The power of regret: using hindsight as a tool for growth

Daniel Pink’s 2022 book, called The Power of Regret: How Looking Backward Moves Us Forward has some important takeaways that can be applied to classroom teaching scenarios.

If you’re not familiar with Daniel Pink, he’s a number-one New York Times bestselling author of When (about the optimal timing for completing tasks), Drive (about motivation), and several other books I’ve enjoyed. The Power of Regret is his most recent title. In this book, Pink draws on research in psychology, neuroscience, economics, and biology to challenge widely held assumptions about emotions and behavior.

His argument is that trying to live with “no regrets” is nonsense, even dangerous. Pink has found that everybody has regrets, that they’re a fundamental part of our lives, and if we reckon with them in fresh and imaginative ways, we can enlist our regrets to make smarter decisions, perform better at work and school, and deepen our sense of meaning and purpose.

Pink uses the largest sampling of American attitudes about regret ever conducted, as well as his own World Regret Survey, which has collected regrets from more than 16,000 people in 105 countries. From all that data, he identifies the four core regrets that most people have. By understanding what people regret the most, we can understand what they value the most. And by following the simple, science-based, three-step process that he sets out, we can transform our regrets into a positive force for working smarter and living better.

I thought this was an especially relevant topic for educators, because who among us doesn’t look back on choices we made or didn’t make and feel guilt or shame because of it. The emotional labor of teaching and the responsibility of having such a profound impact, for good or bad, on so many kids’ lives can be a lot to carry. So this is a fresh approach that might help you experience more resilience moving forward.

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Regret is an unavoidable part of the human experience

Pink writes that regret is about comparison. We compare what we think could have happened with what did, then we blame ourselves for making the wrong choice.

But this doesn’t have to be a bad thing, depending on how we use it. Regrets can improve decisions, boost performance by increasing persistence, and deepen meaning.

The key to turning regret into something positive is to use your emotions to understand when you’re feeling regret, think about why you’re feeling it, and then use it to improve your future.

Four regret categories (and their solutions)

Pink’s survey about regret found that the top regrets people have are related to interactions with family, interactions with romantic partners, education and career and finances, health, and friends.

So what are we supposed to do with that information?

What I like about the way Daniel Pink uses this research is that he’s categorized those regrets into larger behavioral patterns. Thinking about our regrets in this way makes it easier for us to recognize when we’re making a choice we won’t feel great about later, and easier to find a way to turn things around.

Regrets tend to fall into one of four types: foundation regrets, boldness regrets, moral regrets, and connection regrets. Let’s look at each one.

Foundation regrets stem from neglecting essential aspects of our lives, like health, finances, and relationships. They arise from our failure to plan and make wise decisions. They sound like, “If only I’d done the work.” The solution to foundation regrets is to start today.

Boldness regrets arise when we don’t seize opportunities or take risks. They come from playing it safe. They sound like, “If only I’d taken that risk.” The lesson here is to act. Do the thing that scares you a bit.

Moral regrets involve actions that go against our values, leading to guilt and shame. They happen when we make a choice we realize was cowardly or out of line with what we believe. Bullying and cheating on a partner were the most widely reported regrets in this category. Moral regrets sound like, “If only I’d done the right thing.” The learning here is, when in doubt, do the right thing.

Connection regrets occur when we can’t maintain or cultivate meaningful relationships with others. These are regrets about not starting or maintaining a relationship, and they sound like, “If only I’d reached out.” Connection regrets tend to be either rifts, started by an event that breaks the relationship, or drifts, when relationships slowly fade. The solution is to do your part to make the relationship happen and to maintain it.

Before we get into how to actually process those regrets, I want to take a quick moment to tell you about my book, Awakened: Change Your Mindset to Transform Your Teaching. The second edition is out, and it speaks to what we’re talking about here. 

Awakened is all about developing the resilient, flexible mindset that teaching actually requires. It pulls from stress management research, cognitive behavioral therapy, acceptance and commitment therapy, mindfulness practices, and a lot of stories and examples from real teachers.

