The Myth of Regret


Life is hard. 

It’s hard looking forward, but it can be even harder looking back. 

We are essentially living two lives — we are characters living in the story of the present moment (I am sitting in my kitchen writing this article), and we are also characters in the story we’re telling ourselves about the past (I have had a good life). 

In order to be fully content, it seems as though we need to find peace with both lives. 

In this article, we’re going to focus on the latter — life looking back — and the ever-present phenomenon that seems to get in the way: regret.

What is regret?

According to psychologist Melanie Greenberg, “regret is a negative cognitive or emotional state that involves blaming ourselves for a bad outcome, feeling a sense of loss or sorrow at what might have been, or wishing we could undo a previous choice that we made.”

We look back and see something that we wish wasn’t there (“I wish I hadn’t said that”), or we look back and imagine something that we wish was there (“I wish I’d traveled more”). In both cases, we suffer.

There are many forms of suffering that we inevitably encounter as we go through life yet regret is, I believe, one of the most prevalent, powerful, and unnecessary forms of suffering. 

Buddhism teaches us that the antidote to suffering is understanding. Let’s see if we can understand exactly what’s going on when we experience regret. 

When we look under the hood of regret, we notice that its’ engine is made up of four separate components: a memory, a judgment, a forecast, and a desire.

(1) A memory — you recall a past experience

(2) A judgment — you judge this experience

(3) A forecast — you forecast what life would have been like if the experience were added, removed, or changed

(4) A desire — you wish things were different

Bring any regret to mind and you will notice all four of these aspects at play. 

What we want to figure out is whether or not each of these aspects is accurate. Are we seeing things clearly? Is the suffering we feel from regret based on an accurate reflection of reality, or is our suffering misguided?

The myth of regret

The myth of regret is not that regret doesn’t exist — it does exist. The myth is about where regret comes from.

The story we’re told about regrets is that they are inevitable and that the goal should be to live your life in such a way as to minimize the number of regrets you have. Live the right way, do the right things, and there’s a promise of a life with no regrets. Live the wrong way, do the wrong things, and the dark cloud of regret may hover over you for the rest of your days.

This cultural view of regret can be seen quite clearly through a quick google search on the topic. Here are just a few of the articles that pop up:

  • How To Live Life Without Major Regrets: 8 Lessons From Older Americans
  • The 25 Biggest Regrets In Life. What Are Yours?
  • Older People’s Most Common Regrets
  • How To Limit 10 Of Life’s Biggest Regrets

But there’s something that all of these articles miss. Their approach to minimizing regrets is to direct one to rearrange the external circumstances of their life. And herein lies the myth. Regrets are not rooted in what you do or don’t do in your life. They are rooted in what you think about what you did or didn’t do in your life. 

In other words, it is our internal world that holds the key to unlocking the oppressive emotion of regret. And when we look closer to the internal mechanism of regret we come to find that it stems from not seeing things clearly. In its essence, regret is a thinking error. 

“I suspect you will find that a great many of your negative feelings are in fact based on thinking errors.” 

David Burns

Your mind deceives you

Regret is not just a thinking error — it is a string of thinking errors. To demonstrate what I mean, let’s take the following regret from one of the articles above:

“I regret marrying my partner.”

When you experience this regret, you are actually thinking four separate thoughts and believing them. The four thoughts might sound something like this:

A memory — I accurately recall the circumstances surrounding my decision to marry this person.

A judgment — I should not have married this person.

A forecast — I am certain that my life would have been better if I had not married this person.

A desire — I wish I had not married this person.

Our goal here is to comb through each of these thoughts to see if they are accurate reflections of reality. Are we seeing things clearly? 


The entire phenomenon of regret has its foundation in memory, and it turns out that this isn’t a particularly sturdy foundation. When it comes to remembering the past, evidence shows that we’re like a cheap camera — poor resolution and often out of focus.

To understand how remembering works, consider the “telephone game.” In this game, one person quietly whispers a message to the person beside them, who then passes it on to the next person in line, and so on.

Each time the message is passed, some parts might be misheard or misunderstood, others might get innocently altered, improved, or forgotten. Over time the message can become very different from the original.

The same can happen to our memories. There are countless reasons why tiny mistakes or embellishments might happen each time we recall past events, ranging from what we believe is true or wish were true, to what someone else told us about the event, or what we want that person to think. And whenever these flaws happen, they can have long-term effects on how we’ll recall that memory in the future.

According to Donna Bridge, a postdoctoral fellow at Northwestern University Feinberg School of Medicine, 

“A memory is not simply an image produced by time-traveling back to the original event — it can be an image that is somewhat distorted because of the prior times you remembered it. Your memory of an event can grow less precise even to the point of being totally false with each retrieval.”

