Why Regret Is (Actually) Good for Us

In one of the final scenes in Leo Tolstoy’s novella “The Death of Ivan Ilyich,” the protagonist lies in bed, dying a slow but imminent death.

With nothing else to do his mind begins to review the past and all the mistakes he’s made: an unhappy family life, a dull and unfulfilling job, the endless pursuit of money and status. Overwhelmed, he tells himself: “I must not think about these things. It’s too painful.” ¹

Many of us would probably feel the same as Ivan Ilyich if we were in his shoes. After a lifetime of mediocre choices and missed opportunities, who would want to start exploring possible regrets? It’s natural to think, “There’s nothing I can do now, so what’s the point?”

“Regret” is a melancholy word on the whole. It’s ladled with connotations of failure and futility. In our forward-looking, achievement-focused culture it can almost be taboo at times. “No regrets,” is a sentiment many of us like to live by (and occasionally etch in tattoo). Who has time for regret – especially when it can be so painful?

The truth is that regret is perhaps one of the most valuable things in life for helping us find greater meaning and satisfaction. And it need not lead to existential torment, either.

Psychology professor and author Janet Landman in her remarkable book Regret: the Persistence of the Possible notes:

“Regret need not necessarily be a futile waste of time, a failure of rationality, or a ‘perilous slope’ down to depression. Regret can also constitute a path leading onward and upward. Regret is better viewed as a form of practical reason appropriately informed by emotion. Like anything human, it can go wrong. It all depends on what you do with it.” ²

This opens the question up to us: what should we do with our regrets?

Regret Makes Us Better

Unless we go through life incapacitated in some form, we will have to make many important choices over time. Some of our choices will seem obvious, but not all of them will be.

Choosing between more than one option always leaves room for the possibility that one choice is better than the other – and that we just might end up making the not-as-good choice. In fact, because we are human, at some point we will make the not-as-good choice. Or even a flat-out bad choice.

Regret, then, is a metric that helps us figure out how to live better.

“People value their regrets substantially more than they value other negative emotions,” researchers discovered in two different studies on regret. ³ What they found is that regret, unlike jealousy, boredom, or anxiety, has the ability to motivate us to improve ourselves. Regret isn’t fun, but if we learn from it, we can correct our course and live the rest of our lives (however much is left) even more meaningfully.

There’s another important consideration here, too: if you have the capacity to experience regret, it’s a sign that your moral compass is functioning. In Landman’s words, “It is better to have (right) values, even at the cost of the pain of regret, than to be devoid of them.”

In other words, regret makes us both human and humane.

The Price of Not Regretting

Because regret isn’t usually pleasant, and learning isn’t always easy, there will always be those who try to bypass thinking about regret altogether.

This can feel like a good idea at first, but failing to question your life choices over a long period of time (or failing to make choices at all) puts you at risk of being the proverbial ostrich with your head in the sand. In the worst case, you end up like Ivan Ilyich.

More likely still, you’ll end up like Sterling Ainsley.

Sterling is the fictitious name of one of the men from the famous Harvard Study – a longitudinal study aimed at uncovering important factors in lifelong happiness. On the outside, Sterling’s life is both peaceful and quiet.

He doesn’t argue with his wife, since he doesn’t live under the same roof as her. His relationship with his kids is pretty good – but then again, he only sees them once in a blue moon. Because he doesn’t “need” his family (or friends), he doesn’t have to worry about social conflict or being a burden to anyone. In the meantime, he’s free to focus on tending his garden, mowing his lawn for exercise, and watching TV at night with his 87-year-old neighbor.

Regret can be an uncomfortable thing, but what’s truly tragic is not making use of that discomfort to improve the amount of time that’s still left in your life.

Because Sterling is so anxious to not think about any regrets he’s had over his relationships, he tries to frame everything in terms of the positive. “But when asked to look more deeply in the mirror…it became clear that deep down he felt quite alone, and he had little understanding of how isolated he was.” The only person in Sterling’s life who offers any real emotional support to him is his elderly neighbor. “I don’t know what I’ll do if she dies,” he admits. ⁴

How did 64-year-old Sterling Ainsley get to this point in his life? While the authors don’t say it point blank, it’s clear that avoiding any kind of negative thinking and regret has, ironically, only made Sterling’s life lonelier and more unbearable over the years. Because he won’t admit what’s gone wrong, there’s no way to make things right.

It’s Never Too Late

You might still sympathize with Sterling and wonder: “Is there a point of no return when it comes to regret? At some point in our lives are we actually better off stuffing our regrets in the closet?”

Such an attitude might make sense, but only for those who don’t value being honest with themselves or others. It may be painful to examine our regrets, but cognitive dissonance is a heavy price to pay. By acknowledging our mistakes – especially long-term and chronic ones – we exercise courage, build character, and choose to live in reality rather than an eternal bubble.