What we cover in the book is how to change your perception of setbacks by replacing judgment with curiosity. How to observe your thoughts and pick the ones that actually create the results you want. How to let go of unrealistic expectations and comparisons. How to practice radical acceptance when you’re not seeing the results you want yet. And how to feel a sense of accomplishment in a job that, let’s be honest, is truly never finished.

It’s available now in paperback, Kindle, and on Audible if you want to listen. I’ll link to it in the show notes, and thank you, as always, for supporting me and my work.

Now, back to the episode, and …

How to respond to regrets of action (things we did or didn’t do)

I’m sure by this point you’re thinking about at least one thing you regret. The first move, if it’s possible, is to try to undo the consequences.

When you’ve done something you wish you hadn’t, ask yourself two questions. If you’ve harmed others, which is often the case with moral and connection regrets, can you make amends through an apology or some form of emotional or material restitution? And if you’ve harmed yourself, which is the case for many foundation regrets and some connection regrets, can you fix the mistake? Can you start paying down the debt? Can you reach out immediately to the person whose connection you let slip? If the regret can be undone, that’s where to start.

But a lot of regrets can’t be undone, and that’s where Pink offers a really useful reframe. He says when you can’t undo something, “at least” it. Instead of staying stuck in “if only,” try to find an “at least.”

Here’s what I mean. Several women in the World Regret Survey listed marrying a previous husband as their greatest regret. But the ones who were mothers tended to say something like, “I regret marrying a loser, but at least I got these great kids.”

Finding a silver lining doesn’t negate the existence of a cloud. It just offers another perspective on it.

Or imagine you bought a new car and now you regret it because you wish you’d picked a different make and model. Assuming the car is safe and functional, the type of car you drive isn’t going to make or break your happiness. So while you might pull a lesson from it for next time, like, check the consumer guides more carefully before buying, you can also “at least” it. “At least I got a good deal.” “At least it’s paid off.” “At least I didn’t get that other model with less trunk space.”

“At leasts” make us feel better. “If onlys” make us feel worse. “If only I’d made that investment sooner.” “If only I’d gotten my master’s degree then.” “If onlys” keep you stuck. “At leasts” give you somewhere to stand while you figure out the next move.

Three steps to make every regret count

One criticism of Daniel Pink’s work is that his conclusions are obvious and self-evident, and maybe you’re thinking that at this point. It’s nothing you didn’t already know intuitively.

But I’ve found that naming the behaviors and thinking about them consciously helps solidify better thinking habits. And it makes it easier to make wise choices in the future because I’ve actually sat with the regret instead of pushing it away because it felt uncomfortable. The discomfort is there to teach us something, if we’re willing to stay with it.

Rather than ignoring the negative emotion of regret, or worse, wallowing in it, we can use three steps Daniel Pink has outlined to process the regret in a healthy way. Disclose, reframe the way we view it and ourselves, and extract a lesson from the experience.

Step 1: Self-Disclosure (Relive and Relieve)

Once you’ve identified what you regret and figured out which of the four types it falls into, the first move is to actually talk about it. Or write about it. Just get it out of your head somehow.

I know that feels counterintuitive, because most of us want to bury the stuff we’re not proud of. Admitting that you yelled at a kid in front of the whole class, or that you let a friendship with a colleague quietly die after they got the position you wanted, none of that feels good to say out loud.

But disclosing what you’re feeling, whether you tell a trusted friend or just write it in a journal nobody will ever read, is linked to lower blood pressure, better coping, improved cognitive function, and even higher academic performance in students. Your body and brain do measurably better when you stop locking all your shameful behavior and lowest moments inside.

Pink’s point is that denying our regrets is exhausting. It takes up mental real estate we could be using for other things. And on the flip side, clutching them too tightly, replaying them on a loop at 2 a.m., that’s just rumination, and rumination doesn’t help anyone.

The middle path is to relive it just enough to relieve it. Say it, write it, name it, and let some of the air out of the balloon.

For teachers, this might look like talking to a colleague, friend, or partner that you trust about a parent interaction you handled badly. It might be an apology, when an apology is warranted, to a student, a parent, a coworker, or a former version of yourself.

And if an apology is part of it, a real one, not the corporate “I’m sorry you feel that way” version, Pink’s research is clear about what makes apologies actually work. You name what you did, without adding excuses or justifications. You acknowledge how it affected the other person. And you show, through what you do next, that you’re committed to something different. Apologies don’t undo the regret, but they often release some of its grip on you.

Step 2: Self-Compassion (Normalize and Neutralize)

Once you’ve said the regret out loud, you’re exposed. You’ve brought it into the light. This is where most of us tend to veer into unhealthy territory.

We might continue to be really hard on ourselves about it: “I should have known better, I’m a terrible teacher, this kid is going to remember this forever, and it’s my fault.” We tend to think this kind of self-flagellation is somehow productive, like if we beat ourselves up hard enough, we’ll never do the thing again.

But research says the opposite. Self-criticism, when it’s about who you are rather than about a specific behavior, mostly just leads to more rumination and hopelessness. It feels like accountability, but it functions more like inner-directed virtue signaling. You’re proving to yourself how seriously you take the failure, but you’re not actually changing anything.

We might also have a tendency to gloss over the regret, deny it, or pump ourselves up with affirmations. “I’m a great teacher, I’m doing my best, I shouldn’t feel bad about this.” That’s not effective either, because you know it’s not quite true.

What works is self-compassion, which Pink describes as replacing harsh judgment with basic kindness. You’re recognizing, as researcher Kristin Neff puts it, that being imperfect and making mistakes is part of the shared human experience.

You are not the only teacher who has ever blown it. You are not the worst person in your building. You are a human doing one of the hardest jobs there is.

Pink offers three questions to help you actually get to a place of self-compassion.

First, if a friend or a colleague came to you with the exact same regret you’re carrying, would you treat them with kindness, or with contempt? If your answer is kindness, that’s the approach you owe yourself. If your answer is contempt, try a different answer, because contempt isn’t a teaching tool, even when you’re directing it inward.

Second, is this kind of regret something other humans have experienced, or are you the only person on earth who has ever felt this? Because I can almost guarantee, whatever you’re carrying, another teacher somewhere is carrying the same thing. You’re not uniquely broken.

And third, does this regret represent one moment of your life, or does it define your entire life? One unpleasant memory inside a long and complicated career is very different from a regret that you’ve allowed to become the whole story of who you are. And if you really believe a single moment defines you, ask someone who loves you what they think. They’ll set you straight.

When we normalize what we’re feeling, we neutralize a lot of its power. We’re conscious of our tendency to either suppress it, or exaggerate it and make it more all-encompassing. Instead, we let it be what it actually is, which is a human moment, not a verdict on your worth as a teacher or your value as a human being.

Step 3: Self-Distancing (Analyze and Strategize)

The final step in processing regret in a healthy way is to turn that regret into something useful.

When you’re stuck in regret, the temptation is to dive deeper into the feeling. To analyze it from the inside, replay every detail, examine every angle from up close. The problem is that this almost always becomes rumination dressed up as reflection. You’re not actually learning anything new, you’re just sitting in the muck.

What actually works is moving in the opposite direction. Pulling back. Zooming out. Looking at the regret with a little bit of distance and a lot more curiosity.

Pink uses this metaphor I love. Instead of being the scuba diver swimming around in the murky depths of your regret, become the oceanographer flying over the water and studying the shape of the coastline. Same body of water, totally different vantage point, totally different information.

There are a few ways to actually do this, and you don’t need to use all of them. Just pick whichever one resonates and try it on.

One way is to imagine a friend or a colleague you adore is sitting across from you with the exact same regret you’re holding. What would you tell them? What lesson would you say this regret is offering them? Be specific. Be kind. Now go follow your own advice, because the advice you’d give someone else is almost always wiser than the advice you give yourself.