What was that relationship like with your partner before you decided to get married? What was good, and what was bad about the relationship? 

What was it that led to you making the decision to marry this person? 

What were you thinking? What were you feeling? 

What else was going on in your life?

More often than not, the very memory of the event which you are regretting is not entirely accurate. 

That’s our starting point.


The next step we take in forming a regret is to judge the potentially inaccurate memory. This is when the pain starts. The judgment usually surfaces as a “should/shouldn’t” thought. 

  • “I should not have sent that email.”
  • “I should have spent more time with my kids.”
  • “I should have traveled more.”

Or in our example:

  • “I should not have married this person.”

If you’ve ever watched a professional sports game with a group of enamored fans you would have inevitably noticed an interesting phenomenon. People sitting at the bar, with a beer, who have never played professional sports, judging every decision made by the players on the court. “They should’ve passed…they should’ve shot…the coach should’ve run a different play…the player should have kept running down the field…these guys are idiots!”

Who is in the best position to make the decisions — the players on the field, or the fans off the field?

I think we’d all agree that the players on the field are in the best position to make the decision. Why? The players on the field have the most information and the most up-to-date data on the situation on hand. They are the ones who are actually in the game.

The same cognitive error is at play with regrets. 

In our example, someone chose a partner to marry, and then sometime later started believing that they should not have married that person. But if you look closely you’ll notice that there are actually two characters involved here: there is the person who made the decision (Person A), and there is the person who now believes they should not have made that decision (Person B).

These are not the same people. 

We are not the same individual throughout the course of our lives — we change, moment to moment, year to year. Every experience we have, every encounter, every book we read, every success, and every failure, all change us.

See if you can connect with that reality. See if you can connect with the fact that you are not the same person that you are remembering.

Let’s say that Person A made the decision to marry in 2015 and that now, in 2020, Person B believes that Person A made the wrong decision. Person B is judging Person A. But who was in the best position to make the decision, Person A or Person B? Who had the most accurate, up-to-date information at the time the decision was made?

Person A.

Person A made the decision on the court. Person B, similar to the rowdy fans in the sports bar, is making a judgment off the court.

Don’t judge Person A. They made the best decision they could with who they were and what they knew at the time. You are in no place to judge.


With our unreliable memory and our misplaced judgment, we are now on to phase three of the process of regret: forecasting. 

Similar to judgment, forecasting is yet another thought. But whereas the judgment in regret is a thought about the past, forecasting is a thought about the future. Specifically, forecasting is a thought about which path would have been better.

  • Person B is certain that Person A would have had a better life if they had not married their partner.
  • You are certain that your life would have been better if you traveled more.
  • You are certain that your life would have been better if you had had the courage to start your own business.

How can we be so certain?

It turns out that we are actually quite bad at predicting what will make us happy. Dan Gilbert, in his widely-acclaimed book, Stumbling On Happiness, hammers this point home with great rigor. Dan presents countless studies that show how our brains fall victim to a wide range of biases that ultimately cause our predictions of the future to be inaccurate. Because of these mental errors, it is remarkably difficult to predict what will make us feel happy. 

The biggest error we make in forecasting our happiness is the impact and duration that we think one particular life event will have on our lives.

He shares an extreme example of becoming a paraplegic versus winning the lottery. 

I am sure that you, like me, are certain that you would be much happier if you won the lottery and much less happy if you became a paraplegic. But you’d be wrong. A year after losing the use of their legs, and a year after winning the lotto, lottery winners and paraplegics both found their way back to their “baseline” level of happiness. 

Everyone in the study agreed that both events would have a dramatic and lasting effect on their overall life satisfaction, but the results of the study proved them wrong.

As the authors of the study explain, we are too damn adaptive. Whatever life throws at us, regardless of how good or how bad, we eventually just…get used to it:

“Eventually, the thrill of winning the lottery will itself wear off. If all things are judged by the extent to which they depart from a baseline of past experience, gradually even the most positive events will cease to have impact as they themselves are absorbed into the new baseline against which further events are judged. Thus, as lottery winners become accustomed to the additional pleasures made possible by their new wealth, these pleasures should be experienced as less intense and should no longer contribute very much to their general level of happiness.”

We shouldn’t feel bad about our poor forecasting capabilities since, according to Gilbert, “the part of our brain that enables us to think about the future is one of nature’s newest inventions, so it isn’t surprising that when we try to use this new ability to imagine our futures, we make some rookie errors.”

You are certain that if you could go back in time and ‘make right’ whatever regret is looming over your head that you’d be much happier in your life. 

Don’t be so sure.


If you’ve made it this far in the article with a regret still intact, then we have one final cognitive knot to untie for you. 

Imagine a good friend coming to you and lamenting over the fact that it rained on their graduation day over ten years ago. Every time they think back on their life the rain on their graduation day surfaces and they suffer. “I can’t believe it rained on my graduation day. I really wish it hadn’t rained, ugh, so frustrating.”

What would you tell them?

The truth is this: it rained. And it rained for a reason. Do you know why it rained? This is why it rained: heat from the sun turned moisture from plants and leaves, as well as oceans, lakes, and rivers, into water vapor, which disappeared into the air. That vapor then rose, cooled, and changed into tiny water droplets, which formed clouds. When the water droplets got too large and heavy, they fall as rain.

In other words, there is no way it could have not rained, due to the cause-and-effect laws that govern our universe.

Whatever it is that did or didn’t happen in the past, it could not have been otherwise. If it could have been otherwise, it would have been otherwise

If you regret something you said or did, understand that there are reasons why you said or did those things. Understand that the past you at that time in those circumstances could never have not said those things, any more than the rain could have not fallen on graduation day. 

The person who regrets marrying their partner falsely thinks that they could have not married that person. If they could have not married that person then they would not have married that person. What they’re really saying is that they wish they (themselves) were a different person back then and that the entire circumstances surrounding their decision were different. They are wishing that the heat from the sun didn’t turn to moisture. They are wishing that clouds didn’t form and produce rain.

It is this desire for reality to be other than what it is that forms the fourth and final thinking error in the phenomenon of regret. You must come to see reality as it is, not how you would like it to be. 

This requires acceptance.

Breaking through the myth 

Regret, as we’ve seen, is a string of thinking errors, otherwise known as cognitive distortions. Cognitive distortions are biased perspectives we take on ourselves and the world around us. They are irrational thoughts and beliefs that we unknowingly reinforce over time.

All cognitive distortions are:

  • Tendencies or patterns of thinking or believing;
  • That are false or inaccurate;
  • And have the potential to cause psychological damage.

Despite what we’ve been told, regret is not a natural part of life that we can only ever hope to minimize and manage. We can, in fact, dismantle it altogether, and the way to do that is to address these thinking errors one at a time. Each error can be seen as a kind of gate between us and emotional freedom, and we can free ourselves at any one of the four gates we’ve outlined in this article.

Don’t trust your memory: the more time that’s passed the more likely your memory is to be distorted. As you recall the past, put in extra effort to fill in more detail. Consider what you may be leaving out. Ask other people who were there what they recall. 

Challenge your judgment: recognize that the person you are today and the person you were in the past are actually two different people. When you regret the past you are in effect placing judgment on your previous self. 

There is an incredibly effective way to challenge your judgments. It consists of just three steps and can be done in less than ten minutes: 

  1. write down your regret as a statement, using the words “should” or “shouldn’t,” — ie I should have spent more time with my children
  2. write the inverse of this statement — ie I should not have spent more time with my children
  3. come up with as much evidence as you can to prove the inverse statement — ie I should not have spent more time with my children because work was my top priority back then

The magic happens in step three so spend most of your time there. Think of as much proof as you can to prove the inverse of your regret statement. You will slowly begin to see reality (← operative word!) more clearly

Recognize your faulty forecast: when we feel regret we are absolutely certain about what could have been or what would have been if we had acted differently. But the truth is that we are very bad forecasters. We can never know what would have been, and we overestimate the impact that one change would have made on our lives. Challenge your forecast by writing down all the reasons why your life would not have been better if you could go back and change whatever it is that you regret.

Disable your desire: you want so much for things to be different. You look back and see something that you wish you could remove. You look back and see something missing and you wish you could add it, or change it. In essence, you want reality to be other than what it is. If there were ever a recipe for prolonged suffering, this would be it. The only solution here is acceptance of reality. The good news is that whatever did or didn’t occur, it is now in the past. Bring your attention back to the present moment. 

In Conclusion

Unlike other forms of suffering, regret has the capacity to loom over us for months, years, or decades. 

We all make mistakes in life, and it’s important to learn from these mistakes so that we may not repeat them, but sustained regret is a different beast altogether. It really is a cognitive disease of sorts, working its way deep into our hearts and souls and carving out a home for itself.

The most effective approach to regret is not to tip-toe timidly through life, aiming to do all the “right” things and avoiding all the “wrong” things. The best approach is to understand regret itself; to see through the thinking errors it entails such that we’re able to release ourselves from its grip. In doing so we can free ourselves to live fully in today and tomorrow, regardless of what did or did not happen yesterday.

By Ryan Paugh

Hi there!

With decades spent exploring the outer world and the inner world, I share some of the insights I have learned along the way.

Topics include mindfulness, spirituality, growth, perspective, and career.

Start Here