Nor is it ever truly too late to transition from an empty life to a full one. One of the most powerful examples in the same Harvard study is Andrew Dearing, a depressed, unhappily married gentleman who never went anywhere or did anything new for years. At times he even felt suicidal; the only thing that brought meaning was his work repairing cuckoo clocks, but then his eyesight failed and he no longer even had that.

After finally separating from his wife at age 68, he tentatively ventured out and joined a health club. Though it was slow-going at first, he eventually started making new friends. They started having get-togethers and watching old movies – and Andrew’s social life continued to bloom. He went from never leaving his home or seeing other people, to visiting with others every single day. ⁵

Even the miserable and tormented Ivan Ilyich finds redemption and peace in his final days of life when he observes the genuine kindness of one of his caretakers and sees that love, compassion, and goodness are real things that exist in the world. While it’s too late for him to take much personal advantage of these things, his eyes are opened and his perspective is completely changed.

Regret Is Not Rumination

For many people, the word “regret” conjures the image of a brooding, bitter person who can’t let go of the past. Someone like Miss Havisham from Great Expectations, still wearing her wedding dress some forty years later, surrounded by rotting food and completely unable to move forward in life.

Rumination is never a good thing, but it’s not the same thing as regret for one key reason: regret is a natural part of human existence, and rumination is a choice.

Regret is a reaction – a normal, healthy one – for any of us who allow ourselves to reflect on life choices for long enough. Unless we intentionally avoid doing this, like Sterling and Ivan Ilyich, we’re going to have regrets at some point: the question becomes, what do we do about them? While regret itself is neither a state of action nor inaction, it’s a data point that we can take and use to inform our future decisions.

To use a navigation analogy, moments of regret act as opportunities for course correction. Starting out in life, we may have a particular idea in mind for what we want to do and so begin down that path. When we realize that certain choices are coming at the cost of other things that matter more, we can then adjust course to prevent those regrets from growing or recurring. We can even hone the skill of “anticipatory” regret to avoid making regrettable choices in the first place.

In the end, none of our “flight paths” will be straight – all of them in fact will be filled with plenty of detours and missed opportunities – but when we learn from smaller regrets we can avoid bigger ones later on and make it to our final destination (which may or may not be the same as our original destination).

On the other hand, rumination is the choice to not take action and instead allow the “whys”, “what ifs”, and “what might have beens” to cloud your view of reality until you can no longer even see the path in front of you. Instead of charting a course through life based on what you’ve learned, you’re at the mercy of the weather patterns.

Regret can be an uncomfortable thing, but what’s truly tragic is not making use of that discomfort to improve the amount of time that’s still left in your life.

Finding a Balance Between Regret and “Good Enough”

Regret only exists because the human brain is capable of counterfactual thinking.

We humans are both blessed and cursed by the ability to imagine, daydream, theorize, postulate, and build for ourselves virtual time machines that allow us to fly forward and backward in time. Movies and literature are filled with stories about people who are able to “undo the past” and save others in the future. We find this cathartic because we understand how flawed reality can be.

Daniel Pink, a journalist who has done extensive research on regret, puts it this way:

Regret is the quintessential upward counterfactual – the ultimate If Only. The source of its power, scientists are discovering, is that it muddles the conventional pain-pleasure calculus. Its very purpose is to make us feel worse – because by making us feel worse today, regret helps us to do better tomorrow. ⁶

But what about feeling happy today? As we’ve seen with rumination it’s not good to be stuck in the past, but is it any better to always be living in an idealized future?

“To unite the thought and feeling of regret is, in my view, to make a kind of living poetry of the raw material of one’s life.”

Here is where wisdom must intervene. Counterfactual thinking is a tool that, when used skillfully, makes our lives better. But like any tool, you can be overkill and sabotage your original purpose. Just like a scalpel should be used to only scrap away what’s needed (otherwise it destroys your whole project), counterfactual thinking should serve as a helpful guide in life but not be allowed to have full rein to our thoughts.

The other issue with counterfactual thinking is that it’s the ultimate Catch-22. We have no scientific controls for it: because we have no actual time machine, we can’t find out for sure just how much better or worse things would have been if we had chosen differently. We can be pretty sure it was a bad idea to cheat on our taxes or our spouse, for example, but it’s harder to know if we should have had three kids instead of two. Or if we really would have been happier going back to graduate school.

Wisdom and careful reflection should be able to tell us in more obvious instances when our regret is valid. At other times, it may be better to adopt a mindset that embraces the present reality as the best possible one. In each case, self-knowledge is crucial. No one can know or dictate our regrets except us.

Some regret in life is inevitable, but the good news is that it’s in our power to make the most of it. Or as Landman so poetically puts it: