty much guarantee that all of us will mess up. The essay was as much a reminder to me as to anyone who reads it. Regret is just part of our allotment in life. Glad you found it provocative.

      Liked by 1 person

  2. Good thoughts for those of us in the “final” years of life. It’s a great feeling to have no regrets. And to have the freedom (and resources) to “design” our own days now.

    Liked by 2 people

    • Thanks, Lois. I think the years before the final one’s are best for breaking the mold. While it is true that the struggle simply to make a living can be all-consuming, there are often more possibilities for fulfilling action than we see or take the time to consider. None of us has complete freedom of action, but without thoughtful attention to what might be available it is too easy to become static, lost in regret and hopelessness. I know you to be a brave soul. You were/are this, early and late. Brava!

      Liked by 1 person

  3. Thank you. I felt like this article is just in time to tell me something. I am at this intersection of my life and I am lost. Thank you for such a beautiful article.

    Liked by 1 person

  4. I agree that this is a very insightful, helpful article–Thank you!


  5. Very good points. I need to pay more attention to some of these things.


  6. Dr. Stein, thanks for yet another insightful post. Lots to chew on. Learning to forgive myself for my failures and bad choices took years, but was the greatest defining moment in my life. I have no regrets: just gratitude for lessons learned, the people who helped me along the journey, and shared lived experiences.


  7. Making the jump… taking that leap of faith is its own therapeutic process, but you have to be ready or the parachute won’t deploy.


  8. This reminds me of Grendel’s (John Gardner’s) words: “Things fade and alternatives exclude.” When I first read this quote, I began to understand (finally) that for every “yes” decision we make, we have, in a sense, made a “no” decision thus setting the stage for regret. We choose a spouse and let go of the other possibilities which may come back to haunt us. “One with a hungering heart unsatisfied, mourns for imagined joys that were denied.” Ella Wheeler Wilcox, 1906.


    • Thank you for these quotations, Evelyn. Those who maintain a faithful practice within an organized religious community know that the exclusions give the choices meaning. Even (and especially) to the point of private acts (say, not drinking alcohol or eating the flesh of some animals). In a different way, I suppose, paying for psychotherapy gives meaning and fuels dedication to treatment in a way that would not be matched by if therapy were a gift or an entitlement. I am quite sure you know all of this. The other thought I had to your Wilcox quote is that one rarely comes up with a new idea. We simply offer those ideas others have thought of and said and written, as if they were new, because they might be new to us. Do let me know if I come up with something new! 😉

      Liked by 1 person

      • What I meant by sharing the Wilcox quote was to show how regret is a part of the human condition. Her words are just as timely read in 2016. I’m sure you could find examples in the ancient philosophers you enjoy studying. It’s your perspective that is new. Dr. G. You bring many years of professional experience to these universal ideas and present them to us in a fresh, and sometimes startling, manner. It’s a wonderful gift.


      • Well, Evelyn, you’ve made my day, and not in the Clint Eastwood sense! A quote I’ve used often in these essays is one you might know from Kafka, “A book is like an ax to break the frozen sea within us.” If I can startle without alienating then I’ve done my job. And thanks for your clarification of the Wilcox quote; a view, of course, which I share.

        Liked by 1 person

  9. drgeraldstein

    Reblogged this on Dr. Gerald Stein and commented:

    Regret is one of those things embedded in the human condition. It fits a discussion in most any time. I wrote this in 2016.


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