Another way comes from the late Andy Grove, who used to run the company Intel. When he was wrestling with a tough decision, he’d ask himself, “If I were replaced tomorrow, what would my successor do?” It’s a really useful question because it strips out all the ego and the embarrassment and the history you have with the situation, and it just asks, what would a fresh-eyed person do here? You can apply that to your classroom too. If a brand new teacher walked in tomorrow and inherited your situation, what would they do that you’ve been too close to see?

And one more, which I think is especially good for teachers. Imagine it’s ten years from now, and you’re looking back with pride on how you handled this regret. What did you do? Where did it lead you? What’s the version of this story you’d want to be telling at retirement? That future version of you, the one who’s already come through this, usually has the clearest sense of what the present version needs to do.

When you self-distance like this, the regret stops being a wound you’re trapped inside, and it starts being information you can actually use.

So that’s the sequence for processing regret. Disclose, then normalize, then analyze. It’s not complicated, but it does require you to sit with discomfort long enough to learn from it instead of running from it.

And the payoff Pink offers, the line that’s stuck with me since I first read this book, is this. If we know what we truly regret, we know what we truly value. Your regrets are a map. They’re pointing you toward what matters most to you. The things you regret about your classroom practice are usually the things you care about most deeply. Those regrets can be your greatest learning tool, and they can help you understand yourself so much better.

How to avoid unnecessary regret in the future

Now, if you’ve been listening this whole time thinking, “Okay great, but how do I just not pile up new regrets going forward?” Pink has thoughts on that too, and they’re practical.

His framework comes down to one big idea. You cannot agonize over every decision. You’ll burn out, and you’ll end up with decision fatigue that affects the choices that actually do matter. So he distinguishes between two modes, and learning when to use which one is a truly important life skill.

The first mode is satisficing. This is a word coined by the economist Herbert Simon, and it just means “satisfy” plus “suffice.” Good enough, in other words.

For the vast majority of decisions you make in a day, satisficing is the move. Which lesson plan template should I use? Where should we go for dinner? Should I email this parent today or tomorrow? What should I wear today? Pick a reasonable option, commit to it, and move on. You don’t need to research it, second-guess it, or make a spreadsheet of options.

Most of what people regret isn’t the small stuff. So stop treating the small stuff like it deserves the same energy as the big stuff.

The second mode is maximizing, which is where you actually do slow down, weigh options carefully, and try to get it right. But you only pull this mode out when you’re facing a decision that touches one of those four core regrets. Is this about my foundation, my health and finances, and long-term wellbeing? Is this about boldness, where I’m being too safe when I should be taking a real risk? Is this about a moral choice, where I know what the right thing is but it’s hard? Or is this about connection, about reaching out and showing up for the people who matter to me?

When you’re facing one of those, slow way down. Pink suggests projecting yourself into the future, ten years out, twenty years out, and asking which choice will most help you build a solid foundation, take a sensible risk, do the right thing, or strengthen a connection. That future version of you usually knows.

So in your daily work as an educator, it might play out like this. The decision about whether to redo your bulletin board? Satisfice. Pick something, slap it up, move on. The decision about whether to apply for that leadership role you’ve been dreaming about? That’s a boldness regret in the making. Maximize. Take it seriously. Don’t dismiss it because you’re tired.

The decision about which assessment to use this Friday? Satisfice. The decision about whether to confront the colleague who’s been making your work life harder, or whether to finally tell your principal that the workload isn’t sustainable? Connection and moral regret territory. Maximize.

You don’t have infinite emotional energy. Use it where it counts.

Your takeaway truth for the week ahead is this.

Your regrets aren’t proof that you’ve failed, they’re a map of what you care about. Every time you look back and wish you’d done something differently, you’re getting information about what actually matters to you, and that information is too valuable to waste on shame or rumination. Name the regret, treat yourself with the same kindness you’d offer a friend, pull back far enough to actually learn from it, and then let it guide what you do next.

You’re allowed to have regrets. You’re allowed to have made mistakes. You’re a human being doing one of the most emotionally complex jobs there is, and of course you’re going to look back sometimes and wish you’d handled things differently. That’s not a flaw in your character. That’s evidence that you care.